(3'RS,3'SR)-Astaxanthin (CHEM032459)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:24:28 UTC
Update Date2016-11-09 01:20:43 UTC
Accession NumberCHEM032459
Identification
Common Name(3'RS,3'SR)-Astaxanthin
ClassSmall Molecule
DescriptionA carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S,3's)-AstaxanthinChEBI
3,3'-Dihydroxy-beta,beta-carotene-4,4'-dioneChEBI
3,3'-Dihydroxy-beta-carotene-4,4'-dioneChEBI
all-trans-(3S,3's)-AstaxanthinChEBI
AstaxanthineChEBI
e 161JChEBI
OvoesterChEBI
(3S,3's)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dioneKegg
3,3'-Dihydroxy-b,b-carotene-4,4'-dioneGenerator
3,3'-Dihydroxy-β,β-carotene-4,4'-dioneGenerator
3,3'-Dihydroxy-b-carotene-4,4'-dioneGenerator
3,3'-Dihydroxy-β-carotene-4,4'-dioneGenerator
(3S,3's)-3,3'-Dihydroxy-b,b-carotene-4,4'-dioneGenerator
(3S,3's)-3,3'-Dihydroxy-β,β-carotene-4,4'-dioneGenerator
(3S,3's)-all-trans-AstaxanthinHMDB
all-trans-3,3'-Dihydroxy-b-carotene-4,4'-dione (8ci)HMDB
all-trans-3,3'-Dihydroxy-beta-carotene-4,4'-dione (8ci)HMDB
all-trans-AstaxanthinHMDB
AstaREALHMDB
Astaxanthin (6ci)HMDB
BioAstinHMDB
BioAstin oleoresinHMDB
Carophyll pinkHMDB
Lucantin pinkHMDB
NatupinkHMDB
trans-AstaxanthinHMDB
e-AstaxanthinHMDB
(3S,3’S)-3,3’-dihydroxy-β,β-carotene-4,4’-dioneHMDB
(3S,3’S)-astaxanthinHMDB
(3S,3’S)-all-trans-astaxanthinHMDB
(S,S)-AstaxanthinHMDB
all-trans-(3S,3’S)-astaxanthinHMDB
AstaxanthinHMDB
Chemical FormulaC40H52O4
Average Molecular Mass596.839 g/mol
Monoisotopic Mass596.387 g/mol
CAS Registry Number71772-51-5
IUPAC Name(6S)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-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
Traditional Nameastaxanthin
SMILESC\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)C(O)CC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)C(O)CC1(C)C
InChI IdentifierInChI=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+
InChI KeyMQZIGYBFDRPAKN-HDQLMXHPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Cyclohexenone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00067 g/LALOGPS
logP7.4ALOGPS
logP8.05ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.98 m³·mol⁻¹ChemAxon
Polarizability73.77 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2000090000-c6336112eb898c2f0a48Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-3000019000-6b5720849187b199d6bfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Astaxanthin,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0961030000-dc7a74c186ee85f204faSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0961030000-368bb77cba4aef27a5cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000090000-ce16b33770cb7a4b2ff7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0232390000-f37e3530214c99f63306Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1296830000-ac8ea41a53a053acb7c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0185910000-7af6a00762ad7e8ee75dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-248171e80348a7e1d17eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000090000-b9759de23c7494bb7b2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0333390000-074ea5de5d017bafdb5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004m-0142590000-4e72a5bda186fd51912cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0195650000-3ee8ba797d4a2fb9c80fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01u3-0013900000-71e9a6336700d9e8fca6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0001090000-836dc358b0a566457c26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-0117190000-07d5d205542df36e4f5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-0239230000-7be6270484a4c641a468Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06543
HMDB IDHMDB0002204
FooDB IDFDB018640
Phenol Explorer IDNot Available
KNApSAcK IDC00000918
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3671
PDB IDNot Available
Wikipedia LinkAstaxanthin
Chemspider ID4444636
ChEBI ID40968
PubChem Compound ID5281224
Kegg Compound IDC08580
YMDB IDNot Available
ECMDB IDM2MDB005295
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21833799
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21883294
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22119431
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22188802
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22189778
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22221991
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22267192
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22279065
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22309505
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22349894
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22406426
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22428137
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22432539
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22455145
15. Berg, Michael; Essl, Stefan; Hugentobler, Max. Process for the preparation of astaxanthin. PCT Int. Appl. (2007), 19pp.
16. Berg, Michael; Essl, Stefan; Hugentobler, Max. Process for the preparation of astaxanthin. PCT Int. Appl. (2007), 19pp.
17. Hussein G, Sankawa U, Goto H, Matsumoto K, Watanabe H: Astaxanthin, a carotenoid with potential in human health and nutrition. J Nat Prod. 2006 Mar;69(3):443-9.
18. Higuera-Ciapara I, Felix-Valenzuela L, Goycoolea FM: Astaxanthin: a review of its chemistry and applications. Crit Rev Food Sci Nutr. 2006;46(2):185-96.
19. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
20. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
21. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
22. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
23. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
24. The lipid handbook with CD-ROM