Bishomoretinoic acid

Base Information

• Chemical Name: Bishomoretinoic acid
• CAS No.: 857473-23-5
• Molecular Formula: C₂₂H₃₀O₂
• Molecular Weight: 326.479
• UNII: 9ZG6H07U1D
• Nikkaji Number: J698.208E
• ChEMBL ID: CHEMBL225948
• Mol file: 857473-23-5.mol

Synonyms:Bishomoretinoic acid;9ZG6H07U1D;UNII-9ZG6H07U1D;RO-11-0976;14'-Apo-beta,psi-carotenoic acid;2,6,6-Trimethyl-1-(10'-carboxy-3',7'-dimethyldeca-1',3',5',7',9'-pentaenyl)cyclohex-1-ene;2,4,6,8,10-Undecapentaenoic acid, 5,9-dimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (2E,4E,6E,8E,10E)-;6722-00-5;CHEMBL225948;SCHEMBL10623334;14'-APO-.BETA.,.PSI.-CAROTENOIC ACID;(2E,4E,6E,8E,10E)-11-(2,6,6-Trimethyl-1-cyclohexenyl)5,9-dimethylundeca-2,4,6,8,10-pentaenoic acid;857473-23-5

Chemical Property of Bishomoretinoic acid

Chemical Property:

• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 326.224580195
• Heavy Atom Count: 24
• Complexity: 635

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=CC(=O)O)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C(=O)O)/C)/C

Technology Process of Bishomoretinoic acid

There total 2 articles about Bishomoretinoic acid 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:

C24H34O2 → C22H30O2 (857473-23-5)

Guidance literature:

With potassium hydroxide; In methanol; for 2h; Reflux;

DOI:10.1016/j.tet.2012.10.041

Reference yield:

3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal (1436-55-1,52918-36-2,311338-94-0) → C22H30O2 (857473-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate / methanol; tetrahydrofuran / 48 h

2: potassium hydroxide / methanol / 2 h / Reflux

With sodium methylate; potassium hydroxide; In tetrahydrofuran; methanol; 1: |Wittig Olefination;

DOI:10.1016/j.tet.2012.10.041

Reference yield: 65.0%

[1,2']bipyridinyl-2-one (3480-65-7) + C22H30O2 (857473-23-5) → C31H36N2O

Guidance literature:

With di(rhodium)tetracarbonyl dichloride; di-tert-butyl dicarbonate; In 1,4-dioxane; at 130 ℃; for 6h;

DOI:10.1039/c9sc03672e

upstream raw materials:

3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal