11-cis,13-cis-12-carboxyretinoic acid

Base Information

• Chemical Name: 11-cis,13-cis-12-carboxyretinoic acid
• CAS No.: 81176-73-0
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.451
• Mol file: 81176-73-0.mol

Synonyms:11-cis,13-cis-12-carboxyretinoic acid

Chemical Property of 11-cis,13-cis-12-carboxyretinoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-cis,13-cis-12-carboxyretinoic acid

There total 12 articles about 11-cis,13-cis-12-carboxyretinoic 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: 85.0%

diethyl 3-methylpent-2-enedioate (924-59-4) + (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal (3917-41-7) → 11-cis,13-cis-12-carboxyretinoic acid (81176-73-0)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 64h;

Reference yield:

13-cis-12-carboxyretinoic anhydride (83860-26-8) → 11-cis,13-cis-12-carboxyretinoic acid (81176-73-0) + 13-cis-12-carboxyretinoic acid (81176-74-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 0 ℃; Yields of byproduct given;

DOI:10.1021/jo00349a001

Reference yield:

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol (3917-39-3) → 11-cis,13-cis-12-carboxyretinoic acid (81176-73-0)

Guidance literature:

Multi-step reaction with 2 steps

1: petroleum ether; MnO₂ / <30

2: KOH

With manganese(IV) oxide; potassium hydroxide; Petroleum ether;

DOI:10.1021/ja01620a043

upstream raw materials:

dimethyl 3-methyl-2-cis-pentenedioate

(2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal

diethyl 3-methylpent-2-enedioate

9-hydroxy-β-ionylideneacetaldehyde dimethyl acetal

Downstream raw materials:

9-cis-retinoic acid

11-cis,13-cis-12-carboxyretinoic anhydride

13-cis-retinoic acid

2-((1E,3E,5E)-3,7-dimethylocta-1,3,5,7-tetraen-1-yl)-1,3,3-trimethylcyclohex-1-ene

Refernces

• 1、 Lewin, Anita H.,Whaley, M. Glenn,Parker, Steven R.,Carroll, F. Ivy. "12-Carboxyretinoic Acids. Synthesis and Structure". . p. 1799 - 1807. Retrieved 2007/10/02.