7,8-Didehydroastaxanthin

Base Information

• Chemical Name: 7,8-Didehydroastaxanthin
• CAS No.: 19866-02-5
• Molecular Formula: C₄₀H₅₀O₄
• Molecular Weight: 594.835
• UNII: MBJ4WSK12V
• DSSTox Substance ID: DTXSID201313436
• Nikkaji Number: J15.741D
• Wikidata: Q27896450
• Metabolomics Workbench ID: 28819
• Mol file: 19866-02-5.mol

Synonyms:7,8-didehydroastaxanthin

Chemical Property of 7,8-Didehydroastaxanthin

Chemical Property:

• PSA: 74.60000
• LogP: 8.35260
• XLogP3: 10
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 594.37091007
• Heavy Atom Count: 44
• Complexity: 1520

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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)/C#CC2=C(C(=O)[C@H](CC2(C)C)O)C)/C)/C

Technology Process of 7,8-Didehydroastaxanthin

There total 7 articles about 7,8-Didehydroastaxanthin 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: 32.0%

Phenoxy-acetic acid (S)-3,5,5-trimethyl-2-oxo-4-((3E,5E,7E,9E,11E)-3,7,12-trimethyl-13-oxo-trideca-3,5,7,9,11-pentaen-1-ynyl)-cyclohex-3-enyl ester + {(2E,4E)-3-Methyl-5-[(S)-2,6,6-trimethyl-3-oxo-4-(2-phenoxy-acetoxy)-cyclohex-1-enyl]-penta-2,4-dienyl}-triphenyl-phosphonium; bromide → all-trans-(3S,3'S)-7,8-Didehydroastaxanthin (19866-02-5)

Guidance literature:

With sodium ethanolate; In ethanol; dichloromethane; 1.) 0 deg C, 1 h 2.) rt, 22 h;

DOI:10.1002/hlca.19800630618

Reference yield:

all-trans-(3S)-3-Hydroxy-4-oxo-7,8-didehydro-12'-apo-β-carotin-12'-al (72523-69-4,72580-11-1) → all-trans-(3S,3'S)-7,8-Didehydroastaxanthin (19866-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Pyridin / CH₂Cl₂ / 0.5 h / 0 °C

2: 32 percent / 1M Natriumaethylat / CH₂Cl₂; ethanol / 1.) 0 deg C, 1 h 2.) rt, 22 h

With pyridine; sodium ethanolate; In ethanol; dichloromethane;

DOI:10.1002/hlca.19800630618

Reference yield:

(all-E)-8-hydroxy-2,7-dimethylocta-2,4,6-trienal (76686-46-9) → all-trans-(3S,3'S)-7,8-Didehydroastaxanthin (19866-02-5)

Guidance literature:

Multi-step reaction with 5 steps

1: Salzsaeure / CH₂Cl₂ / 2.67 h / 0 - 5 °C

2: ethyl acetate / 16 h / Heating

3: 1.) Orthoameisensaeure-trimethylester, p-Toluolsolfonsaeure 2.) Natriumaethylat / 1.) methanol, 30 deg C, 16 h 2.) ethanol, methanol, -20 deg, 30 min then rt, 3.5 h

4: Pyridin / CH₂Cl₂ / 0.5 h / 0 °C

5: 32 percent / 1M Natriumaethylat / CH₂Cl₂; ethanol / 1.) 0 deg C, 1 h 2.) rt, 22 h

With pyridine; hydrogenchloride; Orthoameisensaeure-trimethylester; sodium ethanolate; toluene-4-sulfonic acid; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1002/hlca.19800630618

upstream raw materials:

all-trans-(3S)-3-Hydroxy-4-oxo-7,8-didehydro-12'-apo-β-carotin-12'-al

(all-E)-8-hydroxy-2,7-dimethylocta-2,4,6-trienal

all-trans-(7-Formyl-2-methyl-2,4,6-octatrienyl)triphenylphosphoniumchlorid

(all-E)-8-chloro-2,7-dimethyl-2,4,6-octatrienal

Downstream raw materials:

all-trans-(3S,3'S)-7,8-Didehydroastaxanthin-diacetat

Refernces