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citramalic acid

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Name:2-hydroxy-2-methylbutanedioic acid
CAS Number: 2306-22-1Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J7.390C
XlogP3:-0.90 (est)
Molecular Weight:148.11476000
Formula:C5 H8 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
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Pubchem Patents:Search
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
BOC Sciences
For experimental / research use only.
(+/-)-Potassium citramalate 95%
Safety Information:
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
natural substances and extractives
Recommendation for citramalate usage levels up to:
 not for fragrance use.
Recommendation for citramalate flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :1081
National Institute of Allergy and Infectious Diseases:Data
2-hydroxy-2-methylbutanedioic acid
 2-hydroxy-2-methylbutanedioic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):1081
Pubchem (cas):2306-22-1
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
Golm Metabolome Database:Search
KEGG (GenomeNet):C00815
HMDB (The Human Metabolome Database):HMDB00426
YMDB (Yeast Metabolome Database):YMDB01584
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 cherry sour cherry fruit
Search Trop Picture
 butanedioic acid, 2-hydroxy-2-methyl-
 citramalic acid
2-hydroxy-2-methyl butane dioic acid
2-hydroxy-2-methylbutanedioic acid
alpha-methyl malate


PubMed:Synthesis of citramalic acid from glycerol by metabolically engineered Escherichia coli.
PubMed:Eliminating acetate formation improves citramalate production by metabolically engineered Escherichia coli.
PubMed:Production of citramalate by metabolically engineered Escherichia coli.
PubMed:Metabolic engineering of a synergistic pathway for n-butanol production in Saccharomyces cerevisiae.
PubMed:Identification of an itaconic acid degrading pathway in itaconic acid producing Aspergillus terreus.
PubMed:Improving Functional Annotation in the DRE-TIM Metallolyase Superfamily through Identification of Active Site Fingerprints.
PubMed:Mesaconase/Fumarase FumD in Escherichia coli O157:H7 and Promiscuity of Escherichia coli Class I Fumarases FumA and FumB.
PubMed:Metabolic flux analysis of the halophilic archaeon Haladaptatus paucihalophilus.
PubMed:A Comparative Metabolomic Evaluation of Behcet's Disease with Arthritis and Seronegative Arthritis Using Synovial Fluid.
PubMed:Trauma/hemorrhagic shock instigates aberrant metabolic flux through glycolytic pathways, as revealed by preliminary (13)C-glucose labeling metabolomics.
PubMed:Mesaconase Activity of Class I Fumarase Contributes to Mesaconate Utilization by Burkholderia xenovorans.
PubMed:Itaconic Acid: The Surprising Role of an Industrial Compound as a Mammalian Antimicrobial Metabolite.
PubMed:Pathologic metabolism: an exploratory study of the plasma metabolome of critical injury.
PubMed:New insight into the photoheterotrophic growth of the isocytrate lyase-lacking purple bacterium Rhodospirillum rubrum on acetate.
PubMed:Volatile profiles of members of the USDA Geneva Malus Core Collection: utility in evaluation of a hypothesized biosynthetic pathway for esters derived from 2-methylbutanoate and 2-methylbutan-1-ol.
PubMed:α-Hydroxy coordination of mononuclear vanadyl citrate, malate and S-citramalate with N-heterocycle ligand, implying a new protonation pathway of iron-vanadium cofactor in nitrogenase.
PubMed:Parallel labeling experiments validate Clostridium acetobutylicum metabolic network model for (13)C metabolic flux analysis.
PubMed:Unexpected similarities between the Schizosaccharomyces and human blood metabolomes, and novel human metabolites.
PubMed:Modifying the determinants of α-ketoacid substrate selectivity in mycobacterium tuberculosis α-isopropylmalate synthase.
PubMed:Unfamiliar metabolic links in the central carbon metabolism.
PubMed:Biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) from glucose with elevated 3-hydroxyvalerate fraction via combined citramalate and threonine pathway in Escherichia coli.
PubMed:Metabolic engineering of Escherichia coli for biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) from glucose.
PubMed:Metabolic and pathway engineering to influence native and altered erythromycin production through E. coli.
PubMed:New sputum metabolite markers implicating adaptations of the host to Mycobacterium tuberculosis, and vice versa.
PubMed:Multiple propionyl coenzyme A-supplying pathways for production of the bioplastic poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in Haloferax mediterranei.
PubMed:Identification and characterization of re-citrate synthase in Syntrophus aciditrophicus.
PubMed:Synergy as design principle for metabolic engineering of 1-propanol production in Escherichia coli.
PubMed:Metabolic engineering of Escherichia coli for the production of 1-propanol.
PubMed:Crystal structure of LeuD from Methanococcus jannaschii.
PubMed:Structural and functional characterization of α-isopropylmalate synthase and citramalate synthase, members of the LeuA dimer superfamily.
PubMed:Citramalic acid and salicylic acid in sugar beet root exudates solubilize soil phosphorus.
PubMed:Biosynthesis of polyhydroxyalkanoates containing 2-hydroxybutyrate from unrelated carbon source by metabolically engineered Escherichia coli.
PubMed:Facultative methanotrophy: false leads, true results, and suggestions for future research.
PubMed:Inhibition of aconitase in citrus fruit callus results in a metabolic shift towards amino acid biosynthesis.
PubMed:Metabolic flux analysis of the mixotrophic metabolisms in the green sulfur bacterium Chlorobaculum tepidum.
PubMed:Carbon flow of heliobacteria is related more to clostridia than to the green sulfur bacteria.
PubMed:1-methylmalate from camu-camu (Myrciaria dubia) suppressed D-galactosamine-induced liver injury in rats.
PubMed:Alternative isoleucine synthesis pathway in cyanobacterial species.
PubMed:Carbohydrate metabolism and carbon fixation in Roseobacter denitrificans OCh114.
PubMed:Features of structural organization and expression regulation of malate dehydrogenase isoforms from Rhodobacter sphaeroides strain 2R.
PubMed:Investigation of carbon metabolism in "Dehalococcoides ethenogenes" strain 195 by use of isotopomer and transcriptomic analyses.
PubMed:Characterization of the central metabolic pathways in Thermoanaerobacter sp. strain X514 via isotopomer-assisted metabolite analysis.
PubMed:Molecular basis of the inhibitor selectivity and insights into the feedback inhibition mechanism of citramalate synthase from Leptospira interrogans.
PubMed:[Enzymes of the citramalate cycle in Rhodospirillum rubrum].
PubMed:Directed evolution of Methanococcus jannaschii citramalate synthase for biosynthesis of 1-propanol and 1-butanol by Escherichia coli.
PubMed:Molecular basis of the substrate specificity and the catalytic mechanism of citramalate synthase from Leptospira interrogans.
PubMed:Elucidation of an alternate isoleucine biosynthesis pathway in Geobacter sulfurreducens.
PubMed:Enzymology and evolution of the pyruvate pathway to 2-oxobutyrate in Methanocaldococcus jannaschii.
PubMed:Insights into the autotrophic CO2 fixation pathway of the archaeon Ignicoccus hospitalis: comprehensive analysis of the central carbon metabolism.
PubMed:MAM3 catalyzes the formation of all aliphatic glucosinolate chain lengths in Arabidopsis.
PubMed:A comprehensive survey on isoleucine biosynthesis pathways in seven epidemic Leptospira interrogans reference strains of China.
PubMed:Properties of succinyl-coenzyme A:D-citramalate coenzyme A transferase and its role in the autotrophic 3-hydroxypropionate cycle of Chloroflexus aurantiacus.
PubMed:Properties of succinyl-coenzyme A:L-malate coenzyme A transferase and its role in the autotrophic 3-hydroxypropionate cycle of Chloroflexus aurantiacus.
PubMed:[The mechanism of acetate assimilation in purple nonsulfur bacteria lacking the glyoxylate pathway: enzymes of the citramalate cycle in Rhodobacter sphaeroides].
PubMed:[The mechanism of acetate assimilation in purple nonsulfur bacteria lacking the glyoxylate pathway: acetate assimilation in Rhodobacter sphaeroides cells].
PubMed:Isoleucine biosynthesis in Leptospira interrogans serotype lai strain 56601 proceeds via a threonine-independent pathway.
PubMed:Inhibition of acetate and propionate assimilation by itaconate via propionyl-CoA carboxylase in isocitrate lyase-negative purple bacterium Rhodospirillum rubrum.
PubMed:A bicyclic autotrophic CO2 fixation pathway in Chloroflexus aurantiacus.
PubMed:Significance of two distinct types of tryptophan synthase beta chain in Bacteria, Archaea and higher plants.
PubMed:Bacillus subtilis YxkJ is a secondary transporter of the 2-hydroxycarboxylate transporter family that transports L-malate and citrate.
PubMed:[Dark metabolism of acetate in Rhodospirillum rubrum cells, grown under photoheterotropic conditions].
PubMed:(R)-citramalate synthase in methanogenic archaea.
PubMed:3-Methylaspartate ammonia-lyase as a marker enzyme of the mesaconate pathway for (S)-glutamate fermentation in Enterobacteriaceae.
PubMed:Catalytic Reduction of Hydrazine to Ammonia with MoFe(3)S(4)-Polycarboxylate Clusters. Possible Relevance Regarding the Function of the Molybdenum-Coordinated Homocitrate in Nitrogenase.
PubMed:Increased urinary excretion of analogs of Krebs cycle metabolites and arabinose in two brothers with autistic features.
PubMed:Purification and characterization of a cytoplasmic enzyme component of the Na+-activated malonate decarboxylase system of Malonomonas rubra: acetyl-S-acyl carrier protein: malonate acyl carrier protein-SH transferase.
PubMed:Thermodynamics of the maleate and citraconate hydration reactions catalysed by malease from Pseudomonas pseudoalcaligenes.
PubMed:Purification and Characterization of Maleate Hydratase from Pseudomonas pseudoalcaligenes.
PubMed:13C-NMR study of acetate assimilation in Thermoproteus neutrophilus.
PubMed:Substrate reduction properties of dinitrogenase activated in vitro are dependent upon the presence of homocitrate or its analogues during iron-molybdenum cofactor synthesis.
PubMed:Mechanism of biosynthesis of 2-oxo-3-methylvalerate in Chlorobium vibrioforme.
PubMed:Equilibrium constants of several reactions involved in the fermentation of glutamate.
PubMed:Acetate and CO2 assimilation by Methanothrix concilii.
PubMed:Citramalic acid in cerebrospinal fluid of patients with bacterial meningitis.
PubMed:Relatedness of acyl carrier proteins shown by amino acid compositions.
PubMed:2-hydroxy-2-methylsuccinic acid--a urinary metabolite in propionyl-CoA carboxylase deficiency.
PubMed:Nicotinic acid metabolism. 2,3-Dimethylmalate lyase.
PubMed:Isolation and function of the subunits of citramalate lyase and formation of hybrids with the subunits of citrate lyase.
PubMed:Pathway for isoleucine formation form pyruvate by leucine biosynthetic enzymes in leucine-accumulating isoleucine revertants of Serratia marcescens.
PubMed:Structure of the prosthetic groups of citrate lyase and citramalate lyase.
PubMed:A novel pathway for L-citramalate synthesis in Rhodospirillum rubrum.
PubMed:Metabolism of threo-beta-methylmalate by a soil bacterium.
PubMed:Acetic anhydride: an intermediate analogue in the acyl-exchange reaction of citramalate lyase.
PubMed:The enzyme complex citramalate lyase from Clostridium tetanomorphum.
PubMed:Formation of beta-methylmalate and its conversion to citramalate in Rhodospirillum rubrum.
PubMed:Studies on the metabolic pathway for itatartaric acid formation by Aspergillus terreus. II. Use of (-)citramalate, citraconate and itaconate by cell-free extracts.
PubMed:Amino acid biosynthesis in the spirochete Leptospira: evidence for a novel pathway of isoleucine biosynthesis.
PubMed:Enzymatic cleavage of (+)citramalate into pyruvate and acetyl-CoA in Bacillus sp.
PubMed:Nonfunctional tricarboxylic acid cycle and the mechanism of glutamate biosynthesis in Acetobacter suboxydans.
PubMed:Metabolism of (-)-citramalate.
PubMed:Enzymatic isomerization of -methylmate to (-)citramalate by a soil bacterium.
PubMed:The enzymic degradation of alkyl-substituted gentisates, maleates and malates.
PubMed:Activation of L-citramalate hydrolyase from clostridium tetanomorphum.
PubMed:Purification and properties of L-citramalate hydrolyase.
PubMed:Inhibition of the metabolism of carboxylic acids and amino acids by citramalate and other related compounds in Rhodopseudomonas spheroides.
PubMed:Citramalate lyase of Clostridium tetanomorphum.
PubMed:Assay and purification of (+)-citramalate hydro-lyase components from Clostridium tetanomorphum.
PubMed:Enzymatic hydration of citraconate to (minus)citramalate.
PubMed:Enzymic formation of citramalate from acetyl-coenzyme A and pyruvate in Pseudomonas ovalis Chester, catalysed by "pyruvate transacetase".
PubMed:[On the decarboxylations in wine and the appearance of citramalic acid].
PubMed:[Does the fermentation of citramalic acid occur in wine].
PubMed:The oxidation of citramalic acid and beta-hydroxyglutaric acid to acetoacetic acid and the possible significance of citramalic acid in plant metabolism.
PubMed:The isolation of l-citramalic acid from the peel of the apple fruit.
PubMed:The effect of citrate on the rotation of the molybdate complexes of malate, citramalate and isocitrate.
Citramalic acid is an analog of malic acid. The structure is citramalic acid is similar to the structure of malic acid except it has an extra CH3 group on it. It can inhibit the production of malic acid.
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