Methyl retinoate

Base Information

• Chemical Name: Methyl retinoate
• CAS No.: 339-16-2
• Molecular Formula: C21H30 O2
• Molecular Weight: 314.468
• UNII: WS76I7L4S7
• DSSTox Substance ID: DTXSID401316812
• Nikkaji Number: J432.023I,J669.828J,J109.128J
• Wikidata: Q27292800
• ChEMBL ID: CHEMBL488005
• Mol file: 339-16-2.mol

Synonyms:cis-methyl retinoate;methyl retinoate;methyl retinoate, (13-cis)-isomer;trans-methyl retinoate

Chemical Property of Methyl retinoate

Chemical Property:

• Vapor Pressure: 1.82E-07mmHg at 25°C
• Melting Point: 66-68°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:

99% ^*data from raw suppliers

all-trans-RetinoicAcidMethylEster ^*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: all-trans-Retinoic Acid Methyl Ester (cas# 339-16-2) is a compound useful in organic synthesis.

Technology Process of Methyl retinoate

There total 56 articles about Methyl retinoate 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: 100.0%

all-trans-retinoic-acid (302-79-4) + diazomethyl-trimethyl-silane (18107-18-1) → all-trans-methyl retinoate (339-16-2)

Guidance literature:

In methanol; hexane; benzene; at 20 ℃; for 0.75h;

DOI:10.1021/jm0401457

Reference yield: 98.0%

(1E,3E)-2-methyl-1-[(trifluoromethanesulfonyl)oxy]-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-diene (256518-38-4) + methyl (2E,4E)-3-methyl-5-(tri-n-butylstannyl)penta-2,4-dienoate (212967-48-1) → all-trans-methyl retinoate (339-16-2)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenyl-arsane; In various solvent(s); at 60 ℃; for 0.5h;

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

Reference yield: 98.0%

methanol (67-56-1) + all-trans-Retinal (116-31-4) → all-trans-methyl retinoate (339-16-2)

Guidance literature:

With potassium cyanide; manganese(IV) oxide; acetic acid; In methanol; for 12h; Ambient temperature;

upstream raw materials:

diazomethane

all-trans-retinoic-acid

methyl iodide

methanol

Downstream raw materials:

RETINOL

Methyl ester of 5,6-epoxy-(E)-retinoic acid

4-Oxo-retinoic acid methyl ester

methyl retinoate radical anion

Refernces

• 1、 -. "Preparation method of olefine acid impurity". Paragraph 0054-0056. . Retrieved 2021/01/11.
• 2、 Patel, Jyoti B.,Huynh, Carlic K.,Handratta, Venkatesh D.,Gediya, Lalji K.,Brodie, Angela M. H.,Goloubeva, Olga G.,Clement, Omoshile O.,Nanne, Ivo P.,Soprano, Dianne Robert,Njar, Vincent C. O.. "Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and prostate cancer cells in vitro and a human breast tumor xenograft in nude mice". . p. 6716 - 6729. Retrieved 2007/10/03.