7250-55-7

Basic information

• Product Name: Dimethyl 3-hydroxyglutarate
• Synonyms: 3-hydroxyglutaric acid dimethyl ester;DIMETHYL 3-HYDROXYGLUTARATE;Dimethyl 3-hydroxypentanedioate;Pentanedioic acid, 3-hydroxy-, dimethyl ester;NISTC7250557;Glutaric acid, 3-hydroxy-, dimethyl ester;Nsc30047;Dimethyl 3-hydroxygl
• CAS NO: 7250-55-7
• Molecular Formula: C₇H₁₂O₅
• Molecular Weight: 176.17
• Product Categories: C6 to C7;Carbonyl Compounds;Esters;Aliphatics;Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 7250-55-7.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 139-140 °C8 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.192 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00125mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform
• PKA: 12.60±0.20(Predicted)
• BRN: 1776666
• CAS DataBase Reference: Dimethyl 3-hydroxyglutarate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 3-hydroxyglutarate(7250-55-7)
• EPA Substance Registry System: Dimethyl 3-hydroxyglutarate(7250-55-7)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 7250-55-7(Hazardous Substances Data)

Usage

Description

Dimethyl 3-hydroxyglutarate is an organic compound that serves as a crucial intermediate in the synthesis of various chiral fragments and has been studied for its enantioselective hydrolysis and ammonolysis properties. It is an off-white to pale yellow oil and is derived from glutaric acid.

Uses

Used in Pharmaceutical Industry:
Dimethyl 3-hydroxyglutarate is used as a chiral building block for the synthesis of polyene macrolide pimaricin, which is a complex natural product with potential pharmaceutical applications. It is used in the synthesis of two chiral fragments representing C1-11 and C12-25 of pimaricin, contributing to the development of novel drugs and therapeutic agents.
Used in Chemical Synthesis:
Dimethyl 3-hydroxyglutarate is used as a glutaric acid derivative in the chemical synthesis of various compounds. Its enantioselective hydrolysis and ammonolysis have been studied using immobilized lipase B isolated from Candida antarctica, which can be applied to develop more efficient and selective synthetic methods for producing enantiomerically pure compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C7H12O5/c1-11-6(9)3-5(8)4-7(10)12-2/h5,8H,3-4H2,1-2H3

Upstream product

• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 542-05-2 acetonedicarboxylic acid 
• 77-92-9 citric acid 
• 67-56-1 methanol 
• 32328-03-3 diethyl 3-hydroxyglutarate 
• 66833-29-2 β-Aethylimino-methylglutarat 
• 106-95-6 allyl bromide 

Downstream Products

• 91424-39-4 3-[[(1,1-Dimethylethyl)dimethylsilyl]-oxy]pentanedioic acid,diethyl ester 
• 91424-40-7 3-(tert-butyldimethylsilyloxy)glutaric anhydride 
• 112904-65-1 dimethyl 3-(benzyloxy)pentanedioate 
• 92454-01-8 dimethyl 4-hydroxycyclohexane-1,1-dicarboxylate 

Relevant articles and documents

Synthesis of six-membered carbocyclic ring α,α-disubstituted amino acids and arginine-rich peptides to investigate the effect of ring size on the properties of the peptide

Cell-penetrating peptides (CPPs) have been attracting attention as tools for intracellular delivery of membrane-impermeant functional molecules. Among the variety of CPPs that have been developed, many are composed of both natural and unnatural amino acids. We previously synthesized α,α-disubstituted α-amino acids (dAAs) containing a five-membered carbocyclic ring in its side chain and revealed the utility of dAAs for the development of novel CPPs. In the present study, we designed a six-membered carbocyclic ring dAA with an amino group on the ring and introduced it into arginine (Arg)-rich peptides to further investigate the value of dAAs for developing CPPs. We also assessed the effects of the size of the dAA carbocyclic ring on cellular uptake of dAA-containing peptides. The stability of the peptide's secondary structure and its membrane permeability were both greater in dAA-containing peptides than in an Arg nonapeptide. However, the number of carbon atoms in the dAA side chain ring had little effect. Nevertheless, these results show the utility of cyclic dAAs in the design of novel CPPs containing unnatural amino acids.

Synthetic Access to Benzimidacarbocyanine Dyes to Tailor Their Aggregation Properties

Developing structure-aggregation relationships of cyanine dyes is crucial for controlling their optical properties for various uses. This study develops a synthetic route and the structure-dependent self-assembly of a family of benzimidacarbocyanine dyes for J- or H-aggregation properties. It was found that both the presence and placement of halogen atoms play a defining role in the resulting supramolecular interactions of these compounds.

Intramolecular functional group differentiation as a strategy for the synthesis of bridged bicyclic β-amino acids

Differentiation of identical electrophilic functional groups (carboxylates) by a strategically placed internal nucleophile (an amino group) in cyclic precursors was used as a key general approach to functionalized azabicyclic scaffolds. The utility of the method was demonstrated by the synthesis of three bicyclic β-amino acids (analogues of nipecotic acid), which were prepared in good yields and on a relatively large scale.