499-12-7 Usage
Description
Propene-1,2,3-tricarboxylic acid, also known as aconitic acid, is a tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2, and 3. It has a pleasant, winey, acid taste and is almost odorless. Aconitic acid occurs naturally in beet root, sugarcane, the leaves and tubers of Aconitum napellus, and other natural products like Pelargonium species. It can be synthesized from citric acid by dehydration with sulfuric acid or by catalytic dehydration.
Uses
1. Used in Food Industry:
Propene-1,2,3-tricarboxylic acid is used as a flavoring substance in various food categories for its nutty, vegetative, musty, and slightly caramellic taste characteristics. It is used in alcoholic beverages, baked goods, frozen dairy products, nonalcoholic beverages, and soft candy.
2. Used in Pharmaceutical Industry:
Aconitic acid is used as a metabolic intermediate in the Krebs cycle during the isomerization of citric acid to isocitric acid by the action of enzyme aconitase. This makes it potentially useful in the development of pharmaceuticals targeting metabolic processes.
3. Used in Chemical Synthesis:
Aconitic acid can be synthesized from citric acid by dehydration with sulfuric acid or by catalytic dehydration, making it a useful compound in the chemical synthesis industry for producing other organic compounds.
4. Used in Sugar Cane Processing:
Trans-aconitic acid can be isolated during sugar cane processing by precipitation as the calcium salt from cane sugar or molasses, making it a valuable byproduct in the sugar industry.
5. Used in Flavor and Fragrance Industry:
Aconitic acid's unique taste and odor characteristics make it a potential candidate for use in the flavor and fragrance industry to create specific sensory profiles for various products.
Identification
▼▲
CAS.No.:?
499-12-7?
FL.No.:?
8.033
FEMA.No.:?
2010
NAS.No.:?
2010
CoE.No.:?
33
EINECS.No.:?
207-877-0?
JECFA.No.:?
627
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).
Natural occurrence
Reported found in beet root, sugarcane, the leaves and tubers of Aconitum napellus, and other natural products (Pelargonium species).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 499-12-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 9 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 499-12:
(5*4)+(4*9)+(3*9)+(2*1)+(1*2)=87
87 % 10 = 7
So 499-12-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)
499-12-7Relevant articles and documents
Synthetic method of itaconic acid intermediate 3-carboxy-2-pentene-1,5-diacid
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Paragraph 0007; 0015; 0016, (2016/11/24)
The invention provides a synthetic method of an itaconic acid intermediate 3-carboxy-2-pentene-1,5-diacid. The synthetic method comprises the following steps: adding 310ml of cyclohexane, 1.3mol of 2-bromo-nitrobenzene solution, 1.6-1.9mol of 3-amino-1,3,5-pentanoic triacid solution and 0.56mol of cuprous chloride to a reaction vessel on which a stirrer, a thermometer and a dropping funnel are installed, controlling the stirring speed at 150-190rpm, raising the temperature of the solution to 110-115 DEG C, reacting for 3-5 hours, reducing the temperature of the solution to 60-65 DEG C, controlling the stirring speed at 200-230rpm, continuously reacting for 90-120 minutes, separating out a solid, carrying out suction filtration, adding the solid to 200ml of oxalic acid solution, stirring the materials for 30-50 minutes, carrying out suction filtration, adopting ethyl acetate for washing and a dehydrating agent for dehydration and carrying out recrystallization in nitromethane, thus obtaining the crystal 3-carboxy-2-pentene-1,5-diacid.