10282. Hydroxycitric Acid

Nomenclature

CAS number: 27750-10-3; 6205-14-7 (unspecified stereo)
3-C-Carboxy-2-deoxy-d-erythro-pentaric acid; (1S,2S)-1,2-dihydroxy-1,2,3-propanetricarboxylic acid; ()-2-hydroxycitric acid; garcinia acid.
C6H8O8; mol wt 208.12.
C 34.63%, H 3.87%, O 61.50%.

Description and references

Principal acid found in the fruit of various species of garcinia, q.v., especially the Malabar tamarind, Garcinia cambogia Desr., Guttiferae (alt. Clusiaceae). Nutraceutical used in weight loss preparations. Competitive inhibitor of ATP-citrate lyase, a key enzyme in lipogenesis. Synthesis (unspecified stereo): H. Kiliani, P. Loeffler, Ber. 37, 3612 (1904); of all four stereoisomers: C. Martius, R. Maué, Z. Phys. Chem. 269, 33 (1941). Isoln from G. cambogia: Y. S. Lewis, S. Neelakantan, Phytochemistry 4, 619 (1965) DOI; Y. S. Lewis, Methods Enzymol. 13, 613 (1969) DOI. Abs config of lactone: J. P. Glusker et al., Arch. Biochem. Biophys. 132, 573 (1969) DOI PubMed. Enzyme inhibition: J. A. Watson et al., ibid. 135, 209 (1969) DOI PubMed; and effect on lipogenesis: A. C. Sullivan et al., ibid. 150, 183 (1972) DOI PubMed. HPLC determn in commercial extracts: G. K. Jayaprakasha, K. K. Sakariah, J. Liq. Chromatogr. Relat. Technol. 23, 915 (2000) DOI. GC-MS determn in blood: Y. C. Loe et al., Anal. Biochem. 292, 148 (2001) DOI PubMed. Review of chemistry and biological effects: B. S. Jena et al., J. Agric. Food Chem. 50, 10-22 (2002) DOI PubMed.

Chemical structure

Properties

[α]D20 20°. Rapidly cyclizes to the lactone form.

Derivative

Calcium potassium salt.

Nomenclature

CAS number: 449158-84-3
Super Citrimax (InterHealth).

Description and references

Unspecified mixed calcium and potassium salts. Description and safety assessment: M. G. Soni et al., Food Chem. Toxicol. 42, 1513 (2004) DOI PubMed. Review of clinical experience for weight management: H. G. Preuss et al., J. Med. 35, 33-48 (2004) PubMed.

Properties

Highly sol in water. LD50 orally in rats: >5000 mg/kg; dermally in rabbits: >2000 mg/kg (Preuss).

Derivative

Hydroxycitric acid lactone.

Nomenclature

CAS number: 27750-13-6
Garcinia lactone.
C6H6O7; mol wt 190.11.
C 37.91%, H 3.18%, O 58.91%.

Properties

Slightly hygroscopic needles, mp 178°. [α]D20 +100° (c = 2 in water). Very sol in alcohol, water. Fairly sol in ether.

Derivative

allo-Hydroxycitric acid.

Nomenclature

CAS number: 27750-11-4
3-C-Carboxy-2-deoxy-d-threo-pentaric acid; allohydroxycitric acid; hibiscus acid.

Description and references

Naturally occurring isomer found in hibiscus flowers. Isoln from Hibiscus sabdariffa L., Malvaceae: C. Griebel, Z. Unters. Lebensm. 77, 561 (1939) DOI.

Properties

[α]D20 +31°.

Derivative

allo-Hydroxycitric acid lactone.

Nomenclature

CAS number: 469-72-7
Hibiscus lactone.
C6H6O7; mol wt 190.11.
C 37.91%, H 3.18%, O 58.91%.

Properties

Hygroscopic needles, mp 183°. [α]D20 +122° (c = 2 in water). Very sol in water, alcohol; slightly sol in ether.

Use

Dietary supplement; weight loss aid.