tricarballylic acid
carboxymethylsuccinic acid
Isol. from plants e.g. sugarbeet sap, sap of Acer saccharinum (maple syrup) Propane-1,2,3-tricarboxylic acid, also known as tricarballylic acid, carballylic acid, and beta-carboxyglutaric acid, is a tricarboxylic acid that has three carboxylic acid functional groups. The compound is an inhibitor of the enzyme aconitase and interferes with the Krebs cycle. (Wikipedia)
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      P0490 1,2,3-Propanetricarboxylic Acid
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propane-1,2,3-tricarboxylic acid (Click)
CAS Number: 99-14-9Picture of molecule
Other: 850848-65-6
ECHA EINECS - REACH Pre-Reg: 202-733-3
Nikkaji Web: J4.963H
Beilstein Number: 1783567
MDL: MFCD00002723
XlogP3-AA: -1.20 (est)
Molecular Weight: 176.12496000
Formula: C6 H8 O6
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: buffering agents, sequestrants
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 166.00 °C. @ 760.00 mm Hg
Boiling Point: 266.43 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.002000 mm/Hg @ 25.00 °C. (est)
Flash Point: 265.00 °F. TCC ( 129.20 °C. ) (est)
logP (o/w): -1.420 (est)
Soluble in:
 water, 3.32E+05 mg/L @ 18C (exp)
 water, 1e+006 mg/L @ 25 °C (est)
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Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: buffering agents
chelating agents
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BOC Sciences
For experimental / research use only.
1,2,3-propanetricarboxylic acid 95%
Penta International
Santa Cruz Biotechnology
For experimental / research use only.
Tricarballylic Acid ≥97%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Tricarballylic Acid 99%
For experimental / research use only.
1,2,3-Propanetricarboxylic Acid
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Safety Information:
Preferred SDS: View
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
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Safety in Use Information:
Category: buffering agents, sequestrants
Recommendation for tricarballylic acid usage levels up to:
 not for fragrance use.
Recommendation for tricarballylic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 99-14-9
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 14925
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 propane-1,2,3-tricarboxylic acid
Chemidplus: 0000099149
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 propane-1,2,3-tricarboxylic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 14925
Pubchem (sid): 135023550
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
KEGG (GenomeNet): C19806
HMDB (The Human Metabolome Database): HMDB31193
FooDB: FDB003213
Export Tariff Code: 2917.19.5050
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
None Found
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 beet leaf
Search Trop  Picture
 corn plant
Search Trop  Picture
 sugarbeet sap
Search  Picture
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 carballylic acid
3-carboxyglutaric acid
 carboxymethylsuccinic acid
3-carboxypentane-1,5-dioic acid
3-carboxypentanedioic acid
 propane-1,2,3-tricarboxylic acid
1,2,3-propanetricarboxylic acid
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PubMed: Decreased transport restores growth of a Salmonella enterica apbC mutant on tricarballylate.
PubMed: Reactions of atomic metal anions in the gas phase: competition between electron transfer, proton abstraction and bond activation.
PubMed: Synthesis, characterization and cytocompatibility of a poly(diol-tricarballylate) visible light photo-cross-linked biodegradable elastomer.
PubMed: Molecular structures of citrate and tricarballylate adsorbed on alpha-FeOOH particles in aqueous suspensions.
PubMed: Total synthesis of the sphingolipid biosynthesis inhibitor fumonisin B(1).
PubMed: Regulation of expression of the tricarballylate utilization operon (tcuABC) of Salmonella enterica.
PubMed: Enantioselective desymmetrisation of citric acid catalysed by the substrate-tolerant petrobactin biosynthetic enzyme AsbA.
PubMed: Cell wall component and mycotoxin moieties involved in the binding of fumonisin B1 and B2 by lactic acid bacteria.
PubMed: Involvement of the Cra global regulatory protein in the expression of the iscRSUA operon, revealed during studies of tricarballylate catabolism in Salmonella enterica.
PubMed: Synthesis, chemical speciation and SOD mimic assays of tricarballylic acid-copper(II) and imidazole-tricarballylic acid-copper(II) complexes.
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: Citrate sensing by the C4-dicarboxylate/citrate sensor kinase DcuS of Escherichia coli: binding site and conversion of DcuS to a C4-dicarboxylate- or citrate-specific sensor.
PubMed: Deletion analysis of FUM genes involved in tricarballylic ester formation during fumonisin biosynthesis.
PubMed: Detection of new fumonisin mycotoxins and fumonisin-like compounds by reversed-phase high-performance liquid chromatography/electrospray ionization ion trap mass spectrometry.
PubMed: Biodegradable network elastomeric polyesters from multifunctional aliphatic carboxylic acids and poly(epsilon-caprolactone) diols.
PubMed: A bidomain nonribosomal peptide synthetase encoded by FUM14 catalyzes the formation of tricarballylic esters in the biosynthesis of fumonisins.
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PubMed: Fumonisin-ortho-phthalaldehyde derivative is stabilized at low temperature.
PubMed: The Tricarballylate utilization (tcuRABC) genes of Salmonella enterica serovar Typhimurium LT2.
PubMed: Fumonisin and beauvericin induce apoptosis in turkey peripheral blood lymphocytes.
PubMed: Total fumonisins are reduced in tortillas using the traditional nixtamalization method of mayan communities.
PubMed: Studies into the thermodynamic origin of negative cooperativity in ion-pairing molecular recognition.
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PubMed: Electrospray mass spectrometry for fumonisin detection and method validation.
PubMed: Functional characterization of CitM, the Mg2+-citrate transporter.
PubMed: Insertion of 2-carboxysuccinate and tricarballylic acid fragments into cyclic-pseudopeptides: new antagonists for the human tachykinin NK-2 receptor.
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PubMed: Identification of fumonisin B1 as an inhibitor of argininosuccinate synthetase using fumonisin affinity chromatography and in vitro kinetic studies.
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PubMed: Oxidative deamination of hydrolyzed fumonisin B(1) (AP(1)) by cultures of Exophiala spinifera.
PubMed: Effects of fumonisin B1 and (hydrolyzed) fumonisin backbone AP1 on membranes: a spin-label study.
PubMed: Analysis of fumonisin B1 in corn by capillary electrophoresis.
PubMed: The inhibitory activity of some citrate analogues upon calcium crystalluria: observations using an improved urine evaporation technique.
PubMed: Determination of hydrolysed fumonisin B1 (HFB1) in corn by competitive direct enzyme-linked immunosorbent assay.
PubMed: Identification of an N-acetyl keto derivative of fumonisin B1 in corn cultures of Fusarium proliferatum.
PubMed: Inhibition of colchicine absorption by the fat substitutes, sucrose polyester and tricarballylate triester, in the rat.
PubMed: Fate of a single dose of 14C-labelled fumonisin B1 in vervet monkeys.
PubMed: Cyclosporin absorption is impaired by the fat substitutes, sucrose polyester and tricarballylate triester, in the rat.
PubMed: Ability of Acidaminococcus fermentans to oxidize trans-aconitate and decrease the accumulation of tricarballylate, a toxic end product of ruminal fermentation.
PubMed: Catabolism of isonicotinate by Mycobacterium sp. INA1: extended description of the pathway and purification of the molybdoenzyme isonicotinate dehydrogenase.
PubMed: Effect of fat substitutes, sucrose polyester and tricarballylate triester, on digitoxin absorption in the rat.
PubMed: Transport of tricarballylate by intestinal brush-border membrane vesicles from steers.
PubMed: Structure-activity relationships of fumonisins in short-term carcinogenesis and cytotoxicity assays.
PubMed: Generation of antibodies reactive with fumonisins B1, B2, and B3 by using cholera toxin as the carrier-adjuvant.
PubMed: Superoxide sensitivity of the Escherichia coli aconitase.
PubMed: Effect of the intestinal flora on the urinary organic acid profile of rats ingesting a chemically simplified diet.
PubMed: Effect of tricarballylic acid, a nonmetabolizable rumen fermentation product of trans-aconitic acid, on Mg, Ca and Zn utilization of rats.
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.
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PubMed: Enrichment and Isolation of Rumen Bacteria That Reduce trans- Aconitic Acid to Tricarballylic Acid.
PubMed: Citrate utilization by Escherichia coli: plasmid- and chromosome-encoded systems.
PubMed: Lack of chemotactic response to tricarboxylic acids by Escherichia coli carrying a plasmid determining citrate utilization.
PubMed: NADP-dependent isocitrate dehydrogenase from the mussel Mytilus edulis L. 2. Kinetic studies.
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PubMed: Transport of tricarboxylic acids in Salmonella typhimurium.
PubMed: Tricarballylic acid in the livers of sheep.
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