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472-61-7

Basic Information
CAS No.: 472-61-7
Name: Astaxanthin
Molecular Structure:
Molecular Structure of 472-61-7 (Astaxanthin)
Formula: C40H52O4
Molecular Weight: 596.85
Synonyms: Astaxanthin(3,3-Dihydroxy-Beta,Beta-Carotene-4,4-Dione);Astaxanthin Discontinued;
EINECS: 207-451-4
Density: 1.071 g/cm3
Melting Point: 215-216 °C
Boiling Point: 774 °C at 760 mmHg
Flash Point: 435.8 °C
Solubility:
Appearance: Drak-purple solid
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37/38
Safety: 24/25-36-26
Transport Information:
PSA: 74.60000
LogP: 8.90540
Synthetic route
5056-17-7

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

<5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid

A

472-61-7

(3S,3'S)-astaxanthin

B

71772-51-5

(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

Conditions
ConditionsYield
With sodium methylate In methanol at 0 - 25℃; for 4h;A 94.6%
B 4.2 % Chromat.
In various solvent(s) for 20h; Heating;A 97.7 % Chromat.
B 2.1 % Chromat.
696647-73-1

C12H20O4

[(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Stage #1: C12H20O4; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide With sodium methylate In methanol at 0℃; for 2h; Wittig Reaction;
Stage #2: With acetic acid In methanol; water at 20 - 75℃; for 20h; Heating / reflux;
83%

(3S,3'S)-Astaxanthin-di-(-)-camphanat

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With sodium hydroxide In methanol; dichloromethane for 1.16667h; Ambient temperature;73%
5056-17-7

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

<5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
70.7%
5056-17-7

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

[(2E,4E)-3-Methyl-5-((S)-2,6,6-trimethyl-3-oxo-4-phenoxymethoxycarbonyl-cyclohex-1-enyl)-penta-2,4-dienyl]-triphenyl-phosphonium; bromide

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With sodium hydride In dichloromethane; isopropyl alcohol

(3S,3'S)-astaxanthin disulfate

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With hydrogenchloride In methanol at 40℃;
6094-35-5, 28082-20-4

3,4,3',4'-tetrahydroxy-β,β-carotene

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane

(S)-6-Hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-on

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. HBr / CH2Cl2 / 0.17 h / 0 °C
3: 94.6 percent / NaOMe / methanol / 4 h / 0 - 25 °C
View Scheme

(S)-3-((1E,3E)-5-Bromo-3-methyl-penta-1,3-dienyl)-6-hydroxy-2,4,4-trimethyl-cyclohex-2-enone

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 94.6 percent / NaOMe / methanol / 4 h / 0 - 25 °C
View Scheme
7542-45-2

3,3'-dihydroxy-β,β-carotene-4,4'-dione

A

472-61-7

(3S,3'S)-astaxanthin

B

60760-95-4

(3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

C

71772-51-5

(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

Conditions
ConditionsYield
Resolution of racemate;
72523-68-3

(S)-2,7,11-trimethyl-13-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8,10,12-tridecahexaen-1-al

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
In ethanol for 3h; Heating / reflux;

astaxanthin radical-cation

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
With daidzein dianion In methanol; chloroform at 25℃; Thermodynamic data; Kinetics; Reagent/catalyst;

(4S)-4-acetoxy-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: E-2 / aq. phosphate buffer; acetone / 1 h / 20 - 30 °C / pH 7 / Large scale; Enzymatic reaction
2.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
3.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
4.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
5.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
5.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme

(4S)-4-hydroxy-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
2.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
3.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
4.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
4.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme

(4S)-4-(2-methoxypropan-2-yloxy)-3-oxo-1-(3-oxo-1-butenyl)-2,6,6-trimethyl-1-cyclohexene

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
2.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
3.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
3.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme

1-(3-hydroxy-3-methyl-1,4-pentadienyl)-(4S)-4-(2-methoxypropan-2-yloxy)-3-oxo-2,6,6-trimethyl-1-cyclohexene

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
2.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
2.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
5056-17-7

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

1-(5-bromo-3-methyl-1,3-pentadienyl)-(4S)-4-hydroxy-3-oxo-2,6,6-trimethyl-1-cyclohexene

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Stage #1: 1-(5-bromo-3-methyl-1,3-pentadienyl)-(4S)-4-hydroxy-3-oxo-2,6,6-trimethyl-1-cyclohexene With ethyloxirane; triphenylphosphine In ethyl acetate at 0 - 30℃; for 24h; Large scale;
Stage #2: (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial With ethyloxirane; 2,6-di-tert-butyl-4-methyl-phenol In isopropyl alcohol for 30h; Reflux; Inert atmosphere; Large scale;
1.53 kg

2-[2-((4RS)-4-acetoxy-3-oxo-2,6,6-trimethyl-1-cyclohexenyl)vinyl]-2-methyl-1,3-dioxolane

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: LAY 400-AF / aq. phosphate buffer; toluene / 24 h / 37 °C / pH 7 / Enzymatic reaction
1.2: 3 h / 50 °C
2.1: hydrogenchloride / toluene; methanol; water / 2 h / 20 - 30 °C
3.1: E-2 / aq. phosphate buffer; acetone / 1 h / 20 - 30 °C / pH 7 / Large scale; Enzymatic reaction
4.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
5.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
6.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
7.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
7.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 7 steps
1.1: LAY 400-AF / aq. phosphate buffer; toluene / 24 h / 37 °C / pH 7 / Enzymatic reaction
2.1: hydrogenchloride / toluene; methanol; water / 2 h / 20 - 30 °C
3.1: E-2 / aq. phosphate buffer; acetone / 1 h / 20 - 30 °C / pH 7 / Large scale; Enzymatic reaction
4.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
5.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
6.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
7.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
7.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme

2-[2-((4S)-4-acetoxy-3-oxo-2,6,6-trimethyl-1-cyclohexenyl)vinyl]-2-methyl-1,3-dioxolane

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogenchloride / toluene; methanol; water / 2 h / 20 - 30 °C
2.1: E-2 / aq. phosphate buffer; acetone / 1 h / 20 - 30 °C / pH 7 / Large scale; Enzymatic reaction
3.1: pyridinium p-toluenesulfonate / toluene / 0.5 h / -5 - 5 °C / Large scale
4.1: tetrahydrofuran / 2 h / -75 - -55 °C / Large scale
5.1: hydrogen bromide / dichloromethane / 0.5 h / -21 - -11 °C / Large scale
6.1: triphenylphosphine; ethyloxirane / ethyl acetate / 24 h / 0 - 30 °C / Large scale
6.2: 30 h / Reflux; Inert atmosphere; Large scale
View Scheme
514-78-3

canthaxanthin

472-61-7

(3S,3'S)-astaxanthin

Conditions
ConditionsYield
Stage #1: canthaxanthin With iodosylbenzene; sodium hydroxide In methanol at 10 - 20℃; for 12.5h; Inert atmosphere;
Stage #2: With sulfuric acid In water at 20℃; for 5h; Reagent/catalyst; Temperature; Solvent;
4.48 g
472-61-7

(3S,3'S)-astaxanthin

112-67-4

n-hexadecanoyl chloride

A

5794-22-9

astaxanthin dipalmitate

B

(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

Conditions
ConditionsYield
With pyridine In dichloromethane for 5h; Concentration;A 92.48%
B 0.63%
472-61-7

(3S,3'S)-astaxanthin

C16H23ClO3Si

astaxanthin diferulate

Conditions
ConditionsYield
Stage #1: (3S,3'S)-astaxanthin; C16H23ClO3Si With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With caesium carbonate In water; N,N-dimethyl-formamide for 2h; Inert atmosphere;
80%
472-61-7

(3S,3'S)-astaxanthin

112-76-5

Stearoyl chloride

173422-82-7

astaxanthin dioctadecanoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;80%
472-61-7

(3S,3'S)-astaxanthin

112-67-4

n-hexadecanoyl chloride

5794-22-9

astaxanthin dipalmitate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; Concentration; Reagent/catalyst; Temperature; Solvent;73%
With pyridine
112-16-3

n-dodecanoyl chloride

472-61-7

(3S,3'S)-astaxanthin

astaxanthin didodecanoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;73%
472-61-7

(3S,3'S)-astaxanthin

112-13-0

n-decanoyl chloride

[(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

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;69%
472-61-7

(3S,3'S)-astaxanthin

65-85-0

benzoic acid

4,4'-dioxo-β,β-carotene-3,3'-diyl dibenzoate

Conditions
ConditionsYield
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction;59%
472-61-7

(3S,3'S)-astaxanthin

99-94-5

p-Toluic acid

4,4'-dioxo-β,β-carotene-3,3'-diyl di(4-methylbenzoate)

Conditions
ConditionsYield
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction;58%
59-67-6

nicotinic acid

472-61-7

(3S,3'S)-astaxanthin

4,4'-dioxo-β,β-carotene-3,3'-diyl di(pyridine-3-carboxylate)

Conditions
ConditionsYield
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction;57%
472-61-7

(3S,3'S)-astaxanthin

7693-46-1

4-Nitrophenyl chloroformate

C54H58N2O12

Conditions
ConditionsYield
Stage #1: (3S,3'S)-astaxanthin With n-butyllithium In tetrahydrofuran at -70℃; for 0.25h;
Stage #2: 4-Nitrophenyl chloroformate In tetrahydrofuran at 20℃; for 8h;
56.1%
472-61-7

(3S,3'S)-astaxanthin

4,4'-dioxo-β,β-carotene-3,3'-diyl di(2-hydroxy-2-phenylethanoate)

Conditions
ConditionsYield
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction;55%
472-61-7

(3S,3'S)-astaxanthin

60760-95-4

(3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

71772-51-5

(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione

61319-45-7

N-(all-trans-Retinoyl)-imidazole

B

(3R,3'S)-astaxanthin monoretinoate

Conditions
ConditionsYield
With pyridine; sodium hydride at 20℃; for 3h;A 50%
B 5%
472-61-7

(3S,3'S)-astaxanthin

1010099-33-8

C108H104O22

Conditions
ConditionsYield
With 4 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane at 0℃; for 2h;31%
472-61-7

(3S,3'S)-astaxanthin

A

9-Z-3,3′-dihydroxy-4,4′-dione-β,β′-carotene

B

13-Z-3,3′-dihydroxy-4,4′-dione-β,β′-carotene

Conditions
ConditionsYield
With iodine-doped titanium dioxide In ethyl acetate at 70℃; for 2h; Reagent/catalyst; Temperature; Solvent;A 22.7%
B 16.9%
In acetone; Petroleum ether at 70℃; for 12h;
With I-TiO2 In ethyl acetate at 70℃; for 2h;
472-61-7

(3S,3'S)-astaxanthin

(E)-2-((3-(thiazolidin-3-yl)propyl)imino)acetic acid

A

C48H64N2O5S

B

C56H76N4O6S2

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 48h;A 10.9%
B 15.7%
472-61-7

(3S,3'S)-astaxanthin

(3S,3'S)-15,15'-cis-Astaxanthin

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In dichloromethane
472-61-7

(3S,3'S)-astaxanthin

39637-99-5

(-)-methoxytrifluoromethylphenylacetyl chloride

Conditions
ConditionsYield
With pyridine at 0℃; for 0.75h; determination of enantiomeric composition of partly racemized carotenols by converting them in to diastereomeric esters, HPLC and NMR (in the presence of Eu(fod)3 shift reagent) analysis;
472-61-7

(3S,3'S)-astaxanthin

39637-74-6, 104530-16-7

(-)-camphanic acid chloride

C60H76O10

Conditions
ConditionsYield
With pyridine at 0℃; for 0.666667h;
472-61-7

(3S,3'S)-astaxanthin

6094-35-5, 28082-20-4

3,4,3',4'-tetrahydroxy-β,β-carotene

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol
472-61-7

(3S,3'S)-astaxanthin

A

(3S,3'S)-astaxanthin monosulfate

B

(3S,3'S)-astaxanthin disulfate

Conditions
ConditionsYield
With pyridine; chlorosulfonic acid for 2.5h; Ambient temperature; Yield given;
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  • CAS No. 472-61-7 Astaxanthin

  • Casno:

    472-61-7

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    1.Prompt Goods; 2.Flexible payment terms; 3.Documents & Certificate support. Name: Astaxanthin Molecular Structure: Formula: C40H52O4 Molecular Weight : 596.84 Synonyms: 3,3'-DIHYDROXY-B,B-CAROTENE-4,4'-DIONE;3,3-DIHYDROXY-B,B-CAR

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Specification

The Astaxanthin, with the CAS registry number 472-61-7, is also known as 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione.It belongs to the product categories of Carotenoids;Intermediates & Fine Chemicals;Pharmaceuticals.Its EINECS number is 207-451-4.This chemical's molecular formula is C40H52O4 and molecular weight is 596.85.  What's more,Its systematic name is Astaxanthin.Carotenoid pigment found mostly in animal organisms, but also occuring in plants; thought to be the precursor of Astaxanthin. Animal studies indicate that it reduces blood glucose and ameliorates several parameters of the diabetic metabolic syndrome.

Physical properties about Astaxanthin are: (1)ACD/LogP: 8.163; (2)# of Rule of 5 Violations: 2 ; (3)ACD/LogD (pH 5.5): 8.16; (4)ACD/LogD (pH 7.4): 8.16; (5)ACD/BCF (pH 5.5): 941812.00; (6)ACD/BCF (pH 7.4): 941800.60; (7)ACD/KOC (pH 5.5): 657252.60; (8)ACD/KOC (pH 7.4): 657244.70; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 12; (12)Index of Refraction: 1.595; (13)Molar Refractivity: 189.377 cm3; (14)Molar Volume: 557.098 cm3; (15)Surface Tension: 44.6749992370605 dyne/cm; (16)Density: 1.071 g/cm3; (17)Flash Point: 435.837 °C; (18)Enthalpy of Vaporization: 128.448 kJ/mol; (19)Boiling Point: 774.042 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

The Astaxanthin is harmful by inhalation, in contact with skin and if swallowed.It is irritating to eyes, respiratory system and skin. When you use it ,wear suitable protective clothing, avoid contact with skin and eyes.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES:O=C2/C(=C(/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(/C(=O)C(O)CC1(C)C)C)C)C)C)C)C(C)(C)CC2O)C;
(2)Std. InChI:InChI=1S/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+;
(3)Std. InChIKey:MQZIGYBFDRPAKN-QISQUURKSA-N.

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