34212-59-4

Basic information

• Product Name: (1R)-(-)-DIMENTHYL SUCCINATE
• Synonyms: (-)-Dimenthyl succinate;Bis(2-isopropyl-5-methylcyclohexyl) succinate;Succinic acid, di-(-)-menthyl ester;(1R)-(-)-DIMENTHYL SUCCINATE;(-)-DI[(1R)-MENTHYL] SUCCINATE;bis((1R,2S,5R)-2-isopropyl-5-Methylcyclohexyl) succinate;(1R)-(-)-DIMENTHYL SUCCINATE-3;Bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) succinate
• CAS NO: 34212-59-4
• Molecular Formula: C₂₄H₄₂O₄
• Molecular Weight: 394.59
• Mol File: 34212-59-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 62-64 °C(lit.)
• Boiling Point: 200-205 °C2 mm Hg(lit.)
• Flash Point: 215.5°C
• Appearance: /
• Density: 0.9873 (rough estimate)
• Vapor Pressure: 1.35E-08mmHg at 25°C
• Refractive Index: 1.4460 (estimate)
• BRN: 3220135
• CAS DataBase Reference: (1R)-(-)-DIMENTHYL SUCCINATE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(-)-DIMENTHYL SUCCINATE(34212-59-4)
• EPA Substance Registry System: (1R)-(-)-DIMENTHYL SUCCINATE(34212-59-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 34212-59-4(Hazardous Substances Data)

Usage

Description

(1R)-(-)-DiMenthyl Succinate, also known as Dimethyl Succinate, is an organic compound with the chemical formula C6H10O4. It is a chiral molecule, which means it has a non-superimposable mirror image. The (1R)-(-)-enantiomer is the one being referred to here. It is a colorless liquid with a fruity odor and is used as a building block in the synthesis of various compounds.

Uses

Used in Pharmaceutical Industry:
(1R)-(-)-DiMenthyl Succinate is used as a key intermediate in the synthesis of antifungal agents and synthetic analogues for the pharmaceutical industry. Its chiral nature allows for the creation of specific compounds with targeted effects against fungal infections.
Used in Chemical Synthesis:
In the chemical synthesis industry, (1R)-(-)-DiMenthyl Succinate is used as a versatile building block for the creation of various synthetic analogues. Its unique structure and reactivity make it a valuable component in the development of new molecules with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C24H42O4/c1-15(2)19-9-8-18(6)21(14-19)27-23(25)11-12-24(26)28-22-13-17(5)7-10-20(22)16(3)4/h15-22H,7-14H2,1-6H3

Upstream product

• 110-15-6 succinic acid 
• 2216-51-5 (-)-menthol 
• 108-30-5 succinic acid anhydride 

Downstream Products

• 96055-59-3 (-)-dimenthyl (1S,2S)-cyclopentane-1,2-dicarboxylate 
• 704890-11-9 (-)-(1S,2S)-cyclobutane-1,2-dicarboxylic acid di(-)-menthyl ester 
• 1403755-70-3 bis(2-isopropyl-5-methylcyclohexyl)-2,3-dibenzylsuccinate 
• 1403755-71-4 C₃₀H₅₂O₅ 
• 178685-01-3 (1S,2S)-2-chlorocarbonyl-cyclopropanecarboxylic acid (1R,2S,5R)-5-isopropyl-2-methyl-cyclohexyl ester 
• 175221-03-1 (1S,2S)-cyclopropane-1,2-dicarboxylic acid mono-(1R,2S,5R)-(5-isopropyl-2-methyl-cyclohexyl) ester 
• 130799-04-1 dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate 
• 96149-00-7 (1S,2S)-cyclopropane-1,2-dicarboxylic acid bis-(1R,2S,5R)-(5-isopropyl-2-methyl-cyclohexyl) ester 
• 96055-60-6 (3S,4S)-3,4-bis-(-)-menthyloxycarbonyl-1-methylidenecyclopentane 

Relevant articles and documents

Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids

Hydrogenation of carboxylic acids (CAs) to alcohols represents one of the most ideal reduction methods for utilizing abundant CAs as alternative carbon and energy sources. However, systematic studies on the effects of metal-to-ligand relationships on the catalytic activity of metal complex catalysts are scarce. We previously demonstrated a rational methodology for CA hydrogenation, in which CA-derived cationic metal carboxylate [(PP)M(OCOR)]+ (M = Ru and Re; P = one P coordination) served as the catalyst prototype for CA self-induced CA hydrogenation. Herein, we report systematic trial- and-error studies on how we could achieve higher catalytic activity by modifying the structure of bidentate diphosphine (PP) ligands of molecular Ru catalysts. Carbon chains connecting two P atoms as well as Ar groups substituted on the P atoms of PP ligands were intensively varied, and the induction of active Ru catalysts from precatalyst Ru(acac)3 was surveyed extensively. As a result, the activity and durability of the (PP)Ru catalyst substantially increased compared to those of other molecular Ru catalyst systems, including our original Ru catalysts. The results validate our approach for improving the catalyst performance, which would benefit further advancement of CA self-induced CA hydrogenation.

Identification and Preclinical Development of a 2,5,6-Trisubstituted Fluorinated Pyridine Derivative as a Radioligand for the Positron Emission Tomography Imaging of Cannabinoid Type 2 Receptors

Despite the broad implications of the cannabinoid type 2 receptor (CB2) in neuroinflammatory processes, a suitable CB2-targeted probe is currently lacking in clinical routine. In this work, we synthesized 15 fluorinated pyridine derivatives and tested their binding affinities toward CB2 and CB1. With a sub-nanomolar affinity (Ki for CB2) of 0.8 nM and a remarkable selectivity factor of >12,000 over CB1, RoSMA-18-d6 exhibited outstanding in vitro performance characteristics and was radiofluorinated with an average radiochemical yield of 10.6 ± 3.8% (n = 16) and molar activities ranging from 52 to 65 GBq/μmol (radiochemical purity > 99%). [18F]RoSMA-18-d6 showed exceptional CB2 attributes as demonstrated by in vitro autoradiography, ex vivo biodistribution, and positron emission tomography (PET). Further, [18F]RoSMA-18-d6 was used to detect CB2 upregulation on postmortem human ALS spinal cord tissues. Overall, these results suggest that [18F]RoSMA-18-d6 is a promising CB2 PET radioligand for clinical translation.

Process for making monomenthyl esters

A process for making monomenthyl esters of dicarboxylic acids is disclosed. Menthol reacts with a saturated, cyclic anhydride in the presence of a base catalyst under conditions effective to produce a mixture of mono- and bis-menthyl esters in which the molar ratio of mono- to bis-menthyl esters is enhanced compared with the ratio of esters produced in a similar uncatalyzed process.