Astaxanthin

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
(3S,3′S)-3,3′-Dihydroxy-β,β-carotene-4,4′-dione
Systematic IUPAC name
(6S,6′S)-3,3′-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(6-hydroxy-2,4,4-trimethylcyclohex-2-en-1-one)
Other names
  • β-Carotene-4,4'-dione, 3,3'-dihydroxy-, all-trans-
  • (3S,3'S)-Astaxanthin
  • (3S,3'S)-Astaxanthin
  • (3S,3'S)-all-trans-Astaxanthin
  • (S,S)-Astaxanthin; Astaxanthin, all-trans-
  • all-trans-Astaxanthin
  • trans-Astaxanthin
  • Ovoester[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.776 Edit this at Wikidata
E number E161j (colours)
UNII
  • 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 checkY
    Key: MQZIGYBFDRPAKN-UWFIBFSHSA-N checkY
  • 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
  • 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
C40H52O4
Molar mass 596.84 g/mol
Appearance red solid powder
Density 1.071 g/mL[2]
Melting point 216 °C (421 °F; 489 K)[2]
Boiling point 774 °C (1,425 °F; 1,047 K)[2]
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 checkY☒N ?)

Astaxanthin /æstəˈzænθɪn/ is a keto-carotenoid within a group of chemical compounds known as carotenones or terpenes.[3][4][5] Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups.[3]

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.[3] The presence of the hydroxyl functional groups and the hydrophobic hydrocarbons render the molecule amphiphilic.[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. [7][8] When the algae are stressed by lack of nutrients, increased salinity, or excessive sunshine, they create astaxanthin.[9] Animals who feed on the algae, such as salmon, red trout, red sea bream, flamingos, and crustaceans (shrimp, krill, crab, lobster, and crayfish), subsequently reflect the red-orange astaxanthin pigmentation.[3][10]

Astaxanthin is used as a dietary supplement for human, animal, and aquaculture consumption.[3] Astaxanthin from algae, synthetic and bacterial sources is generally recognized as safe in the United States.[11] The US Food and Drug Administration has approved astaxanthin as a food coloring (or color additive) for specific uses in animal and fish foods.[3][12] The European Commission considers it as a food dye with E number E161j.[13] The European Food Safety Authority has set an Acceptable Daily Intake of 0.2 mg per kg body weight, as of 2019.[14] As a food color additive, astaxanthin and astaxanthin dimethyldisuccinate are restricted for use in Salmonid fish feed only.[15]

  1. ^ SciFinder Web (accessed September 28, 2010). Astaxanthin (472-61-7) Name
  2. ^ a b c SciFinder Web (accessed September 28, 2010). Astaxanthin (472-61-7) Experimental Properties.
  3. ^ a b c d e f "Astaxanthin". PubChem, US National Library of Medicine. May 3, 2024. Retrieved May 10, 2024.
  4. ^ Margalith PZ (1999). "Production of ketocarotenoids by microalgae". Applied Microbiology and Biotechnology. 51 (4): 431–8. doi:10.1007/s002530051413. PMID 10341427. S2CID 123858.
  5. ^ Choi S, Koo S (2005). "Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene". The Journal of Organic Chemistry. 70 (8): 3328–31. doi:10.1021/jo050101l. PMID 15823009.
  6. ^ Ahirwar A (August 3, 2021). "Light modulates transcriptomic dynamics upregulating astaxanthin accumulation in Haematococcus: A review". Bioresource Technology. 340: 125707. doi:10.1016/j.biortech.2021.125707. PMID 34371336. Retrieved November 15, 2023.
  7. ^ "Phaffia rhodozyma M.W. Mill., Yoney. & Soneda - Names Record". www.speciesfungorum.org. Species Fungorum. Retrieved September 9, 2022.
  8. ^ Tsubokura A, Yoneda H, Mizuta H (January 1, 1999). "Paracoccus carotinifaciens sp. nov., a new aerobic Gram-negative astaxanthin-producing bacterium". International Journal of Systematic and Evolutionary Microbiology. 49 (1): 277–282. doi:10.1099/00207713-49-1-277. ISSN 1466-5026. PMID 10028273.
  9. ^ Aizpuru A, González-Sánchez A (July 20, 2024). "Traditional and new trend strategies to enhance pigment contents in microalgae". World Journal of Microbiology and Biotechnology. 40 (9): 272. doi:10.1007/s11274-024-04070-3. ISSN 1573-0972. PMC 11271434. PMID 39030303.
  10. ^ Routray W, Dave D, Cheema SK, Ramakrishnan VV, Pohling J (June 2019). "Biorefinery approach and environment-friendly extraction for sustainable production of astaxanthin from marine wastes". Critical Reviews in Biotechnology. 39 (4): 469–488. doi:10.1080/07388551.2019.1573798. PMID 30939937.
  11. ^ Astaxanthin wins full GRAS status. Nutraingredients-usa.com. Retrieved on April 25, 2013.
  12. ^ "Summary of Color Additives for Use in United States in Foods, Drugs, Cosmetics, and Medical Devices". Food and Drug Administration. March 4, 2022. See Note 1.
  13. ^ E-numbers : E100- E200 Food Colours. Food-Info.net. Retrieved on April 25, 2013.
  14. ^ Safety and efficacy of astaxanthin-dimethyldisuccinate (Carophyll Stay-Pink 10%-CWS) for salmonids, crustaceans and other fish European Food Safety Authority. Retrieved on August 24, 2020.
  15. ^ Summary of Color Additives for Use in the United States in Foods, Drugs, Cosmetics, and Medical Devices. Fda.gov. Retrieved on January 16, 2019.