Methyl 13-cis-4-Oxoretinoate

Base Information

• Chemical Name: Methyl 13-cis-4-Oxoretinoate
• CAS No.: 71748-57-7
• Molecular Formula: C21H28O3
• Molecular Weight: 328.452
• DSSTox Substance ID: DTXSID90440537
• Wikidata: Q82256876
• Mol file: 71748-57-7.mol

Synonyms:71748-57-7;Methyl 13-cis-4-Oxoretinoate;4-Keto 13-cis-Retinoic Acid Methyl Ester;13-cis-4-Oxo-retinoic acid Methyl Ester;(2Z,4E,6E,8E)-Methyl 3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate;methyl (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)nona-2,4,6,8-tetraenoate;METHYL (2Z,4E,6E,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-3-OXOCYCLOHEX-1-EN-1-YL)NONA-2,4,6,8-TETRAENOATE;SCHEMBL17769829;DTXSID90440537;BCP16855;PD056485;(2Z,4E,6E,8E)-Methyl3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

Chemical Property of Methyl 13-cis-4-Oxoretinoate

Chemical Property:

• Melting Point: 68-71°C
• PSA: 43.37000
• LogP: 4.87000
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 328.20384475
• Heavy Atom Count: 24
• Complexity: 653

Purity/Quality:

99%+, ^*data from raw suppliers

4-Keto13-cis-RetinoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 13-cis-4-Oxoretinoate

There total 11 articles about Methyl 13-cis-4-Oxoretinoate 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: 84.0%

4-Hydroxyretinoic acid methyl ester (38030-59-0) → 4-Oxo-retinoic acid methyl ester (71748-57-7,100897-09-4,38030-58-9,163955-59-7)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00348a018

Reference yield: 70.0%

methanol (67-56-1) + 4-keto-all-trans-retinal (33532-44-4) → 4-Oxo-retinoic acid methyl ester (71748-57-7,100897-09-4,38030-58-9,163955-59-7)

Guidance literature:

With sodium cyanide; manganese(IV) oxide; acetic acid; at 4 - 20 ℃;

DOI:10.1023/A:1021245616117

Reference yield: 68.0%

(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) → (2Z,4E,6E,8E)-methyl 3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate (71748-57-7,163955-59-7)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 12h;

DOI:10.1021/jm501792c

upstream raw materials:

methanol

all-trans-retinoic-acid

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

13-cis-retinoic acid

Downstream raw materials:

(2Z,4E,6E,8E)-methyl 9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoate

C₂₀H₂₈O₃

C₂₀H₂₈O₃

rac-(2E,4E,6E,8E)-3,7-dimethyl-9-<2,6-dimethyl-6-(hydroxymethyl)-3-oxo-1-cyclohexen-1-yl>-2,4,6,8-nonatetraenoic acid

Refernces

• 1、 -. "Preparation method of olefine acid impurity". Paragraph 0057-0058. . Retrieved 2021/01/11.
• 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.