(7cis,9cis,13cis)-O~15~-ethylretinoic acid

Base Information

• Chemical Name: (7cis,9cis,13cis)-O~15~-ethylretinoic acid
• CAS No.: 24519-09-3
• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 328.495
• Mol file: 24519-09-3.mol

Synonyms:

Chemical Property of (7cis,9cis,13cis)-O~15~-ethylretinoic acid

Chemical Property:

• Vapor Pressure: 6.32E-08mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7cis,9cis,13cis)-O~15~-ethylretinoic acid

There total 159 articles about (7cis,9cis,13cis)-O~15~-ethylretinoic 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: 98.0%

→ ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate (86708-67-0,24519-09-3)

Guidance literature:

With copper dichloride; In ethanol; for 0.5h;

DOI:10.1021/jo961041+

Reference yield: 97.0%

ethyl (E)-3-iodomethacrylate (34450-61-8) + (1E,3E,5E)-1-tributylstannyl-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5-hexatriene → ethyl (all-E)-retinoate (3899-20-5,24519-09-3)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenyl-arsane; In various solvent(s); at 25 ℃; for 4h;

DOI:10.1016/S0040-4020(99)00962-X

Reference yield: 95.0%

ethanol (64-17-5) + all-trans-retinoic-acid (302-79-4) → ethyl (all-E)-retinoate (3899-20-5,24519-09-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In diethyl ether; 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;

upstream raw materials:

ethyl (E)-3-formyl-2-butenoate

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol

(+/-)-7-hydroxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-⁽⁶⁾-yl)-nonatrien-(1.3t.5t)-oic acid-⁽⁹⁾-ethyl ester

all-trans-retinoic-acid

Downstream raw materials:

ethyl (all-E)-retinoate

9,11,13-tri-cis-ethyl retinoate

9-cis-13,14-dihydroretinoic acid ethyl ester

ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

Refernces

• 1、 -. "METHOD FOR SYNTHESIS OF 9-CIS-BETA-CAROTENE AND FORMULATIONS THEREOF". Paragraph 0056-0057. . Retrieved 2017/12/29.
• 2、 Maj, Jadwiga,Morzycki, Jacek W.,Rárová, Lucie,Wasilewski, Grzegorz,Wojtkielewicz, Agnieszka. "A cross-metathesis approach to the synthesis of new etretinate type retinoids, ethyl retinoate and its 9Z-isomer". . p. 5430 - 5433. Retrieved 2012/11/07.