Astaxanthin

Astaxanthin

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
CAS Number	472-61-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:40968 N
ChEMBL	ChEMBL445751 N
ChemSpider	4444636 Y
ECHA InfoCard	100.006.776
E number	E161j (colours)
PubChem	5281224
UNII	8XPW32PR7I Y
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+/t35-,36-/m0/s1 Y Key: MQZIGYBFDRPAKN-UWFIBFSHSA-N Y InChI=1/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+ Key: MQZIGYBFDRPAKN-QISQUURKBE InChI=1/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 Key: MQZIGYBFDRPAKN-UWFIBFSHBJ
SMILES O=C2\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@@H](O)CC1(C)C)C)C)C)C)C)C(C)(C)C[C@@H]2O)C
Properties
Chemical formula	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  (what is YN ?)
Infobox references

Astaxanthin /æstəˈzænθᵻn/ is a keto-carotenoid. It belongs to a larger class of chemical compounds known as terpenes (in Asthaxanthin's case, a tetraterpenoid); terpenes 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.