339-16-2

Basic information

• Product Name: Retinoic acid, methyl ester
• Synonyms: Retinoic acid, methyl ester;methyl retinoate;all-trans-Vitamin A acid methyl ester;Methyl retinate;Ro-4-3781;All-trans-methylretinoate;beta-Retinoic acid methyl ester;Brn 2059353
• CAS NO: 339-16-2
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.46
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Retinoids
• Mol File: 339-16-2.mol

Chemical Properties

• Melting Point: 66-68°C
• Boiling Point: 426.1°Cat760mmHg
• Flash Point: 229.8°C
• Appearance: /
• Density: 0.975g/cm³
• Vapor Pressure: 1.82E-07mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Amber Vial, -86°C Freezer
• CAS DataBase Reference: Retinoic acid, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Retinoic acid, methyl ester(339-16-2)
• EPA Substance Registry System: Retinoic acid, methyl ester(339-16-2)

Safety Data

• Hazardous Substances Data: 339-16-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Retinoic acid, methyl ester is used as a synthetic intermediate for the production of various compounds in the field of organic synthesis. Its chemical structure allows it to be a versatile building block in the creation of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
Retinoic acid, methyl ester is used as an active pharmaceutical ingredient (API) for the development of drugs that target various health conditions. Its role in the synthesis of these drugs is crucial, as it can be modified and combined with other molecules to create effective treatments.
Used in Cosmetics Industry:
In the cosmetics industry, Retinoic acid, methyl ester is used as a key ingredient in anti-aging and skin care products. Its ability to promote cell turnover and improve skin texture makes it a valuable component in formulations designed to reduce the appearance of fine lines, wrinkles, and other signs of aging.
Used in Research and Development:
Retinoic acid, methyl ester is also utilized in research and development settings, where it serves as a valuable tool for studying the effects of retinoids on cellular processes and understanding their potential applications in medicine and other fields.

InChI:InChI=1/C21H30O2/c1-16(9-7-10-17(2)15-20(22)23-6)12-13-19-18(3)11-8-14-21(19,4)5/h7,9-10,12-13,15H,8,11,14H2,1-6H3/b10-7+,13-12+,16-9+,17-15+

Upstream product

• 186581-53-3 diazomethane 
• 302-79-4 all-trans-retinoic-acid 
• 74-88-4 methyl iodide 
• 43059-51-4 (2E,6E,8E)-5-Acetoxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienoic acid methyl ester 
• 41551-56-8 5-Benzolsulfonyl-3,7-dimethyl-9-(2',6',6'-trimethylcyclohex-1-enyl)-nona-2,6,8-triensaeuremethylester 
• 22030-20-2 (2E,4E)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dien-1-ol 
• 67-56-1 methanol 
• 116-31-4 all-trans-Retinal 
• 83802-77-1 retinoyl fluoride 
• 146558-55-6 8-<2-(methylthio)-1,3-dithian-2-yl>-3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)octa-1E,3E,5E,7E-tetraene 
• 85329-46-0 5,9-Bis-benzenesulfonyl-3,7-dimethylene-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nonanoic acid methyl ester 
• 138846-06-7 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene 
• 212967-48-1 methyl (2E,4E)-3-methyl-5-(tri-n-butylstannyl)penta-2,4-dienoate 
• 59057-30-6 (1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol 

Downstream Products

• 68-26-8 RETINOL 
• 7432-30-6 Methyl ester of 5,6-epoxy-(E)-retinoic acid 
• 71748-57-7 4-Oxo-retinoic acid methyl ester 
• 339-16-2 methyl retinoate radical anion 
• 138093-43-3 methyl 14-methyl-20,14-retro-retinoate 
• 163808-81-9 methyl 4-methoxyretinoate 
• 163955-59-7 (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-oxo-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid methyl ester 
• 4159-20-0 3,4-didehydroretinoic acid 
• 38030-59-0 4-Hydroxyretinoic acid methyl ester 
• 303731-03-5 (±)-4-(4H-1,2,4-triazol-4-yl) methyl retinoate 
• 303731-00-2 (±)-4-(1H-imidazol-1-yl)-methyl retinoate 
• 303731-02-4 (±)-4-(1H-1,2,4-triazol-1-yl) methyl retinoate 
• 303731-01-3 4-(1H-imidazole-1-yl)retinoic acid 

Relevant articles and documents

Visual Pigments. 11. Spectroscopy and Photophysics of Retinoic Acids and all-trans-Methyl Retinoate

The photophysics of hydrogen-bonded complexes of retinoic acid and its 9-cis and 13-cis isomers and the photophysics of the dimers of these isomers of retinoic acid were studied.The ivestigation indicated that complexes of retinoic acid and molecules that

Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations

Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.

Preparation method of olefine acid impurity

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of an olefine acid impurity. The impurity is (13E) -3, 7-dimethyl -9 -[(3RS) -3-methoxy -2, 6, 6-trimethyl cyclohexenyl] -2, 4, 6, 8-azela

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

Novel retinoic acid metabolism blocking agents (RAMBAs) have been synthesized and characterized. The synthetic features include introduction of nucleophilic ligands at C-4 of all-trans-retinoic acid (ATRA) and 13-cis-retinoic acid, and modification of ter

Correlation of fluorescence quenching in carotenoporphyrin dyads with the energy of intramolecular charge transfer states. Effect of the number of conjugated double bonds of the carotenoid moiety

The electrochemistry of a series of non-symmetric synthetic carotenoids, with different conjugated double bounds chain lengths (5 to 11) is reported. The values of the first oxidation potentials of the carotenoids were evaluated by digital simulation of t

Potent inhibition of retinoic acid metabolism enzyme(s) by novel azolyl retinoids

Novel (±)-4-azolyl retinoic acid analogues 4, 5, 7 and 8 have been designed and synthesized and have been shown to be powerful inhibitors of hamster microsomal all-trans-retinoic acid 4-hydroxylase enzyme(s). (±)-4-(1H-Imidazol-1-yl)retinoic acid (4) is t

A comprehensive survey of Stille-type C(sp2)-C(sp2) single bond forming processes in the synthesis of retinoic acid and analogs

The synthesis of the retinoid skeleton has been exhaustively explored using the Stille coupling for the formation of the side- chain single bonds. On employing the experimental catalytic conditions developed by Farina [Pd2(dba)3, AsPh3, NMP] we have modified the electronic and steric requirement of the coupling partners, alkenyl stannanes and electrophiles (alkenyl iodides and triflates). The comprehensive survey afforded appropriately matched components for every bond formation considered. Moreover, from the comparison of the reactivities of different coupling partners with different degrees of steric hindrance, the sensitivity of the Stille coupling to steric effects was confirmed. Besides providing a variety of building blocks for retinoid synthesis, the study highlights some trends that might be useful for the application of the Stille reaction to the synthesis of unsubstituted conjugated polyenes.

Preparation of 9-(Z)-retinoic acid

A process for preparing 9-(Z)-retinoic acid from mother liquors from the industrial preparation of C15 -triarylphosphonium salts of the general formula I STR1 where R1 to R3 are each aryl and X? is halogen or (HSO4)?, in an organic solvent, which comprises A. increasing the proportion of 9-(Z)-C15 -triarylphosphonium salt in the C15 -triarylphosphonium salts isolated from the mother liquor by treatment with isopropanol at elevated temperature, cooling and separating off the all-(E)-C15 -triarylphosphonium salt which has crystallized out, B. subjecting the resulting C15 -triarylphosphonium salt to a Wittig reaction with an alkyl β-formylcrotonate of the general formula STR2 and C. hydrolyzing the resulting oily retinoic ester mixture in a C3 -C9 -alkanol, preferably in a propanol or butanol, precipitating the resulting 9-(Z)-retinoic acid where appropriate by adding methanol as crystals, with all-(E)-retinoic acid and other retinoic acid isomers remaining in the alkanolic solution.

Low-valent titanium reductive elimination: a direct and highly stereoselective synthesis of vitamin A aldehyde and all-trans retinoic acid orthothioester

It is shown that low-valent titanium reductive elimination can be carried out in the presence of a thioacetal or an orthothioester group.The application to the synthesis of vitamin A aldehyde and all-trans retinoic acid orthothioester is described.Keywords - Ti(0) reductive elimination / vitamin A aldehyde / all-trans retinoic acid

SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS LII. SYNTHESIS OF RETINOIC AND DIHYDRORETINOIC ESTERS BY THE REFORMATSKII REACTION

The esters of 7,8- and 7,14-dihydroretinoic acids were obtained by the reaction of 6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5-octadien-2-one with bromoacetic ester in the Reformatskii reaction followed by dehydration.The 7,8- and 7,14-dihydroretinoic