149-61-1

Basic information

• Product Name: ANION STANDARD - MALATE
• Synonyms: 2-Hydroxysuccinate;2-Hydroxysuccinic acid dianion;R-116301;Butanedioic acid, hydroxy-, ion(2)-;Hydroxybutanedioate;Malate, L-;ANION STANDARD - MALATE;2-hydroxybutanedioate
• CAS NO: 149-61-1
• Molecular Formula: C₄H₄O₅
• Molecular Weight: 132.07156
• Mol File: 149-61-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 306.4°Cat760mmHg
• Flash Point: 153.4°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 7.19E-05mmHg at 25°C
• CAS DataBase Reference: ANION STANDARD - MALATE(CAS DataBase Reference)
• NIST Chemistry Reference: ANION STANDARD - MALATE(149-61-1)
• EPA Substance Registry System: ANION STANDARD - MALATE(149-61-1)

Safety Data

• Hazardous Substances Data: 149-61-1(Hazardous Substances Data)

Usage

Definition

ChEBI: A C4-dicarboxylate resulting from deprotonation of both carboxy groups of malic acid.

InChI:InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/p-2

Upstream product

• 142-42-7 fumarate 
• 149-63-3 oxaloacetate 

Downstream Products

• 530-59-6 trans-3,5-dimethoxy-4-hydroxycinnamic acid 
• 149-63-3 oxaloacetate 
• 57-60-3 piruvate 
• 58-68-4 NADH 

Relevant articles and documents

Direct Photoconversion of Pyruvate to Lactate in Aqueous TiO2 Dispersions

Pyruvate is efficiently converted to lactate under illumination of aqueous suspensions of titanium dioxide powder.This photoconversion does not require additional catalysts and its efficiency depends on the pH and the electron donor present in solution.Other keto carboxylic acids can also be photoreduced by the same process.The kinetics of reduction has been studied by monitoring the interfacial electron transfer occuring at the surface of colloidal TiO2 semiconducting particles using laser photolysis.

L-2-Hydroxyglutarate production arises from noncanonical enzyme function at acidic pH

The metabolite 2-hydroxyglutarate (2HG) can be produced as either a D-R- or L-S- enantiomer, each of which inhibits α-ketoglutarate (αKG)-dependent enzymes involved in diverse biologic processes. Oncogenic mutations in isocitrate dehydrogenase (IDH) produce D-2HG, which causes a pathologic blockade in cell differentiation. On the other hand, oxygen limitation leads to accumulation of L-2HG, which can facilitate physiologic adaptation to hypoxic stress in both normal and malignant cells. Here we demonstrate that purified lactate dehydrogenase (LDH) and malate dehydrogenase (MDH) catalyze stereospecific production of L-2HG via 'promiscuous' reduction of the alternative substrate αKG. Acidic pH enhances production of L-2HG by promoting a protonated form of αKG that binds to a key residue in the substrate-binding pocket of LDHA. Acid-enhanced production of L-2HG leads to stabilization of hypoxia-inducible factor 1 alpha (HIF-1α) in normoxia. These findings offer insights into mechanisms whereby microenvironmental factors influence production of metabolites that alter cell fate and function.