Astaxanthin

[6] Astaxanthin is produced naturally in the freshwater microalgae Haematococcus pluvialis, the yeast fungus Xanthophyllomyces dendrorhous (also known as Phaffia rhodozyma) and the bacteria Paracoccus carotinifaciens.

[13] The European Food Safety Authority has set an Acceptable Daily Intake of 0.2 mg per kg body weight, as of 2019.

[17] In shellfish, astaxanthin is almost exclusively concentrated in the shells, with only low amounts in the flesh itself, and most of it only becomes visible during cooking as the pigment separates from the denatured proteins that otherwise bind it.

[23] The cost of astaxanthin extraction, high market price, and lack of efficient fermentation production systems, combined with the intricacies of chemical synthesis, discourage its commercial development.

The metabolic engineering of bacteria (Escherichia coli) enables efficient astaxanthin production from beta-carotene via either zeaxanthin or canthaxanthin.

[3][24][25][26] In addition to structural isomeric configurations, astaxanthin also contains two chiral centers at the 3- and 3′-positions, resulting in three unique stereoisomers (3R,3′R and 3R,3'S meso and 3S,3'S).

[28] Astaxanthin exists in two predominant forms, non-esterified (yeast, synthetic) or esterified (algal) with various length fatty acid moieties whose composition is influenced by the source organism as well as growth conditions.

[3][17] The primary use of synthetic astaxanthin today is as an animal feed additive to impart coloration, including farm-raised salmon and chicken egg yolks.

[3][33] Synthetic carotenoid pigments colored yellow, red or orange represent about 15–25% of the cost of production of commercial salmon feed.

[35] Class action lawsuits were filed against some major grocery store chains for not clearly labeling the astaxanthin-treated salmon as "color added".

Litigation persisted with the suit for damages, but a Seattle judge dismissed the case, ruling that enforcement of the applicable food laws was up to government and not individuals.

Skeletal formula of astaxanthin
Space-filling model of the astaxanthin molecule
The shell and smaller parts of the bodily tissue of Pandalus borealis (Arctic shrimp) are colored red by astaxanthin, and are used and sold as an extractable source of astaxanthin.
A Haematococcus pluvialis cyst filled with astaxanthin (red)
Krill also are used as an astaxanthin source.
Astaxanthin biosynthesis starts with three molecules of isopentenyl pyrophosphate (IPP) and one molecule of dimethylallyl pyrophosphate (DMAPP) that are combined by IPP isomerase and converted to geranylgeranyl pyrophosphate (GGPP) by GGPP synthase. Two molecules of GGPP are then coupled by phytoene synthase to form phytoene. Next, phytoene desaturase creates four double bonds in the phytoene to form lycopene. Then, lycopene cyclase first forms γ-carotene then subsequently forms β-carotene. From β-carotene, hydrolases (blue) and ketolases (green) form multiple intermediate molecules until the final molecule, astaxanthin is obtained.
Astaxanthin biosynthesis starts with three molecules of isopentenyl pyrophosphate (IPP) and one molecule of dimethylallyl pyrophosphate (DMAPP) that are combined by IPP isomerase and converted to geranylgeranyl pyrophosphate (GGPP) by GGPP synthase. Two molecules of GGPP are then coupled by phytoene synthase to form phytoene. Next, phytoene desaturase creates four double bonds in the phytoene to form lycopene. Then, lycopene cyclase first forms γ-carotene then subsequently forms β-carotene. From β-carotene, hydrolases (blue) and ketolases (green) form multiple intermediate molecules until the final molecule, astaxanthin is obtained.
Synthesis of astaxanthin by Wittig reaction