13-cis Retinoic Acid Methyl Ester

Base Information

• Chemical Name: 13-cis Retinoic Acid Methyl Ester
• CAS No.: 16760-45-5
• Molecular Formula: C21H30 O2
• Molecular Weight: 314.468
• Mol file: 16760-45-5.mol

Synonyms:13-cis Retinoic Acid Methyl Ester;Methyl 13-cis-Retinoate;16760-45-5;methyl (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate;13-cis-Methyl retinoate;SCHEMBL17769828

Chemical Property of 13-cis Retinoic Acid Methyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 426.1°Cat760mmHg
• Flash Point: 229.8°C
• PSA: 26.30000
• Density: 0.975g/cm³
• LogP: 5.69100
• Storage Temp.: Amber Vial, -86°C Freezer
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 581

Purity/Quality:

97% ^*data from raw suppliers

13-cisRetinoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)OC)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C\C(=O)OC)/C)/C
• Uses: Retinoic acid derivative.

Technology Process of 13-cis Retinoic Acid Methyl Ester

There total 30 articles about 13-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: 83.0%

13-cis-retinoic acid (4759-48-2) + diazomethyl-trimethyl-silane (18107-18-1) → (2Z,4E,6E,8E)-methyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate (16760-45-5)

Guidance literature:

In methanol; hexane; benzene;

DOI:10.1021/jm501792c

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

upstream raw materials:

diazomethane

13-cis-retinoic acid

methanol

8-<2-(methylthio)-1,3-dithian-2-yl>-3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)octa-1E,3E,5E,7E-tetraene

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF 4-OXOISOTRETINOIN". Page/Page column 12. . Retrieved 2022/02/28.
• 2、 Mbatia, Hannah W.,Ramalingam, Senthilmurugan,Ramamurthy, Vidya P.,Martin, Marlena S.,Kwegyir-Afful, Andrew K.,Njar, Vincent C. O.. "Novel C-4 heteroaryl 13- cis -retinamide Mnk/AR degrading agents inhibit cell proliferation and migration and induce apoptosis in human breast and prostate cancer cells and suppress growth of MDA-MB-231 human breast and CWR22Rv1 human prostate tumor xenografts in mice". . p. 1900 - 1914. Retrieved 2015/04/27.