Basic information
- Standard SMILES
O=C(O)C=C(CC(=O)O)C(=O)O- InChIKey
GTZCVFVGUGFEME-UHFFFAOYSA-N- Molecular formula
- C6H6O6
- Average molar mass
- 174.11 g/mol
- Monoisotopic mass
- 174.01643791
Names & identifiers
- Preferred name
- Aconitic Acid
- IUPAC
- prop-1-ene-1,2,3-tricarboxylic acid
- English name
- Aconitic Acid
- Molecular formula
- C6H6O6
- Molecular weight
- 174.11
Names & synonyms
Show more names
Database identifiers
- CAS
499-12-7- PubChem CID
- 309
- DTXSID
DTXSID9060102- ChEMBL
CHEMBL153658- ChEBI
CHEBI:22211- EC Number
- 207-877-0
Properties
Computed structural properties
- XLogP
- -1
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 251
Physicochemical properties
- Melting point
- 192 °C · 192°C (rough estimate)
- Boiling point
- 225.05 °C · 225.05°C (rough estimate)
- Density
- 1.4285 · 1.4285 (rough estimate)
- refractive index
- 1.586 · 1.5860 (estimate)
- FEMA
- 2010 · 2010 | ACONITIC ACID
- FLAVIS Number
- 8.033 · 08.033 | Prop-1-ene-1,2,3-tricarboxylic acid
- solubility
- 16 % · Soluble 16 % in water at 13 ℃, 33% in water at 25 ℃. Decomposes when heated to 200° C. Soluble in alcohol and most perfume and flavor materials, poorly soluble in hydrocarbons (Terpenes, etc.).
- form
- Solid
- pka
- 2.39 · 2.39±0.36(Predicted)
- color
- Colorless (white) crystal leaves or plates
- Odor
- Vegetative, musty and nutty with a dry, toasted nuance
- JECFA Number
- 627 · 627
- LogP
- 0.63 · 0.63
- SCOGS (Select Committee on GRAS Substances)
- Aconitic Acid
- Substances Added to Food (formerly EAFUS)
- ACONITIC ACID
- FDA 21 CFR
- 184.1007 · 184.1007
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 93371 T1BXP · 93371T1BXP
- EPA Substance Registry System
- 1 · 1-Propene-1,2,3-tricarboxylic acid (499-12-7)
- TSCA
- TSCA listed
- Hazardous Substances Data
- 499 · 499-12-7(Hazardous Substances Data)
- Toxicity
- 50 intravenous · LD50 intravenous in mouse: 180mg/kg
Safety & regulation
Safety data
- tsca
- TSCA listed
- Toxicity
- LD50 intravenous in mouse: 180mg/kg
- Hazardous Substances Data
- 499-12-7(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionAconitic acid has pleasant, winey, acid taste; almost odorless. Aconitic acid of the trans-configuration can be isolated during the processing of sugarcane by precipitating it as the calcium salt from cane syrup or molasses. The concentration in molasses ranges from 1.8 to 2.5%. Aconitic acid may be synthesized from citric acid by dehydration with sulfuric acid or by catalytic dehydration. The cis-configuration is somewhat unstable and is readily rearranged to the trans form by heating. Trans-aconitic acid is decarboxylated to itaconic acid by heating to 180°F. The cis form occurs in plant and animal tissues as a metabolic intermediate in the Krebs cycle during the isomerization of citric acid to isocitric acid by the action of enzyme aconitase.
OccurrenceReported found in beet root, sugarcane, the leaves and tubers of Aconitum napellus, and other natural products (Pelargonium species).
UsesAconitic Acid is a flavoring substance which occurs in the leaves and tubers of aconitum napellus l. And other ranunculaceae. Transaconitic acid can be isolated during sugar cane processing, by precipitation as the calcium salt from cane sugar or molasses. It may be synthesized by sulfuric acid dehydration of citric acid but not by the methanesulfonic acid method. It is used in a maximum level, as served, of 0.003% for baked goods, 0.002% for alcoholic beverages, 0.0015% for frozen dairy products, 0.0035% for soft candy, and 0.0005% or less for all other food categories.
Preparation methods
PreparationBy dehydration of citric acid with concentrated H2SO4: Aconitic acid prepared by this or other methods has the transconfiguration; the cis-isomer is little known. Trans-aconitic acid can be isolated during sugarcane processing by precipitation as the calcium salt from cane sugar or molasses.
Upstream & downstream products
Downstream products
Suppliers13 total
Additional notes
DefinitionChEBI: A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.
Related reactions
Linked notes
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