(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial
A
(3S,3'S)-astaxanthin
B
(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; dichloromethane for 1.16667h; Ambient temperature; | 73% |
Conditions | Yield |
---|---|
70.7% |
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane; isopropyl alcohol |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 40℃; |
3,4,3',4'-tetrahydroxy-β,β-carotene
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
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 |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 94.6 percent / NaOMe / methanol / 4 h / 0 - 25 °C View Scheme |
3,3'-dihydroxy-β,β-carotene-4,4'-dione
A
(3S,3'S)-astaxanthin
B
(3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
C
(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
Conditions | Yield |
---|---|
Resolution of racemate; |
(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
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
In ethanol for 3h; Heating / reflux; |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
With daidzein dianion In methanol; chloroform at 25℃; Thermodynamic data; Kinetics; Reagent/catalyst; |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
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 |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
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 |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
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 |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
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 |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 5h; Concentration; | A 92.48% B 0.63% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; | 80% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; Concentration; Reagent/catalyst; Temperature; Solvent; | 73% |
With pyridine |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; | 73% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; | 69% |
Conditions | Yield |
---|---|
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction; | 59% |
Conditions | Yield |
---|---|
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction; | 58% |
Conditions | Yield |
---|---|
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction; | 57% |
Conditions | Yield |
---|---|
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% |
(3S,3'S)-astaxanthin
MANDELIC ACID
Conditions | Yield |
---|---|
With Novozyme 435 In methanol; toluene at 37℃; for 6h; Darkness; Enzymatic reaction; | 55% |
(3S,3'S)-astaxanthin
(3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
(3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione
N-(all-trans-Retinoyl)-imidazole
A
astacene
Conditions | Yield |
---|---|
With pyridine; sodium hydride at 20℃; for 3h; | A 50% B 5% |
β-1-bromo-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
(3S,3'S)-astaxanthin
C108H104O22
Conditions | Yield |
---|---|
With 4 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane at 0℃; for 2h; | 31% |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
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; |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
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% |
(3S,3'S)-astaxanthin
Conditions | Yield |
---|---|
With hydrogen; Lindlar's catalyst In dichloromethane |
(3S,3'S)-astaxanthin
(-)-methoxytrifluoromethylphenylacetyl chloride
C60H66F6O8
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With pyridine at 0℃; for 0.666667h; |
(3S,3'S)-astaxanthin
3,4,3',4'-tetrahydroxy-β,β-carotene
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol |
Conditions | Yield |
---|---|
With pyridine; chlorosulfonic acid for 2.5h; Ambient temperature; Yield given; |
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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