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472-61-7 molecular structure
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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 and InChIs

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

Cite this record

CBID:131155 http://www.chembase.cn/molecule-131155.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
472-61-7
EC Number
207-451-4
MDL Number
MFCD00672621
PubChem SID
162225433
24277721
PubChem CID
5368397

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5368397 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.071698  H Acceptors
H Donor LogD (pH = 5.5) 8.047382 
LogD (pH = 7.4) 8.047381  Log P 8.047382 
Molar Refractivity 195.9826 cm3 Polarizability 71.7522 Å3
Polar Surface Area 74.6 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Apperance
Dark-Purple Solid expand Show data source
powder expand Show data source
Melting Point
220-225 °C expand Show data source
223-225°C expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
≥98.5% (HPLC) expand Show data source
Grade
analytical standard, for food analysis expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
from synthetic expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Shipped in
wet ice expand Show data source
Empirical Formula (Hill Notation)
C40H52O4 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - A3236 external link
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 external link
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 external link
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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