astaxanthin

Also known as E 161j, AstaREAL, trans-Astaxanthin, (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, Astaxanthin (6CI), BioAstin, All-trans-Astaxanthin, Natupink

Astaxanthin is a keto-carotenoid within a group of chemical compounds known as carotenoids, a subclass of the broad group of phytochemicals known as terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups.

Chemical data

Formula: C40H52O4
Molecular weight: 596.8 g/mol
IUPAC name: (6S)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethylcyclohex-2-en-1-one
SMILES: CC1=C(C(C[C@@H](C1=O)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C(=O)[C@H](CC2(C)C)O)C)\C)\C)/C)/C
InChIKey: MQZIGYBFDRPAKN-UWFIBFSHSA-N
XLogP: 10.3
Polar surface area: 74.6 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

~11 min read

Encyclopedic overview

13 sections

Contents

Natural sources
Biosynthesis
Synthetic sources
Metabolic engineering
Structure
Stereoisomers
Esterification
Uses
For seafood and animals
Dietary supplement
Role in the food chain
Regulations
References

It is a lipid-soluble pigment with red coloring properties, which result from the extended chain of conjugated (alternating double and single) double bonds at the center of the compound. The presence of the hydroxyl functional groups and the hydrophobic hydrocarbons render the molecule amphiphilic.

Excerpted from Wikipedia’s “astaxanthin” article, available under the CC BY-SA 4.0 licence.