Chlorocitric acid

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Chlorocitric acid
Chlorocitric acid.svg
Names
IUPAC name
1-chloro-2-hydroxypropane-1,2,3-tricarboxylic acid
Other names
Chlorocitrate, (−)-threo-chlorocitric acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C6H7ClO7/c7-3(4(10)11)6(14,5(12)13)1-2(8)9/h3,14H,1H2,(H,8,9)(H,10,11)(H,12,13)
    Key: PLYZXLXZNMQAAU-UHFFFAOYSA-N
  • OC(=O)CC(O)(C(Cl)C(O)=O)C(O)=O
Properties
C6H7ClO7
Molar mass 226.57 g·mol−1
soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chlorocitric acid is a organochlorine compound, a derivative of citric acid, belonging to the group of tricarboxylic acids and their derivatives, characterized by the presence of three carboxyl groups. [1] Its chemical formula is C6H7ClO7. [2] [3]

Contents

Natural occurrence

The acid has been detected in human blood. Chlorocitric acid is not a naturally occurring metabolite; it is found exclusively in individuals who have been exposed to this compound or its derivatives. From a scientific perspective, chlorocitric acid is considered to be part of the human exposome, which encompasses all exposures that individuals encounter throughout their lifetime and their impact on health. These exposures begin before birth and include environmental and occupational factors. [4]

Synthesis

Chlorocitric acid is obtained by the action of hypochlorous acid on aconitic acid in aqueus solution. [5]

Physical properties

The acid is uncrystallizible, soluble in water and ether. The compound decomposes when heated, releasing hydrochloric acid and oxycitric acid. [5]

Uses

There are reports suggesting that chlorocitric acid might be used as an anti-obesity agent. [6] [7]

See also

References

  1. ↑ Official Gazette of the United States Patent and Trademark Office: Patents. U.S. Department of Commerce, Patent and Trademark Office. 1984. p. 1278. Retrieved 8 April 2025.
  2. ↑ "NCATS Inxight Drugs — CHLOROCITRIC ACID". drugs.ncats.io. Retrieved 8 April 2025.
  3. ↑ "chlorocitric acid". chemsrc.com. Retrieved 9 April 2025.
  4. ↑ "Human Metabolome Database: Showing metabocard for Chlorocitric acid (HMDB0242538)". hmdb.ca. Retrieved 8 April 2025.
  5. 1 2 Watts (F.C.S.), Henry (1879). A dictionary of chemistry and the allied branches of other sciences. p. 510. Retrieved 9 April 2025.
  6. ↑ Sullivan, Ann C.; Dairman, Wallace; Triscari, Joseph (1 August 1981). "(−)-threo-chlorocitric acid: A novel anorectic agent" . Pharmacology Biochemistry and Behavior . 15 (2): 303–310. doi:10.1016/0091-3057(81)90192-1. ISSN   0091-3057. PMID   7312900 . Retrieved 9 April 2025.
  7. ↑ "CHLOROCITRIC ACID WEIGHT REDUCTION EFFECT". Citeline. 23 February 1987. Retrieved 9 April 2025.
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