Astaxanthin (BioCAD00000006873)

blood feces plant natural products microbial natural products

Metabolite Card

Formula: C40H52O4 (596.3865)
SMILES: C\C(\C=C\C=C(/C)\C=C\C1=C(C)C(=O)[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)[C@@H](O)CC1(C)C

Synonyms [en]

astaxanthin; (3S,3'S)-Astaxanthin; (3S,3'S)-3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione; 3,3'-Dihydroxy-beta,beta-carotene-4,4'-dione; astaxanthine; Ovoester

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Astaxanthin. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000006873). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Astaxanthin is the main carotenoid pigment found in aquatic animals. It is also found in some birds, such as flamingoes, quails, and other species. This carotenoid is included in many well-known seafoods such as salmon, trout, red seabream, shrimp, lobster, and fish eggs. Astaxanthin, similar to other carotenoids, cannot be synthesized by animals and must be provided in the diet. Mammals, including humans, lack the ability to synthesize astaxanthin or to convert dietary astaxanthin into vitamin A. Astaxanthin belongs to the xanthophyll class of carotenoids. It is closely related to beta-carotene, lutein, and zeaxanthin, sharing with them many of the general metabolic and physiological functions attributed to carotenoids. In addition, astaxanthin has unique chemical properties based on its molecular structure. The presence of the hydroxyl (OH) and keto (CdO) moieties on each ionone ring explains some of its unique features, namely, the ability to be esterified and a higher antioxidant activity and a more polar nature than other carotenoids. In its free form, astaxanthin is considerably unstable and particularly susceptible to oxidation. Hence it is found in nature either conjugated with proteins (e.g. salmon muscle or lobster exoskeleton) or esterified with one or two fatty acids (monoester and diester forms) which stabilize the molecule. Various astaxanthin isomers have been characterized on the basis of the configuration of the two hydroxyl groups on the molecule. The geometrical and optical isomers of astaxanthin are distributed selectively in different tissues and levels of free astaxanthin in the liver are greater than the corresponding concentration in the plasma, suggesting concentrative uptake by the liver. Astaxanthin, similar to other carotenoids, is a very lipophilic compound and has a low oral bioavailability. This criterion has limited the ability to test this compound in well-defined rodent models of human disease (PMID: 16562856). Astaxanthin is a carotenoid widely used in salmonid and crustacean aquaculture to provide the pink colour characteristic of that species. This application has been well documented for over two decades and is currently the major market driver for the pigment. Additionally, astaxanthin also plays a key role as an intermediary in reproductive processes. Synthetic astaxanthin dominates the world market but recent interest in natural sources of the pigment has increased substantially. Common sources of natural astaxanthin are the green algae Haematococcus pluvialis (the red yeast), Phaffia rhodozyma, as well as crustacean byproducts. Astaxanthin possesses an unusual antioxidant activity which has caused a surge in the nutraceutical market for the encapsulated product. Also, health benefits such as cardiovascular disease prevention, immune system boosting, bioactivity against Helicobacter pylori, and cataract prevention, have been associated with astaxanthin consumption. Research on the health benefits of astaxanthin is very recent and has mostly been performed in vitro or at the pre-clinical level with humans (PMID: 16431409). Astaxanthin is used in fish farming to induce trout flesh colouring.

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 113085-05-5
  • CAS Registry Number: 472-61-7
  • CAS Registry Number: 60760-95-4
  • CAS Registry Number: 71772-51-5
  • CAS Registry Number: 7542-45-2
  • PubChem: 5281224
  • PubChem: 5368397
  • ChEBI: ChEBI:40968
  • HMDB: HMDB0002204
  • LipidMaps: LMPR01070263
  • LipidMaps: LMPR01070800
  • KEGG: C08580
  • BioCyc: CPD-11473
  • BioCyc: CPD-7847
  • NCBI MeSH: astaxanthine
  • Wikipedia: Astaxanthin
  • DrugBank: DB06543
  • RefMet: RM0118472
  • MoNA: Bruker_HCD_library001486
  • MoNA: CA000004
  • MoNA: MSJ00122
  • MoNA: MSJ00123
  • MoNA: MSJ00124
  • MoNA: MSJ00125
  • MoNA: PM015401
  • MoNA: PM015420
  • MoNA: VF-NPL-LTQ006223
  • MoNA: VF-NPL-LTQ006224
  • MoNA: VF-NPL-QEHF003103
  • MoNA: VF-NPL-QEHF003104
  • MoNA: VF-NPL-QEHF003105
  • MoNA: VF-NPL-QEHF003106
  • MoNA: VF-NPL-QEHF003107
  • MoNA: VF-NPL-QEHF003108
  • MoNA: VF-NPL-QEHF003109
  • MoNA: VF-NPL-QEHF003110
  • MoNA: VF-NPL-QEHF003111
  • Metlin: METLIN_3671
  • Coconut NaturalProduct: CNP0190579.1
  • Coconut NaturalProduct: CNP0190579.2
  • Coconut NaturalProduct: CNP0190579.3
  • Coconut NaturalProduct: CNP0190579.4
  • Coconut NaturalProduct: CNP0316160.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R07572 1.14.15.24 phoenicoxanthin,reduced ferredoxin [iron-sulfur] cluster:oxygen 3'-oxidoreductase
KEGG:R07573 1.14.99.64 adonixanthin,donor:oxygen oxidoreductase (astaxanthin-forming)
KEGG:R08102 C08580<=>C16486
Rhea:RHEA:56773 1.14.99.64 all-trans-adonixanthin + 2 AH2 + 2 O2 => all-trans-(3S,3'S)-astaxanthin + 2 A + 3 H2O
Rhea:RHEA:56774 1.14.99.64 all-trans-(3S,3'S)-astaxanthin + 2 A + 3 H2O => all-trans-adonixanthin + 2 AH2 + 2 O2
Rhea:RHEA:56775 1.14.99.64 all-trans-adonixanthin + 2 AH2 + 2 O2 <=> all-trans-(3S,3'S)-astaxanthin + 2 A + 3 H2O
BioCyc:RXN-18969 CPD-20427 --> CPD-7847 + WATER
BioCyc:RXN-19151 1.14.15.24 CPD-7851 + 4 Reduced-ferredoxins + 2 OXYGEN-MOLECULE + 4 PROTON --> CPD-7847 + 4 Oxidized-ferredoxins + 2 WATER
BioCyc:RXN-8190 1.14.99.64 CPD-7852 + 2 Donor-H2 + 2 OXYGEN-MOLECULE --> CPD-7847 + 2 Acceptor + 3 WATER
BioCyc:RXN-16438 1.14.13.- astaxanthin hydroxylase
BioCyc:RXN-16436 1.14.13.- CPD-7847 + NADH + PROTON + OXYGEN-MOLECULE --> CPD-17665 + NAD + WATER
BioCyc:RXN-8187 CPD-7849 + 2 Reduced-ferredoxins + 2 PROTON + OXYGEN-MOLECULE --> CPD-7847 + 2 Oxidized-ferredoxins + WATER
BioCyc:RXN-16244 2.4.1.- CPD-7847 + 2 CPD-353 --> CPD-17491 + 2 GDP + 2 PROTON
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Organism Source

Taxonomy Source

  1. A new engineered strain of Bacillus subtilis [PbdhA] [ncbi taxid: ]
  2. A new engineered strain of Escherichia coli BL21(DE3) [aroAT gdh YDR380w YGL157w] [ncbi taxid: ]
  3. Actinoplanes sp. QQ-1 [acb cluster treY] [ncbi taxid: ]
  4. Adonis aestivalis [ncbi taxid: 113211]
  5. Adonis vernalis [ncbi taxid: 46985]
  6. Agrobacterium aurantiacum [ncbi taxid: 44155]
  7. Alcaligenes PC1 [ncbi taxid: ]
  8. Brevundimonas sp. strain SD212 [ncbi taxid: ]
  9. Carassius auratus [ncbi taxid: 7957]
  10. Centropages furcatus [ncbi taxid: 399975]
  11. Cetraria australiensis [ncbi taxid: 425280]
  12. Chlorella fusca [ncbi taxid: ]
  13. Chlorella zofingiensis [ncbi taxid: ]
  14. Chlorococcum citriforme [ncbi taxid: 1521711]
  15. Clione limacina [ncbi taxid: 71516]
  16. Coelastrum proboscideum [ncbi taxid: 795112]
  17. Ettlia carotinosa [ncbi taxid: 707317]
  18. Euchaeta russelli [ncbi taxid: ]
  19. Euglena rubida mainx [ncbi taxid: ]
  20. Fusinus perplexus [ncbi taxid: ]
  21. Gelliodes callista [ncbi taxid: 1336858]
  22. Glenodinium sp. [ncbi taxid: ]
  23. Gymnogobius castaneus [ncbi taxid: 255296]
  24. Haematococcus pluvialis [ncbi taxid: ]
  25. Haematococcus pluvialis Phaffia rhodozyma AS2-1557 [ncbi taxid: ]
  26. Homo sapiens [ncbi taxid: 9606]
  27. Liobagrus reinii [ncbi taxid: 78875]
  28. Lophelia pertusa [ncbi taxid: ]
  29. Muriella aurantiaca [ncbi taxid: ]
  30. Muriellopsis sp. [ncbi taxid: ]
  31. Nannochloropsis gaditana [ncbi taxid: 72520]
  32. Nannochloropsis oculata [ncbi taxid: 43925]
  33. Nannochloropsis salina [ncbi taxid: ]
  34. Neochloris wimmeri [ncbi taxid: ]
  35. Oriolus cruentus [ncbi taxid: 370835]
  36. Paedoclione doliiformis [ncbi taxid: ]
  37. Paracoccus carotinifaciens sp. nov. [ncbi taxid: ]
  38. Paragorgia arborea [ncbi taxid: 318094]
  39. Pelteobagrus nudiceps [ncbi taxid: ]
  40. Pfaffia rhodozyma [ncbi taxid: ]
  41. Phoenicoparrus andinus [ncbi taxid: 704177]
  42. Phoenicoparrus jamesi [ncbi taxid: 704178]
  43. Phoenicoparrus ruber [ncbi taxid: ]
  44. Primnoa resedaeformis [ncbi taxid: 328424]
  45. Protosiphon botryoides [ncbi taxid: 44656]
  46. Protousnea sp. [ncbi taxid: ]
  47. Pycnococcus provasolii [ncbi taxid: 41880]
  48. Rhacophorus bipunctatus [ncbi taxid: 191205]
  49. Salvelinus alpinus [ncbi taxid: 8036]
  50. Scenedesmus vacuolatus [ncbi taxid: 77546]
  51. Scotiellopsis oocystiformis [ncbi taxid: ]
  52. Temora turbinata [ncbi taxid: 749012]
  53. Tetracystis sp. [ncbi taxid: 2976233]
  54. Tovellia sanguinea [ncbi taxid: 363794]
  55. Undinula vulgaris [ncbi taxid: 184747]
  56. Xanthophyllomyces dendrorhous [ncbi taxid: ]
  57. Xipholena punicea [ncbi taxid: 114392]
  58. Phaffia rhodozyma [ncbi taxid: 264483]
  59. Xanthophyllomyces dendrorhous [ncbi taxid: ]
  60. Carassius auratus [ncbi taxid: 7957]
  61. Cyprinus carpio [ncbi taxid: 7962]
  62. Fenneropenaeus orientalis [ncbi taxid: ]
  63. Homarus gammarus [ncbi taxid: 6707]
  64. Penaeus orientalis [ncbi taxid: 70917]
  65. Rhizobium lupini [ncbi taxid: ]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-7623 astaxanthin dirhamnoside biosynthesis
BioCyc:META_PWY-5288 astaxanthin biosynthesis (bacteria, fungi, algae)
BioCyc:META_PWY-7637 2,2'-dihydroxyketocarotenoids biosynthesis
BioCyc:META_PWY-7636 astaxanthin biosynthesis (flowering plants)
WikiPathways:WP1259 Retinol metabolism
WikiPathways:WP1038 Vitamin A and carotenoid metabolism
WikiPathways:WP1297 Retinol metabolism
WikiPathways:WP716 Vitamin A and carotenoid metabolism
WikiPathways:WP805 Retinol metabolism
WikiPathways:WP3843 Vitamin A and carotenoid metabolism
View All Pathways