Aconitic Acid

HCID 309CAS 499-12-7

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

ACONITIC ACIDAchilleic acid499-12-71-Propene-1,2,3-tricarboxylic acidCitridic acidEquisetic acid3-Carboxy-2-pentenedioic acidDTXSID9060102CHEBI:22211Propene-1,2,3-tricarboxylic acidFEMA No. 201093371T1BXP
Show more names
aconiticaci3-carboxyglutaconic acidAconitic Acid, 10 mM in DMSOTRAN-1,2,3-PROPENE TRICARBOXYLIC ACIDAconic acid(1,2,3-Propenetricarboxylic acid)
NSC-7616RefChem:388769DTXCID5040756207-877-02-Pentenedioic acid, 3-carboxy-Achilleaic acidCitridinic AcidGlutaconic acid, 3-carboxy-

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

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

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 · 3 items

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 · 1 item

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

成都彼样生物科技有限公司18108052721 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]

Additional notes

DefinitionChEBI: A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.

Related reactions

1 records

Linked notes

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