Record Information
Version1.0
Creation date2010-04-08 22:13:50 UTC
Update date2015-07-21 06:29:35 UTC
Primary IDFDB018640
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3S,3'S)-Astaxanthin
DescriptionAstaxanthin (pronounced as-tuh-zan'-thin) is a carotenoid. It belongs to a larger class of phytochemicals known as terpenes. It is classified as a xanthophyll, which means "yellow leaves". Like many carotenoids, it is a colorful, lipid-soluble pigment. Astaxanthin is produced by microalgae, yeast, salmon, trout, krill, shrimp, crayfish, crustaceans, and the feathers of some birds. Professor Basil Weedon was the first to map the structure of astaxanthin.; Astaxanthin 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); Astaxanthin, unlike some carotenoids, does not convert to Vitamin A (retinol) in the human body. Too much Vitamin A is toxic for a human, but astaxanthin is not. However, it is a powerful antioxidant; it is claimed to be 10 times more capable than other carotenoids. However, other sources suggest astaxanthin has slightly lower antioxidant activity than other carotenoids.; While astaxanthin is a natural nutritional component, it can be found as a food supplement. The supplement is intended for human, animal, and aquaculture consumption. The commercial production of astaxanthin comes from both natural and synthetic sources.
CAS Number472-61-7
Structure
Thumb
Synonyms
SynonymSource
(3S,3'S)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dionebiospider
(3S,3'S)-all-trans-Astaxanthinbiospider
(3S,3'S)-Astaxanthinbiospider
3,3'-Dihydroxy-,-carotene-4,4'-dionebiospider
3,3'-dihydroxy-4,4'-diketo-beta,beta-carotenebiospider
3,3'-Dihydroxy-b-carotene-4,4'-dioneGenerator
3,3'-Dihydroxy-b,b-carotene-4,4'-dioneGenerator
3,3'-Dihydroxy-beta-carotene-4,4'-dionebiospider
3,3'-Dihydroxy-beta,beta-carotene-4,4'-dionebiospider
3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione, (3S,3'S)-biospider
3,3'-Dihydroxy-β-carotene-4,4'-dioneGenerator
3,3'-Dihydroxy-β,β-carotene-4,4'-dioneGenerator
3S,3'S-astaxanthinbiospider
all-trans-(3S,3'S)-astaxanthinChEBI
all-trans-3,3'-dihydroxy-b-Carotene-4,4'-dione (8CI)biospider
all-trans-3,3'-dihydroxy-beta-Carotene-4,4'-dione (8CI)biospider
All-trans-astaxanthinbiospider
Astarealbiospider
ASTAXANTHINChEBI
Astaxanthin (6CI)biospider
Astaxanthin, (3S,3'S)-biospider
Astaxanthin, all-trans-, (3S,3'S)-biospider
Astaxanthinebiospider
beta,beta-Carotene-4,4'-dione, 3,3'-dihydroxy-, (3S,3'S)-biospider
Bioastinbiospider
Bioastin oleoresinbiospider
Carophyll pinkbiospider
e 161JChEBI
Lucantin pinkbiospider
Natupinkbiospider
Ovoesterbiospider
Trans-astaxanthinbiospider
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
Polarizability72.68 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H52O4
IUPAC name6-hydroxy-3-[(1E,3E,5E,7Z,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
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 KeyInChIKey=MQZIGYBFDRPAKN-HDQLMXHPSA-N
Isomeric SMILESCC(=C\C=C\C=C(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\C1=C(C)C(=O)C(O)CC1(C)C
Average Molecular Weight597
Monoisotopic Molecular Weight596
Classification
DescriptionThis compound 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 DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 80.50%; H 8.78%; O 10.72%DFC
Melting PointMp 223-225°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 492 () (CHCl3)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2000090000-c6336112eb898c2f0a48View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-3000019000-6b5720849187b199d6bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0232390000-f37e3530214c99f63306View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1296830000-ac8ea41a53a053acb7c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0185910000-7af6a00762ad7e8ee75dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-248171e80348a7e1d17eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000090000-b9759de23c7494bb7b2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0333390000-074ea5de5d017bafdb5eView in MoNA
ChemSpider ID4444636
ChEMBL IDCHEMBL1255871
KEGG Compound IDC08580
Pubchem Compound ID5281224
Pubchem Substance IDNot Available
ChEBI ID602736
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02204
CRC / DFC (Dictionary of Food Compounds) IDLMC61-X:LMC63-Z
EAFUS ID266
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000918
HET IDAXT
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAstaxanthin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference