Aconitic Acid

Aconitic Acid Structure
CAS No.
499-12-7
Chemical Name:
Aconitic Acid
Synonyms
aconiticaci;ACONITIC ACID;citridinic acid;achilleaic acid;3-carboxyglutaconic acid;3-carboxy-2-pentenedioic acid;1-Propene-1,2,3-tricarboxylic acid;TRAN-1,2,3-PROPENE TRICARBOXYLIC ACID;Aconic acid;(1,2,3-Propenetricarboxylic acid)
CBNumber:
CB5928806
Molecular Formula:
C6H6O6
Molecular Weight:
174.11
MOL File:
499-12-7.mol
Modify Date:
2024/7/2 8:55:12

Aconitic Acid 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
solubility 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±0.36(Predicted)
color Colorless (white) crystal leaves or plates
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

Risk and Safety Statements

Toxicity LD50 intravenous in mouse: 180mg/kg

Aconitic Acid Chemical Properties,Uses,Production

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.

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.

Definition

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

Aconitic Acid Preparation Products And Raw materials

Raw materials

Preparation Products

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1-Propene-1,2,3-tricarboxylic acid 3-carboxy-2-pentenedioic acid 3-carboxyglutaconic acid achilleaic acid citridinic acid TRAN-1,2,3-PROPENE TRICARBOXYLIC ACID ACONITIC ACID Aconic acid;(1,2,3-Propenetricarboxylic acid) aconiticaci 499-12-7