[ CAS No. 472-61-7 ] {[proInfo.proName]}

Name: 472-61-7|(6S,6'S)-3,3'-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)bis(6-hydroxy-2,4,4-trimethylcyclohex-2-enone)|95%
Brand: Ambeed
SKU: A186372
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Quality Control of [ 472-61-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 472-61-7 ]

Product Details of [ 472-61-7 ]

CAS No. :	472-61-7	MDL No. :	MFCD00672621
Formula :	C₄₀H₅₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MQZIGYBFDRPAKN-UWFIBFSHSA-N
M.W :	596.84	Pubchem ID :	5281224
Synonyms :

Calculated chemistry of [ 472-61-7 ]

Physicochemical Properties

Num. heavy atoms :	44
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.4
Num. rotatable bonds :	10
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	187.16
TPSA :	74.6 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-2.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	6.59
Log Po/w (XLOGP3) :	10.27
Log Po/w (WLOGP) :	8.91
Log Po/w (MLOGP) :	5.09
Log Po/w (SILICOS-IT) :	10.33
Consensus Log Po/w :	8.24

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	-9.35
Solubility :	0.000000266 mg/ml ; 0.0000000004 mol/l
Class :	Poorly soluble
Log S (Ali) :	-11.77
Solubility :	0.000000001 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-5.68
Solubility :	0.00124 mg/ml ; 0.00000208 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	6.53

Safety of [ 472-61-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 472-61-7 ]

* 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 [ 472-61-7 ]
Downstream synthetic route of [ 472-61-7 ]

[ 472-61-7 ] Synthesis Path-Upstream 1~8

1
[ 696647-73-1 ]
[ 472-61-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: With sodium methylate In methanol at 0℃; for 2 h; Stage #2: With acetic acid In methanol; water at 20 - 75℃; for 20 h; Heating / reflux	71,9 g (0, 125 mol) ASTAXANTHIN-C15-PHOSPHONIUMSALZ P5 (X~ = BRO- mid) wurden in 150 ML Methanol vorgelegt. Bei 0C gab man 11,4 g GIO-DIAL Ia (95percent ig ; das entspricht 0,0475 mol) zu. Dann tropfte man innerhalb von 1H bei 0C 24,8 g einer 30percent igen Lsung von Natriummethylat in Methanol (= 0,137 mol NaOMe) zu, rhrte eine weitere Stunde bei 0C nach und lies dann auf Raumtemperatur kom- men. Man tropfte eine Lsung von 1,5 G (25 mmol) Essigsure in 115 ml Wasser zu, erhitzte auf Rckfluss (ca. 75C) und rhrte 20 h unter Rckfluss nach. Man lies auf Raumtemperatur kommen und filtrierte das Kristallisat ab. Der Filterkuchen wurde zweimal MIT JE 100 ML EINES 60 : 40 (V/V) -GEMISCHES AUS METHANOL/WASSER, einmal mit heiem Wasser (100 ml) und einmal mit Methanol (100 ml ; 25C) gewaschen und im Vakuumtrockenschrank bei +50C getrocknet. Auswaage : 23,5 g Astaxanthin = 83, 0percent Ausbeute (bezogen auf eingesetztes Ia) ; Reinheit nach HPLC : 99, 17percent

Reference： [1] Patent: WO2004/48323, 2004, A1, . Location in patent: Page 10

2
[ 5056-17-7 ]
[ 472-61-7 ]

Yield	Reaction Conditions	Operation in experiment
1.53 kg	Stage #1: With ethyloxirane; triphenylphosphine In ethyl acetate at 0 - 30℃; for 24 h; Large scale Stage #2: With ethyloxirane; 2,6-di-tert-butyl-4-methyl-phenol In isopropyl alcohol for 30 h; Reflux; Inert atmosphere; Large scale	The concentrated solution of Example 6 was added dropwise to a solution of triphenylphosphine (11.8 kg) and 1,2-epoxybutane (130 g) in ethyl acetate (44 kg) at 0 to 30 ° C., and the reaction mixture was added dropwise at the same temperature And the mixture was stirred for 24 hours. The precipitated solid was collected by filtration and the wet crystals were dissolved in methylene chloride (39 kg). The obtained solution was added dropwise to ethyl acetate (305 kg) while stirring, and solid precipitation was confirmed. The precipitated solid was collected by filtration and dried in vacuo to give the title compound (3.95 kg, purity 87.5percent (trans form), 5.8percent (cis form)) as a white solid. The purity of the product was determined by high performance liquid chromatography (column: YMC-PAC ODS-A manufactured by YMC and mobile phase: acetonitrile with 0.1percent trifluoroacetic acid / 0.1percent aqueous trifluoroacetic acid = 5-95 / 45 to 5). 2,7-dimethylocta-2,4,6-triene-1,8-dialdehyde (0.484 kg), the compound of Example 7 (1) (3.90 kg), 2,6-di-t-butyl-p-cresol (32.5 g) and 1,2-epoxybutane (1.9 kg) were suspended in 2-propanol (15 kg) and the suspension was heated under reflux for 30 hours under a nitrogen atmosphere. The reaction mixture was cooled to -5 to 5 ° C. and stirred for 1 hour, and the precipitated solid was collected by filtration to give the title compound (1.53 kg, yield 86.9percent, purity 98.8percent, optical purity 97. 9percent ee) as a deep violet solid. The purity of the product was determined by high performance liquid chromatography (column: Triart C 18 ExRS Plus manufactured by YMC and mobile phase: acetonitrile with 0.025percent trifluoroacetic acid / 0.025percent aqueous trifluoroacetic acid = 30 to 98 / 2), respectively. The optical purity of the product was determined using high performance liquid chromatography (column: YMC CHIRAL Cellulose-SB manufactured by YMC and mobile phase: hexane / tetrahydrofuran = 85/15)

Reference： [1] Patent: JP2018/131390, 2018, A, . Location in patent: Paragraph 0032

3
[ 5056-17-7 ]
[ 472-61-7 ]
[ 71772-51-5 ]

Reference： [1] Helvetica Chimica Acta, 1981, vol. 64, # 7, p. 2405 - 2418
[2] Helvetica Chimica Acta, 1981, vol. 64, # 7, p. 2405 - 2418

4
[ 72523-68-3 ]
[ 472-61-7 ]

Reference： [1] Patent: WO2006/39685, 2006, A2, . Location in patent: Page/Page column 43

5
[ 7542-45-2 ]
[ 472-61-7 ]
[ 60760-95-4 ]
[ 71772-51-5 ]

Reference： [1] Patent: WO2006/39685, 2006, A2, . Location in patent: Page/Page column 58

6
[ 5056-17-7 ]
[ 472-61-7 ]

Reference： [1] Helvetica Chimica Acta, 1978, vol. 61, # 7, p. 2609 - 2615

7
[ 6094-35-5 ]
[ 472-61-7 ]

Reference： [1] Journal of the Chemical Society. Perkin transactions 1, 1975, # 21, p. 2195 - 2204

8
[ 5056-17-7 ]
[ 472-61-7 ]

Reference： [1] Helvetica Chimica Acta, 1981, vol. 64, # 7, p. 2447 - 2462

[ 472-61-7 ] Synthesis Path-Downstream 1~60

1
[ 5056-17-7 ]
[(2E,4E)-3-Methyl-5-((S)-2,6,6-trimethyl-3-oxo-4-phenoxymethoxycarbonyl-cyclohex-1-enyl)-penta-2,4-dienyl]-triphenyl-phosphonium; bromide [ No CAS ]
[ 472-61-7 ]

Reference： [1]Helvetica Chimica Acta,1978,vol. 61,p. 2609 - 2615

2
[ 472-61-7 ]
(3S,3'S)-15,15'-cis-Astaxanthin [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1978,vol. 61,p. 2609 - 2615

3
[ 472-61-7 ]
[ 112-67-4 ]
[ 5794-22-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridine; In dichloromethane; at 20℃;	10120] 7.6 g (12.7 mmol) of astaxanthin and 2.98 g (37.7 mmol) of pyridine are charged in 75.9 g of dichloromethane and 9.42 g (34.3 mmol) of hexadecanoyl chloride are added dropwise at 20 C. over 5 minutes. The reaction mixture is allowed to react overnight, the mixture diluted with 75.9 g of dichloromethane, 0.37 g of methanol and, 30 mm later, 11.4 g of water are added and the phases separated. The lower phase is washed with 11.4 g of 10% hydrochloric acid and then twice with 11.4 g of water. The organic phase is rotary evaporated at 50 C., the residue is taken up in ca. 217 ml of t-butyl methyl ether and again thlly concentrated. The residue is virtually dissolved in 217 ml of ethyl acetate at 50 C. and 108 ml of ethanol is added dropwise. The mixture is initially cooled to 45 C. and then to 0 C. over 17 h. The precipitated crystalline solid is filtered off under suction, washed twice with 72 ml of ethanol each time and dried at 40 C. in a vacuum drying cabinet. 10 g (73% yield) of astaxanthin dihexadecanoate (m.p. 79.7 C.) are obtained.

Reference： [1]Patent: US2017/305849,2017,A1 .Location in patent: Paragraph 0103; 0104; 0105; 0106; 0107; 0108-0110; 0120
[2]Helvetica Chimica Acta,1978,vol. 61,p. 2609 - 2615

4
[ 5056-17-7 ]
<5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid [ No CAS ]
[ 472-61-7 ]

Reference： [1]Helvetica Chimica Acta,1981,vol. 64,p. 2447 - 2462

5
[ 5056-17-7 ]
<5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid [ No CAS ]
[ 472-61-7 ]
[ 71772-51-5 ]

Reference： [1]Helvetica Chimica Acta,1981,vol. 64,p. 2405 - 2418
[2]Helvetica Chimica Acta,1981,vol. 64,p. 2405 - 2418

6
[ 472-61-7 ]
[ 39637-99-5 ]
[ 84432-72-4 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1982,vol. 36,p. 499 - 504

7
[ 472-61-7 ]
[ 39637-74-6 ]
C₆₀H₇₆O₁₀ [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 711 - 715

8
[ 472-61-7 ]
[ 6094-35-5 ]

Reference： [1]Chemistry of Natural Compounds,1984,vol. 20,p. 407 - 409
Khimiya Prirodnykh Soedinenii,1984,vol. 20,p. 431 - 433

9
[ 472-61-7 ]
(3S,3'S)-astaxanthin monosulfate [ No CAS ]
(3S,3'S)-astaxanthin disulfate [ No CAS ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1985,vol. 39,p. 629 - 638

10
(3S,3'S)-astaxanthin disulfate [ No CAS ]
[ 472-61-7 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1985,vol. 39,p. 629 - 638

11
(3S,3'S)-Astaxanthin-di-(-)-camphanat [ No CAS ]
[ 472-61-7 ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 1654 - 1664

12
[ 6094-35-5 ]
[ 472-61-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1975,p. 2195 - 2204

13
(S)-6-Hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-on [ No CAS ]
[ 472-61-7 ]

Reference： [1]Helvetica Chimica Acta,1981,vol. 64,p. 2405 - 2418

14
(S)-3-((1E,3E)-5-Bromo-3-methyl-penta-1,3-dienyl)-6-hydroxy-2,4,4-trimethyl-cyclohex-2-enone [ No CAS ]
[ 472-61-7 ]

Reference： [1]Helvetica Chimica Acta,1981,vol. 64,p. 2405 - 2418

15
[ 696647-73-1 ]
[(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide [ No CAS ]
[ 472-61-7 ]

Yield	Reaction Conditions	Operation in experiment
83%		71,9 g (0, 125 mol) ASTAXANTHIN-C15-PHOSPHONIUMSALZ P5 (X~ = BRO- mid) wurden in 150 ML Methanol vorgelegt. Bei 0C gab man 11,4 g GIO-DIAL Ia (95% ig ; das entspricht 0,0475 mol) zu. Dann tropfte man innerhalb von 1H bei 0C 24,8 g einer 30% igen Lsung von Natriummethylat in Methanol (= 0,137 mol NaOMe) zu, rhrte eine weitere Stunde bei 0C nach und lies dann auf Raumtemperatur kom- men. Man tropfte eine Lsung von 1,5 G (25 mmol) Essigsure in 115 ml Wasser zu, erhitzte auf Rckfluss (ca. 75C) und rhrte 20 h unter Rckfluss nach. Man lies auf Raumtemperatur kommen und filtrierte das Kristallisat ab. Der Filterkuchen wurde zweimal MIT JE 100 ML EINES 60 : 40 (V/V) -GEMISCHES AUS METHANOL/WASSER, einmal mit heiem Wasser (100 ml) und einmal mit Methanol (100 ml ; 25C) gewaschen und im Vakuumtrockenschrank bei +50C getrocknet. Auswaage : 23,5 g Astaxanthin = 83, 0% Ausbeute (bezogen auf eingesetztes Ia) ; Reinheit nach HPLC : 99, 17%

Reference： [1]Patent: WO2004/48323,2004,A1 .Location in patent: Page 10

16
[ 7542-45-2 ]
[ 472-61-7 ]
[ 60760-95-4 ]
[ 71772-51-5 ]

Yield	Reaction Conditions	Operation in experiment
	Resolution of racemate;	A Regis Pirkle Covalent D-phenylglycine, 5 A, 4.6 X 250 nm chiral HPLC column was used. The detector was set EPO <DP n="61"/>at 474 nm. A 10 muL sample was injected into the column. The sample was passed through the column using a mobile phase of 75% Heptane, 24% dichloromethane, and 1% ethanol at a flow rate of 1.5 mL/min. Racemic astaxanthin (e.g., 3S,3'S, meso (3R,3'S), and 3R,3'R in a 1:2:1 ratio) was run through the chiral HPLC column and the retention time for 3S,3'S ("S,S")-astaxanthin was 32.763 min, meso-astaxanthin was 31.165, and 3R,3'R ("R,R")-astaxanthin was.29.937. The total run time was 60 minutes.

Reference： [1]Patent: WO2006/39685,2006,A2 .Location in patent: Page/Page column 58

17
[ 72523-68-3 ]
[ 472-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 3h;Heating / reflux;	To a mixture of phosphonium salt (S)-102a (463 g, 0.804 mol, 2.2 eq), 4A MS (100 g) and Ci0 -dialdehyde (2,7-dimethyl-2,4,6-octatrienedial 122) (60 g, 0.365 mol, 1 eq) in DCM (7 L) at 0 0C, MeONa in MeOH (30 wt %, 151 mL, 0.804 mol, 2.2 eq) was added dropwise. After 4h, the additional 42 g of phosphonium salt (S)-102a (42 g, 0.2 mol) and 14 mL of MeONa in MeOH (30 wt %, 0.2 mol) was added. After 21h, the mixture was filtered through a silica gel pad (eluents: DCM/ EtOAc ~DCM/MeOH). Concentrated and filtered to obtain 110 g of crude product. The crude product (297 g) was mixed with 1000 ml of ethyl alcohol refluxed for 3h. After cooling, filtered and washed with ethyl alcohol (50 ml x 2) to obtain 221 g of (3S,3'S)-all-£'-astaxanthin. 1H NMR (CDCl3, 300 MHz): delta 1.21 (s, 6H), 1.32 (s, 6H), 1.81(t, J= 13.2 Hz, 2H), 1.94 (s, 6H), 1.99 (s, 6H) and 2.00 (s, 6H), 2.15 (dd, J= 12.6, 5.7 Hz, 2H), 4.32 (dd, J= 13.8, 5.7 Hz, 2H), 6.18-6.72 (m, ~14H).

Reference： [1]Patent: WO2006/39685,2006,A2 .Location in patent: Page/Page column 43

18
[ 114682-36-9 ]
[ 472-61-7 ]
[ 1010099-33-8 ]

Reference： [1]Phytochemistry,2008,vol. 69,p. 479 - 490

19
astaxanthin radical-cation [ No CAS ]
[ 472-61-7 ]

Reference： [1]Journal of Physical Chemistry A,2010,vol. 114,p. 126 - 132

21
[ 472-61-7 ]
C₄₀H₅₂O₄*Ca⁽²⁺⁾ [ No CAS ]

Reference： [1]Journal of Physical Chemistry B,2010,vol. 114,p. 16968 - 16977

22
[ 472-61-7 ]
[ 60760-95-4 ]
[ 71772-51-5 ]
[ 61319-45-7 ]
[ 34026-74-9 ]
(3R,3'S)-astaxanthin monoretinoate [ No CAS ]

Reference： [1]Natural Product Research,2011,vol. 25,p. 511 - 525

23
[ 472-61-7 ]
heptakis(6-(2-hydroxypropyl))-β-cyclodextrin [ No CAS ]
C₄₀H₅₂O₄*C₆₃H₁₁₂O₄₂ [ No CAS ]

Reference： [1]Carbohydrate Polymers,2012,vol. 89,p. 492 - 496

24
[ 472-61-7 ]
[ 897031-66-2 ]

Reference： [1]Marine Drugs,2012,vol. 10,p. 1391 - 1399

25
[ 472-61-7 ]
C₄₀H₅₂O₄^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium methanolate; dimethyl sulfoxide; In methanol; at 20℃;Inert atmosphere;	General procedure: Cn:N (0.5 mg) was dissolved under N2 in dry DMSO (3 mL). MeOK (25% in MeOH, 1 mL) was added and stirred at r.t. The reaction to Cn:N+12- became evident by a fast color change (Figure 2S). C50:19 gave a color change without forming a transparent solution. The obtained dispersion prevented the exact measurement of lmax. The characteristic color conversion was also observed with C30:11 replacing N2 with N2O.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4522 - 4525

26
[ 472-61-7 ]
astaxanthin radical-cation [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 14660 - 14670

27
[ 472-61-7 ]
C₄₀H₅₂O₄*2Sc⁽³⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 14660 - 14670

28
[ 108-30-5 ]
[ 472-61-7 ]
[ 264254-35-5 ]

Reference： [1]Organic Process Research and Development,2004,vol. 8,p. 796 - 801

29
[ 472-61-7 ]
(3S,3'S)-sodium succinate mono-(4-{18-[4-(3-carboxypropionyloxy)-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl) ester [ No CAS ]

Reference： [1]Organic Process Research and Development,2004,vol. 8,p. 796 - 801

32
[ 472-61-7 ]
C₁₆H₂₃ClO₃Si [ No CAS ]
astaxanthin diferulate [ No CAS ]

Reference： [1]Free Radical Research,2014,vol. 49,p. 102 - 111

33
[ 472-61-7 ]
9-Z-3,3′-dihydroxy-4,4′-dione-β,β′-carotene [ No CAS ]
13-Z-3,3′-dihydroxy-4,4′-dione-β,β′-carotene [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2017,vol. 65,p. 818 - 826
[2]Asian Journal of Chemistry,2016,vol. 28,p. 1185 - 1190
[3]Journal of Agricultural and Food Chemistry,2017,vol. 65,p. 10223 - 10232

34
[ 334-48-5 ]
[ 472-61-7 ]
[(1S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-decanoyloxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-2-oxocyclohex-3-en-1-yl] decanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 6h;	It was confirmed that astaxanthin didecanoate was produced by reacting free astaxanthin and a heavy chain fatty acid with an activating agent in an organic solvent in a conventional manner as conventionally used. Specifically, dichloromethane was dissolved in anhydrous 200 mg (0.34 mM) of astaxanthin (commercially available from Sigma) was dissolved in 5 ml of dry dichloromethane obtained by drying with calcium chloride (CaCl2) and then distilled. The resulting solution was dissolved in a 25 ml round-bottomed flask, 121.2 mg (0.70 mM) of decanoic acid and 160.5 mg (0.84 mM) of ethyl 3- (3-dimethylaminopropyl) -carbodiimide (EDCI) and 4- (dimethylamino) pyridine 81.9 mg (0.67 mM) were successively added thereto, followed by stirring at 20 C for 6 hours.
24.3 mg	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 6h;	It has been confirmed that astaxanthin didecanoate is produced by reacting free astaxanthin and heavy chain fatty acid with an activating agent in an organic solvent in the manner conventionally used in the prior art. Specifically, dichloromethane was dried with anhydrous calcium chloride (CaCl2) and then 5 ml of dry dichloromethane obtained by distillation was used as a solvent. 200 mg (0.34 mM) of astaxanthin (commercially available from Sigma) was dissolved in a 25-ml round-bottomed flask, and 121.2 mg (0.70 mM) of decanoic acid was used as the heavy chain fatty acid. 160.5 mg (0.84 mM) of 3-dimethylaminopropyl] -carbodiimide (EDCI) and 81.9 mg (0.67 mM) of 4- (dimethylamino) pyridine were successively added thereto and reacted at 20 C for 6 hours with stirring

Reference： [1]Patent: KR2015/134828,2015,A .Location in patent: Paragraph 0029-0031
[2]Patent: KR2017/5886,2017,A .Location in patent: Paragraph 0029-0031

35
[ 334-48-5 ]
[ 472-61-7 ]
astaxanthin monodecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2h;	In the present invention, astaxanthin monoester having better absorption effect than diester type was produced in a short time in a high yield by selectively reacting only one of two hydroxyl groups of astaxanthin.Specifically, 200 mg (0.34 mM) of free astaxanthin was dissolved in a 25 ml round-bottomed flask using 5 ml of dry dichloromethane obtained by drying dichloromethane with anhydrous calcium chloride (CaCl2) 20.2 mg (0.12 mM) of decanoic acid as a heavy chain fatty acid, 26.7 mg (0.14 mM) of EDCI and 13.7 mg (0.11 mM) of 4- (dimethylamino) pyridine as an activator were successively mixed and stirred at 20 C for 2 hours (Primary reaction).Subsequently, 20.2 mg of decanoic acid, 26.7 mg of EDCI and 13.7 mg of 4- (dimethylamino) pyridine were sequentially added to the reaction mixture, followed by stirring for 2 hours (secondary reaction). Further, 20.2 mg of decanoic acid, And 13.7 mg of 4- (dimethylamino) pyridine were successively added thereto, followed by reaction at 20 C for 2 hours (tertiary reaction). The mixture of the final reaction mixture and 50 ml of dichloromethane was washed with 20 ml of a 1 N aqueous hydrochloric acid solution, washed with distilled water, dried over anhydrous sodium sulfate (Na2SO4), filtered and then dichloromethane And evaporated.
130.8 mg	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 6h;	In the present invention, the astaxanthin monoester having an absorption effect superior to the diester type was produced in a short time in a high yield by selectively reacting with only one of the two hydroxyl groups of astaxanthin.Specifically, 200 mg (0.34 mM) of free astaxanthin was dissolved in 25 ml of a round-bottomed flask using 5 ml of dry dichloromethane obtained by drying dichloromethane with anhydrous calcium chloride (CaCl 2) and distillation, 20.2 mg (0.12 mM) of decanoic acid as a heavy chain fatty acid, 26.7 mg (0.14 mM) of EDCI and 13.7 mg (0.11 mM) of 4- (dimethylamino) pyridine as an activator were sequentially mixed and stirred at 20 C for 2 hours (Primary reaction).Subsequently, 20.2 mg of decanoic acid, 26.7 mg of EDCI and 13.7 mg of 4- (dimethylamino) pyridine were sequentially added to the reaction mixture, followed by stirring for 2 hours (secondary reaction). Further, 20.2 mg of decanoic acid, And 13.7 mg of 4- (dimethylamino) pyridine were sequentially added thereto, followed by reaction at 20 C for 2 hours (tertiary reaction). The mixture of the final reaction mixture and 50 ml of dichloromethane was washed with 20 ml of 1 N aqueous hydrochloric acid solution, washed with distilled water, and dried over anhydrous sodium sulfate (Na2SO4), filtered, and then dichloromethane And evaporated.

Reference： [1]Patent: KR2015/134828,2015,A .Location in patent: Paragraph 0032-0035
[2]Patent: KR2017/5886,2017,A .Location in patent: Paragraph 0032-0035

36
[ 472-61-7 ]
[ 112-67-4 ]
[ 5794-22-9 ]
(6S)-6-palmitoyloxy-3-[(all-E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.48%; 0.63%	With pyridine; In dichloromethane; for 5h;	In examples 5a, Sb, Sc and Sd, 0.4 g (0.67 mmol) of astaxanthin 2 was in each case charged in 3.35 ml (4.46 g, 52.48 mmol) of dichloromethane and 0.17 g (178.51 pi, 2.21 mmol) of pyridine was added in each case. Then, 550 mg (609.99 pi, 2.01 mmol) of palmitoyl chloride was added in example Sa, 520mg (569.32 jtl, 1.89 mmol) of palmitoyl chloride in example Sb, 480 mg (528.66 pi, 1.75 mmol) of palmitoyl chloride in example Sc and 440 mg (487.99 pi, 1.60 mmol) of palmitoyl chloride in example Sd. The mixtures were allowed to react for S hours and a sample from each example was analyzed by HPLC under the following conditions. Column: Zorbax Eclipse XDB-C18 1.8 tm S0*4.6 mm from Agilent. Eluent: -A: 0.OS% by volume triethylamine inwater10114] B: tetrahydrofuran Detector: UV detector X=470 nm, BW=S0 nmFlow rate: 1.2 ml/min Injection: 5 jtlTemperature: 50 C. Run time: 12 mm Pressure: ca. 260 bar The results are presented in Table 1 below. It can be seen that astaxanthin 2 elutes at a retention time of 3.2 minutes, astaxanthin monopalmitate at a retention time of 5.3 minutes and astaxanthin dipalmitate at a retention time of 6.5 minutes. Example 5a affords the best result. According to the integrated peaks, 92.48% of astaxanthin dipalmitate and 0.63% of astaxanthin monopalmitate are obtained. The astaxanthin 2 starting material is no longer present. Therefore, a particularly good yield of astaxanthin dipalmitate is obtained when the molar ratio of palmitoyl chloride to astaxanthin 2 is 3.

Reference： [1]Patent: US2017/305849,2017,A1 .Location in patent: Paragraph 0111; 0112; 0113; 0114; 0115; 0116; 0117

37
[ 472-61-7 ]
[ 112-13-0 ]
[(1S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-decanoyloxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-2-oxocyclohex-3-en-1-yl] decanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With pyridine; In dichloromethane; at 20℃;	10 g (16.75 mmol) of astaxanthin 2 and 4.37 g (55.29 mmol) of pyridine are charged in 111.4 g of dichloromethane and 10.65 g (50.26 mmol) of decanoyl chloride are added dropwise at 20 C. over 5 minutes. The reaction mixture is allowed to react overnight, the mixture diluted with 111.4 g of dichloromethane, 0.54 g of methanol and, 30 mm later, 16.8 g of water are added and the phases separated. The lower phase is washed with 17.59 g of 10% hydrochloric acid and then twice with 16.75 g of water. The organic phase is rotary evaporated at 50 C., the residue is taken up in ca. 250 ml of t-butyl methyl ether and again thlly concentrated. The residue is dissolved in 67 ml of t-butyl methyl ether and 201 ml of ethanol is added dropwise. The mixture is heated to 45 C. and then cooled to 0 C. over 17 h. The precipitated crystalline solid is filtered off under suction, washed twice with 150 ml of ethanol each time and dried at 40 C. in a vacuum drying cabinet. 10.4 g (69% yield) of astaxanthin didecanoate (m.p. 104.8 C.) are obtained.

Reference： [1]Patent: US2017/305849,2017,A1 .Location in patent: Paragraph 0118

38
[ 112-16-3 ]
[ 472-61-7 ]
astaxanthin didodecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridine; In dichloromethane; at 20℃;	10 g (16.75 mmol) of astaxanthin 2 and 4.37 g (55.29 mmol) of pyridine are charged in 111.4 g of dichloromethane and 12.2 g (50.26 mmol) of dodecanoyl chloride are added dropwise at 20 C. over 5 minutes. The reaction mixture is allowed to react overnight, the mixture diluted with 111.4 g of dichloromethane, 0.54 g of methanol and, 30 mm later, 16.8 g of water are added and the phases separated. The lower phase is washed with 17.59 g of 10% hydrochloric acid and then twice with 16.75 g of water. The organic phase is rotary evaporated at 50 C., the residue is taken up in ca. 250 ml of t-butyl methyl ether and again fully concentrated. The residue is virtually dissolved in 117 ml of t-butyl methyl ether at 67 C. and 201 ml of ethanol is added dropwise. The mixture is initially cooled to 45 C. and then to 0 C. over 17 h. The precipitated crystalline solid is filtered off under suction, washed twice with 200 ml of ethanol each time and dried at 40 C. in a vacuum drying cabinet. 11.7 g (73% yield) of astaxanthin didodecanoate (m.p. 130.0 C.) are obtained.

Reference： [1]Patent: US2017/305849,2017,A1 .Location in patent: Paragraph 0119

39
[ 472-61-7 ]
[ 112-76-5 ]
[ 173422-82-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine; In dichloromethane; at 20℃;	10121] 10g (16.75 mmol) ofastaxanthin and 4.37 g (55.29 mmol) of pyridine are charged in 111.4 g of dichloromethane and 16.9 g (50.26 mmol) of octadecanoyl chloride are added dropwise at 20 C. over 5 minutes. The reaction mixture is allowed to react overnight, the mixture diluted with 111.4 g of dichloromethane, 0.54 g of methanol and, 30 mm later, 16.8 g of water are added and the phases separated. The lower phase is washed with 17.59 g of 10% hydrochloric acid and then twice with 16.75 g of water. The organic phase is rotary evaporated at 50 C., the residue is taken up in ca. 250 ml of t-butyl methyl ether and again fully concentrated. The residue is dissolved in 67 ml of t-butyl methyl ether and 201 ml of ethanol at 53 C. The mixture is cooled to 45 C., seeded and then cooled to 0 C. over 17 h. The precipitated crystalline solid is filtered off under suction, washed twice with 200 ml of ethanol each time and dried at 40 C. in a vacuum drying cabinet. 15.1 g (80% yield) of astaxanthin dioctadecanoate (m.p. 70.5 C.) are obtained.

Reference： [1]Patent: US2017/305849,2017,A1 .Location in patent: Paragraph 0121

40
[ 472-61-7 ]
[ 57-10-3 ]
[ 5794-22-9 ]
(6S)-6-palmitoyloxy-3-[(all-E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3 g (11.7 mmol) of palmitic acid were charged in47.37 ml (53 g, 740 mmol) of dichloromethane and 2.21 g (17.55 mmol) of N,N-diisopropylcarbodiimide (DIC) was added at room temperature over 5 minutes. Afier 2 hours, 142.93 mg (1.17 mmol) of 4-dimethylaminopyridine (DMAP) and 2.3 g (3.86 mmol) of astaxanthin 2 were added and the mixture heated to reflux for 20 hours. After cooling, the conversion to astaxanthin dipalmitate was evaluated by thin-layer chromatography (cyclohexane/ethyl acetate=1 :2). As can be seen in FIG. 2, even afier 20 h large proportions of astaxanthin 2 are unreacted, a further large proportion reacted to give astaxanthin monopalmitate and only a fraction of astaxanthin 2 used formed astaxanthin dipalmitate.

Reference： [1]Patent: US2017/305849,2017,A1 .Location in patent: Paragraph 0091; 0092

41
[ 472-61-7 ]
[ 57-10-3 ]
(6S)-6-palmitoyloxy-3-[(all-E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3 g (11.7 mmol) of palmitic acid were charged in47.37 ml (53 g, 740 mmol) of dichloromethane. 2.85 g (17.55 mmol) of 1,1 ?-carbonyldiimidazole (CDI) were added at room temperature in three portions at intervals of 5 minutes each. The mixture was stirred overnight and 3.49 g (5.85 mmol) of astaxanthin 2 were added on the following day. A sample was analyzed by thin-layer chromatography afier 6 hours, then 133.8 jil of acetic acid were added and the mixture stirred overnight at room temperature. Afier 20 hours, a thrther sample was analyzed by thin-layer chromatography. (Eluent for both chromatograms was cyclohexane/ ethyl acetate=1 :2.). FIG. 4 shows that no astaxanthin dipalmitate forms afier 6 hours. At best, traces of astaxanthin monopalmitate are detectable. Even after 20 hours, large amounts of unreacted astaxanthin 2 still remain and a certain fraction of astaxanthin monopalmitate is present. The desired astaxanthin dipalmitate can only be detected in very low amounts.

Reference： [1]Patent: US2017/305849,2017,A1 .Location in patent: Paragraph 0096; 0097

42
[ 472-61-7 ]
C₁₁H₁₉NO₄S [ No CAS ]
C₆₂H₈₆N₂O₁₀S₂ [ No CAS ]

Reference： [1]International Journal of Biological Macromolecules,2018,vol. 118,p. 252 - 262

43
(4S)-4-acetoxy-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene [ No CAS ]
[ 472-61-7 ]

Reference： [1]Patent: JP2018/131390,2018,A

44
(4S)-4-hydroxy-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene [ No CAS ]
[ 472-61-7 ]

Reference： [1]Patent: JP2018/131390,2018,A

45
(4S)-4-(2-methoxypropan-2-yloxy)-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene [ No CAS ]
[ 472-61-7 ]

Reference： [1]Patent: JP2018/131390,2018,A

46
1-(3-hydroxy-3-methyl-1,4-pentadienyl)-(4S)-4-(2-methoxypropan-2-yloxy)-3-oxo-2,6,6-trimethyl-1-cyclohexene [ No CAS ]
[ 472-61-7 ]

Reference： [1]Patent: JP2018/131390,2018,A

47
[ 5056-17-7 ]
1-(5-bromo-3-methyl-1,3-pentadienyl)-(4S)-4-hydroxy-3-oxo-2,6,6-trimethyl-1-cyclohexene [ No CAS ]
[ 472-61-7 ]

Yield	Reaction Conditions	Operation in experiment
1.53 kg		The concentrated solution of Example 6 was added dropwise to a solution of triphenylphosphine (11.8 kg) and 1,2-epoxybutane (130 g) in ethyl acetate (44 kg) at 0 to 30 C., and the reaction mixture was added dropwise at the same temperature And the mixture was stirred for 24 hours. The precipitated solid was collected by filtration and the wet crystals were dissolved in methylene chloride (39 kg). The obtained solution was added dropwise to ethyl acetate (305 kg) while stirring, and solid precipitation was confirmed. The precipitated solid was collected by filtration and dried in vacuo to give the title compound (3.95 kg, purity 87.5% (trans form), 5.8% (cis form)) as a white solid. The purity of the product was determined by high performance liquid chromatography (column: YMC-PAC ODS-A manufactured by YMC and mobile phase: acetonitrile with 0.1% trifluoroacetic acid / 0.1% aqueous trifluoroacetic acid = 5-95 / 45 to 5). 2,7-dimethylocta-2,4,6-triene-1,8-dialdehyde (0.484 kg), the compound of Example 7 (1) (3.90 kg), 2,6-di-t-butyl-p-cresol (32.5 g) and 1,2-epoxybutane (1.9 kg) were suspended in 2-propanol (15 kg) and the suspension was heated under reflux for 30 hours under a nitrogen atmosphere. The reaction mixture was cooled to -5 to 5 C. and stirred for 1 hour, and the precipitated solid was collected by filtration to give the title compound (1.53 kg, yield 86.9%, purity 98.8%, optical purity 97. 9% ee) as a deep violet solid. The purity of the product was determined by high performance liquid chromatography (column: Triart C 18 ExRS Plus manufactured by YMC and mobile phase: acetonitrile with 0.025% trifluoroacetic acid / 0.025% aqueous trifluoroacetic acid = 30 to 98 / 2), respectively. The optical purity of the product was determined using high performance liquid chromatography (column: YMC CHIRAL Cellulose-SB manufactured by YMC and mobile phase: hexane / tetrahydrofuran = 85/15)

Reference： [1]Patent: JP2018/131390,2018,A .Location in patent: Paragraph 0032

48
2-[2-((4RS)-4-acetoxy-3-oxo-2,6,6-trimethyl-1-cyclohexenyl)vinyl]-2-methyl-1,3-dioxolane [ No CAS ]
[ 472-61-7 ]

Reference： [1]Patent: JP2018/131390,2018,A
[2]Patent: JP2018/131390,2018,A

49
2-[2-((4S)-4-acetoxy-3-oxo-2,6,6-trimethyl-1-cyclohexenyl)vinyl]-2-methyl-1,3-dioxolane [ No CAS ]
[ 472-61-7 ]

Reference： [1]Patent: JP2018/131390,2018,A

50
[ 472-61-7 ]
C₅₂H₇₀N₂O₆S₂ [ No CAS ]

Reference： [1]Patent: CN107021961,2018,B

51
[ 472-61-7 ]
[ 7693-46-1 ]
C₅₄H₅₈N₂O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.1%		Astaxanthin (1.79 g, 3.0 mmol) was dissolved in anhydrous tetrahydrofuran (60 ml).n-Butyllithium (2.5 M, 3 mL, 7.5 mmol) was added dropwise at -70 C.After stirring at -70 C for 15 minutes, 4-nitrophenoxycarbonyl chloride(1.51 g, 7.5 mmol) was added.A solution of tetrahydrofuran (40 ml) was slowly warmed to room temperature and stirred for 8 hours.After completion of the reaction, water (80 ml) was added, and ethyl acetate (60 ml × 3)The combined organic phases were washed with brine (80 ml).It was then distilled under reduced pressure to give a yellow oil.The crude product was purified by silica gel column chromatography (eluent: dichloromethane: methanol = 100:1).Obtained a red solid (1.56 g, 56.1%).

Reference： [1]Patent: CN107021961,2018,B .Location in patent: Paragraph 0084-0087

52
[ 472-61-7 ]
(E)-2-((3-(thiazolidin-3-yl)propyl)imino)acetic acid [ No CAS ]
C₄₈H₆₄N₂O₅S [ No CAS ]
C₅₆H₇₆N₄O₆S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.9%; 15.7%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 48h;	Astaxanthin (597 mg, 1.0 mmol) was dissolved in dichloromethane (20 ml).(E)-2-((3-(thiazol-3-yl)propyl)imide)acetic acid (1.01 g, 5.0 mmol),Triethylamine (505 mg, 5.0 mmol), HOBT (1.01 g, 7.5 mmol) and EDCI (1.44 g, 7.5 mmol),The reaction was stirred at room temperature for 48 hours. After the reaction, water (50 ml) was added, and the mixture was combined with methylene chloride (50 ml × 3), and the organic phase was combined and washed with water (50 ml) and brine (50 ml).It was then distilled under reduced pressure to give a yellow oil.The crude product was purified by silica gel column chromatography (eluent: dichloromethane: methanol = 100:1).Obtained red solid -((1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-methyl-3-cyclohexane-1-en-1-yl))-(3,7,12,16-tetramethyloctadecane-1,3,5,7,9,11,13,15,17-nonen-1-yl)-(3,5,5-trimethyl-2-oxocyclohex-3-en-1-yl)-(E)-2-(3-((thiazolidin-3-yl)propyl)imino)acetic acid (85mg, 10.9%).

Reference： [1]Patent: CN107021961,2018,B .Location in patent: Paragraph 0094; 0104-0107

53
[ 472-61-7 ]
[ 65-85-0 ]
4,4'-dioxo-β,β-carotene-3,3'-diyl dibenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With Novozyme 435; In methanol; toluene; at 37℃; for 6h;Darkness; Enzymatic reaction;	General procedure: 50 mL of toluene and 5 mL of methanol were added to a mixture of 2 mmol of lutein or astaxanthin and 4 mmol of the acid (benzoic, 4-methylbenzoic, nicotinic, or mandelic. 0.1 g of catalyst (Novozyme 435) was added to the mixture. The mixture was stirred during 6 h at 37, protecting from light. The obtained mixture was passed through a column filled with 2.5 g of alumina, collecting the second colored fraction. The obtained fraction was washed with 95% ethanol and water and dried in vacuum (20-25 mmHg) during 2 h at 40.

Reference： [1]Russian Journal of General Chemistry,2019,vol. 89,p. 913 - 917
Zh. Obshch. Khim.,2019,vol. 89,p. 721 - 725,5

54
[ 59-67-6 ]
[ 472-61-7 ]
4,4'-dioxo-β,β-carotene-3,3'-diyl di(pyridine-3-carboxylate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With Novozyme 435; In methanol; toluene; at 37℃; for 6h;Darkness; Enzymatic reaction;	General procedure: 50 mL of toluene and 5 mL of methanol were added to a mixture of 2 mmol of lutein or astaxanthin and 4 mmol of the acid (benzoic, 4-methylbenzoic, nicotinic, or mandelic. 0.1 g of catalyst (Novozyme 435) was added to the mixture. The mixture was stirred during 6 h at 37, protecting from light. The obtained mixture was passed through a column filled with 2.5 g of alumina, collecting the second colored fraction. The obtained fraction was washed with 95% ethanol and water and dried in vacuum (20-25 mmHg) during 2 h at 40.

Reference： [1]Russian Journal of General Chemistry,2019,vol. 89,p. 913 - 917
Zh. Obshch. Khim.,2019,vol. 89,p. 721 - 725,5

55
[ 472-61-7 ]
[ 99-94-5 ]
4,4'-dioxo-β,β-carotene-3,3'-diyl di(4-methylbenzoate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With Novozyme 435; In methanol; toluene; at 37℃; for 6h;Darkness; Enzymatic reaction;	General procedure: 50 mL of toluene and 5 mL of methanol were added to a mixture of 2 mmol of lutein or astaxanthin and 4 mmol of the acid (benzoic, 4-methylbenzoic, nicotinic, or mandelic. 0.1 g of catalyst (Novozyme 435) was added to the mixture. The mixture was stirred during 6 h at 37, protecting from light. The obtained mixture was passed through a column filled with 2.5 g of alumina, collecting the second colored fraction. The obtained fraction was washed with 95% ethanol and water and dried in vacuum (20-25 mmHg) during 2 h at 40.

Reference： [1]Russian Journal of General Chemistry,2019,vol. 89,p. 913 - 917
Zh. Obshch. Khim.,2019,vol. 89,p. 721 - 725,5

56
[ 472-61-7 ]
[ 611-71-2 ]
4,4'-dioxo-β,β-carotene-3,3'-diyl di(2-hydroxy-2-phenylethanoate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With Novozyme 435; In methanol; toluene; at 37℃; for 6h;Darkness; Enzymatic reaction;	General procedure: 50 mL of toluene and 5 mL of methanol were added to a mixture of 2 mmol of lutein or astaxanthin and 4 mmol of the acid (benzoic, 4-methylbenzoic, nicotinic, or mandelic. 0.1 g of catalyst (Novozyme 435) was added to the mixture. The mixture was stirred during 6 h at 37, protecting from light. The obtained mixture was passed through a column filled with 2.5 g of alumina, collecting the second colored fraction. The obtained fraction was washed with 95% ethanol and water and dried in vacuum (20-25 mmHg) during 2 h at 40.

Reference： [1]Russian Journal of General Chemistry,2019,vol. 89,p. 913 - 917
Zh. Obshch. Khim.,2019,vol. 89,p. 721 - 725,5

57
[ 472-61-7 ]
C₄₀H₅₂O₄ [ No CAS ]
C₄₀H₅₂O₄ [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 6222 - 6231

58
[ 124-07-2 ]
[ 472-61-7 ]
[ 622836-60-6 ]

Reference： [1]International Journal of Molecular Sciences,2020,vol. 21

59
[ 3049-35-2 ]
[ 84592-32-5 ]
[ 472-61-7 ]

Yield	Reaction Conditions	Operation in experiment
96.8%	With sodium methylate In dichloromethane at -20℃; for 5h; Inert atmosphere;	1-3; 9-10 Preparation of S6 Astaxanthin: Take 47 g of compound 5 (0.082 mol) and 5.74 g (0.035 mol) of compound 6 and dissolve them in 200 ml of dichloromethane, then lower the temperature to -20°C under nitrogen protection, and then add 14.76 g of 30% sodium methoxide methanol dropwise Solution (containing 0.082 mole of sodium methoxide), drip for 1 hour, after dripping, maintain this temperature and react for 5 hours, then wash with 50ml×3 water, recover dichloromethane, add 200ml ethanol and reflux for 1 hour, cool to room temperature and filter to get 17.5 The gram content is 96.8%, and the yield is 83.9%.

Reference： [1]Current Patent Assignee: GUANGZHOU WISDOM BIO TECH - CN113461583, 2021, A Location in patent: Paragraph 0063-0064; 0077-0078; 0090-0091; 0107-0112

60
[ 5056-17-7 ]
[ CAS Unavailable ]
[ 472-61-7 ]

Yield	Reaction Conditions	Operation in experiment
96.35%	With anhydrous sodium oxalate; potassium hydroxide In ethanol; dichloromethane; lithium hydroxide monohydrate at -15 - -10℃; for 7h;	1; 1-4 Prepare strong alkali solution: put 3.92g of sodium hydroxide in a single-neck bottle, add 70g of ethanol (water content 10wt%), stir and dissolve until the solution is transparent and no obvious potassium hydroxide remains, then transfer to a constant pressure dropping funnel. At the beginning of the reaction, flush the 500ml four-necked flask with nitrogen for at least 10min.After that, put 40 g of compound II, 5.65 g of compound III, 100 g of dichloromethane, 30 g of ethanol (water content 10 wt %) and 7.50 g of sodium oxalate in a flask,When the mixed solution in the flask is cooled to -15°C, potassium hydroxide is added dropwise, the rate of addition is controlled, and it is added dropwise for 4 hours.After the dripping was completed, the reaction was continued to be stirred and incubated for 3 hours at a temperature of less than -10 °C. After the reaction was completed, 5.88 g of glacial acetic acid was used for neutralization at a constant temperature. Then, the neutralized reaction mixture was washed with 200 ml of water for 4 times respectively. During the washing with water, each time was extracted with 50 ml of dichloromethane, and the oil phase was separated and collected.The oil phase is concentrated by vacuum distillation, 200-230ml of dichloromethane is recovered, and the concentration is stopped. 300 ml of ethanol was added to the concentrated material, and the mixture was placed in a heating device at 100°C for heating.Then (internal temperature is about 78 , heat source is 100 ), after 100 ml of solvent is extracted, 100 ml of ethanol is added, and then under the condition of boiling point, total reflux is carried out for 3 hours.After the complete reflux, the material was cooled to 20-30°C, suction filtration was carried out, the filter cake was washed twice with 50ml of ethanol, and then dried in a vacuum drying oven for 6 hours; 20.12g of finished astaxanthin was obtained. Yield: According to high performance liquid chromatography detection, in the product, the content of all-trans astaxanthin is 98.47%, the content of semi-astaxanthin is 0.64%, the content of astaxanthin is 0.18%, and the content of cis-astaxanthin is 0.14%; The molar yield of all-trans astaxanthin was calculated to be 96.35% based on compound III.

Reference： [1]Current Patent Assignee: SHANGSHENXIANG AND ZHENGCHENG BIOCHEMICAL ENGINEERING LTD; ZHEJIANG XINJIANG - CN114369048, 2022, A Location in patent: Paragraph 0004; 0016-0040

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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.
P363	Wash contaminated clothing before reuse.
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.
P374	Fight fire with normal precautions from a reasonable distance.
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.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
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. 472-61-7 ] {[proInfo.proName]}

Quality Control of [ 472-61-7 ]

Related Doc. of [ 472-61-7 ]

Product Details of [ 472-61-7 ]

Calculated chemistry of [ 472-61-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 472-61-7 ]

Application In Synthesis of [ 472-61-7 ]

[ 472-61-7 ] Synthesis Path-Upstream 1~8

[ 472-61-7 ] Synthesis Path-Downstream 1~60

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry