Aconitic Acid
Basic information
- CAS
499-12-7- 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
Overview
Aconitic acid is a tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3. It is a conjugate acid of an aconitate(3-).
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 ACID499-12-71-Propene-1,2,3-tricarboxylic acidAchilleic acidCitridic acid3-Carboxy-2-pentenedioic acidDTXSID9060102Propene-1,2,3-tricarboxylic acidCHEBI:22211FEMA No. 201093371T1BXPNSC-7616
Show more names
aconiticaci3-carboxyglutaconic acidAconitic Acid, 10 mM in DMSOTRAN-1,2,3-PROPENE TRICARBOXYLIC ACIDAconic acid(1,2,3-Propenetricarboxylic acid)
RefChem:388769DTXCID5040756207-877-02-Pentenedioic acid, 3-carboxy-Achilleaic acidCitridinic AcidEquisetic 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
- Formal charge
- 0
- Complexity
- 251
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Organic Acids
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Color/Form
LEAFLETS & PLATES FROM WATER
WHITE CRYSTALLINE POWDER
WHITE OR YELLOWISH CRYSTALLINE SOLID
Solubility
1 G DISSOLVES IN 5.5 ML WATER @ 13 °C, 2 ML @ 25 °C; SOL IN 2 PARTS 88% ALCOHOL @ 12 °C; SLIGHTLY SOL IN ETHER
soluble in water and alcohol
(in ethanol)
DecompositionWhen heated to decomp ... emits acrid smoke.
Melting Point194-195 °C (WITH DECOMP)
Physical Description
White to yellowish solid; [Hawley]
colourless or yellow crystals, leaves, or plates; pleasant winey acid taste; almost odourless
Dissociation ConstantsK1 AT 25 °C= 1.58X10-3; K2= 3.5X10-5
Other Experimental Properties
DECOMP @ 209 °C (ELECTRICALLY HEATED BAR); DECOMP 198-199 °C (CAPILLARY IN OIL BATH @ 190 °C), 204-205 °C (CAPILLARY IN OIL BATH @ 195 °C)
NEEDLES FROM WATER; SOL IN WATER; SLIGHTLY SOL IN ETHER; MAX ABSORPTION (WATER): 389 NM (LOG E= 2.69); 411 NM (LOG E= 2.78) /CIS/
LEAFLETS FROM WATER & NEEDLES FROM WATER & ETHER; VERY SOL IN WATER; SOL IN ALCOHOL; SLIGHTLY SOL IN ETHER; SADTLER REF NUMBER: 23512 (IR, PRISM); MAX ABSORPTION: 411 NM (LOG E= 2.88); 432 NM (LOG E= 2.88) /TRANS/
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 information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 97.8% (89 of 91) of all reports.
Not Classified
Aggregated GHS information provided per 91 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 1-Propene-1,2,3-tricarboxylic acid
1-Propene-1,2,3-tricarboxylic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazards SummaryEmergency treatment: non-toxic ingestion; Generally regarded as safe (GRAS) in food; [HSDB] Safe when used as a flavoring agent in food; [JECFA]
FDA RequirementsFDA GRAS
Hazard Classes and CategoriesNot Classified
Toxicology
Natural Pollution Sources
...IN LEAVES & TUBERS OF ACONITUM NAPELLUS L, RANUNCULACEAE, IN VARIOUS SPECIES OF ACHILLEA (COMPOSITAE) & EQUISETUM (EQUISETACEAE), IN BEET ROOT & IN SUGAR CANE.
...ISOLATED FROM EQUISETUM PALUSTRE (MARSH HORSETAIL)...
Regulatory information
FDA RequirementsFDA GRAS
Safety data
- tsca
- TSCA listed
- Toxicity
- LD50 intravenous in mouse: 180mg/kg
- Hazardous Substances Data
- 499-12-7(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Naturally present in the leaves and tubers of beet root, sugar cane, and other plants; Used as a plasticizer for buna rubber and plastics and to make itaconic acid;; [Merck Index] Used as a flavor, antioxidant, and in the preparation of plasticizers and wetting agents; [HSDB]
MFR ITACONIC ACID; AS PLASTICIZER FOR BUNA RUBBER & PLASTICS; USED AS TRIETHYL OR TRIBUTYL ESTER
SYNTHETIC FLAVORING SUBSTANCE & ADJUVANT
PREPN OF PLASTICIZERS & WETTING AGENTS; ANTIOXIDANT; ORG SYNTHESES
U.S. Exports(1986) No Data
U.S. Imports(1986) No Data
U.S. Production(1986) No Data
Methods of Manufacturing
...COMMERCIALLY FROM CALCIUM MAGNESIUM ACONITATE RECOVERED FROM SUGAR CANE JUICE: MCCALIP, SEIBERT, IND ENG CHEM 33, 637 (1941); FROM MOLASSES: REGNA, BRUINS, IND ENG CHEM 48, 1268 (1956). MOST OF COMMERCIAL ACONITIC ACID IS, HOWEVER, MANUFACTURED BY SULFURIC ACID DEHYDRATION OF CITRIC ACID: BRUCE, ORG SYN COLL VOL II, P 12 (1943); BY USING METHANESULFONIC ACID INSTEAD OF SULFURIC: CRANSTON, US PATENT 2,727,066 (1955 TO DANIEL F KELLY). ...PREPD BY ANY OF ABOVE METHODS HAS THE TRANS-CONFIGURATION...
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
1-Propene-1,2,3-tricarboxylic acid: INACTIVE
REPORTED USES: NON-ALCOHOLIC BEVERAGES 0.20-2.0 PPM; ALCOHOLIC BEVERAGES 20 PPM; ICE CREAM, ICES, ETC 0.60 PPM; CANDY 0.60-3O PPM; BAKED GOODS 0.60-15 PPM; CHEWING GUM 28 PPM
FEMA NUMBER 2010
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
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
Compound notes
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