 Home > Encyclopedia > Aconitic acid

Aconitic acid

Aconitic acid structure

CAS No:
499-12-7
Formula:
C6H6O6
Chemical Name:
Aconitic acid
Synonyms:
1-Propene-1,2,3-tricarboxylic acid;Achilleaic acid;Achilleic acid;Aconitic acid;Citridic acid;Citridinic acid;Equisetic acid;3-Carboxyglutaconic acid;Pyrocitric acid;2-Pentenedioic acid,3-carboxy-;NSC 7616
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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-a

colourless or yellow crystals, leaves, or plates; pleasant winey acid taste; almost odourless

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-).|A tricarboxylic acid with the formula (COOH)-CH2-C(COOH)=CH-COOH.

Aconitic acid Basic Attributes

Molecular Weight：

174.10800

Exact Mass：

174.11

EC Number：

209-564-4

DSSTox ID：

DTXSID9060102

Color/Form：

LEAFLETS & PLATES FROM WATER|WHITE CRYSTALLINE POWDER|WHITE OR YELLOWISH CRYSTALLINE SOLID

Characteristics

PSA：

111.90000

XLogP3：

-0.44330

Appearance：

Solid

Density：

1.66g/cm3

Melting Point：

194-195 °C (decomp)

Boiling Point：

542.6ºC at 760 mmHg

Flash Point：

296ºC

Refractive Index：

1.57

Water Solubility：

2.45 M

Vapor Pressure：

3.29E-13mmHg at 25°C

Toxicity：

LD50 intravenous in mouse: 180mg/kg

Dissociation Constants：

K1 AT 25 °C= 1.58X10-3; K2= 3.5X10-5

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/

Safety Information

FDA Requirements：

FDA GRAS

Toxicity

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)...

Drug Information

MeSH Entry Terms：

Achilleic Acid

Aconitic acid Use and Manufacturing

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...

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.

Production

(1986) No Data

Manufacturing Info：

1-Propene-1,2,3-tricarboxylic acid, (1E)-: ACTIVE|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

Use Classification：

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index

Food Additive Classes：

Flavoring Agents

Computed Properties

Molecular Weight:174.11
XLogP3:-1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:174.01643791
Monoisotopic Mass:174.01643791
Topological Polar Surface Area:112
Heavy Atom Count:12
Complexity:251
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes