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Astaxanthin information


Astaxanthin
Skeletal formula of astaxanthin
Space-filling model of the astaxanthin molecule
Names
IUPAC name
(3S,3S)-3,3-Dihydroxy-β,β-carotene-4,4-dione
Systematic IUPAC name
(6S,6S)-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
CAS Number
  • 472-61-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:40968 ☒N
ChEMBL
  • ChEMBL445751 ☒N
ChemSpider
  • 4444636 checkY
ECHA InfoCard 100.006.776 Edit this at Wikidata
E number E161j (colours)
PubChem CID
  • 5281224
UNII
  • 8XPW32PR7I checkY
CompTox Dashboard (EPA)
  • DTXSID00893777 Edit this at Wikidata
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 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
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[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 ?)
Infobox references

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

Astaxanthin is produced naturally in the freshwater microalgae Haematococcus pluvialis and the yeast fungus Xanthophyllomyces dendrorhous (also known as Phaffia rhodozyma).[6] When the algae are stressed by lack of nutrients, increased salinity, or excessive sunshine, they create astaxanthin. 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.

Astaxanthin is used as a dietary supplement for human, animal, and aquaculture consumption. Astaxanthin from algae, synthetic and bacterial sources is generally recognized as safe in the United States.[7] The US Food and Drug Administration has approved astaxanthin as a food coloring (or color additive) for specific uses in animal and fish foods.[8] The European Commission considers it as a food dye with E number E161j.[9] The European Food Safety Authority has set an Acceptable Daily Intake of 0.2 mg per kg body weight, as of 2019.[10] As a food color additive, astaxanthin and astaxanthin dimethyldisuccinate are restricted for use in Salmonid fish feed only.[11]

  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. ^ Margalith PZ (1999). "Production of ketocarotenoids by microalgae". Applied Microbiology and Biotechnology. 51 (4): 431–8. doi:10.1007/s002530051413. PMID 10341427. S2CID 123858.
  4. ^ 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.
  5. ^ 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.
  6. ^ "Phaffia rhodozyma M.W. Mill., Yoney. & Soneda - Names Record". www.speciesfungorum.org. Species Fungorum. Retrieved September 9, 2022.
  7. ^ Astaxanthin wins full GRAS status. Nutraingredients-usa.com. Retrieved on April 25, 2013.
  8. ^ "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.
  9. ^ E-numbers : E100- E200 Food Colours. Food-Info.net. Retrieved on April 25, 2013.
  10. ^ 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.
  11. ^ Summary of Color Additives for Use in the United States in Foods, Drugs, Cosmetics, and Medical Devices. Fda.gov. Retrieved on January 16, 2019.

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Astaxanthin

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Haematococcus pluvialis

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content of the strong antioxidant astaxanthin, which is important in aquaculture, and cosmetics. The high amount of astaxanthin is present in the resting cells...

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Limonene

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Canthaxanthin

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pluvialis are known. Due to the nature of canthaxanthin, relative to astaxanthin (a carotenoid of significant commercial value) these beta-carotene ketolase...

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Krill oil

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per 100 grams of oil. Krill oil also contains appreciable content of astaxanthin at 0.1 to 1.5 mg/ml, depending on processing methods, which is responsible...

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Pink

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pigment called astaxanthin. Their shells, naturally blue-green, turn pink or red when cooked. The flesh of the salmon also contains astaxanthin, which makes...

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Salmon

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diseases.[citation needed] Farm-raised salmon are fed the carotenoids astaxanthin and canthaxanthin to match their flesh colour to wild salmon to improve...

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Haematococcus

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pluvialis, which is used in cosmetic products due to its production of astaxanthin, a powerful antioxidant carotenoid, under stress conditions. Drawing...

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Salmon as food

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The natural color of salmon results from carotenoid pigments, largely astaxanthin and canthaxanthin in the flesh. Wild salmon get these carotenoids from...

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Watermelon snow

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species of green algae containing a secondary red carotenoid pigment (astaxanthin) in addition to chlorophyll. Unlike most species of fresh-water algae...

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Psittacofulvin

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offers an advantage: it creates a more deep-red color when compared to astaxanthin, the pigment's counterpart in most other birds. Birds have tetrachromatic...

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Crustacyanin

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their blue colour. β-Crustacyanin (β-CR), is composed of two stacked astaxanthin carotenoids that absorb at λ = 580–590 nm (2.10–2.14 eV). α-crustacyanin...

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Chlamydomonas nivalis

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taking account of the photoprotective effect of its secondary carotenoid, astaxanthin, among the other adaptive mechanisms to its extreme habitat, it can be...

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Roseate spoonbill

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consisting of the carotenoid pigment canthaxanthin. Another carotenoid, astaxanthin, can also be found deposited in flight and body feathers. The colors...

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Dietary fiber

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Albinism

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rate and fertility. Astaxanthin is the main carotenoid in marine crustaceans (and fish). It has been shown that adding astaxanthin to the feed can improve...

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Capsaicin

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Carotenoid

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methyl ester Methyl 3',4'-didehydro-β,γ-caroten-16'-oate Ketones Astacene Astaxanthin Canthaxanthin a.k.a. Aphanicin, Chlorellaxanthin β,β-Carotene-4,4'-dione...

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Sphingomonas astaxanthinifaciens

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in Japan. Sphingomonas astaxanthinifaciens has the ability to produce astaxanthin. LPSN lpsn.dsmz.de Straininfo of Sphingomonas astaxanthinifaciens UniProt...

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Lobster

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lobster's taste once cooked; except for albinos, all lobsters possess astaxanthin, which is responsible for the bright red color lobsters turn after being...

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Zeaxanthin

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hydroxylase proteins are known. Due to the nature of zeaxanthin, relative to astaxanthin (a carotenoid of significant commercial value) beta-carotene hydroxylase...

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Carotene

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Ngorongoro Crater, Tanzania. The pink colour of wild flamingos is due to astaxanthin (a carotenoid) they absorb from their diet of brine shrimp. If fed a...

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Chronic obstructive pulmonary disease

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Evidence is growing for the effectiveness of Astaxanthin against lung disease including COPD. Astaxanthin is a potent antioxidant with anti-inflammatory...

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Giant oarfish

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bladder. The liver of R. glesne is orange or red, the likely result of astaxanthin in its diet. The lateral line begins above and behind the eye then, descending...

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Menthol

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