Astaxanthin

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Astaxanthin (Wikipedia)
Not to be confused with Anthoxanthin, a subclass of flavonoids.
Astaxanthin
Skeletal formula of astaxanthin
Space-filling model of the astaxanthin molecule
Names
IUPAC name
(6S)-6-Hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone
Other names
3,3'-dihydroxy-ß-carotene-4,4'-dione; Astaxanthin (6CI); β-Carotene-4,4'-dione, 3,3'-dihydroxy-, all-trans- (8CI); (3S,3'S)-Astaxanthin; (3S,3'S)-Astaxanthin; (3S,3'S)-all-trans-Astaxanthin; (S,S)-Astaxanthin; Aquasta; AstaREAL; AstaXin; Astared; Astaxanthin, all-trans-; Astots 10O; Astots 5O; BioAstin; BioAstin oleoresin; Carophyll Pink; Lucantin Pink; NatuRose; Natupink; Ovoester; all-trans-Astaxanthin; trans-Astaxanthin
Identifiers
472-61-7 YesY
ChEBI CHEBI:40968 N
ChEMBL ChEMBL445751 N
ChemSpider 4444636 YesY
Jmol 3D image Interactive graph
PubChem 5281224
UNII 8XPW32PR7I YesY
Properties
C40H52O4
Molar mass 596.84 g/mol
Appearance red solid powder
Density 1.071 g/mL
Melting point 216 °C (421 °F; 489 K)
Boiling point 774 °C (1,425 °F; 1,047 K)
Solubility 30 g/L in DCM; 10 g/L in CHCl3; 0.5 g/L in DMSO; 0.2 g/L in acetone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Astaxanthin /æstəˈzænθn/ is a keto-carotenoid. It belongs to a larger class of chemical compounds known as terpenes, which are built from five carbon precursors; isopentenyl diphosphate (or IPP) and dimethylallyl diphosphate (or DMAPP). Astaxanthin is classified as a xanthophyll (originally derived from a word meaning "yellow leaves" since yellow plant leaf pigments were the first recognized of the xanthophyll family of carotenoids), but currently employed to describe carotenoid compounds that have oxygen-containing moities, hydroxyl (-OH) or ketone (C=O), such as zeaxanthin and canthaxanthin. Indeed, astaxanthin is a metabolite of zeaxanthin and/or canthaxanthin, containing both hydroxyl and ketone functional groups. Like many carotenoids, astaxanthin is a colorful, lipid-soluble pigment. This colour is due to the extended chain of conjugated (alternating double and single) double bonds at the centre of the compound. This chain of conjugated double bonds is also responsible for the antioxidant function of astaxanthin (as well as other carotenoids) as it results in a region of decentralized electrons that can be donated to reduce a reactive oxidizing molecule.

Astaxanthin is found in microalgae, yeast, salmon, trout, krill, shrimp, crayfish, crustaceans, and the feathers of some birds. It provides the red color of salmon meat and the red color of cooked shellfish. Professor Basil Weedon's group was the first to prove the structure of astaxanthin by synthesis, in 1975.

Astaxanthin, unlike several carotenes and one other known carotenoid, is not converted to vitamin A (retinol) in the human body. Like other carotenoids, astaxanthin has self-limited absorption orally and such low toxicity by mouth that no toxic syndrome is known. It is an antioxidant with a slightly lower antioxidant activity in some model systems than other carotenoids. However, in living organisms the free-radical terminating effectiveness of each carotenoid is heavily modified by its lipid solubility, and thus varies with the type of system being protected.

While astaxanthin is a natural dietary component, it can also be used 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.

The U.S. Food and Drug Administration (FDA) has approved astaxanthin as a food coloring (or color additive) for specific uses in animal and fish foods. The European Commission considers it food dye and it is given the E number E161j. Natural astaxanthin is generally recognized as safe (GRAS) by the FDA, but as a food coloring in the United States it is restricted to use in animal food.

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