6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

• ChemBase ID: 131155
• Molecular Formular: C40H52O4
• Molecular Mass: 596.83848
• Monoisotopic Mass: 596.38656014
• SMILES: CC1=C(C(CC(C1=O)O)(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(CC1(C)C)O)C)\C)\C)/C)/C
• Canonical SMILES: C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C(=O)C(CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)C(=O)C(CC1(C)C)O)\C
• 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+
• InChIKey: MQZIGYBFDRPAKN-QISQUURKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one; 6-hydroxy-3-[18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
• IUPAC Traditional name: astaxanthin; 6-hydroxy-3-[18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
• Synonyms: 3,3’-Dihydroxy-β,β-carotene-4,4’-dione; 3,3’-Dhydroxy-4,4’-diketo-β-carotene; Ovoester; AstaxanthinDiscontinued; Astaxanthin; 3,3′-Dihydroxy-β,β-carotene-4,4′-dione; 3,3′-二羟基-β,β-胡萝卜素-4,4′-二酮; 虾青素

Database IDs

• CAS Number: 472-61-7
• EC Number: 207-451-4
• MDL Number: MFCD00672621
• PubChem SID: 162225433; 24277721
• PubChem CID: 5368397

CALCULATED PROPERTIES

• Acid pKa: 13.071698
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 8.047382
• LogD (pH = 7.4): 8.047381
• Log P: 8.047382
• Molar Refractivity: 195.9826 cm^3
• Polarizability: 71.7522 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Dark-Purple Solid; powder
• Melting Point: 220-225 °C; 223-225°C

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC); ≥98.5% (HPLC)
• Grade: analytical standard, for food analysis
• Biological Source: from synthetic
• Shelf Life: (limited shelf life, expiry date on the label)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C40H52O4

DETAILS

Sigma Aldrich - A3236

Biochem/physiol Actions
Astaxanthin is a potent carotenoid antioxidant found in marine algae, red yeast and many other plant and animal sources. Animal studies indicate that it reduces blood glucose and ameliorates several parameters of the diabetic metabolic syndrome. It improves blood flow and vascular tone in models of hypertension. In vitro studies indicate that it upregulates connexin 43 and thus, may be chemopreventive against cancer.

Sigma Aldrich - A9335

Biochem/physiol Actions
虾青素是在海藻、红酵母和许多植物和动物来源中发现的强效类胡萝卜素抗氧化剂。动物试验表明，它可降低血糖并改善糖尿病代谢综合征的若干指标。可改善高血型模型的血流和血管张力。体外研究表明，它上调间隙联接蛋白 43，可用于化学防癌。

Sigma Aldrich - 41659

Biochem/physiol Actions
Astaxanthin is a potent carotenoid antioxidant found in marine algae, red yeast and many other plant and animal sources. Animal studies indicate that it reduces blood glucose and ameliorates several parameters of the diabetic metabolic syndrome. It improves blood flow and vascular tone in models of hypertension. In vitro studies indicate that it upregulates connexin 43 and thus, may be chemopreventive against cancer.

Toronto Research Chemicals - A790025

Carotenoid pigment found mostly in animal organisms, but also occuring in plants; thought to be the precursor of astacin. Animal studies indicate that it reduces blood glucose and ameliorates several parameters of the diabetic metabolic syndrome. It impro

REFERENCES

• Schroeder, W.A., et al.: J. Biol. Chem., 270, 18374 (1995)
• Bertram, J.S., et al.: Biochem. Biophys. Acta, 1740, 170 (1995)
• Hussein, G., et al.: J. Nat. Prod., 69, 443 (2006)