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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2019-03-14 18:02:27 UTC
HMDB IDHMDB0002204
Secondary Accession Numbers
  • HMDB02204
Metabolite Identification
Common NameAstaxanthin
DescriptionAstaxanthin is the main carotenoid pigment found in aquatic animals. It is also found in some birds, such as flamingoes, quails, and other species. This carotenoid is included in many well-known seafoods such as salmon, trout, red seabream, shrimp, lobster, and fish eggs. Astaxanthin, similar to other carotenoids, cannot be synthesized by animals and must be provided in the diet. Mammals, including humans, lack the ability to synthesize astaxanthin or to convert dietary astaxanthin into vitamin A. Astaxanthin belongs to the xanthophyll class of carotenoids. It is closely related to beta-carotene, lutein, and zeaxanthin, sharing with them many of the general metabolic and physiological functions attributed to carotenoids. In addition, astaxanthin has unique chemical properties based on its molecular structure. The presence of the hydroxyl (OH) and keto (CdO) moieties on each ionone ring explains some of its unique features, namely, the ability to be esterified and a higher antioxidant activity and a more polar nature than other carotenoids. In its free form, astaxanthin is considerably unstable and particularly susceptible to oxidation. Hence it is found in nature either conjugated with proteins (e.g., salmon muscle or lobster exoskeleton) or esterified with one or two fatty acids (monoester and diester forms), which stabilize the molecule. Various astaxanthin isomers have been characterized on the basis of the configuration of the two hydroxyl groups on the molecule. the geometrical and optical isomers of astaxanthin are distributed selectively in different tissues and that levels of free astaxanthin in the liver are greater than the corresponding concentration in the plasma, suggesting concentrative uptake by the liver. Astaxanthin, similar to other carotenoids, is a very lipophilic compound and has a low oral bioavailability. This criterion has limited the ability to test this compound in well-defined rodent models of human disease. (PMID: 16562856 ). Astaxanthin is a carotenoid widely used in salmonid and crustacean aquaculture to provide the pink color characteristic of that species. This application has been well documented for over two decades and is currently the major market driver for the pigment. Additionally, astaxanthin also plays a key role as an intermediary in reproductive processes. Synthetic astaxanthin dominates the world market but recent interest in natural sources of the pigment has increased substantially. Common sources of natural astaxanthin are the green algae Haematococcus pluvialis, the red yeast, Phaffia rhodozyma, as well as crustacean byproducts. Astaxanthin possesses an unusual antioxidant activity which has caused a surge in the nutraceutical market for the encapsulated product. Also, health benefits such as cardiovascular disease prevention, immune system boosting, bioactivity against Helycobacter pylori, and cataract prevention, have been associated with astaxanthin consumption. Research on the health benefits of astaxanthin is very recent and has mostly been performed in vitro or at the pre-clinical level with humans. (PMID: 16431409 ).
Structure
Data?1547234208
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
Chemical FormulaC40H52O4
Average Molecular Weight596.852
Monoisotopic Molecular Weight596.386560154
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
CAS Registry Number472-61-7
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)[C@@H](O)CC1(C)C
InChI Identifier
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+/t35-,36-/m0/s1
InChI KeyMQZIGYBFDRPAKN-UWFIBFSHSA-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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2000090000-c6336112eb898c2f0a48JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-3000019000-6b5720849187b199d6bfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0232390000-f37e3530214c99f63306JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1296830000-ac8ea41a53a053acb7c8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0185910000-7af6a00762ad7e8ee75dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-248171e80348a7e1d17eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000090000-b9759de23c7494bb7b2dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0333390000-074ea5de5d017bafdb5eJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.092 +/- 0.025 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06543
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018640
KNApSAcK IDC00000918
Chemspider ID4444636
KEGG Compound IDC08580
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAstaxanthin
METLIN ID3671
PubChem Compound5281224
PDB IDNot Available
ChEBI ID40968
References
Synthesis ReferenceBerg, Michael; Essl, Stefan; Hugentobler, Max. Process for the preparation of astaxanthin. PCT Int. Appl. (2007), 19pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:16562856 ]
  2. 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. [PubMed:16431409 ]