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

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

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

Downstream Products

• 638-18-6 diethyl 3-hydroxypentanedioate 
• 66833-33-8 β-Hydroxyglutarsaeure-bis-homoveratrylamid 
• 112904-65-1 dimethyl 3-(benzyloxy)pentanedioate 
• 87118-53-4 (R)-3-hydroxypentanedioic acid monomethyl ester 
• 87118-64-7 Monomethyl (3S)-(-)-3-hydroxypentanedioate 
• 137847-71-3 dimethyl 3-(phenylacetyloxy)glutarate 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 927403-88-1 dimethyl 3-(dimethylphenylsilyloxy)glutarate 
• 927403-97-2 (S)-[3-(dimethylphenylsilyloxy)-5-hydroxypentan-1-yl] acetate 
• 927404-08-8 (S)-[5-azido-3-(dimethylphenylsilyloxy)pentan-1-yl] acetate 
• 288591-47-9 3-O-(6-O-tosyl-β-D-glucopyranosyl)dimethyl glutarate 
• 87118-55-6 (R)-((3-tert-butyldiphenylsillyl)oxy)pentanedioic acid monomethyl ester 
• 106064-61-3 (R)-3-[(tert-butyldiphenylsilyl)oxy]pentanoic acid lactone 
• 106064-60-2 (R)-3-[(tert-butyldiphenylsilyl)oxy]pentanoic acid methyl ester 

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.

Efficient synthesis of 1,3,5-oxygenated synthons from dimethyl 3-oxoglutarate: First use of borane-dimethyl sulfide complex as a regioselective reducing agent of 3-oxygenated glutarate derivatives

The selective reduction of dimethyl 3-oxoglutarate was accomplished in different levels. A high yielding sodium borohydride reduction of the keto group is fully described leading to dimethyl 3-hydroxyglutarate. When borane-dimethyl sulfide (BMS) complex was used, a diol or a triol compound can be obtained by selective or total reduction of 3-hydroxy-or 3-oxoglutarate, respectively, allowing an efficient and practical route to 1,3,5-oxygenated compounds.

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.

Method for preparing silicon compounds

The invention provides a method for preparing silicon compounds, and belongs to the field of chemical synthesis. The method for preparing the silicon compounds comprises the following processes that citric acid is used as a raw material for performing oxidative decarboxylation to obtain a compound 1,3-acetone dicarboxylic acid; esterification reaction is carried out to obtain a compound 1,3-acetone dicarboxylic acid dimethyl ester; catalytic hydrogenation reduction is carried out to obtain a compound 3-hydroxyglutaric acid dimethyl ester; etherification reaction is carried out to obtain a compound3-tertiary butyl dimethyl siloxy dimethyl glutarate; saponification, dehydration and purification are carried out to obtain 3-tert-butyl-dimethylsiloxyglutaric anhydride; and a catalyst for catalytic hydrogenation is Cu/ZnO/Al2O3 prepared by a precipitation reduction method. According to the method for preparing the silicon compounds, the catalyst for catalytic hydrogenation is optimized, so that in the hydrogenation reduction reaction, the hydrogenation activity of a Cu catalyst is significantly improved, the selectivity is increased, and the generation of by-products is reduced; and theproduct yield and purity are significantly improved by recrystallization with a mixed solvent.

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.

Synthesis and anti-tubercular activity of 2-nitroimidazooxazines with modification at the C-7 position as PA-824 analogs

Tuberculosis (TB) is a major global health problem, and new drug targets and scaffolds need to be identified to combat the emergence of drug resistant TB. The nitroimidazooxazine PA-824 represents a new class of bio-reductive drug to treat TB. In this study we report a 2-nitroimidazooxazine derivative with modification at the C-7 position that exhibited better activity than PA-824 against Mycobacterium tuberculosis (Mtb) H37Rv strain in vitro. From 7a as a key intermediate, we functionalized with benzyl ether (8), phenyl ether (9), benzyl carbonate (10) and benzyl carbamate (11). Among the 23 compounds produced, 8a-R (MIC = 0.078 μM) with trifluoromethoxy benzyl group was 5-fold more potent than PA-824 (MIC = 0.390 μM) in the in vitro assays against the wild-type Mtb, and the phenyl ether compound 9g-R (MIC = 0.050 μM) exhibited the most potent antimycobacterial activity.

Amidine dications as superelectrophiles

2-Dimethylalkylammonium pyridinium and 2-dimethylalkylammonium pyrimidinium ditriflate salts are very powerful methylating agents toward phosphorus (triphenylphosphine) and nitrogen (triethylamine) nucleophiles. In competition experiments with triethylamine as nucleophile, these N-methyl disalts are more reactive methylating agents than dimethyl sulfate. Reaction of the pyridinium dications with water as an oxygen nucleophile leads to attack at the 2-position of the heteroaromatic ring and displacement of an ammonium group; 2-hydroxypyridinium compounds are formed in the first instance, which are easily converted to 2-pyridones. Extending the scope of the reactions, a tricationic 2,6-bis(dimethylalkylammonium) pyridinium salt has also been prepared and characterized and its reactivity as a methylating agent assessed in comparison with that of the dications.

Dual macrolactonization/pyran-hemiketal formation via acylketenes: Applications to the synthesis of (-)-callipeltoside A and a lyngbyaloside B model system

Two for one: Thermal generation of acylketenes in diol-containing substrates results in the title transformation. This transformation expands the scope of acylketene macrolactonizations and their application to the synthesis of complex macrolides. Triol and tetraol substrates have also been cyclized in highly regioselective fashion. Additionally, the challenging macrolactonization of a tertiary alcohol was achieved. (Chemical Equation Presented).

Scandium triflate catalyzed transesterification of carboxylic esters

The direct transesterification of carboxylic esters is efficiently catalyzed with Sc(OTf)3 (10 mol%) in boiling alcoholic solvent. Methyl, ethyl, isopropyl, and allyl esters were prepared from a broad range of different substrates in high yields. The application of microwave irradiation led to significantly reduced reaction times. Georg Thieme Verlag Stuttgart.

Optical resolution of 3-(silyloxy)glutaric acid half esters and their utilization for enantioconvergent synthesis of a HMG-CoA reductase inhibitor

Useful chiral synthons, (3R)- and (3S)-[(tert- butyldimethylsilyl)oxy]pentanedioic acid monomethyl ester, (R)-1 and (S)-1, were obtained by optical resolution of a racemic mixture of 1. Sulfoxide 8 has been developed from (S)-1 as a new building block for preparing HMG-CoA reductase inhibitors. Two alternate chiral synthons 2 and 8, synthesized from (R)-1 and (S)-1, respectively, were employed for enantioconvergent synthesis of potent inhibitor 15 containing a pyrrole moiety.