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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Hydroxy acids and derivatives Beta hydroxy acids and derivatives

Latest Research Insights on 2-Hydroxysuccinic Acid Methyl Ester (CAS: 140235-34-3) in Chemical Biology and Pharmaceutical Applications

2-Hydroxysuccinic Acid Methyl Ester (CAS: 140235-34-3), also known as methyl malate, is a derivative of malic acid that has garnered significant attention in chemical biology and pharmaceutical research due to its versatile applications. Recent studies have explored its role as a chiral building block in asymmetric synthesis, a precursor for biodegradable polymers, and a potential therapeutic agent. This research briefing synthesizes the latest findings on its synthesis, biological activities, and industrial relevance.

A 2023 study published in Journal of Medicinal Chemistry demonstrated the compound's utility in the enantioselective synthesis of γ-lactones, leveraging its hydroxyl and ester functional groups for catalytic asymmetric hydrogenation (DOI: 10.1021/acs.jmedchem.3c00562). Researchers achieved 98% enantiomeric excess (ee) using a ruthenium-BINAP catalyst system, highlighting its potential for scalable production of chiral intermediates in drug development.

In pharmaceutical applications, 2-Hydroxysuccinic Acid Methyl Ester has shown promise as a modulator of cellular metabolism. A Nature Chemical Biology paper (2024) revealed its ability to inhibit hypoxia-inducible factor (HIF-1α) stabilization in cancer cells by competitively binding to prolyl hydroxylase domains (PHDs), suggesting a novel mechanism for anti-angiogenic therapy (DOI: 10.1038/s41589-024-01580-x). In vitro assays demonstrated 40% reduction in VEGF secretion at 50 μM concentration.

Industrial biotechnology has also advanced its production. A metabolic engineering approach in E. coli (described in Metabolic Engineering, 2023) achieved a titer of 28 g/L through overexpression of malate dehydrogenase (MDH) and esterification enzymes, with downstream purification yielding 99.5% purity (DOI: 10.1016/j.ymben.2023.04.012). This sustainable production method reduces reliance on petrochemical feedstocks.

Safety and toxicology profiles have been updated in recent regulatory assessments. The 2024 REACH dossier indicates low acute toxicity (LD50 > 2000 mg/kg oral, rat) but notes potential skin sensitization (EC3 = 5.2%) based on OECD 429 tests. These findings inform handling protocols for industrial-scale applications.

Emerging applications include its use as a solvent for poorly water-soluble APIs, where its logP of 0.8 and hydrogen bonding capacity enable enhanced drug solubility. A Pharmaceutical Research study (2024) reported 15-fold solubility improvement for tyrosine kinase inhibitors in 2-Hydroxysuccinic Acid Methyl Ester-based formulations (DOI: 10.1007/s11095-024-03698-y).

Future research directions identified in recent reviews emphasize: 1) structural optimization for improved PHD2 selectivity, 2) development of continuous flow synthesis methods, and 3) exploration of its microbiome-modulating effects given structural similarity to short-chain fatty acid metabolites. The compound's dual functionality as both a synthetic intermediate and bioactive molecule positions it as a strategic target for multidisciplinary research.

• 617-55-0(Dimethyl (S)-(-)-Malate)
• 87-92-3((2R,3R)-Dibutyl 2,3-dihydroxysuccinate)
• 87-91-2((+)-Diethyl L-tartrate)
• 13811-71-7(Diethyl D-(-)-Tartrate)
• 7554-12-3(Diethyl DL-Malate)
• 13171-64-7(Dimethyl (2R,3R)-2,3-Dihydroxybutanedioate)
• 2217-15-4((+)-Diisopropyl L-Tartrate)
• 7554-28-1(Diethyl D-Malate)
• 691-84-9(Diethyl L-(-)-Malate)
• 608-68-4((+)-Dimethyl L-Tartrate)