Identification

Nameaconitic acid
IUPACprop-1-ene-1,2,3-tricarboxylic acid
CAS Number499-12-7
EINECS207-877-0
FDA UNII93371T1BXP
Molecular FormulaC6 H6 O6
Molecular Weight174.10902000
Nikkaji NumberJ71.033D
Beilstein1725828
CoE Number33

Regulatory

FDA/DG SANTE Petitions, Reviews, Notices184.1007
JECFA Food Flavoring627 aconitic acid
DG SANTE Food Flavourings08.033 prop-1-ene-1,2,3-tricarboxylic acid
FEMA Number2010
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)499-12-7 ; ACONITIC ACID
FDA RegulationFDA PART 184 -- DIRECT FOOD SUBSTANCES AFFIRMED AS GENERALLY RECOGNIZED AS SAFE

Physical Properties

Appearance colorless to yellow crystals (est)
Assay 98.00 to 100.00
Additional Assay Information tridodecylamine: max 0.10 mg/kg
Food Chemicals Codex Listed No
Melting Point 195.00 to 196.00 °C. @ 760.00 mm Hg
Boiling Point 542.00 to 543.00 °C. @ 760.00 mm Hg (est)
Flash Point 564.00 °F. TCC ( 295.56 °C. )
logP (o/w) -0.179 (est)
Soluble in water, 333000 mg/L @ 15 °C (exp)
Similar Items note

Organoleptic Properties

Odor Strength none
Odor Description
at 100.00 %.
Vegetative, musty and nutty with a dry, toasted nuance
Taste Description at 25.00 ppm.

Safety Information

Oral/Parenteral Toxicityintravenous-mouse LD50 180 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00189']

Safety in Use

Categoryflavoring agents and adjuvants
Recommendation for aconitic acid usage levels up tonot for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU)0.012 (μg/capita/day)
baked goods0.60000
beverages(nonalcoholic)0.20000
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy0.60000
imitation dairy-
instant coffee / tea-
jams / jellies-
meat products-
milk products-
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy-
soups-
sugar substitutes-
sweet sauces-

No supplier data available

Potential Uses

None Found

Natural Occurrence

aconitum napellus barley root beet plant corn root corn shoot oat plant potato plant sunflower leaf

Synonyms

achilleaic acid achilleic acid 2- carboxy glutaconic acid 3- carboxy-2-pentene dioic acid 3- carboxy-2-pentenedioic acid 3- carboxyglutaconic acid citridic acid citridinic acid equisetic acid glutaconic acid, 3-carboxy- 2- pentenedioic acid, 3-carboxy- prop-1-ene-1,2,3-tricarboxylic acid 1,2,3- propene tricarboxylic acid 1- propene-1,2,3-tricarboxylic acid 1,2,3- propenetricarboxylic acid pyrocitric acid PubMed: Effects of nitrogen treatments and harvesting stages on the aconitic acid, invert sugar and fiber in sweet sorghum cultivars. PubMed: Characterization of taste-active fractions in red wine combining HPLC fractionation, sensory analysis and ultra performance liquid chromatography coupled with mass spectrometry detection. PubMed: Metabonomic analysis of the toxic effects of TM208 in rat urine by HPLC-ESI-IT-TOF/MS. PubMed: A HPLC-Q-TOF-MS-based urinary metabolomic approach to identification of potential biomarkers of metabolic syndrome. PubMed: Urinary Loss of Tricarboxylic Acid Cycle Intermediates As Revealed by Metabolomics Studies: An Underlying Mechanism to Reduce Lipid Accretion by Whey Protein Ingestion? PubMed: Hydrophilic interaction chromatography-mass spectrometry for anionic metabolic profiling of urine from antibiotic-treated rats. PubMed: Guidance of growth mode and structural character in organic-inorganic hybrid materials - a comparative study. PubMed: On-line capillary electrophoresis enrichment by combining chitosan trapping with surfactant assisted sample stacking for the ultratrace determination of organic acids in Plateau alfalfa roots. PubMed: Biochemistry of microbial itaconic acid production. PubMed: Different methods of detaching adherent cells significantly affect the detection of TRAIL receptors. PubMed: Anionic metabolic profiling of urine from antibiotic-treated rats by capillary electrophoresis-mass spectrometry. PubMed: Antifungal activity of homoaconitate and homoisocitrate analogs. PubMed: Metabolic profiling reveals sphingosine-1-phosphate kinase 2 and lyase as key targets of (phyto-) estrogen action in the breast cancer cell line MCF-7 and not in MCF-12A. PubMed: Cis-aconitic anhydride ethyl ester and phenolic compounds from the seeds of Alisma orientale. PubMed: Analysis of urinary metabolic signatures of early hepatocellular carcinoma recurrence after surgical removal using gas chromatography-mass spectrometry. PubMed: Metabolomic profiling of the autosomal dominant polycystic kidney disease rat model. PubMed: Metabolic profiling and predicting the free radical scavenging activity of guava (Psidium guajava L.) leaves according to harvest time by 1H-nuclear magnetic resonance spectroscopy. PubMed: [Analysis of transporter function and development to clinical application]. PubMed: Effects of nitrogen treatments and harvesting stages on the aconitic acid, invert sugar and fiber in sweet sorghum cultivars. PubMed: Application of NMR-based metabolomics to the investigation of salt stress in maize (Zea mays). PubMed: Urinary metabonomics study in a rat model in response to protein-energy malnutrition by using gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry. PubMed: LC-MS analysis of low molecular weight organic acids derived from root exudation. PubMed: Biochemical characterisation of aconitase from Corynebacterium glutamicum. PubMed: Characterization of taste-active fractions in red wine combining HPLC fractionation, sensory analysis and ultra performance liquid chromatography coupled with mass spectrometry detection. PubMed: Flavonoid glucuronides and a chromone from the aquatic macrophyte Stratiotes aloides. PubMed: Enhancing itaconic acid production by Aspergillus terreus. PubMed: [Metabonomic profiling of plasma metabolites in Wistar rats to study the effect of aging by means of GC/TOFMS-based techniques]. PubMed: A novel monoclonal antibody specific to peptide pdnaelvlltlgqawqg. PubMed: Synthesis and properties of polycarboxylate-type green surfactants with S- or N-linkages. PubMed: Biotechnological production of itaconic acid and its biosynthesis in Aspergillus terreus. PubMed: A surface transporter family conveys the trypanosome differentiation signal. PubMed: Microbiology: Signals for change. PubMed: Aconitate and methyl aconitate are modulated by silicon in powdery mildew-infected wheat plants. PubMed: Abnormal tricarboxylic acid cycle metabolites in isovaleric acidaemia. PubMed: Preparation and characterization of a novel monoclonal antibody specific to human CAD protein. PubMed: A high-throughput method to measure NaCl and acid taste thresholds in mice. PubMed: Antifeedants of Indian barnyard millet, Echinochloa frumentacea link, against brown planthopper, Nilaparvata lugens (Stål). PubMed: Metabolite profiling of blood from individuals undergoing planned myocardial infarction reveals early markers of myocardial injury. PubMed: Cloning and functional characterization of the cis-aconitic acid decarboxylase (CAD) gene from Aspergillus terreus. PubMed: Metabonomic analysis of hepatitis B virus-induced liver failure: identification of potential diagnostic biomarkers by fuzzy support vector machine. PubMed: Tricarballylate catabolism in Salmonella enterica. The TcuB protein uses 4Fe-4S clusters and heme to transfer electrons from FADH2 in the tricarballylate dehydrogenase (TcuA) enzyme to electron acceptors in the cell membrane. PubMed: The three-dimensional crystal structure of the PrpF protein of Shewanella oneidensis complexed with trans-aconitate: insights into its biological function. PubMed: Bacillus decisifrondis sp. nov., isolated from soil underlying decaying leaf foliage. PubMed: [Simultaneous determination of twenty-one organic acids in food by ion chromatography with eluent autogeneration]. PubMed: Isolation, structure determination, and sensory activity of mouth-drying and astringent nitrogen-containing phytochemicals isolated from red currants (Ribes rubrum). PubMed: Detection of new fumonisin mycotoxins and fumonisin-like compounds by reversed-phase high-performance liquid chromatography/electrospray ionization ion trap mass spectrometry. PubMed: The FAD-dependent tricarballylate dehydrogenase (TcuA) enzyme of Salmonella enterica converts tricarballylate into cis-aconitate. PubMed: High-speed counter-current chromatography for the study of defense metabolites in wheat. Characterization of 5,6-O-methyl trans-aconitic acid. PubMed: Efficient preparation and improved sensitivity of molecularly imprinted polymers using room temperature ionic liquids. PubMed: Purification and characterization of cis-aconitic acid decarboxylase from Aspergillus terreus TN484-M1. PubMed: Antiproliferative properties of chemically modified recombinant IFN-alpha2b. PubMed: Allelopathic effects of aconitic acid on wild poinsettia (Euphorbia heterophylla) and morningglory (Ipomoea grandifolia). PubMed: Cold shock and regulation of surface protein trafficking convey sensitization to inducers of stage differentiation in Trypanosoma brucei. PubMed: Chemical interactions of Brachiaria plantaginea with Commelina bengalensis and Acanthospermum hispidum in soybean cropping systems. PubMed: Depressive symptoms and taste reactivity in humans. PubMed: 3-Isopropylmalate is the major endogenous substrate of the Saccharomyces cerevisiae trans-aconitate methyltransferase. PubMed: Basolateral localization of flounder Na+-dicarboxylate cotransporter (fNaDC-3) in the kidney of Pleuronectes americanus. PubMed: Efficient scavenger receptor-mediated hepatic targeting of proteins by introduction of negative charges on the proteins by aconitylation: the influence of charge density and size of the proteins molecules. PubMed: HPMA copolymers with pH-controlled release of doxorubicin: in vitro cytotoxicity and in vivo antitumor activity. PubMed: Unexpected anthracycline-mediated alterations in iron-regulatory protein-RNA-binding activity: the iron and copper complexes of anthracyclines decrease RNA-binding activity. PubMed: Massive and selective delivery of lipid-coated cationic lipoplexes of oligonucleotides targeted in vivo to hepatic endothelial cells. PubMed: The influence of charge clustering on the anti-HIV-1 activity and in vivo distribution of negatively charged albumins. PubMed: [Effect of organic acids on soil chemical behavior of lead and cadmium and their toxicity to plants]. PubMed: The methylcitric acid pathway in Ralstonia eutropha: new genes identified involved in propionate metabolism. PubMed: The applicability of rat and human liver slices to the study of mechanisms of hepatic drug uptake. PubMed: [Characteristics of NADP-dependent isocitrate dehydrogenase functioning in pea leaves during salt stress]. PubMed: Distinct reactions catalyzed by bacterial and yeast trans-aconitate methyltransferases. PubMed: In vitro conversion of propionate to pyruvate by Salmonella enterica enzymes: 2-methylcitrate dehydratase (PrpD) and aconitase Enzymes catalyze the conversion of 2-methylcitrate to 2-methylisocitrate. PubMed: [The use of liposomal form of phenylimide of cis-aconitic acid in herpes therapy]. PubMed: A novel selection regime for differentiation defects demonstrates an essential role for the stumpy form in the life cycle of the African trypanosome. PubMed: The use of transgenic Trypanosoma brucei to identify compounds inducing the differentiation of bloodstream forms to procyclic forms. PubMed: Resistance of the human immunodeficiency virus to the inhibitory action of negatively charged albumins on virus binding to CD4. PubMed: Anti-HIV-1 activity of combinations and covalent conjugates of negatively charged human serum albumins (NCAs) and AZT. PubMed: Molecular mechanisms of the adsorption of a model protein (human serum albumin) on poly(methylidene malonate 2.1.2) nanoparticles. PubMed: Lactoferrin. Antiviral activity of lactoferrin. PubMed: Lectin-mediated drug targeting: preparation, binding characteristics, and antiproliferative activity of wheat germ agglutinin conjugated doxorubicin on Caco-2 cells. PubMed: Citrate promotes attachment of Prevotella nigrescens (intermedia) ATCC 25261 to hydroxyapatite. PubMed: Mild acid stress as a differentiation trigger in Trypanosoma brucei. PubMed: Cell density triggers slender to stumpy differentiation of Trypanosoma brucei bloodstream forms in culture. PubMed: Commitment to differentiation and cell cycle re-entry are coincident but separable events in the transformation of African trypanosomes from their bloodstream to their insect form. PubMed: Massive targeting of liposomes, surface-modified with anionized albumins, to hepatic endothelial cells. PubMed: Detection and molecular analysis of plant- and insect-associated bacteria harboring aconitate isomerase involved in biosynthesis of trans-aconitic acid as antifeedant in brown planthoppers. PubMed: Enzymes and symmetrical molecules. PubMed: Fermentation of trans-aconitate via citrate, oxaloacetate, and pyruvate by Acidaminococcus fermentans. PubMed: Antiviral effects of milk proteins: acylation results in polyanionic compounds with potent activity against human immunodeficiency virus types 1 and 2 in vitro. PubMed: Preliminary determination of a molecular basis of chronic fatigue syndrome. PubMed: Preparation and characterization of conjugates of (modified) human serum albumin and liposomes: drug carriers with an intrinsic anti-HIV activity. PubMed: Comparative pharmacokinetic, immunologic and hematologic studies on the anti-HIV-1/2 compounds aconitylated and succinylated HSA. PubMed: A new patient with alpha-ketoglutaric aciduria and progressive extrapyramidal tract disease. PubMed: Ability of Acidaminococcus fermentans to oxidize trans-aconitate and decrease the accumulation of tricarballylate, a toxic end product of ruminal fermentation. PubMed: Emendation of the description of Acidaminococcus fermentans, a trans-aconitate- and citrate-oxidizing bacterium. PubMed: Kinetics of enzymes with iso-mechanisms: dead-end inhibition of fumarase and carbonic anhydrase II. PubMed: Crystal structures of aconitase with trans-aconitate and nitrocitrate bound. PubMed: Studies on compounds promoting the in vitro transformation of Trypanosoma brucei from bloodstream to procyclic forms. PubMed: Experimental visceral leishmaniasis: role of trans-aconitic acid in combined chemotherapy. PubMed: Altered intracellular polyamines in bloodstream form Trypanosoma brucei brucei: transformation to procyclic trypomastigotes. PubMed: Novel, negatively charged, human serum albumins display potent and selective in vitro anti-human immunodeficiency virus type 1 activity. PubMed: Automated docking in crystallography: analysis of the substrates of aconitase. PubMed: Transport of tricarballylate by intestinal brush-border membrane vesicles from steers. PubMed: Immunotargeting of daunomycin to localized and metastatic human colon adenocarcinoma in athymic mice. PubMed: Effects of birth asphyxia on urinary organic acid excretion. PubMed: Phloretin and citrate promote the differentiation rate from epimastigote to metacyclic forms of Trypanosoma cruzi. PubMed: Alterations in Krebs cycle enzyme activities and carbohydrate catabolism in two strains of Trypanosoma brucei during in vitro differentiation of their bloodstream to procyclic stages. PubMed: Inhibition of protein synthesis results in super-induction of procyclin (PARP) RNA levels. PubMed: Tumor reactive cis-aconitylated monoclonal antibodies coupled to daunorubicin through a peptide spacer are unable to kill tumor cells. PubMed: Daunorubicin coupled to monoclonal antibodies via a cis-aconitic anhydride linker: biochemical and cytotoxic properties revisited. PubMed: Evaluation of antileishmanial activity of trans-aconitic acid. PubMed: Erythrocyte membrane-bound daunorubicin as a delivery system in anticancer treatment. PubMed: Effect of tricarballylic acid, a nonmetabolizable rumen fermentation product of trans-aconitic acid, on Mg, Ca and Zn utilization of rats. PubMed: The arrhythmogenic effect of platelet activating factor (PAF) is inhibited by PAF antagonist and by substances influencing eicosanoids. PubMed: Repression and reactivation of the variant surface glycoprotein gene in Trypanosoma brucei. PubMed: Genetic mapping, distribution, and properties of an aconitase isozyme in Anopheles albimanus (Diptera:Culicidae). PubMed: The effect of citrate/cis-aconitate on oxidative metabolism during transformation of Trypanosoma brucei. PubMed: Trypanosoma brucei: cis-aconitate and temperature reduction as triggers of synchronous transformation of bloodstream to procyclic trypomastigotes in vitro. PubMed: Production of tricarballylic acid by rumen microorganisms and its potential toxicity in ruminant tissue metabolism. PubMed: 17O electron nuclear double resonance characterization of substrate binding to the [4Fe-4S]1+ cluster of reduced active aconitase. PubMed: Trypanosoma brucei: differentiation of in vitro-grown bloodstream trypomastigotes into procyclic forms. PubMed: [Pharmacological effect of the organic acid of Achillea alpina]. PubMed: Enrichment and Isolation of Rumen Bacteria That Reduce trans- Aconitic Acid to Tricarballylic Acid. PubMed: Presence and regulation of the alpha-ketoglutarate dehydrogenase multienzyme complex in the filamentous fungus Aspergillus niger. PubMed: pH profiles and isotope effects for aconitases from Saccharomycopsis lipolytica, beef heart, and beef liver. alpha-Methyl-cis-aconitate and threo-Ds-alpha-methylisocitrate as substrates. PubMed: Mutagenic investigation of flavourings: dimethyl succinate, ethyl pyruvate and aconitic acid are negative in the Salmonella/mammalian-microsome test. PubMed: Wheat pasture poisoning. I. An evaluation of cereal pastures as related to tetany in beef cows. PubMed: Citrate utilization by Escherichia coli: plasmid- and chromosome-encoded systems. PubMed: Organic acids or urine in multiple sclerosis. PubMed: Fluorometric determination of carbodiimides with trans-aconitic acid. PubMed: The effect of thermal history on the transition temperature of citric acid glass. PubMed: Metabolism of trans-Aconitic Acid in Maize : II. Regulatory Properties of Two Compartmented Forms of Citrate Dehydrase. PubMed: Metabolism of trans-Aconitic Acid in Maize : I. PURIFICATION OF TWO MOLECULAR FORMS OF CITRATE DEHYDRASE. PubMed: Stimulating effect of citrate and cis-Aconitate on the transformation of Trypanosoma brucei bloodstream forms to procyclic forms in vitro. PubMed: Kinetic studies of cytoplasmic and mitochondrial aconitate hydratases from rat liver. PubMed: Structural basis for aconitase activity inactivation by butanedione and binding of substrates and inhibitors. PubMed: cis- and trans-Aconitic acids as inhibitors of glutamate decarboxylase. PubMed: [Oxidation of Krebs cycle substrates by Eurytrema pancreaticum mitochondria]. PubMed: Regulation of citrate synthase in Brevibacterium flavum, a glutamate-producing bacterium. PubMed: The structure and function of ribonuclease T1. XXIII. Inactivation of ribonuclease T1 by reversible blocking of amino groups with cis-aconitic anhydride and related dicarboxylic acid anhydrides. PubMed: Urinary organic acid profiles of Reye's syndrome patients. PubMed: Growth and synthesis of rubratoxin by Penicillium rubrum in a chemically defined medium fortified with organic acids and intermediates of the tricarboxylic acid cycle. PubMed: [The identification of cis- and trans-aconitic acid with paper chromatographic methods. 30. The chemistry and physiology of metaboloically, chemically important acids]. PubMed: Gas-liquid chromatography of organic acids in citrus tissues. PubMed: Phthalonic acid, an inhibitor of alpha-oxoglutarate transport in mitochondria. PubMed: Stimulation of citrate oxidation and transport in human placental mitochondria by L-malate. PubMed: Regulation of progesterone biosynthesis in human placental mitochondria by Krebs cycle metabolites. PubMed: Effect of acetic and trans-aconitic acids on citric acid production by Aspergillus niger. PubMed: Inhibition of Mn2+ of citrate supported progesterone biosynthesis in mitochondrial fractions of human term placentae. PubMed: [2 methods of preparing solvent systems for the chromatographic separation of organic acids]. PubMed: Purification and kinetic properties of ATP: citrate oxaloacetate lyase from rat brain. PubMed: [The significance of the cis-aconitic acid for the biological inactivation of the 3,4-benzopyrene cancerogenesis (author's transl)]. PubMed: [Prevention of 3,4-benzpyrene carcinogenesis by naturally occurring and synthetic compounds]. PubMed: Reinforced polycarboxylate cements. PubMed: The mechanism of aconitase action. Evidence for an enzyme isomerization by studies of inhibition by tricarboxylic acids. PubMed: Oxidation, accumulation, and turnover of citrate in normal and diabetic rats. PubMed: [Biochemical characteristics of the facultatively parasitic strain Bdellovibrio bacteriovorus]. PubMed: Comparison of the amino acid sequences of the variable regions of light chains derived from two homogeneous rabbit anti-pneumococcal antibodies. PubMed: Urinary excretion of non-nitrogenous organic acids by healthy infants and children. PubMed: Separation and determination of 14C-labelled intermediates of the citric acid cycle and related compounds. PubMed: Modulation of mitochondrial adenylate kinase by citric-acid-cycle intermediates. PubMed: The magnitude of enzyme transition state analog binding constants. PubMed: Rapid sampling of yeast cells and automated assays of adenylate, citrate, pyruvate and glucose-6-phosphate pools. PubMed: [Physicochemical methods of studying aconitine and the prospects for utilizing them in toxicological analysis]. PubMed: Effects of modifying urea hydrolysis in acute nephrectomy on survival, ammonia in cecal contents and blood metabolites. PubMed: Organic acids and iron translocation in maize genotypes. PubMed: Effects of urea in rats deprived of arginine. PubMed: Transport of tricarboxylic acids in Salmonella typhimurium. PubMed: Fluorocitrate inhibition of aconitate hydratase and the tricarboxylate carrier of rat liver mitochondria. PubMed: Separation of Krebs cycle intermediates on a low-bleed gas chromatographic column. Temperature dependence of methylene unit values. PubMed: Sarcosomal aconitase of silkworm. PubMed: [Effect of organic acids on the activity of malate synthase from Acinetobacter calco-aceticus]. PubMed: The content of trans-aconitic acid in Asarum europaeum L. determined by means of a chromatogram spectrophotometer. PubMed: Colorimetric determination of aconitic acid in Avena sativa (oat). PubMed: alpha-Methyl-cis-aconitic acid. Aconitase substrate. II. Substrate properties and aconitase mechanism. PubMed: Alpha-methyl-cis-aconitic acid, cis-aconitase substrate. I. Synthesis. PubMed: Trans-Aconitic Acid in Range Grasses in Early Spring. PubMed: Isolation of trans-Aconitic Acid from the Moss Mnium affine. PubMed: Triethyl alpha-fluoroaconitate. PubMed: Selective antibacterial activity of aconitic acid. PubMed: [Formation of an ester of aconitic acid during the stabilization of plant material and during the extraction of organic acids by ethyl alcohol]. PubMed: Biosynthesis of itaconic acid in Aspergillus terreus. III. The properties and reaction mechanism of cis-aconitic acid decarboxylase. PubMed: [Colorimetric microdetermination of citric acid and of cis-aconitic acid]. PubMed: Aconitic acid, a by-product in the manufacture of sugar. PubMed: The effect of pH on the stability of cis-aconitic acid in dilute solution. PubMed: Some pharmacological properties of the monoanilide of aconitic acid.