Astaxanthin

Base Information

• Chemical Name: Astaxanthin
• CAS No.: 472-61-7
• Molecular Formula: C40H52O4
• Molecular Weight: 596.85
• Hs Code.: 29339990
• European Community (EC) Number: 207-451-4
• UNII: 8XPW32PR7I
• ChEMBL ID: CHEMBL1255871
• DSSTox Substance ID: DTXSID00893777
• Metabolomics Workbench ID: 157533
• NCI Thesaurus Code: C63653
• Nikkaji Number: J11.883D
• Wikidata: Q413740
• Wikipedia: Astaxanthin
• Mol file: 472-61-7.mol

Synonyms:astaxanthin;astaxanthine;E-astaxanthin

Chemical Property of Astaxanthin

Chemical Property:

• Appearance/Colour: Drak-purple solid
• Melting Point: 215-216 °C
• Refractive Index: 1.4760 (estimate)
• Boiling Point: 774 °C at 760 mmHg
• PKA: 12.33±0.70(Predicted)
• Flash Point: 435.8 °C
• PSA: 74.60000
• Density: 1.071 g/cm³
• LogP: 8.90540
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble1mg/mL (warmed)
• XLogP3: 10.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 596.38656014
• Heavy Atom Count: 44
• Complexity: 1340

Purity/Quality:

1%,5%,10%, ^*data from raw suppliers

Astaxanthin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(CC(C1=O)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(C(=O)C(CC2(C)C)O)C)C)C
• Isomeric 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
• Recent ClinicalTrials: Clinical Trial of Anti-oxidant Astaxanthin in Insulin-resistant Subjects
• Recent NIPH Clinical Trials: Clinical study of astaxanthin on glucose metabolism and vascular function
• Chemical Composition and Structure: Astaxanthin is a carotenoid pigment composed of 40 carbon atoms arranged in a tetraterpene structure, with linked isoprene units. It contains a linear polyene chain and two terminal β rings. Astaxanthin has two hydroxyl (OH) groups located at asymmetric carbons C3 and C3', and a keto (=O) group at carbons C4.
• Sources: Astaxanthin is naturally found in aquatic environments, where it gives pink and red colors to the meat of fish such as salmon, trout, and shrimp, as well as to crustacean shells and feathers of certain birds. It is synthesized by algae and plankton crustaceans, which convert carotenoid precursors (chiefly β-carotene and zeaxanthin) into astaxanthin.
• Categories: Astaxanthin is classified as a xanthophyll, which is a type of carotenoid pigment. It is also categorized as a dietary supplement, nutraceutical, and cosmetic ingredient.
• Uses: Feed Industry:; Astaxanthin is widely used in the feed industry for pigmentation of salmon, trout, shrimp, and aquarium fish. It enhances the color of egg yolks and meat tissue in broiler chickens.; Nutraceuticals:; Due to its strong antioxidant properties, astaxanthin is used in nutraceuticals to prevent and treat diseases associated with reactive oxygen species, such as cancers, neurodegenerative diseases, eye diseases, atherosclerosis, and type 2 diabetes. It exhibits immunomodulatory effects and may protect against UV radiation.; Cosmetics:; Astaxanthin is utilized in cosmetics, including creams, balms, oils, and anti-aging serums, for skin health. It reduces wrinkles, age spots, and improves skin elasticity, texture, and moisture content. It provides protection from solar radiation.; Food Technology:; Astaxanthin is used in food technology for designing functional foods and active packages. Its limited use is attributed to differences between natural and synthetic astaxanthin structures and the high cost of natural astaxanthin sources.
• Pharmacokinetics: Astaxanthin easily permeates the blood-brain barrier and blood-retinal barrier, making it effective in preventing inflammations in these organs. Recommended daily doses for health benefits range from 2 to 12 mg, depending on the source and form of astaxanthin.
• Market Data: The global astaxanthin market was estimated at USD 1.0 billion in 2019, with a projected compound annual growth rate of 16.2% from 2019 to 2027, reaching USD 3398.8 million by 2027. Chemical synthesis of astaxanthin dominates over 95% of the feed market due to cost-effectiveness, while natural astaxanthin is preferred in pharmaceutical, cosmetic, and food industries.

Technology Process of Astaxanthin

There total 31 articles about Astaxanthin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.8%

2,7-dimethyl-2,4,6-octanetriene-1,8-dialdehyde (5056-17-7,3049-35-2) + 3-methyl-5-(2,6,6-trimethyl-4-hydroxy-1-cyclohexene-3-carbonyl)-2,4-pentadiene-1-bromotriphenylphosphine (84592-32-5) → (3S,3'S)-astaxanthin (472-61-7)

Guidance literature:

With sodium methylate; In dichloromethane; at -20 ℃; for 5h; Reagent/catalyst; Solvent; Inert atmosphere;

Reference yield: 94.6%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + <5-((S)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid → (3S,3'S)-astaxanthin (472-61-7) + (3R,3'S)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione (71772-51-5)

Guidance literature:

With sodium methylate; In methanol; at 0 - 25 ℃; for 4h;

DOI:10.1002/hlca.19810640749

Reference yield: 83.0%

C12H20O4 (696647-73-1) + [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide → (3S,3'S)-astaxanthin (472-61-7)

Guidance literature:

C₁₂H₂₀O₄; [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide; With sodium methylate; In methanol; at 0 ℃; for 2h;

With acetic acid; In methanol; water; at 20 - 75 ℃; for 20h; Heating / reflux;

upstream raw materials:

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

3,4,3',4'-tetrahydroxy-β,β-carotene

C₁₂H₂₀O₄

3,3'-dihydroxy-β,β-carotene-4,4'-dione

Downstream raw materials:

3,4,3',4'-tetrahydroxy-β,β-carotene

astacene

astaxanthin dipalmitate

astaxanthin dioctadecanoate

Refernces

• 1、 -. "Synthetic method of astaxanthin". . . Retrieved 2021/10/05.
• 2、 -. "METHOD FOR PRODUCING OPTICALLY ACTIVE ASTAXANTHIN". . . Retrieved 2018/09/19.