[ CAS No. 302-79-4 ] {[proInfo.proName]}

Name: 302-79-4|(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid|98%
Brand: Ambeed
SKU: A126336
Price: 10.0 USD
Availability: InStock
Rating: 99 (22 reviews)

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Cat. No.: {[proInfo.prAm]}

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Limited Quantity	USD 15-60
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Inaccessible (Haz class 6.1), International	USD 150+
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Quality Control of [ 302-79-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 302-79-4 ]

Product Details of [ 302-79-4 ]

CAS No. :	302-79-4	MDL No. :	MFCD00001551
Formula :	C₂₀H₂₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	300.44	Pubchem ID :	-
Synonyms :	Vitamin A acid;all-trans-Retinoic acid;ATRA;Vitinoin;StievaA Forte;StievaA;RetisolA;Eudyna;EpiAberel;Dermairol;RetinA MICRO;RetinA;Renova;Avita;Aknoten;Vitamin A Acid. US brand names: Aberel;tretinoinum;trans vitamin A acid;trans retinoic acid;TRA;betaretinoic acid;alltrans vitamin A acid;RA;NSC 122758;NSC 122578;Tretinoin	Chemical Name :	(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

Calculated chemistry of [ 302-79-4 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.45
Num. rotatable bonds :	5
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	95.28
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.68
Log Po/w (XLOGP3) :	6.3
Log Po/w (WLOGP) :	5.6
Log Po/w (MLOGP) :	4.28
Log Po/w (SILICOS-IT) :	5.21
Consensus Log Po/w :	5.01

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-5.34
Solubility :	0.00137 mg/ml ; 0.00000455 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.87
Solubility :	0.0000403 mg/ml ; 0.000000134 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-3.17
Solubility :	0.205 mg/ml ; 0.000684 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.1

Safety of [ 302-79-4 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P201-P202-P264-P270-P273-P280-P301+P312+P330-P302+P352-P308+P313-P332+P313-P391-P405-P501	UN#:	3077
Hazard Statements:	H302-H315-H360-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 302-79-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 302-79-4 ]
Downstream synthetic route of [ 302-79-4 ]

[ 302-79-4 ] Synthesis Path-Upstream 1~2

1
[ 302-79-4 ]
[ 123-30-8 ]
[ 65646-68-6 ]

Reference： [1] Synthetic Communications, 1998, vol. 28, # 16, p. 2945 - 2958
[2] Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 501 - 506
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4378 - 4387

2
[ 302-79-4 ]
[ 65646-68-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 836 - 840
[2] Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 501 - 506
[3] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 6, p. 745 - 751

[ 302-79-4 ] Synthesis Path-Downstream 1~88

1
[ 638-10-8 ]
[ 54226-17-4 ]
[ 302-79-4 ]

Reference： [1]Journal of Vitaminology,1958,vol. 4,p. 190,192

2
[ 302-79-4 ]
[ 302-79-4 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 4111,4117

3
[ 186581-53-3 ]
[ 302-79-4 ]
[ 58526-50-4 ]

Reference： [1]Magnetic Resonance in Chemistry,1989,vol. 27,p. 707 - 709

4
[ 41891-54-7 ]
[ 20110-08-1 ]
[ 302-79-4 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 408 - 414

5
[ 302-79-4 ]
[ 132788-52-4 ]
C₅₀H₅₈N₁₀O₁₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 1917 - 1920

6
[ 302-79-4 ]
[ 15356-74-8 ]
[ 79-77-6 ]
[ 432-25-7 ]
[ 129454-99-5 ]
[ 129454-95-1 ]
[ 3012-76-8 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7679 - 7694

7
[ 86708-67-0 ]
[ 302-79-4 ]

Reference： [1]Synlett,2001,p. 800 - 802
[2]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3931 - 3942
[3]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[4]Journal of Organic Chemistry,2001,vol. 66,p. 8483 - 8489
[5]Journal of Organic Chemistry,1997,vol. 62,p. 4343 - 4348
[6]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 757 - 759
[7]Journal of Organic Chemistry,1995,vol. 60,p. 1195 - 1200

8
[ 302-79-4 ]
(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyl fluoride [ No CAS ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 1355 - 1361

9
(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid ethyl ester [ No CAS ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 3542 - 3544

10
[ 58526-50-4 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

11
[ 302-79-4 ]
[ 123-30-8 ]
[ 65646-68-6 ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 2945 - 2958
[2]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 501 - 506
[3]Journal of Medicinal Chemistry,2011,vol. 54,p. 4378 - 4387

12
[ 61644-18-6 ]
[ 302-79-4 ]
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid isobutyryloxymethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2962 - 2966

13
[ 302-79-4 ]
[ 65646-68-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 836 - 840
[2]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 501 - 506
[3]Journal of Pharmaceutical Sciences,1984,vol. 73,p. 745 - 751

14
(1E,3Z,5E)-1-tributylstannyl-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5-hexatriene [ No CAS ]
[ 302-79-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3931 - 3942

15
[ 2408-37-9 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 8483 - 8489
[2]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

16
[ 189633-82-7 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 8483 - 8489
[2]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[3]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[4]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290

17
[ 189633-81-6 ]
[ 302-79-4 ]

18
[ 252930-80-6 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 8483 - 8489
[2]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290

19
ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(tri-n-butylstannyl)-nona-2,4,6,8-tetraenoate [ No CAS ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 8483 - 8489
[2]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290

20
[ 54226-17-4 ]
[ 302-79-4 ]

Reference： [1]Synlett,2001,p. 800 - 802
[2]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[3]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 757 - 759
[4]Journal of the American Chemical Society,1955,vol. 77,p. 4111,4117

21
[ 25576-26-5 ]
[ 302-79-4 ]

Reference： [1]Synlett,2001,p. 800 - 802

22
2-((1E,3Z,5Z)-6-Iodo-3-methyl-hexa-1,3,5-trienyl)-1,3,3-trimethyl-cyclohexene [ No CAS ]
[ 302-79-4 ]

Reference： [1]Synlett,2001,p. 800 - 802

23
[ 154307-85-4 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 2696 - 2705

24
[ 210700-52-0 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 2696 - 2705

25
[ 210700-50-8 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 2696 - 2705

26
[ 6153-05-5 ]
[ 302-79-4 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[2]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[3]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

27
[ 2408-37-9 ]
EtX (X=halogen) [ No CAS ]
[ 302-79-4 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[2]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[3]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290

28
[ 3917-40-6 ]
[ 302-79-4 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[2]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 757 - 759
[3]Journal of the American Chemical Society,1955,vol. 77,p. 4111,4117
[4]Journal of Vitaminology,1958,vol. 4,p. 190,192

29
[ 99747-72-5 ]
[ 302-79-4 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290

30
(2Z,4E)-5-Iodo-3-methyl-penta-2,4-dien-1-ol [ No CAS ]
[ 302-79-4 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290

31
C₁₁H₂₁BO₂ [ No CAS ]
[ 302-79-4 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290
[2]Tetrahedron Letters,1999,vol. 40,p. 8287 - 8290

32
[ 25529-00-4 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

33
[ 67567-19-5 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

34
[ 187339-51-1 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

35
[ 14398-58-4 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

36
[ 14398-59-5 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

37
[ 187409-93-4 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

38
[ 187339-52-2 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

39
[ 78769-76-3 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

40
[ 187339-53-3 ]
[ 302-79-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 39,p. 1 - 10

41
[ 302-79-4 ]
(2S,3S,4S,5R,6S)-6-[(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid [ No CAS ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 1355 - 1361

42
[ 162376-82-1 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 1195 - 1200

43
[ 162376-86-5 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 1195 - 1200

44
[ 162376-83-2 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 1195 - 1200

45
5,6-Dihydro-4-methyl-6-(2,6,6-trimethylcyclohexa-1,4-dien-1-yl)-2H-pyran-2-ol [ No CAS ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 1195 - 1200

46
[ 162376-87-6 ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 1195 - 1200

47
Ethyl (4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)nonatetraenoate [ No CAS ]
[ 302-79-4 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 1195 - 1200

48
[ 79-77-6 ]
[ 302-79-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 757 - 759

49
[ 29789-62-6 ]
[ 302-79-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 757 - 759

50
[ 81061-91-8 ]
[ 302-79-4 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 4111,4117

51
[ 6703-19-1 ]
[ 302-79-4 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 4111,4117

52
[ 14398-44-8 ]
[ 302-79-4 ]

Reference： [1]Journal of Vitaminology,1958,vol. 4,p. 190,192

53
[ 57-55-6 ]
[ 302-79-4 ]
C₁₇H₂₀O₂ [ No CAS ]
C₁₇H₂₂O₂ [ No CAS ]
C₁₇H₂₀O₂ [ No CAS ]
C₁₇H₂₀O₂ [ No CAS ]
C₁₇H₂₀O₂ [ No CAS ]
C₁₇H₂₂O₂ [ No CAS ]
C₁₇H₂₀O₂ [ No CAS ]
C₁₈H₂₄O [ No CAS ]
C₂₁H₃₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	salicylic acid; at 187℃; for 2h;	In a 2-liter vessel, a solution was prepared containing 2 g of retinoic acid in 300 ml of propylene glycol; the esterification reaction of the retinoic acid was initiated by adding 1 mg of salicylic acid as a catalyst and by bringing the solution to a (boiling) temperature of 187C; the reaction was continued for an hour at the same temperature, and the resulting solution - referred to as solution n.1 - was cooled and added to an equal volume of distilled water. The mixture was extracted in three successive stages using 150, 100 and 100 ml respectively of 1,1,2 trichloro-2,2,1 trifluoro-ethane in a separating funnel; the organic extract was then washed with 100 ml of a 0.1% aqueous solution of potassium bicarbonate (KHCO3) and with 100 ml of distilled water to eliminate the catalyst. The solvent was removed in a Rotavapor in a stream of nitrogen (known technique). Solution n.1 was then analyzed to determine the compounds present. Elementary analysis showed the presence of about 70% of the crude formula compound C21H30O3 of molecular weight 330; and spectrographic and, in particular, infrared analyses determined the following structural formula: A second sample was prepared in the same way, but with a two-hour hot reaction between the retinoic acid and propylene glycol; and the resulting solution - referred to as solution n.2 - was purified and analyzed in the same way as solution n.1. In addition to about 20% of the formula IV compound, solution n.2 was found to contain crude formula compounds C17H20O2 and C18H24O of molecular weight 256 and C17H22O2 of molecular weight 258, corresponding to the following formu Solution n.2 was found to contain about 70% of isomers of molecular weight 256 and less than 10% of those of molecular weight 258.

Reference： [1]Patent: EP1119538,2004,B1 .Location in patent: Page 4-6

54
[ 57-55-6 ]
[ 302-79-4 ]
C₂₁H₃₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	salicylic acid; at 187℃; for 1h;	In a 2-liter vessel, a solution was prepared containing 2 g of retinoic acid in 300 ml of propylene glycol; the esterification reaction of the retinoic acid was initiated by adding 1 mg of salicylic acid as a catalyst and by bringing the solution to a (boiling) temperature of 187C; the reaction was continued for an hour at the same temperature, and the resulting solution - referred to as solution n.1 - was cooled and added to an equal volume of distilled water. The mixture was extracted in three successive stages using 150, 100 and 100 ml respectively of 1,1,2 trichloro-2,2,1 trifluoro-ethane in a separating funnel; the organic extract was then washed with 100 ml of a 0.1% aqueous solution of potassium bicarbonate (KHCO3) and with 100 ml of distilled water to eliminate the catalyst. The solvent was removed in a Rotavapor in a stream of nitrogen (known technique). Solution n.1 was then analyzed to determine the compounds present. Elementary analysis showed the presence of about 70% of the crude formula compound C21H30O3 of molecular weight 330; and spectrographic and, in particular, infrared analyses determined the following structural formula:

Reference： [1]Patent: EP1119538,2004,B1 .Location in patent: Page 4

55
potassium 3-methyl-4-oxocrotonoate [ No CAS ]
[(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride [ No CAS ]
[ 302-79-4 ]

Yield	Reaction Conditions	Operation in experiment
		In an argon atmosphere 40.4 g (278.5 mmol) ETHYL-3-METHYL-4-OXOCROTONATE were taken up in 80 ml of ethanol. 30.6 g (272.7 mmol) of a 50% aqueous solution of potassium hydroxide was then carefully added in the course of 20 minutes thereby keeping the reaction temperature at 0 to 5C. The mixture was then stirred at this temperature until the ester disappeared in the HPLC chromatograph. Thereafter 258.0 g of an ethanolic solution OF 9-(Z)-CLS-TRIPHENYLPHSPHONIUMCHLORIDE (content 38.8 %, 199.5 mmol) was carefully added in the course of 20 minutes. During the addition the reaction temperature was kept at 0 to 5C. Then 29.8 g (265.6 mmol) of a 50% aqueous solution of potassium hydroxide was then carefully added in the course of 20 minutes thereby keeping the reaction temperature at 0 to 5C. The mixture was then stirred at this temperature until the phosphonium salt disappeared in the HPLC chromatograph. To the orange suspension so formed 900ML deionized water were added whereby a clear orange solution was formed. The mixture was stirred for another 10 minutes, then 400 ml of deionized water and 260 ml methylene chloride were added and stirred for another 10 minutes. The organic phase was separated; the water phase then was three times extracted with a total volume of 540 ML methylene chloride. The organic phase was separated. The water phase was adjusted to a pH of 3.5 to 4.0 with 21 ml of phosphoric acid 85% and stirred for 20 minutes at 20 to 30C under argon atmosphere. The water phase was then extracted with 200 ml methylene chloride and the water phase further extracted two times with a total of 160 ml of methylene chloride. The combined organic phase was filtered. An exchange of solvent towards methanol was achieved by distilling off methylene chloride starting at 30C/250 mbar and ending at 40C/700 mbar and by at the same time adding 800 ml methanol. 9- (Z)-RETINOIC acid starts to crystallise out in the course of the distillation. The suspension was then cooled down to 0 to 5C and stirred for 2 hours. The yellow-orange suspension was filtered, washed with a total of 170 ml of methanol of 0 to 5C and the so obtained crystals were dried in the vacuum at 40 to 50C/ 30 mbar overnight. 10.6 g (17.7%) of the product was obtained in the form of yellow crystals and with a content of 98.5%.

Reference： [1]Patent: WO2004/89887,2004,A1 .Location in patent: Page 5-6

56
[ 302-79-4 ]
[ 53839-60-4 ]
[ 34781-86-7 ]
(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoyl]-(2,4-dihydroxy)phenylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With thionyl chloride; triethylamine; In N,N-dimethyl-formamide;	Example 2 (2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoyl]-(2,4-dihydroxy)phenylamide (KCBG08) A mixture of anhydrous DMF (2 mL) and SOCl2 (0.072 mL, 0.99 mmol) was stirred under argon for 1 h. To the mixture was added a solution of retinoic acid (0.10 g, 0.33 mmol) in anhydrous DMF (2 mL). After stirring at 0 C. for 45 min, the clear deep red retinoyl chloride solution was added dropwise to a cooled solution distilled triethylamine (0.14 mL, 0.99 mmol) and 4-amino resorcinol.HCl (0.10 g, 0.66 mmol) in dry, degassed DMF (2 mL). The reaction was quenched with NH4Cl (aq.), extracted with EtOAc (30 mL). The extracts were washed with H2O (2*30 mL) and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc:hexane=1:4) to give KCBG08 (0.11 mg, 86%) as a yellow solid. 1H-NMR (200 MHz, CDCl3): delta 7.78 (br s, 1H, NH), 6.97 (dd, 1H, J=15.00), 6.76 (d, 1H, J=8.60, Ar-H), 6.09~6.43 (m, 6H), 5.83 (s, 1H), 2.37 (s, 3H), 1.99~2.03 (m, 2H), 1.98 (s, 3H), 1.71 (s 3H), 1.58~1.62 (m, 2H), 1.45~1.47 (m, 2H), 1.02 (s, 6H). 13C NMR (100 MHz, CDCl3): delta 166.89, 154.94, 151.98, 149.80, 139.67, 137.64, 137.25, 135.14, 131.06, 130.01, 129.57, 128.65, 123.60, 119.53, 119.01, 107.88, 105.92, 39.57, 34.23, 33.10, 28.95, 21.76, 19.19, 14.15, 13.82, 12.89.

Reference： [1]Patent: US2003/171339,2003,A1

57
[ 302-79-4 ]
4-OH-9-cis-retinoic acid [ No CAS ]
4-hydroxy-9-cis-retinoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With SeO2; In 1,4-dioxane; Petroleum ether;	Example 11 Synthesis of 4-hydroxy-<strong>[302-79-4]9-cis-retinoic acid</strong> To a solution of <strong>[302-79-4]9-cis-retinoic acid</strong> (51 mg, 0.17 mmole) in 1.4-dioxane (2 ml) was added SeO2 (19 mg, 0.17 mmole) at 60 C. The solution was allowed to stir at that temperature for 3 hours. The reaction mixture was then filtered through a silica bed. The filtrate was concentrated and the residue subjected to flash column chromatography (silica, 75% ether in petroleum ether) to afford 4-OH-<strong>[302-79-4]9-cis-retinoic acid</strong> (21 mg., 40% yield), which is characterized as follows: Oil; TLC Rf=0.25 (silica, 75% ether in petroleum ether); 1 H-NMR (400 MHz, CDCl3) delta 7.08 (dd, J=16, 12 Hz, 1H, olefinic); 6.64 (d, J=16 Hz, 1H, olefinic), 6.21 (d, J=16 HZ, 1H, olefinic), 6.20 (d, J=16 Hz, 1H, olefinic); 6.04 (d, J=12 Hz, olefinic), 5.79 (s, 1H, olefinic), 4.02 (t, J=5 Hz, 1H, CH--O), 2.18 (s, 3H, CH3), 2.02 (s, 3H, CH3), 1.82 (s, 3H, CH3), 2.0-1.6 (m, 4H, CH2 --CH2), 1.05, 1.03 (2s, 23H, 2*CH3).

Reference： [1]Patent: US5932622,1999,A

58
[ 23790-80-9 ]
[ 302-79-4 ]

Yield	Reaction Conditions	Operation in experiment
25%	With sodium hydroxide; silver nitrate; acetic acid; trifluoroacetic acid; In ethanol; water; aluminium; acetonitrile;	EXAMPLE 5 Preparation of 9-cis-Retinoic Acid In 20 mL of 50% ethanol/water, 100 mg of 9-cis-retinal is dissolved in a capped vial wrapped with aluminum foil. After 200 mg of NaOH and 450 mg of AgNO3 is added, the vial is shaken vigorously at room temperature for at least 24 hours until disappearance of the starting retinal. Reaction is followed by HPLC (Vedec C18 column; MeCN/0.1% TFA gradient; 75-85%; 10 minutes, 1 mL/minute, 350 nm, retention time; 10.4 minutes for 9-cis-retinoic acid, and 11.6 minutes for all-trans). Greater than 90% of the products are 9-cis-retinoic acid. For purification, the reaction mixture is acidified by adding acetic acid and 5 mL of water and then filtered with 0.45 mu Whatman disk. The filtrate is pumped through a 900 mg C18 cartridge. 9-cis-retinoic acid is retained on the column. The column is then desalted with a water wash (40 mL). The retinoic acid is washed out with MeOH/MeCN (2:1). The product is concentrated under reduced pressure to dryness. Yield is about 25 mg of title product (25% yield).

Reference： [1]Patent: US5714595,1998,A

59
concentrated aqueous NH₄ OH [ No CAS ]
[ 1201226-02-9 ]
[ 302-79-4 ]
[ 545-06-2 ]
all-trans-retinoylphosphocholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	EXAMPLE 4 all-trans-Retinoylphosphocholine A solution of trichloroacetonitrile (50 mL) and triethylammonium phosphorylcholine (4.98 g, 17.5 mmol) in acetonitrile (500 mL) is added to a solution of all-trans-retinoic acid (2.1 g, 6.99 mmol) in acetonitrile (500 mL), which is protected from light, at room temperature under nitrogen. The resultant mixture is stirred at room temperature under nitrogen for 8 hours. The reaction mixture is cooled to 0 C. and is neutralized by addition of concentrated aqueous NH4 OH (3 mL) over a 30 minute period. The resultant mixture is concentrated in vacuo and purified to yield all-trans-retinoylphosphocholine as a yellow powder by column chromatography followed by drying in vacuo.

Reference： [1]Patent: US5776915,1998,A

60
[ 302-79-4 ]
N-hexadecyl-N,N,N-trimethyl-ammonium all-trans-retinoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol; n-heptane;	Table I 5 g (16.6 mmol) of all-trans-retinoic acid, which was previously dissolved in 50 ml of anhydrous tetrahydrofuran, were added to a solution of 5.25 g (8.3 mmol) of freshly purified and dried hexadecyltrimethylammonium carbonate dissolved in 50 ml of anhydrous methanol; the mixture was stirred for 2 hours at 30 C., away from the light and under an inert atmosphere, then the solvents were evaporated off under high vacuum and the residue obtained was taken up in heptane; the solution was filtered and the solvent was evaporated off under high vacuum. 9.7 g (quantitative yield) of N-hexadecyl-N,N,N-trimethylammonium all-trans-retinoate were obtained in the form of a maroon paste.

Reference： [1]Patent: US4857525,1989,A

61
benzene-n-hexane [ No CAS ]
[ 302-79-4 ]
[ 1073-42-3 ]
[ 150-76-5 ]
2-Cyclohexylethyl all-trans-Retinoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium iodide; potassium carbonate; In tetrahydrofuran; hexane; aluminium;	EXAMPLE VI 2-Cyclohexylethyl all-trans-Retinoate The following were refluxed in an aluminum foil-covered flask under nitrogen for 28 hours: 5.0 g. of all-trans-retinoic acid; 3.5 g. of cyclohexylethyl bromide; 15.0 g. of anhydrous potassium carbonate; 0.05 g. of potassium iodide; 0.05 g. of p-methoxyphenol; and 50 ml. of tetrahydrofuran. The reaction mixture was then diluted with 200 ml. of n-hexane and filtered through a one-half-inch-thick pad of alumina. The pad was eluted with 100 ml. of 1:1 benzene-n-hexane and the washings were combined with the original filtrate. The solvents were removed on a rotary evaporater, and the residual yellow oil was placed on a silica gel column (100 g.) with 20 ml. of n-hexane. The column was eluted with 600 ml. of 1:1 benzene-n-hexane. The first 200 ml. of eluted solution were discarded; the next 300 ml. were collected, and the solvent was evaporated. The yellow oil residue was evacuated for two days at a pressure of 0.03 mm. and room temperature. The proton magnetic resonance spectrum of the resulting oil was consistent with the structure. Anal. Calcd. for C28 H42 O2: C, 81.9; H, 10.3. Found: C, 81.8; H, 10.3.

Reference： [1]Patent: US4190594,1980,A

62
[ 6066-82-6 ]
[ 302-79-4 ]
[ 7719-12-2 ]
succinimidyl 9-cis-retinoate [ No CAS ]
[ 53839-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; isopropyl alcohol; benzene;	EXAMPLE V N-(All-trans-Retinoyloxy)-Succinimide A solution of retinoyl chloride was prepared by magnetically stirring 3.00 g. of all-trans-retinoic acid and 0.92 g. of phosphorous trichloride for two hours in 50 ml. of dry benzene at room temperature. This solution was added dropwise during 30 minutes at room temperature to a stirred solution of 5.75 g. of N-hydroxysuccinimide dissolved in 10 ml. of dry, N,N-dimethylformamide. The reaction mixture was stirred for 1.5 hours longer, then immersed in an 80 C. oil bath for 15 minutes. The reaction mixture was diluted with 150 ml. ethyl ether, and the thick red oil which did not dissolve was discarded. The ether solution was washed with five 30-ml. portions of ice water and dried over sodium sulfate. Evaporation of the solvents left a yellow powder which was recrystallized twice from 1:2 chloroform-n-hexane (7.5 ml. per gram) and once from isopropanol (25 ml. per gram). Product melting point was 177-179 C. The proton magnetic resonance spectrum was consistent with the structure. Anal. Calcd. for C 24 H31 NO4: C, 72.5; H, 7.86; N, 3.52. Found: C, 72.5; H, 7.91; N, 3.50.

Reference： [1]Patent: US4190594,1980,A

63
[ 60-29-7 ]
[ 302-79-4 ]
[ 7719-12-2 ]
[ 53839-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In ethylene glycol; benzene;	EXAMPLE III 2-HYDROXYETHYL all-trans-RETINOATE A solution of retinoyl chloride was prepared from 3.0 g of all-trans-retinoic acid and 0.92 g of phosphorous trichloride in 25 ml of benzene. This solution was added gradually to a solution of 6 ml of ethylene glycol and 8 ml of pyridine during a period of 40 minutes. The moderate reaction exotherm was controlled by cooling the reaction flask in an ice bath. The reaction was then stirred under a nitrogen atmosphere for 30 minutes longer. The orange reaction mixture was placed directly on 80 ml of activated alumina in a chromatographic column, and the column was eluted with 1.4 liters of anhydrous ethyl ether.

Reference： [1]Patent: US4055659,1977,A

64
[ 302-79-4 ]
[ 79-07-2 ]
all-trans RETINOYLOXYACETAMIDE [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; nitrogen; sodium carbonate; potassium carbonate; In water; ethyl acetate;	EXAMPLE I all-trans RETINOYLOXYACETAMIDE In a 1000 ml 3-necked round-bottom flask equipped with reflux condenser, stirrer, and nitrogen inlet were placed ethyl acetate (500 ml), all-trans-retinoic acid (10 g; 0.30 mole), anhydrous potassium carbonate (4.6 g, 0.30 mole), 2-chloroacetamide (30 g, 0.32 mole) and sodium iodide (5.0 g, 0.30 mole). This mixture was stirred at reflux temperature for eighteen hours under nitrogen atmosphere. At the end of the eighteen-hour period, the mixture was cooled to room temperature and extracted with three 500-ml portions of water, three 500-ml portions of 10% sodium carbonate in water, and one 500-ml portion of water. After each extraction the upper layer was retained and the lower layer discarded. The final upper layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure, leaving an orange oil. The oil was dried at ambient temperature and 0.5 mm pressure, causing it to turn to an orange-yellow solid, melting at 62-64 C. The crude product was recrystallized from hot toluene yielding pure all-trans-retinoyloxyacetamide, melting at 133-134 C. The proton magnetic resonance spectrum of the compound was consistent with the structure written. Anal. Calcd. for C22 H31 NO3: C, 74.4 H, 8.2 N, 3.9; Found: C, 74.4 H, 8.5 N. 3.9.

Reference： [1]Patent: US4055659,1977,A

65
potassium(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1yl)nona-2,4,6,8-tetraenoate [ No CAS ]
methanolic potassium hydroxide [ No CAS ]
[ 302-79-4 ]
[ 100-11-8 ]
4-NITROBENZYL all-trans-RETINOATE [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;	EXAMPLE V 4-NITROBENZYL all-trans-RETINOATE Potassium retinoate was made by neutralizing 3.00 g of all-trans-retinoic acid in 30 ml of tetrahydrofuran with 15.6 ml of 0.640 N methanolic potassium hydroxide. The solvent was evaporated on a rotary evaporator and the residue dried at a pressure of less than 0.5 mm. for several hours. Powdered potassium retinoate (3.03 g) in 20 ml of hexamethylphosphoramide was stirred overnight at room temperature with 2.16 g of 4-nitrobenzyl bromide. The reaction mixture was poured into 30 ml of cold 5% hydrochloric acid, precipitating a bright-yellow gum. The gum was washed by decantation with 60 ml of cold water, then was dissolved in 300 ml of ethyl ether. The ether solution was washed with four 40-ml portions of ice water and dried over sodium sulfate. Evaporation of the ether left a bright-yellow powder. The material was recrystallized twice from 50:50 chloroform-methanol (6 ml per gram), giving tiny, bright-yellow prisms, melting point 130-131 C. The proton magnetic resonance spectrum was consistent with the structure. Anal. Calcd. for C27 H33 NO4: C, 74.4 H, 7.63 N, 3.22; Found: C, 74.3 H, 7.73 N, 3.14.

Reference： [1]Patent: US4055659,1977,A

66
[ 302-79-4 ]
[ 57-88-5 ]
[ 7719-12-2 ]
[ 53839-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In diethyl ether; N,N-dimethyl-aniline; benzene;	EXAMPLE II Cholesteryl all-trans-Retinoate A solution of retinoyl chloride was prepared from 3.0 g of all-trans-retinoic acid and 0.92 g. of phosphorous trichloride in 20 ml. of benzene. This solution was added during 18 minutes to 3.48 g. of cholesterol and 28 ml. of N,N-dimethylaniline with stirring and heating to 90 C. in an open-neck flask. Stirring was continued for an additional 40 minutes, during which most of the benzene evaporated. The reaction mix was dissolved in 300 ml. of ethyl ether, and the ether solution was successively extracted with three 50-ml. portions of cold 2 N sulfuric acid, two 50-ml. portions of cold saturated sodium bicarbonate solution, and four 50-ml. portions of cold water.

Reference： [1]Patent: US4190594,1980,A

67
potassium(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1yl)nona-2,4,6,8-tetraenoate [ No CAS ]
methanolic potassium hydroxide [ No CAS ]
[ 51490-01-8 ]
[ 302-79-4 ]
All-trans-Retinoyloxyacetyl-3,4,5-Trimethoxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water;	EXAMPLE VIII All-trans-Retinoyloxyacetyl-3,4,5-Trimethoxybenzene: Potassium retinoate was made by neutralizing 3.00 g. of all-trans-retinoic acid in 30 ml. of tetrahydrofuran with 15.6 ml. of 0.640 N methanolic potassium hydroxide. The solvent was evaporated in a rotary evaporator, and the residue was dried at a pressure of less than 0.5 mm. for several hours. Powdered potassium retinoate (3.03 g.) in 20 ml. of hexamethylphosphoramide was stirred overnight at room temperature with 2.89 g. of 2-bromo-3',4',5'-trimethoxyacetophenone. The turbid yellow reaction mixture was poured into 30 ml. of cold 5% hydrochloric acid, precipitating a sticky yellow solid. The solid hardened when washed by decantation with 60 ml. of cold water. The solid was dissolved in 200 ml. ethyl ether, and the ether solution was washed with five 25-ml. portions of cold water. After drying over sodium sulfate, the ether solution was evaporated leaving a yellow powder. The powder was recrystallized twice from 1:2 chloroform-methanol (7.5 ml. per gram), giving yellow crystals, melting point 123.0-123.5 C. The proton magnetic resonance spectrum of the product was consistent with the structure. Anal. Calcd. for C31 H40 O6: C, 73.2; H, 7.93. Found: C, 73.3; H, 7.93.

Reference： [1]Patent: US4190594,1980,A

68
[ 302-79-4 ]
[ 7719-12-2 ]
[ 53839-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine; In diethyl ether; benzene;	EXAMPLE IV Trans-beta-Ionone (All-trans-Retinoyl)-Hydrazone A solution of retinoyl chloride was prepared from 3.0 g. of all-trans-retinoic acid and 0.92 g. of phosphorous trichloride in 50 ml. of benzene by stirring at room temperature for 2.2 hours. This solution was added dropwise to a stirred solution of 4.80 g. of dry hydrazine in 20 ml. of anhydrous ethyl ether during 30 minutes while cooling in an ice bath. Stirring was continued for three hours at room temperature, then for an additional hour at 50-60 C. The reaction mixture was diluted with 150 ml. of ethyl ether, then extracted with four 25-ml. portions of ice water.

Reference： [1]Patent: US4190594,1980,A

69
[ 302-79-4 ]
[ 103-72-0 ]
N-phenyl-N-retinoyl thiocarbamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; dimethyl sulfoxide;	Synthesis of N-Phenyl-N-Retinoyl Thiocarbamic Acid All-trans-retinoic acid 1 gm is dissolved in 5 ml of dimethylsulfoxide, and phenylisothiocyanate 1.2 ml is added to the solution. After reacting at 45 C. for 16 hours the mixture is slowly poured into 500 gm of cold water. The yellowish solid thus formed is filtered and is washed with water. N-phenyl-N-retinoyl thiocarbamic acid thus synthesised is practically pure as shown by infrared spectroscopy and thin-layer chromatography with a mobility of 0.93 on a solvent system of methanol:benzene, 1:3.

Reference： [1]Patent: US4216224,1980,A

70
[ 1040124-47-7 ]
[ 4759-48-2 ]
[ 302-79-4 ]
[ 302-79-4 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 3744 - 3746

71
[ 302-79-4 ]
[ 4759-48-2 ]
[ 302-79-4 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 3744 - 3746
[2]Dalton Transactions,2019,vol. 48,p. 10581 - 10595

72
[ 116-31-4 ]
[ 4759-48-2 ]
[ 302-79-4 ]
[ 302-79-4 ]

Yield	Reaction Conditions	Operation in experiment
	tetracycline-induced HEKK-mouse retinol saturase (RetSat) cells;Enzymatic reaction;Product distribution / selectivity;	FIG. 7 shows RetSat activity towards all-trans-retinoic acid; Incubation of cells with retinoic acid indicated that it is not substrate for saturation by RetSat (FIG. 7A). Synthetic 13-14-dihydroretinoic acid standards were examined on the same HPLC system to establish their elution conditions (FIG. 7B). Even though, 13-cis retinoic acid (peak 1, FIG. 7A) coelutes with all-trans-13,14-dihydroretinoic (peak 7, FIG. 7B) the absorbance spectrum of the two compounds is different (FIGS. 7A and B insets) and allowed us to conclude that 13,14-dihydroretinoic acid cannot be detected in RetSat-expressing cells incubated with retinoic acid.FIG. 7 shows RetSat activity towards all-trans-retinoic acid. (A) Analysis of retinoic acid conversion in RetSat-expressing cells. Tet-induced HEKK-RetSat or untransfected cells were incubated overnight with pure all-trans-retinoic acid (>90% pure by HPLC, assayed before incubation). Following incubation retinoic acid was extracted and analyzed by reverse-phase HPLC System II. The appearance of 13,14-dihydroretinoic acid isomers was monitored at 290 nm (expected 25-30 minutes after injection). Peak numbers represent 13-cis-retinoic acid, 9,13-di-cis-retinoic acid, 9-cis-retinoic acid and all-trans-retinoic acid. Ruiz, et al. J Biol Chem 274:3834-3841, 1999; Batten, et al. J Biol Chem 279:10422-10432, 2004; Kuksa, et al. Vision Res 43:2959-2981, 2003; Imanishi, et al. J Cell Biol 164:373-383, 2004. (B) Mixture of isomers of synthetic standards of 13,14-dihydroretinoic acid were examined by reverse-phase HPLC System II in order to establish product elution profile. Inset shows the spectra of the different isomers of 13,14-dihydroretinoic acid. Star (*) indicates an unrelated compound. The experiment was performed in triplicate samples and repeated.
	untransfected HEKK cells;Enzymatic reaction;Product distribution / selectivity;	FIG. 7 shows RetSat activity towards all-trans-retinoic acid; Incubation of cells with retinoic acid indicated that it is not substrate for saturation by RetSat (FIG. 7A). Synthetic 13-14-dihydroretinoic acid standards were examined on the same HPLC system to establish their elution conditions (FIG. 7B). Even though, 13-cis retinoic acid (peak 1, FIG. 7A) coelutes with all-trans-13,14-dihydroretinoic (peak 7, FIG. 7B) the absorbance spectrum of the two compounds is different (FIGS. 7A and B insets) and allowed us to conclude that 13,14-dihydroretinoic acid cannot be detected in RetSat-expressing cells incubated with retinoic acid.FIG. 7 shows RetSat activity towards all-trans-retinoic acid. (A) Analysis of retinoic acid conversion in RetSat-expressing cells. Tet-induced HEKK-RetSat or untransfected cells were incubated overnight with pure all-trans-retinoic acid (>90% pure by HPLC, assayed before incubation). Following incubation retinoic acid was extracted and analyzed by reverse-phase HPLC System II. The appearance of 13,14-dihydroretinoic acid isomers was monitored at 290 nm (expected 25-30 minutes after injection). Peak numbers represent 13-cis-retinoic acid, 9,13-di-cis-retinoic acid, 9-cis-retinoic acid and all-trans-retinoic acid. Ruiz, et al. J Biol Chem 274:3834-3841, 1999; Batten, et al. J Biol Chem 279:10422-10432, 2004; Kuksa, et al. Vision Res 43:2959-2981, 2003; Imanishi, et al. J Cell Biol 164:373-383, 2004. (B) Mixture of isomers of synthetic standards of 13,14-dihydroretinoic acid were examined by reverse-phase HPLC System II in order to establish product elution profile. Inset shows the spectra of the different isomers of 13,14-dihydroretinoic acid. Star (*) indicates an unrelated compound. The experiment was performed in triplicate samples and repeated.

Reference： [1]Patent: US2008/249042,2008,A1 .Location in patent: Page/Page column 2; 23-24; Sheet 7/24
[2]Patent: US2008/249042,2008,A1 .Location in patent: Page/Page column 2; 23-24; Sheet 7/24

73
[ 86708-67-0 ]
potassium hydroxide [ No CAS ]
[ 302-79-4 ]

Reference： [1]Chemical Communications,2008,p. 6330 - 6332

74
[ 2744-08-3 ]
[ 302-79-4 ]
[ 1311276-24-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4378 - 4387

75
[ 302-79-4 ]
[ 33311-29-4 ]
[ 1311276-38-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4378 - 4387

76
[ 302-79-4 ]
[ 107622-80-0 ]
[ 1311276-20-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4378 - 4387

77
[ 23790-80-9 ]
[ 302-79-4 ]
[ 302-79-4 ]

Reference： [1]Journal of Lipid Research,2012,vol. 53,p. 587 - 598

78
[ 1620084-74-3 ]
[ 74-88-4 ]
[ 4759-48-2 ]
[ 302-79-4 ]
[ 302-79-4 ]

Yield	Reaction Conditions	Operation in experiment
10%; 0.5%; 32%		[Pd2(dba)3](0.5 mg, 0.54 mol),P(o-tolyl)3(0.7 mg, 2.2 mol),K2CO3(0.3 mg, 2.2 mol)were placed under Ar in a 2-mL Schlenk tube. Then, the solutions ofboronic acid ester 15(2.4 mg, 5.4 mol)in 90:10 DMF/H2O(v/v)(400 L)and methyl iodide (0.1 M DMF solution, 6.0 L,0.60 mol)were added successively under dim light. After stirring a mixture at60 C for 5 min, a solution of 10 M KOH in 30:70 CH3OH-H2O(v/v)(500 L)was added and heated at 100 C for 2 min. The resulting mixturewas rapidly cooled in an ice bath and acidified by HCOOH (500 L).The mixture was filtered through a short column of silica gel (0.5g), eluted with acetonitrile (ca. 2 mL), followed by the addition ofpyrene (85 mM acetonitrile solution, 20 L,1.7 mol)as an internal standard. The resulting solution was analyzed by HPLC(mobile phase, acetonitrile:0.2% HCOOH in water = 85:15; column,Inertsil ODS-2 (GL science), 4.6 150 mm, 5 m;flow rate, 1 mL/min; UV detection, 360 nm; column temp., 40 C;retention time, 6.7 min) to give ATRA (1)in 32% yield based on the starting methyl iodide. The identificationof the product 1was confirmed by co-injection with an authentic sample usinganalytical HPLC under the same conditions. The 13- and 9-cisRAs, 2and 3were also observed as minor products in10 and 0.5% yields at 5.8and 6.1 min, respectively.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3622 - 3625

79
[(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride [ No CAS ]
[ 54168-84-2 ]
[ 302-79-4 ]

Yield	Reaction Conditions	Operation in experiment
82.3%		426 g [3-methyl-5-(2,6,6-trimethylcyclohexene-1-yl)-2Z,4E-pentadiene]-triphenyl phosphonic chloride was dissolved into 830 ml isopropanol; 75.4 g trans-beta-formyl crotonic acid was added with nitrogen filling; as the solution was stirred to be transparent, at -50-40 C., 752 ml NaOH isopropanol solution whose concentration is 2N was added dropwise with temperature kept at -50-40 C.; After reaction was performed for 24 hours, pH was adjusted to 8-9 by hydrochloric acid, and 19 mg palladium acetate was added with temperature increased to 80 C.; the reaction result was detected by HPLC; After isomerization was completed, the reaction liquid was poured into water, neutralized with concentrated hydrochloric acid, filtrated to gain crude product with suction filter, crystallized by ethyl acetate to obtain 204.2 g product with purity of 99.8% and yield of 82.3%.

Reference： [1]Patent: US8835680,2014,B1 .Location in patent: Page/Page column 10; 11

80
[ 302-79-4 ]
(R)-2-amino-3-methoxy-3-oxopropane-1-sulfonic acid [ No CAS ]
N-(9-cis-retinoyl)-L-cysteic acid methyl ester sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60 mg	With triethylamine; trimethylamine; isobutyl chloroformate; In tetrahydrofuran; methanol; at -10 - 20℃; for 3h;	<strong>[302-79-4]9-cis-retinoic acid</strong> (50 mg, 0.17 mmol) is dissolved in 0.5 ml_ anhydrous THF followed by the addition of 0.035 mL of triethylamine. The obtained mixture is chilled to ca. -10 C and 0.033 mL of isobutyl chloroformate is added under stirring. In a separate flask 0.09 g of L-cysteic acid methyl ester is dissolved in 2 mL methanol in the presence of 0.14 mL of trimethylamine. The obtained solution is added to the stirred mixture containing mixed anhydride of the <strong>[302-79-4]9-cis-retinoic acid</strong>. The obtained solution is stirred for 3 hours at room temperature and then subjected to work up in a usual manner. The obtained crude product is purified on RP-18 silica using MeOH-water mixture as eluent to give 60 mg of the product as a yellow oil. After purification, N-(9-cis-retinoyl)-L-cysteic acid methyl ester sodium salt was dissolved in methanol and stored under argon in a freezer NMR and High resolution Mass Spectrum the purified product corresponded to the expected structure.

Reference： [1]Patent: WO2017/99662,2017,A1 .Location in patent: Page/Page column 16; 17

81
[ 623-57-4 ]
[ 302-79-4 ]
C₄₅H₆₅NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		All-trans retinoic acid (2 g) and CDI (2.0 g) were dissolved in 20 mL of dichloromethane, stirred at 25 ° C for 2 h, and filtered. To the filtrate was added 3,3-dimethylamino-1,2-propanediol (1.2 g), DBU (1 g) and heated to reflux for 24 h. The reaction solution was washed three times with dilute hydrochloric acid, dried over Na2S04, and the dry solvent was evaporated to give the product 1 bis-all-trans-retinoic acid-3,3-dimethylamino-1,2-propanediol ester. The reaction was carried out by TLC (developing solvent: methanol: dichloromethane / 1: 1, UV detection (lambda = 254 nm)); mass spectrometry was used to determine the product structure.

Reference： [1]Patent: CN104368011,2017,B .Location in patent: Paragraph 0150

82
[ 302-79-4 ]
N-hydroxy-9-cis-retinoic carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Dissolve 30 mg of 9-cis retinoic acid in 10 ml of anhydrous dichloromethane.Add 60mg DIC, 12.2mg DMAP and 50mul DIPEA, react at room temperature for 12h,Retinoic acid NHS ester solution.Another 14 mg of hydroxylamine hydrochloride was dissolved in 8 ml of methanol.Add 2 ml of 0.1M fresh ethanolic sodium ethoxide solution,Filter out sodium chloride precipitation,Hydroxylamine alcohol solution. Mix the above retinoid NHS ester solution with hydroxylamine alcohol solution,Reaction in ice-water mixture for 48h,A crude N-hydroxy-9-cis-retinamide solution was obtained.The N-hydroxyl trans-retinamide crude solution is evaporated to dryness.Add 60% ethanol 5ml dissolved,Transfer to a DM-301 macroporous resin column equilibrated with 60% ethanol.Elution to the effluent with 60% ethanol is essentially free of UV absorption.Then eluted with 80% ethanol, the effluent was collected, concentrated by rotary evaporation, freeze-dried,N-hydroxy-9-cis-retinamide pure product. The product was detected by high resolution mass spectrometry.The anion excimer peak is 314.21255,Meet the target product characteristics.

Reference： [1]Patent: CN107628970,2018,A .Location in patent: Paragraph 0036; 0037; 0038; 0042; 0043; 0044
[2]Patent: CN108069877,2018,A

83
[ 302-79-4 ]
4-Oxo-9-cis-retinoic acid [ No CAS ]

Reference： [1]Molecular Pharmacology,2018,vol. 93,p. 489 - 503

84
[ 302-79-4 ]
C₂₀H₂₈O₃ [ No CAS ]
C₂₀H₂₈O₃ [ No CAS ]
4-Oxo-9-cis-retinoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With CYP26C1; reductase; for 0.25h;Enzymatic reaction;	General procedure: The stereoselectivity in the formation of 4-OH-RA by CYP26C1 was determined for individual RA isomers by incubating atRA, 13-cis-RA, or 9-cis-RA at 0.75 mM with 15 nM CYP26C1 and 30 nM reductase for 15 minutes. For comparison, CYP26A1 was incubated under identical conditions with the same substrates. Samples were extracted and analyzed by LC-UV using an Agilent 1200 series HPLC system coupled with a Chiralcel OD-RH column (5 mm, 2.1 150 mm; Chiral Technologies Inc., West Chester,PA) as described previously to detect 4(S)- and 4(R)-OH-RA formation (Fig. 2; Shimshoni et al., 2012). The peak area ratio of 4(S)- and 4(R)-OH-RA was calculated and used as an indicator of the stereoselectivity of 4-OH-RA formation.

Reference： [1]Molecular Pharmacology,2018,vol. 93,p. 489 - 503

85
[ 6066-82-6 ]
[ 302-79-4 ]
C₂₄H₃₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In dichloromethane; at 20℃; for 12h;	The 30mg 9- cis retinoic acid was dissolved in 10ml of anhydrous dichloromethanewas added 60mg DIC, 12.2mg DMAP and 50mul DIPEA, rt 12h, retinoic acid NHS ester to givea solution. Separately, 14mg of hydroxylamine hydrochloride was dissolved in 8ml ofmethanol was added freshly prepared solution of sodium ethoxide in ethanol 2ml0.1M,sodium chloride precipitate filtered off to give an alcoholic solution of hydroxylamine.The above-described retinoic acid NHS ester solution was mixed with hydroxylaminealcohol solution, the reaction for 48h ice-water mixture, to give N- hydroxy-9-cisretinoiccarboxamide crude solution.

Reference： [1]Patent: CN108069877,2018,A .Location in patent: Paragraph 0031; 0032; 0038

86
[ 302-79-4 ]
[ 575-03-1 ]
C₃₀H₃₁F₃O₄ [ No CAS ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 8805 - 8814

87
[ 68-26-8 ]
[ 4759-48-2 ]
[ 302-79-4 ]
[ 302-79-4 ]

Reference： [1]Patent: US2008/249042,2008,A1

88
[ 302-79-4 ]
[ 85622-93-1 ]
[ 339-16-2 ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 1857 - 1862
Angew. Chem.,2020,vol. 132,p. 1873 - 1878,6

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A1356859[ 13497-05-7 ]

Sodium (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

Reason: Free-salt

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Precautionary Statements-General
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Prevention
Code	Phrase
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P284	Wear respiratory protection.
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Response
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P304	IF INHALED:
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P321
P322
P330	Rinse mouth.
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P337	If eye irritation persists:
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 302-79-4 ] {[proInfo.proName]}

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[ 302-79-4 ] Synthesis Path-Upstream 1~2

[ 302-79-4 ] Synthesis Path-Downstream 1~88

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