9-CIS-RETINOIC ACID METHYL ESTER

Base Information

• Chemical Name: 9-CIS-RETINOIC ACID METHYL ESTER
• CAS No.: 58526-50-4
• Molecular Formula: C21H30O2
• Molecular Weight: 314.468
• Mol file: 58526-50-4.mol

Synonyms:9-CIS-RETINOIC ACID METHYL ESTER;9-cis-Methyl Retinoate

Chemical Property of 9-CIS-RETINOIC ACID METHYL ESTER

Chemical Property:

• PSA: 26.30000
• LogP: 5.69100
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Hexane (Slightly)

Purity/Quality:

≥99% ^*data from raw suppliers

9-cis-RetinoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 9-cis-Retinoic Acid Methyl Ester is a cis-Vitamin A derivative.

Technology Process of 9-CIS-RETINOIC ACID METHYL ESTER

There total 30 articles about 9-CIS-RETINOIC ACID METHYL ESTER 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%

methyl 7,14-dihydroretinoate (140476-17-1) → retinoic acid methyl ester (339-16-2,16760-45-5,25428-67-5,58526-50-4,68070-31-5,68070-32-6,68070-33-7,71423-65-9,71423-66-0,74464-49-6,84415-26-9,98462-65-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 50 ℃; for 1.5h;

Reference yield: 78.0%

5,9-Bis-benzenesulfonyl-3,7-dimethylene-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nonanoic acid methyl ester (85329-46-0) → retinoic acid methyl ester (339-16-2,16760-45-5,25428-67-5,58526-50-4,68070-31-5,68070-32-6,68070-33-7,71423-65-9,71423-66-0,74464-49-6,84415-26-9,98462-65-8)

Guidance literature:

With sodium methylate; In methanol; for 7h; Heating;

DOI:10.1016/S0040-4039(00)85696-8

Reference yield: 19.0%

methyl 7,8-dihydroretinoate (51077-56-6) → retinoic acid methyl ester (339-16-2,16760-45-5,25428-67-5,58526-50-4,68070-31-5,68070-32-6,68070-33-7,71423-65-9,71423-66-0,74464-49-6,84415-26-9,98462-65-8) + methyl (7E,9E,11E,13E)-9,13-dimethyl-7-(1,1,5-trimethyl-3,5-cyclohexadien-6-yl)-7,9,11,13-nonatetraen-15-oate (24041-43-8,25428-47-1,25428-48-2,25537-54-6,62697-31-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 80 ℃; for 1.5h;

upstream raw materials:

diazomethane

9-cis-retinoic acid

(Z)-3-methylpent-2-en-4-ynol

2,2,6-trimethylcyclohexan-1-one

Downstream raw materials:

9-cis-retinol

[7t.9c.11t.13t]retinal semicarbazone

9-cis vitamin A aldehyde

9-cis-retinoic acid

Refernces

• 1、 Tutorskaya, O. O.,Miropol'skaya, M. A.,Samokhvalov, G. I.. "SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS LII. SYNTHESIS OF RETINOIC AND DIHYDRORETINOIC ESTERS BY THE REFORMATSKII REACTION". . p. 1237 - 1240. Retrieved 2007/10/02.
• 2、 Mandai, Tadakatsu,Yanagi, Terumi,Araki, Kunio,Morisaki, Yoshihiro,Kawada, Mikio,Otera, Junzo. "NOVEL SYNTHESIS OF ACETYLENES AND POLYENES VIA DESULFONYLATION REACTION". . p. 3670 - 3672. Retrieved 2007/10/02.