Aconitic Acid Chemical Properties

Melting point:

192°C (rough estimate)

Boiling point:

225.05°C (rough estimate)

Density 

1.4285 (rough estimate)

refractive index 

1.5860 (estimate)

FEMA 

2010 | ACONITIC ACID

pka

2.39±0.36(Predicted)

Odor

Vegetative, musty and nutty with a dry, toasted nuance

JECFA Number

627

LogP

0.63

EPA Substance Registry System

1-Propene-1,2,3-tricarboxylic acid (499-12-7)

Safety Information

Hazardous Substances Data

499-12-7(Hazardous Substances Data)

Toxicity

LD50 intravenous in mouse: 180mg/kg

Aconitic Acid Usage And Synthesis

Identification

Description

Aconitic 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.

Regulatory Status

CoE: Approved. Bev.: 2 ppm; Food: 15 ppm
FDA: 21 CFR: 184.1007, 582.60
FDA (other): n/a
JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1999).

Usage

Reported uses (ppm): (FEMA, 1994)

Natural occurrence

Reported found in beet root, sugarcane, the leaves and tubers of Aconitum napellus, and other natural products (Pelargonium species).

Chemical Properties

Aconitic 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

Occurrence

Reported found in beet root, sugarcane, the leaves and tubers of Aconitum napellus, and other natural products (Pelargonium species).

Uses

Aconitic 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.

Definition

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

Preparation

By 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.

Taste threshold values

Taste characteristics at 25 ppm: nutty, vegetative, musty and slightly caramellic