[ CAS No. 55079-83-9 ] {[proInfo.proName]}

Name: 55079-83-9|(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid|98%
Brand: Ambeed
SKU: A470794
Price: 5.0 USD
Availability: InStock
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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 55079-83-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 55079-83-9 ]

SDS Specification

Alternatived Products of [ 55079-83-9 ]

Product Details of [ 55079-83-9 ]

CAS No. :	55079-83-9	MDL No. :	MFCD00866632
Formula :	C₂₁H₂₆O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IHUNBGSDBOWDMA-AQFIFDHZSA-N
M.W :	326.43	Pubchem ID :	5284513
Synonyms :	Ro 10-1670;all-trans Acitretin;Neotigason.;Soriatane;U0279;Ro 10-1670/000;Etretin	Chemical Name :	(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

Calculated chemistry of [ 55079-83-9 ]

Physicochemical Properties

Num. heavy atoms :	24
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	6
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	101.54
TPSA :	46.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.75 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.79
Log Po/w (XLOGP3) :	6.4
Log Po/w (WLOGP) :	5.06
Log Po/w (MLOGP) :	4.12
Log Po/w (SILICOS-IT) :	5.7
Consensus Log Po/w :	5.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.68
Solubility :	0.000674 mg/ml ; 0.00000207 mol/l
Class :	Moderately soluble
Log S (Ali) :	-7.17
Solubility :	0.0000221 mg/ml ; 0.0000000677 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-4.17
Solubility :	0.0221 mg/ml ; 0.0000676 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.53

Safety of [ 55079-83-9 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P201-P202-P264-P273-P280-P302+P352-P305+P351+P338-P312-P332+P313-P337+P313-P391-P405-P501	UN#:	3077
Hazard Statements:	H303-H315-H319-H360-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 55079-83-9 ]

* 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.

Downstream synthetic route of [ 55079-83-9 ]

[ 55079-83-9 ] Synthesis Path-Downstream 1~38

1
[ 54757-46-9 ]
[ 69427-46-9 ]

Reference： [1]Journal of Pharmaceutical Sciences,1990,vol. 79,p. 444 - 446
[2]Journal of Pharmaceutical Sciences,1994,vol. 83,p. 623 - 628

2
[ 69427-46-9 ]
[ 54757-46-9 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 710 - 715
Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 792 - 797
[2]Journal of Pharmaceutical Sciences,1990,vol. 79,p. 444 - 446

3
[ 54757-46-9 ]
[ 541-41-3 ]
C₂₄H₃₀O₅ [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1990,vol. 60,p. 2246 - 2249
Zhurnal Obshchei Khimii,1990,vol. 60,p. 2511 - 2515

4
[ 160024-33-9 ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
88.5%	With potassium hydroxide In ethanol for 0.75h; Heating;

Reference： [1]Samokhvalov, G. I.; Zakharova, N. I.; Sokolova, N. N.; Filippova, T. M.; Raigorodskaya, O. I.; et al. [Pharmaceutical Chemistry Journal, 1994, vol. 28, # 5, p. 343 - 348][Khimiko-Farmatsevticheskii Zhurnal, 1994, vol. 28, # 5, p. 43 - 47]

5
[ CAS Unavailable ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With iodine; toluene-4-sulfonic acid 1.) methylene dichloride, reflux, 15 min; 2.) diethyl ether/benzene, rt, 7 h;

Reference： [1]Aurell, Maria J.; Ceita, Luisa; Mestres, Ramon; Parra, Margarita; Tortajada, Amparo [Tetrahedron, 1995, vol. 51, # 13, p. 3915 - 3928]

6
[ 478496-93-4 ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine In dichloromethane at 20℃; for 24h;

Reference： [1]Andriamialisoa, Zo; Valla, Alain; Cartier, Dominique; Labia, Roger [Helvetica Chimica Acta, 2002, vol. 85, # 9, p. 2926 - 2929]

7
[ 22035-53-6 ]
[ 54757-46-9 ]

Reference： [1]Helvetica Chimica Acta,2002,vol. 85,p. 2926 - 2929

8
[ CAS Unavailable ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Triton B / methanol / 12 h / 20 °C 2: 9 g / NaOH / H₂O; methanol / 2 h / 20 °C 3: 85 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

Reference： [1]Andriamialisoa, Zo; Valla, Alain; Cartier, Dominique; Labia, Roger [Helvetica Chimica Acta, 2002, vol. 85, # 9, p. 2926 - 2929]

9
[ CAS Unavailable ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 9 g / NaOH / H₂O; methanol / 2 h / 20 °C 2: 85 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

Reference： [1]Andriamialisoa, Zo; Valla, Alain; Cartier, Dominique; Labia, Roger [Helvetica Chimica Acta, 2002, vol. 85, # 9, p. 2926 - 2929]

10
[ 55079-83-9 ]
[ 113473-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) PCl₃ / 1.) benzene, 1.5 h, 30 deg C; 2.) ether, 2 h 2: 2.75 percent / H₂O / 6 h / Irradiation

Reference： [1]Pfoertner; Englert; Schoenholzer [Tetrahedron, 1987, vol. 43, # 7, p. 1321 - 1334]

11
[ 54350-48-0 ]
[ 54757-46-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium hydroxide; In ethanol; ethyl acetate;	This etretinate was then dissolved in 20 ml of ethanol, 3 ml of 4N KOH, and enough acetone to make the solution one phase. The solution was stirred at room temperature for 2 1/2 days, acidified to pH 3 with 3N HCl, and extracted with ethyl acetate. The ethyl acetate was washed with brine, dried over Na2 SO4, filtered and concentrated to give a 69% yield of acitretin.
	In ethyl acetate;	Acitretin was obtained by stirring the contents of thirty 25 mg capsules of etretinate in ethyl acetate for 4 days, filtering and concentrating to dryness to give recovery of greater than 90% of the theoretical quantity of etretinate.

Reference： [1]Patent: US5808111,1998,A
[2]Patent: US5808111,1998,A

12
[ 54757-46-9 ]
[ 530-62-1 ]
[ 99792-29-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; dichloromethane; water;	The imidazolide used as the starting material was prepared as follows: 25.1 g of 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid and 37.3 g of N,N-carbonyldiimidazole were dissolved in 890 ml of tetrahydrofuran and stirred at room temperature for 18 hours. The reaction mixture was then poured into 9 l of water while stirring, stirred for 15 minutes and filtered. The residue was dissolved in 1 l of methylene chloride, dried over sodium sulphate and evaporated. Recrystallization from methylene chloride-pentane yielded 1-[9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoyl]imidazole in the form of orange-yellow crystals of melting point 184-185.

Reference： [1]Patent: US4565863,1986,A

13
1-N sulfuric acid [ No CAS ]
[ 108518-66-7 ]
5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-penta-2,4-diene-1-triphenylphosphonium bromide [ No CAS ]
[ 74479-40-6 ]
[ 111-92-2 ]
[ 123-38-6 ]
[ 6295-06-3 ]
[ 54757-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium hydroxide; sodium chloride; lead(IV) tetraacetate; sodium hydrogencarbonate; In N-methyl-acetamide; ice-water; ethanol; hexane; dichloromethane; water; mineral oil; benzene;	1775 Grams of lead tetraacetate (90) were gradually introduced within 30 minutes into a solution of 1000 g of L(+) tartaric acid dibutyl ester in 3850 ml of benzene at 25-30. The mixture was subsequently stirred for 1 hour at room temperature. The sediment was filtered off and extracted with 500 ml of benzene. The benzene extract was evaporated under reduced pressure. The residual glyoxalic acid butyl ester boiled at 50-65 /12 Torr after rectification. 836 Grams of the foregoing glyoxalic acid butyl ester were introduced into 376 g of propionaldehyde. The mixture was treated dropwise with 40.8 g of di(n-butyl)amine at 60. In so doing, the temperature rose to about 106. The mixture was then stirred for 2 hours at 106-111, cooled and taken up in ether. The ether extract was washed successively with 500 ml of 1-N sulfuric acid, 700 ml of water, 1000 ml of a 5% aqueous solution of sodium bicarbonate and subsequently with 1000 ml of water, dried over sodium sulfate and evaporated under reduced pressure. The residual 3-formyl-crotonic acid butyl ester boiled at 93-105 /14 Torr after rectification. 228 Grams of 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-penta-2,4-diene-1-triphenylphosphonium bromide were introduced into 910 ml of dimethylformamide under nitrogen gassing and treated within 20 minutes with 17.5 g of a suspension of sodium hydride (ca 50%) in mineral oil while cooling to 5-10. The mixture was stirred for 1 hour at about 10, then treated dropwise with 61.8 g of 3-formyl-crotonic acid butyl ester at 5-8, heated for 2 hours at 65, subsequently introduced into 8 liters of ice-water and, after the addition of 300 g of sodium chloride, thoroughly extracted with a total of 18 liters of hexane. The extract was washed five times with 1 liter positions of methanol/water (6:4) and twice with 1.5 liters portions of water, dried over sodium sulfate and evaporated under reduced pressure. The residual 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid butyl ester of melting point 80-81 was converted into a free acid as follows: 125.8 Grams of 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid butyl ester were introduced into 2000 ml of absolute ethanol and treated with a solution of 125.8 g of potassium hydroxide in 195 ml of water. The mixture was heated to boiling for 30 minutes under nitrogen gassing, then cooled, introduced into 10 liters of ice-water and after the addition of ca 240 ml of concentrated hydrochloric acid (pH 2-4), thoroughly extracted with a total of 9 liters of methylene chloride. The extract was washed neutral with about 6 liters of water, dried over calcium chloride and evaporated under reduced pressure. The residue was taken up in 700 ml of hexane. The precipitated 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid melted at 228-230.

Reference： [1]Patent: US4021574,1977,A

14
Diethylaminoethyl chloride [ No CAS ]
[ 54757-46-9 ]
[ 74479-44-0 ]
[ 75-03-6 ]
9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid (3-pyridyl) methyl ester [ No CAS ]
[ 74479-47-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 45 By the procedure of Example 21: 9-(4-methoxy-2,3,5,6-tetramethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester (melting point 105-106 C.) is manufactured from 9-(4-methoxy-2,3,5,6-tetramethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid and ethyl iodide; 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid 2-diethylaminoethyl ester (bright-yellow oil) is manufactured from 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid and diethylaminoethyl chloride; and 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid (3-pyridyl) methyl ester (melting point 113-114 C.) is manufactured from 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid and beta-picoline chloride.

Reference： [1]Patent: US4215215,1980,A

15
[ 55079-83-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
		47 EXAMPLE 47 EXAMPLE 47 By the procedure of Example 46: 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid allyl ester (melting point 66°-68° C.) is manufactured from 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid and allyl alcohol.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US4215215, 1980, A

16
[ 74479-40-6 ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
75.1%	With palladium on activated charcoal; water; triphenylphosphine; potassium hydroxide In acetonitrile at 80℃; for 5h;	5 Example 5 Isomerization reaction to obtain all-trans medicinal acitretin 10 g of acetonitrile, 0.27 g of palladium on carbon and 1.62 g of triphenylphosphine were added to a 100 ml beaker, and the mixture was stirred well to completely dissolve the triphenylphosphine.The prepared palladium carbon composite catalyst was added to the mixture prepared in the same manner as in Example 1, and the mixture was heated to 80 ° C for 3 hours, and filtered to recover palladium carbon.Then, 60 g of potassium hydroxide solution (18 g of potassium hydroxide, 42 g of an aqueous medium) was added to the filtrate, and the hydrolysis reaction was kept for 2 hours.After completion, the temperature was lowered to 30 ° C, the pH was adjusted to 5.0 with glacial acetic acid, 600 g of purified water was added, and the mixture was warmed to 60 ° C and filtered.The filter cake was transferred to a 500 ml three-necked flask, and 450 g of acetone was added thereto with stirring, and the temperature was raised to 55 ° C, and the temperature was kept for 2 hours.After suction filtration and drying, 19.3 g of all-trans medicinal acitretin was obtained, the yield was 75.1%, and the content was 99.7%.
60%	With potassium hydroxide In ethanol; water Reflux;	5 Preparation of acitretin (I) Aqueous solution of potassium hydroxide (155.2 g in 600 ml water) was added to a solution ofbutyl {(2E,4E,6E,8E)-9-(4-methoxy-2,3 ,6-trimethyl) phenyl-3 ,7-dimethyl-nona-2,4,6,8}tetraenoate, VI (300.0 g) in ethanol (1800 ml) at 25-30°C and the reaction mixture wasstirred at reflux temperature till completion of the reaction. After completion, as monitored byHPLC, the reaction mixture was quenched with water, and hydrochloric acid was added till pHwas between 2.5 and 3.5. The mass was heated at 70°C, stirred, cooled to 40-50°C and filtered.Recrystallization of the resulting solid from tetrahydrofuran gave acitretin (I).Yield: 154.0 g (60%)Desired trans isomer: > 98%
	With hydrogenchloride; potassium hydroxide In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; dichloromethane; water	2 EXAMPLE 2 EXAMPLE 2 125.8 g of 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid butyl ester are introduced into 2000 ml of abs. ethanol and treated with a solution of 125.8 g of potassium hydroxide in 195 ml of water. The mixture is heated to boiling under nitrogen gassing for 30 minutes, then cooled, introduced into 10 l of ice-water and, after the addition of about 240 ml of conc. hydrochloric acid [pH 2-4], thoroughly extracted with a total of 9 l of methylene chloride. The extract is washed with about 6 l of water to neutrality, dried over calcium chloride and evaporated under reduced pressure. The residue is taken up in 700 ml of hexane. The precipitated 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid melts at 228°-230° C.

Reference： [1]Current Patent Assignee: HUAPONT LIFE SCIENCES CO LTD - CN108610252, 2018, A Location in patent: Paragraph 0059-0070
[2]Current Patent Assignee: EMCURE PHARMACEUTICALS LTD. - WO2016/42573, 2016, A1 Location in patent: Page/Page column 11
[3]Current Patent Assignee: ROCHE HOLDING AG - US4215215, 1980, A

17
[ CAS Unavailable ]
[ 55079-83-9 ]
[ 1114539-87-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-ethyl-N,N-diisopropylamine In chloroform; N,N-dimethyl-formamide at 25℃; for 3h;

Reference： [1]Location in patent: experimental part Militsopoulou, Maria; Bariamis, Stavros E.; Athanassopoulos, Constantinos M.; Papaioannou, Dionissios [Synthesis, 2008, # 21, p. 3433 - 3442]

18
[ 54757-46-9 ]
[ 62442-57-3 ]
[ 1114539-85-3 ]

Reference： [1]Synthesis,2008,p. 3433 - 3442

19
[ 54757-46-9 ]
[ 121-44-8 ]
C₆H₁₅N*C₂₁H₂₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; at 15 - 25℃;Product distribution / selectivity;	A mixture of 260 ml of ethanol and 60 ml of water under nitrogen atmosphere is added with 38 g of triethylamine.50 g of crude <strong>[54757-46-9]Acitretin</strong> is poured in the mixture with stirring, keeping stirring at temperature of 15 C.-25 C. until complete dissolution.The solution is added with 220 ml of ethanol and slowly with 27 g of acetic acid, with cooling, thereby precipitating <strong>[54757-46-9]Acitretin</strong>.The mixture is left under stirring for not less than 2 hours and the solid is filtered and washed with ethanol, to obtain Pure <strong>[54757-46-9]Acitretin</strong> (46 g on average).
	In methanol; water; at 15 - 25℃;Product distribution / selectivity;	A mixture of 400 ml of methanol and 60 ml of water under nitrogen atmosphere is added with 38 g of triethylamine.50 g of crude <strong>[54757-46-9]Acitretin</strong> are poured in the mixture, stirring at a temperature of 15 C.-25 C. until complete dissolution.The solution is slowly added with 27 g of acetic acid, with cooling, thereby precipitating <strong>[54757-46-9]Acitretin</strong>, which after about 2 hours is separated from reaction mixture by filtration to obtain about 45 g of pure <strong>[54757-46-9]Acitretin</strong>.

Reference： [1]Patent: US2009/118538,2009,A1 .Location in patent: Page/Page column 2
[2]Patent: US2009/118538,2009,A1 .Location in patent: Page/Page column 2

20
[ CAS Unavailable ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In ethanol; water for 2h; Cooling;	1 A mixture of 260 ml of ethanol and 60 ml of water under nitrogen atmosphere is added with 38 g of triethylamine.50 g of crude Acitretin is poured in the mixture with stirring, keeping stirring at temperature of 15° C.-25° C. until complete dissolution.The solution is added with 220 ml of ethanol and slowly with 27 g of acetic acid, with cooling, thereby precipitating Acitretin.The mixture is left under stirring for not less than 2 hours and the solid is filtered and washed with ethanol, to obtain Pure Acitretin (46 g on average).
	With acetic acid In methanol; water for 2h; Cooling;	2 A mixture of 400 ml of methanol and 60 ml of water under nitrogen atmosphere is added with 38 g of triethylamine.50 g of crude Acitretin are poured in the mixture, stirring at a temperature of 15° C.-25° C. until complete dissolution.The solution is slowly added with 27 g of acetic acid, with cooling, thereby precipitating Acitretin, which after about 2 hours is separated from reaction mixture by filtration to obtain about 45 g of pure Acitretin.

Reference： [1]Current Patent Assignee: P&R SPA - US2009/118538, 2009, A1 Location in patent: Page/Page column 2
[2]Current Patent Assignee: P&R SPA - US2009/118538, 2009, A1 Location in patent: Page/Page column 2

21
[ 6066-82-6 ]
[ 54757-46-9 ]
[ 538-75-0 ]
[ 666854-55-3 ]
[ 1160953-96-7 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 2689 - 2695

22
[ 828-27-3 ]
[ 54757-46-9 ]
[ 1197356-78-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 4h;Cooling with ice bath;	In a reaction flask, etretin of 0.53g, p-trifluoromethoxyphenol of 0.4g, 4-dimethylaminopyridine (DMAP) of 0.4g and dichloromethane of 5ml are added and stirred in the condition of ice bath with white insoluble substances generated; DDC of 0.4g and dichloromethane solution are added and stirred to react with one another for 4h; and saturated ammonium chloride solution is added to stop the reaction, followed by extraction by dichloromethane, washing by saturated sodium chloride aqueous solution, drying by anhydrous sodium sulphate, concentration, and recrystallization by ethanol to obtain a yellow solid of 0.67g, mp 145.0-147.9 C 1H-NMR(CDCl3), delta(ppm): 7.26 (s,1H); 7.24(s,1H); 7.19-7.11 (m,3H); 6.77(d,1H); 6.63 (s,1H); 6.40(d,1H); 6.27(t,2H); 6.01 (s,1H); 3.84(s,3H); 2.44(s,3H); 2.33 (s,3H); 2.26(s,3H); 2.17(s,3H); 2.15(s,3H) 13C-N-MR(CDCl3), delta(ppm): 13.06; 156.37; 156.17; 149.17; 146.40; 140.36; 138.07; 136.01; 135.15; 134.01; 132.17; 130.19; 129.80; 129.23; 123.16; 122.89; 122.06; 116.97; 110.10; 55.59; 21.48; 17.53; 14.21; 13.09; 11.91 High-resolution MS: m/z: 486.2015 (theoretical value: 486.2018) molecular formula: C28H29F3O4
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0℃; for 4h;	Example 21 (4-trifluoromethoxyphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dim ethyl-2,4,6,8-nonatetraenoate (5b-01) In a reaction flask, etretin of 0.53 g, p-trifluoromethoxyphenol of 0.4 g, 4-dimethylaminopyridine (DMAP) of 0.4 g and dichloromethane of 5 ml are added and stirred in the condition of ice bath with white insoluble substances generated; DDC of 0.4 g and dichloromethane solution are added and stirred to react with one another for 4 h; and saturated ammonium chloride solution is added to stop the reaction, followed by extraction by dichloromethane, washing by saturated sodium chloride aqueous solution, drying by anhydrous sodium sulphate, concentration, and recrystallization by ethanol to obtain a yellow solid of 0.67 g, mp 145.0-147.9 C. 1HNMR (CDCl3), delta(ppm): 7.26 (s, 1H); 7.24 (s, 1H); 7.19-7.11 (m, 3H); 6.77 (d, 1H); 6.63 (s, 1H); 6.40 (d, 1H); 6.27 (t, 2H); 6.01 (s, 1H); 3.84 (s, 3H); 2.44 (s, 3H); 2.33 (s, 3H); 2.26 (s, 3H); 2.17 (s, 3H); 2.15 (s, 3H) 13CNMR (CDCl3), delta(ppm): 13.06; 156.37; 156.17; 149.17; 146.40; 140.36; 138.07; 136.01; 135.15; 134.01; 132.17; 130.19; 129.80; 129.23; 123.16; 122.89; 122.06; 116.97; 110.10; 55.59; 21.48; 17.53; 14.21; 13.09; 11.91 High-resolution MS: m/z: 486.2015 (theoretical value: 486.2018) molecular formula: C28H29F3O4

Reference： [1]Patent: EP2279999,2011,A1 .Location in patent: Page/Page column 21-22
[2]Patent: US2011/77298,2011,A1 .Location in patent: Page/Page column 17

23
[ 98-17-9 ]
[ 54757-46-9 ]
[ 1197356-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 4h;Cooling with ice bath;	In a reaction flask, etretin of 0.53g, m-trifluoromethylphenol of 0.4g, 4-dimethylaminopyridine (DMAP) of 0.4g and dichloromethane of 5ml are added and stirred in the condition of ice bath with white insoluble substances generated; DDC of 0.4g and dichloromethane solution are added and stirred to react with one another for 4h; and saturated ammonium chloride, solution is added to stop the reaction, followed by extraction by dichloromethane, washing by saturated sodium chloride aqueous solution, drying by anhydrous sodium sulphate, concentration, and recrystallization by ethanol to obtain a yellow solid of 0.62g, mp 121.5-123.1 C 1H-NMR(CDCl3), delta(ppm): 7.48(d,2H); 7.41 (s,1H); 7.32 (m,1H); 7.14(dd,1H); 6.76(d,1H); 6.71 (s,1H); 6.42 (d,1H); 6.29(d,1H); 6.22 (s,1H); 6.00(s,1H); 3.82 (s.3H); 2.43 (s,3H); 2.3 (s,3H); 2.24(s,5H); 2.15 (s,3H); 2.13 (s,3H) 13C-NMR(CDCl3), delta(ppm): 164.72; 156.48; 156.37; 151.02; 140.47; 138.07; 136.02; 135.11; 134.02; 132.31; 132.09; 131.76; 130.18; 129.90; 129.80; 129.28; 125.50; 122.90; 122.35; 119.18; 116.78; 110.10; 55.60; 21.49; 17.54; 14.26; 13.11; 11.92 High-resolution MS: m/z: 470.2076 (theoretical value: 470.2069) molecular formula: C28H29F3O3
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0℃; for 4h;	Example 14 (3-trifluoromethylphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimet hyl-2,4,6,8-nonatetraenoate (2b-01) In a reaction flask, etretin of 0.53 g, m-trifluoromethylphenol of 0.4 g, 4-dimethylaminopyridine (DMAP) of 0.4 g and dichloromethane of 5 ml are added and stirred in the condition of ice bath with white insoluble substances generated; DDC of 0.4 g and dichloromethane solution are added and stirred to react with one another for 4 h; and saturated ammonium chloride solution is added to stop the reaction, followed by extraction by dichloromethane, washing by saturated sodium chloride aqueous solution, drying by anhydrous sodium sulphate, concentration, and recrystallization by ethanol to obtain a yellow solid of 0.62 g, mp 121.5-123.1 C. 1HNMR (CDCl3), delta(ppm): 7.48 (d, 2H); 7.41 (s, 1H); 7.32 (m, 1H); 7.14 (dd, 1H); 6.76 (d, 1H); 6.71 (s, 1H); 6.42 (d, 1H); 6.29 (d, 1H); 6.22 (s, 1H); 6.00 (s, 1H); 3.82 (s, 3H); 2.43 (s, 3H); 2.3 (s, 3H); 2.24 (s, 5H); 2.15 (s, 3H); 2.13 (s, 3H) 13CNMR (CDCl3), delta(ppm): 164.72; 156.48; 156.37; 151.02; 140.47; 138.07; 136.02; 135.11; 134.02; 132.31; 132.09; 131.76; 130.18; 129.90; 129.80; 129.28; 125.50; 122.90; 122.35; 119.18; 116.78; 110.10; 55.60; 21.49; 17.54; 14.26; 13.11; 11.92 High-resolution MS: m/z: 470.2076 (theoretical value: 470.2069) molecular formula: C28H29F3O3

Reference： [1]Patent: EP2279999,2011,A1 .Location in patent: Page/Page column 19
[2]Patent: US2011/77298,2011,A1 .Location in patent: Page/Page column 15

24
[ 77227-90-8 ]
[ 54757-46-9 ]
(2-methyl-4-trifluoromethylphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;	In a reaction flask, etretin, polysubstituted aniline or phenol containing trifluoromethyl or trifluoromethoxyl, 4-dimethylaminopyridine (DMAP), dichloromethane, of 5ml, and dichloromethane solution of DCC are added, stirred at the room temperature for standing overnight; and saturated ammonium chloride solution is added to stop the reaction, followed by extraction by dichloromethane, washing by water, drying by anhydrous sodium sulphate, concentration, column chromatography (petroleum ether: 60-90 C), fraction collection and concentration to obtain the products

Reference： [1]Patent: EP2279999,2011,A1 .Location in patent: Page/Page column 9

25
[ 55079-83-9 ]
[ 74479-50-8 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus trichloride In toluene at 20℃; for 2h;	17 In a reaction flask, etretin of 0.5g, toluene of 10ml and phosphorus trichloride of 0.19ml are added and stirred at the room temperature for 2h, and the resultant solution is added in a solution of m-trifluoromethylaniline of 0.25g and pyridine of 6ml in the cooling condition, and stirred to react with one another at the room temperature for 5h; and the reaction liquid is poured in the crushed ice, followed by extraction by dichloromethane for three times, organic layer washing by saturated sodium bicarbonate, washing by water to neutrality, drying by anhydrous sodium sulphate, filtration, reduced pressure concentration to dryness, column chromatography (silica gel column: 100-200 meshes; mobile phase: petroleum ether: 60-90 °C:ethyl acetate = 15:1), fraction collection, concentration, and recrystallization by methanol to obtain a yellow product of 0.1g, mp 188.6-190.7 °C) 1H-NMR(CDCl3), δ(ppm): 7.88 (s,1H); 7.74(d,1H); 7.43 (t,1H); 7.35 (d,1H); 7.25 (s,1H); 7.06 (q,1H); 6.72 (d,1H); 6.60(s,1H); 6.33 (d,1H); 6.22 (q,2H); 5.79(s,1H); 3.82 (s,3H); 2.45 (s,3H); 2.30(s,3H); 2.24(s,3H); 2.15 (s,3H); 2.10(s,3H) 13C-NMR(CDCl3), δ(ppm): 165.22; 164.69; 156.31; 151.83; 149.87; 139.44; 138.90; 138.41; 138.17; 135.60; 132.13; 131.33; 130.91; 130.31; 129.93; 129.55; 128.73; 128.43; 122.87; 120.76; 118.90; 116.47; 110.14; 55.63; 21.49; 17.54; 13.89; 13.07; 11.91 High-resolution MS: m/z: 469.2234 (theoretical value: 469.2229) molecular formula: C28H30F3NO2
	With phosphorus trichloride In toluene at 20℃; for 2h;	17 Example 17 (3-trifluoromethoxyphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dim ethyl-2,4,6,8-nonatetraenoic acid amide (3b-01) In a reaction flask, etretin of 0.5 g, toluene of 10 ml and phosphorus trichloride of 0.19 ml are added and stirred at the room temperature for 2 h, and the resultant solution is added in a solution of m-trifluoromethylaniline of 0.25 g and pyridine of 6 ml in the cooling condition, and stirred to react with one another at the room temperature for 5 h; and the reaction liquid is poured in the crushed ice, followed by extraction by dichloromethane for three times, organic layer washing by saturated sodium bicarbonate, washing by water to neutrality, drying by anhydrous sodium sulphate, filtration, reduced pressure concentration to dryness, column chromatography (silica gel column: 100-200 meshes; mobile phase: petroleum ether: 60-90° C.:ethyl acetate=15:1), fraction collection, concentration, and recrystallization by methanol to obtain a yellow product of 0.1 g, mp 188.6-190.7° C. 1HNMR (CDCl3), δ(ppm): 7.88 (s, 1H); 7.74 (d, 1H); 7.43 (t, 1H); 7.35 (d, 1H); 7.25 (s, 1H); 7.06 (q, 1H); 6.72 (d, 1H); 6.60 (s, 1H); 6.33 (d, 1H); 6.22 (q, 2H); 5.79 (s, 1H); 3.82 (s, 3H); 2.45 (s, 3H); 2.30 (s, 3H); 2.24 (s, 3H); 2.15 (s, 3H); 2.10 (s, 3H) 13CNMR (CDCl3), δ(ppm): 165.22; 164.69; 156.31; 151.83; 149.87; 139.44; 138.90; 138.41; 138.17; 135.60; 132.13; 131.33; 130.91; 130.31; 129.93; 129.55; 128.73; 128.43; 122.87; 120.76; 118.90; 116.47; 110.14; 55.63; 21.49; 17.54; 13.89; 13.07; 11.91 High-resolution MS: m/z: 469.2234 (theoretical value: 469.2229) molecular formula: C28H30F3NO2

Reference： [1]Current Patent Assignee: ANHI NEW STAR PHARMACEUTICAL DEVELOPMENT; ANHUI MEDICAL UNIVERSITY - EP2279999, 2011, A1 Location in patent: Page/Page column 20
[2]Current Patent Assignee: ANHI NEW STAR PHARMACEUTICAL DEVELOPMENT; ANHUI MEDICAL UNIVERSITY - US2011/77298, 2011, A1 Location in patent: Page/Page column 16

26
[ 54757-46-9 ]
[ 1535-76-8 ]
[ 1197356-76-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane;Cooling with ice bath;	In a reaction flask, etretin of 0.53g, 4-amino-2-trifluoromethylphenol of 0.28g, 4-dimethylaminopyridine (DMAP) of 0.23g and dichloromethane of 5ml are added and stirred in the condition of ice bath with white insoluble substances generated; DDC of 0.4g and dichloromethane solution are added and stirred to react with one another for 4h; and saturated ammonium chloride solution is added to stop the reaction, followed by extraction by dichloromethane, washing by saturated sodium chloride aqueous solution, drying by anhydrous sodium sulphate, concentration, column chromatography (petroleum ether: 60-90 C:ethyl acetate = 20:1) and recrystallization by ethanol to obtain a yellow solid of 60mg, mp 118.7-123.8 C 1H-NMR(CDCl3), delta(ppm): 7.39 (d, 1H 7.26(m,1H); 7.12 (m,1H); 6.75 (d,1H); 6.61 (d,1H); 6.43 (d,1H); 6.30(s,1H); 6.26(d,1H); 6.01 (s,1H); 3.82 (s,3H); 2.42 (s,3H); 2.31 (s,3H); 2.25 (s,3H); 2.14(s,3H); 2.09(s,3H) 13C-NMR(CDCl3), delta(ppm): 165.62; 156.35; 155.93; 144.11; 140.15; 139.81; 138.14; 136.03; 135.33; 134.03; 132.02; 130.28; 129.88; 129.06; 125.43; 122.88; 121.07; 118.67; 116.98; 112.05; 110.10; 55.63; 21.49; 17.54; 14.19; 13.09; 11.92 High-resolution MS: m/z: 485.2177 (theoretical value: 485.2178) molecular formula: C28H30F3NO3
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0℃; for 4h;	Example 20 (4-amino-2-trifluoromethylphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate (4b-02) In a reaction flask, etretin of 0.53 g, 4-amino-2-trifluoromethylphenol of 0.28 g, 4-dimethylaminopyridine (DMAP) of 0.23 g and dichloromethane of 5 ml are added and stirred in the condition of ice bath with white insoluble substances generated; DDC of 0.4 g and dichloromethane solution are added and stirred to react with one another for 4 h; and saturated ammonium chloride solution is added to stop the reaction, followed by extraction by dichloromethane, washing by saturated sodium chloride aqueous solution, drying by anhydrous sodium sulphate, concentration, column chromatography (petroleum ether: 60-90 C.:ethyl acetate=20:1) and recrystallization by ethanol to obtain a yellow solid of 60 mg, mp 118.7-123.8 C. 1HNMR (CDCl3), delta(ppm): 7.39 (d, 1H); 7.26 (m, 1H); 7.12 (m, 1H); 6.75 (d, 1H); 6.61 (d, 1H); 6.43 (d, 1H); 6.30 (s, 1H); 6.26 (d, 1H); 6.01 (s, 1H); 3.82 (s, 3H); 2.42 (s, 3H); 2.31 (s, 3H); 2.25 (s, 3H); 2.14 (s, 3H); 2.09 (s, 3H) 13CNMR (CDCl3), delta(ppm): 165.62; 156.35; 155.93; 144.11; 140.15; 139.81; 138.14; 136.03; 135.33; 134.03; 132.02; 130.28; 129.88; 129.06; 125.43; 122.88; 121.07; 118.67; 116.98; 112.05; 110.10; 55.63; 21.49; 17.54; 14.19; 13.09; 11.92 High-resolution MS: m/z: 485.2177 (theoretical value: 485.2178) molecular formula: C28H30F3NO3

Reference： [1]Patent: EP2279999,2011,A1 .Location in patent: Page/Page column 21
[2]Patent: US2011/77298,2011,A1 .Location in patent: Page/Page column 16-17

27
[ 54757-46-9 ]
[ 445-04-5 ]
[ 1197356-74-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane;Cooling with ice bath;	In a reaction flask, etretin of 0.53g, 4-amino-3-trifluoromethylphenol of 0.28g, 4-dimethylaminopyridine (DMAP) of 0.23g and dichloromethane of 5ml are added and stirred in the condition of ice bath with white insoluble substances generated; DDC of 0.4g and dichloromethane solution are added and stirred to react with one another for 4h; and saturated ammonium chloride solution is added to stop the reaction, followed by extraction by dichloromethane, washing by saturated sodium chloride aqueous solution, drying by anhydrous sodium sulphate, concentration, column chromatography (petroleum ether: 60-90 C:ethyl acetate =20:1) and recrystallization by ethanol to obtain a yellow solid of 60mg, mp 166.7-168.6 C 1H-NMR(CDCl3), delta(ppm): 7.22 (d,1H); 7.12 (m,1H); 7.09(d,1H); 6.79(d,1H); 6.72 (s,1H); 6.62 (d,1H); 6.43 (d,1H); 6.30(s,1H); 6.26(d,1H); 5.98(s,1H); 3.84(s,3H); 2.43 (s,3H); 2.32 (s,3H); 2.26(s,3H); 2.14(s,3H); 2.11 (s,3H) 13C-NMR(CDCl3), delta(ppm): 13.04; 156.35; 155.84; 148.49; 140.21; 138.10; 136.03; 135.36; 134.94; 134.02; 132.01; 130.23; 129.83; 129.12; 126.68; 122.88; 120.00; 118.77; 117.13; 110.10; 55.611; 21.49; 17.53; 14.20; 13.10; 11.92 High-resolution MS: m/z: 485.2176 (theoretical value: 485.2178) molecular formula: C28H30F3NO3
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0℃; for 4h;	Example 19 (4-amino-3-trifluoromethylphenyl)-(all-trans)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate (4b-01) In a reaction flask, etretin of 0.53 g, 4-amino-3-trifluoromethylphenol of 0.28 g, 4-dimethylaminopyridine (DMAP) of 0.23 g and dichloromethane of 5 ml are added and stirred in the condition of ice bath with white insoluble substances generated; DDC of 0.4 g and dichloromethane solution are added and stirred to react with one another for 4 h; and saturated ammonium chloride solution is added to stop the reaction, followed by extraction by dichloromethane, washing by saturated sodium chloride aqueous solution, drying by anhydrous sodium sulphate, concentration, column chromatography (petroleum ether: 60-90 C.:ethyl acetate=20:1) and recrystallization by ethanol to obtain a yellow solid of 60 mg, mp 166.7-168.6 C. 1HNMR (CDCl3), delta(ppm): 7.22 (d, 1H); 7.12 (m, 1H); 7.09 (d, 1H); 6.79 (d, 1H); 6.72 (s, 1H); 6.62 (d, 1H); 6.43 (d, 1H); 6.30 (s, 1H); 6.26 (d, 1H); 5.98 (s, 1H); 3.84 (s, 3H); 2.43 (s, 3H); 2.32 (s, 3H); 2.26 (s, 3H); 2.14 (s, 3H); 2.11 (s, 3H) 13CNMR (CDCl3), delta(ppm): 13.04; 156.35; 155.84; 148.49; 140.21; 138.10; 136.03; 135.36; 134.94; 134.02; 132.01; 130.23; 129.83; 129.12; 126.68; 122.88; 120.00; 118.77; 117.13; 110.10; 55.61; 21.49; 17.53; 14.20; 13.10; 11.92 High-resolution MS: m/z: 485.2176 (theoretical value: 485.2178) molecular formula: C28H30F3NO3

Reference： [1]Patent: EP2279999,2011,A1 .Location in patent: Page/Page column 21
[2]Patent: US2011/77298,2011,A1 .Location in patent: Page/Page column 16

28
[ CAS Unavailable ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate With water; sodium hydroxide In methanol; dimethyl sulfoxide at 65℃; for 2h; Stage #2: With citric acid In water; dimethyl sulfoxide at 0℃;	4.1.9. General procedure for the saponification of tri- or tetraene esters General procedure: To a suspension of crude esters 37-41, 51, 52, 57, 70, 71 and E-72 (0.9 mmol) in MeOH (1.8 mL) and DMSO (0.25 mL), an 8 N aqueous solution of NaOH (0.31 mL) was added. The resulting reaction mixture was heated at 65 °C until completion of the reaction (as indicated by TLC). After evaporation of MeOH, the oily residue was diluted with H2O (5 mL), cooled to 0 °C and acidified with a 5% aqueous solution of citric acid to pH 5. The resulting mixture was extracted twice with EtOAc. The organic layers were combined and washed once with a saturated aqueous solution of NaCl and twice with H2O, dried over Na2SO4 and evaporated to dryness to obtain the corresponding acids 2-12. Acitretin (2) and analogs 3-12 were obtained as all-E acids after crystallization from EtOAc.

Reference： [1]Location in patent: experimental part Magoulas, George E.; Bariamis, Stavros E.; Athanassopoulos, Constantinos M.; Haskopoulos, Anastasios; Dedes, Petros G.; Krokidis, Marios G.; Karamanos, Nikos K.; Kletsas, Dimitris; Papaioannou, Dionissios; Maroulis, George [European Journal of Medicinal Chemistry, 2011, vol. 46, # 2, p. 721 - 737]

29
[ 65527-85-7 ]
[ 54757-46-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 721 - 737
[2]European Journal of Medicinal Chemistry,2011,vol. 46,p. 721 - 737

30
[ 54168-84-2 ]
[ 69365-97-5 ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
85.2%	Stage #1: trans-β-formyl crotonic acid; [3-methyl-5-(4-methoxy-2,3,6-trimethyl-phenyl)-2E,4E-pentadiene]-triphenyl phosphonic chloride With potassium hydroxide In isopropyl alcohol at -30 - -20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride; diamminedichloropalladium(II) In isopropyl alcohol at 30℃;	12 Preparation of 3,7-dimethyl-9-(4-methoxy-2,3,6-trimethyl-phenyl)-2E,4E,6E,8E-nonatetraenoic acid Embodiment 12 Preparation of 3,7-dimethyl-9-(4-methoxy-2,3,6-trimethyl-phenyl)-2E,4E,6E,8E-nonatetraenoic acid 102g [3-methyl-5-(4-methoxy-2,3,6-trimethyl-phenyl)-2E,4E-pentadiene)-triphenyl phosphonic chloride was dissolved into 395ml isopropanol; 32.2g trans-β-formyl crotonic acid was added with nitrogen filling; as the solution was stirred to be transparent, 363ml KOH isopropanol solution whose concentration is 2N was added dropwise with temperature kept at -30∼-20°C; After reaction was performed for 12 hours, pH was adjusted to 7-8 by hydrochloric acid, and 791mg Pd(NH3)2Cl2 was added with temperature increased to 30°C; the reaction result was detected by HPLC; as 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 52.4g product with purity of 99.1 % and yield of 85.2%.
85.2%	Stage #1: trans-β-formyl crotonic acid; [3-methyl-5-(4-methoxy-2,3,6-trimethyl-phenyl)-2E,4E-pentadiene]-triphenyl phosphonic chloride With potassium hydroxide In isopropyl alcohol at -30 - 20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride; cisplatine In isopropyl alcohol at 30℃; Inert atmosphere;	12 Preparation of 3,7-dimethyl-9-(4-methoxy-2,3,6-trimethyl-phenyl)-2E,4E,6E,8E-nonatetraenoic acid 102 g [3-methyl-5-(4-methoxy-2,3,6-trimethyl-phenyl)-2E,4E-pentadiene]-triphenyl phosphonic chloride was dissolved into 395 ml isopropanol; 32.2 g trans-β-formyl crotonic acid was added with nitrogen filling; as the solution was stirred to be transparent, 363 ml KOH isopropanol solution whose concentration is 2N was added dropwise with temperature kept at -30-20° C.; After reaction was performed for 12 hours, pH was adjusted to 7-8 by hydrochloric acid, and 791 mg Pd(NH3)2Cl2 was added with temperature increased to 30° C.; the reaction result was detected by HPLC; as 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 52.4 g product with purity of 99.1% and yield of 85.2%.

Reference： [1]Current Patent Assignee: CHONGQING HUABANGSHENGKAI PHARM - EP2708530, 2014, A1 Location in patent: Paragraph 0045; 0046
[2]Current Patent Assignee: CHONGQING HUABANGSHENGKAI PHARM - US8835680, 2014, B1 Location in patent: Page/Page column 9; 10

31
[ 54757-46-9 ]
[ 286-20-4 ]
C₂₆H₃₆O₂ [ No CAS ]
2-((1E,3E,5E,7E)-8-(4-methoxy-2,3,6-trimethylphenyl)-2,6-dimethylocta-1,3,5,7-tetraen-1-yl)cyclohexan-1-ol [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 11123 - 11126

32
[ 54757-46-9 ]
[ 286-20-4 ]
C₂₆H₃₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); alpha,alpha,alpha-trifluorotoluene; triethylamine hydrochloride; sodium iodide; In 1,4-dioxane; at 90℃; for 24h;Sealed tube; Inert atmosphere;	The reaction formula of this embodiment is as follows: (1) Under the air,Tetrakistriphenylphosphine palladium (Pd(PPh3) 4,8 mol%),1,1'-bis(diphenylphosphino)ferrocene (dppf, 10 mol%),Sodium iodide (NaI, 30 mol%),<strong>[54757-46-9]Acitretin</strong> (0.3mmol) was added to a tube,In a sealed reaction tube containing a magnet, the reaction tube was flushed with argon three times.Under argon protection, add 2 mL of PhCF3 and 0.5 mL of 1,4-dioxane to the reaction tube, then add cyclohexene (2 equiv.) to the reaction solution under argon atmosphere, and plug the piston. The reaction was stirred in a 90 C oil bath for 24 hours.(2) adding the material obtained in the step (1) to ethyl acetate and mixing well.After filtering off the solid residue with a short silica gel column, the organic phase was retained.(3) spinning the solvent in the organic phase obtained in the step (2) to obtain a crude product.The crude product was then purified on a silica gel column. The eluent was a mixture of petroleum ether and ethyl acetate with an isolated yield of 75% and a product purity of 100%.

Reference： [1]Patent: CN110002957,2019,A .Location in patent: Paragraph 0050-0055

33
acitretin [ No CAS ]
[ 10597-60-1 ]
(2E,4E,6E,8E)-3,4-dihydroxyphenethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.83%	With silicomolybdic acid; 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃; for 8h; Inert atmosphere;	1-8 Preparation of Compound of Formula (I) In a 250 mL three-necked flask, 77.0 mg (0.50 mmol) of hydroxytyrosol, 179.4 mg (0.55 mmol) of acitretin and 8.3 mg (0.005 mmol) silicomolybdic acid were dissolved in 100 mL of 1-butyl-3-methylimidazolium tetrafluoroborate under nitrogen atmosphere. After the reactants were fully dissolved, the temperature was raised to 40° C. and the reaction was carried out for 8 hours. Thin layer chromatography was used to track the reaction to completion, heating was stopped, and the protective device was removed. The reaction mixture system was allowed to separate into layers to give a crude product. The crude product was recrystallized with 80 mL methanol, and filtered and dried to obtain 198.3 mg of the title compound, a yield of 85.83%. 1-Butyl-3-methylimidazolium tetrafluoroborate was recovered for reuse.

Reference： [1]Current Patent Assignee: SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY - US10836703, 2020, B1 Location in patent: Page/Page column 1-6; 11-12

34
[ 55079-83-9 ]
[ 2131089-47-7 ]
[ 2639249-68-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	With 1,4-diaza-bicyclo[2.2.2]octane; tris(bipyridine)ruthenium(II) dichloride hexahydrate; 4,4'-di-tert-butyl-2,2'-bipyridine; nickel dichloride In N,N-dimethyl acetamide at 20℃; for 16h; Irradiation; Sealed tube; Inert atmosphere;	5.1; 5.2 Example 5 The reaction formula of this embodiment is as follows: (1) Under air, tris(2,2'-bipyridine)ruthenium hexahydrate (5mol%), nickel chloride (8mol%), 4,4'-di-tert-butyl-2,2'-bipyridine (10mol%), cyclobutanone oxime ester (0.2 mmol), triethylenediamine (2 equivalents), and acitretin (2 equivalents) were added to a sealed reaction tube with a branch tube containing a magnet, and the reaction tube was evacuated with argon three times. At room temperature, the reaction was carried out under 460-465 nm light for 16 hours. (2) Add the materials obtained in step (1) to ethyl acetate to fully mix, concentrate, and purify with a silica gel column to obtain the product. The isolated yield is 63%, and the product purity is 100%.

Reference： [1]Current Patent Assignee: CHUZHOU UNIVERSITY - CN112608208, 2021, A Location in patent: Paragraph 0061-0065

35
[ 104-54-1 ]
[ 55079-83-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
84.95%	With silicomolybdic acid; 1-butyl-3-methylimidazolium Tetrafluoroborate at 25℃; for 10h; Inert atmosphere;	1-8 Preparation of Compound of Formula (I) In a 250 mL three-necked flask, 67.0 mg (0.50 mmol) of cinnamyl alcohol, 179.4 mg (0.55 mmol) of acitretin and 8.3 mg (0.005 mmol) silicomolybdic acid were dissolved in 100 mL of 1-butyl-3-methylimidazolium tetrafluoroborate under nitrogen atmosphere. After full dissolution, the temperature was raised to 25° C. and the reaction was carried out for 10 hours. Thin layer chromatography was used to track the reaction to completion, heating was stopped, and the protective device was removed. The reaction mixture was allowed to separate into layers to give a crude product. The crude product was recrystallized with 70 mL methanol and dried to obtain 187.8 mg of the title compound, a yield of 84.95%. 1-Butyl-3-methylimidazolium tetrafluoroborate was recovered for reuse.

Reference： [1]Current Patent Assignee: SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY - US11084775, 2021, B1 Location in patent: Page/Page column 3-6

36
[ 55079-83-9 ]
[ 2131089-47-7 ]
[ 2639249-68-4 ]
[ 2657769-96-3 ]

Yield	Reaction Conditions	Operation in experiment
66.667 % de	With 1,4-diaza-bicyclo[2.2.2]octane; nickel(II) bromide diethylene glycol dimethyl ether; tris(bipyridine)ruthenium(II) dichloride hexahydrate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide at 20℃; for 16h; Schlenk technique; Inert atmosphere; Irradiation; Overall yield = 63 percent; Overall yield = 44 mg;

Reference： [1]Lu, Xiao-Yu; Xia, Ze-Jie; Gao, Ang; Liu, Qi-Le; Jiang, Run-Chuang; Liu, Chuang-Chuang [Journal of Organic Chemistry, 2021, vol. 86, # 13, p. 8829 - 8842]

37
[ 54145-95-8 ]
[ 84244-59-7 ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: C₃₄H₃₆OP⁽¹⁺⁾*Br^(1-) With sodium methoxide In dichloromethane at -5℃; for 3h; Inert atmosphere; Stage #2: 3-Formyl-crotonsaeure-butylester In dichloromethane at 30℃; for 3h; Inert atmosphere; Stage #3: With lithium hydroxide monohydrate; sodium hydroxide In ethanol at 70 - 80℃; for 2h;	12 Implementation 12All-trans-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nontetraenoic acid (Acitretin ) preparation Under a nitrogen atmosphere, 1143 g of dichloromethane was added to a 3000 ml reaction flask,Add (2E,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-2,4-pentadiene-1-triphenylphosphine bromide 114.3g (0.2mol), after stirring and dissolving,The reaction solution was cooled to below -5°C under ice bath conditions, 64.8 g of 25% sodium methoxide solution was added dropwise, and the dropwise addition was completed in about 2 hours. After the addition was completed, the reaction was continued for 1 hour.Control the reaction temperature to below 30°C, add (E)-3-methyl-4-oxo-2-butenoic acid butyl ester 187g (0.22mol) dropwise, after the dropwise addition, keep the reaction for 3 hours,Add glacial acetic acid to neutralize and adjust pH to about 5-6, add saturated sodium chloride solution, stir and wash,The organic layer was dried with anhydrous magnesium sulfate and filtered. After the filtrate was concentrated under reduced pressure, a solution of 684 ml of ethanol, 12 g of sodium hydroxide and 36 g of water was added, and the reaction solution was heated to 70°C-80°C and reacted for 2 hours. Then, cooled to 30°C, neutralized with glacial acetic acid, adjusted pH to about 5-6, precipitated solid, suction filtered, washed the filter cake with water, sucked dry, added the filter cake to acetone, stirred for 2 hours, suction filtered, dried, 39.2 g of all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nontetraenoic acid were obtained, Yield 60%, purity 99.5%

Reference： [1]Current Patent Assignee: CHONGQING HUBANG HAIKA PHARMACEUTICAL - CN114105737, 2022, A Location in patent: Paragraph 0049-0052

38
[ 54168-84-2 ]
[ 70573-56-7 ]
[ 55079-83-9 ]

Yield	Reaction Conditions	Operation in experiment
49.6%	Stage #1: (E)-1-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-1,4-pentadien-3-ol With sulfuric acid; triphenylphosphine In ethanol at 50 - 60℃; for 6h; Inert atmosphere; Stage #2: With sodium hydroxide In ethanol at 5℃; for 1.5h; Inert atmosphere; Stage #3: trans-β-formyl crotonic acid In ethanol at 30℃; for 3h; Inert atmosphere;	13 Example 13: All-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nontetraenoic acid ( Preparation of Acitretin In a 1000ml reaction flask, under a nitrogen atmosphere, add 100ml of ethanol, 6ml of sulfuric acid, and 26.2g of triphenylphosphine, continue stirring for 30 minutes, and then dropwise add ethyl alcoholAlcohol 300ml and (E)-1-(4-methoxy-2,3,6-trimethylphenyl)-3-methyl-1,4-pentadien-3-ol 24.6g (0.1mol) After mixing the solutions, the reaction solution was heated to 50°C-60°C and reacted for 6 hours. After the reaction solution was concentrated until the flow was stopped, 200 ml of water was added, extracted with 2*150 ml of toluene, and the layers were left to stand, and the toluene layer was discarded. The water layer was transferred to a clean reaction flask, the reaction solution was cooled to below -5°C under ice bath conditions, 24 g of 25% sodium hydroxide solution was added dropwise, and the dropwise addition was completed in about 30 minutes. After one hour, control the reaction temperature to below 30°C, add (E)-3-methyl-4-oxo-2-butenoic acid 18.7g, after the dropwise addition, keep the reaction for 3 hours, add glacial acetic acid for neutralization adjustment At about pH 5-6, a solid was precipitated, suction filtration, and the filter cake was washed with water, dried by suction, the filter cake was added to acetone and stirred for 2 hours, suction filtered, and dried to obtain all-trans-9-(4-methoxy- 2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nontetraenoic acid 16.2 g, yield 49.6%, purity 99.3%.

Reference： [1]Current Patent Assignee: CHONGQING HUBANG HAIKA PHARMACEUTICAL - CN114105737, 2022, A Location in patent: Paragraph 0053-0054

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