(R,R)-Astaxanthin

Base Information

• Chemical Name: (R,R)-Astaxanthin
• CAS No.: 60760-95-4
• Molecular Formula: C₄₀H₅₂O₄
• Molecular Weight: 596.85
• UNII: 8L22ANN83S
• Metabolomics Workbench ID: 157535
• Nikkaji Number: J711.489C
• Wikidata: Q27270688

Synonyms:(R,R)-Astaxanthin;(3R,3'R)-Astaxanthin;Astaxanthin, (R,R)-;60760-95-4;trans-(3R,3'R)-Astaxanthin;8L22ANN83S;3R,3'R-astaxanthin;(3R,3'R)-All-trans-astaxanthin;UNII-8L22ANN83S;beta,beta-Carotene-4,4'-dione, 3,3'-dihydroxy-, (3R,3'R)-;(6R)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethylcyclohex-2-en-1-one;SCHEMBL17519193;MQZIGYBFDRPAKN-OXBRSLPGSA-N;ASTAXANTHIN, (3R,3'R)-;Q27270688;.BETA.,.BETA.-CAROTENE-4,4'-DIONE, 3,3'-DIHYDROXY-, (3R,3'R)-;(6R,6'R)-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)

Chemical Property of (R,R)-Astaxanthin

Chemical Property:

• 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:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

Technology Process of (R,R)-Astaxanthin

There total 9 articles about (R,R)-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: 82.5%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + <(4E)-5-(4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid → (3RS,3'RS)-Astaxanthin (472-61-7,7542-45-2,60760-95-4,64838-38-6,71772-51-5,74601-68-6,111139-31-2,111139-32-3,111139-33-4,113085-04-4,113085-05-5,119478-03-4,122871-99-2,130467-19-5,130548-13-9)

Guidance literature:

With ethyloxirane; water; 1.) reflux; 2.) ethanol, reflux, 18 h; (Z->E) isomerisation in heptane;

DOI:10.1002/hlca.19810640751

Reference yield: 81.2%

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + <5-((R)-4-Hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl)-3-methyl-2,4-pentadienyl>triphenylphosphoniumbromid → (3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione (60760-95-4)

Guidance literature:

DOI:10.1002/hlca.19810640752

Reference yield: 59.0%

(3R,3'R)-Astaxanthin-di-(-)-camphanat → (3R,3'R)-3,3′-dihydroxy-β,β′-caroten-4,4′-dione (60760-95-4)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; for 1.16667h; Ambient temperature;

DOI:10.1002/hlca.19800630635

upstream raw materials:

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

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

Downstream raw materials:

C₄₀H₅₄N₂O₄

astacene

apo-11-astaxanthinal

rac-3-Hydroxy-4-oxo-12'-apo-β-carotin-12'-al

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