Chaulmoogric acid

Structural formula
	( S ) -enantiomer
General
Surname	Chaulmoogric acid
other names	( S ) -Cyclopent-2-en-1-tridecanoic acid; ( S ) -13- (2-cyclopentenyl) tridecanoic acid;
Molecular formula	C 18 H 32 O 2
External identifiers / databases
EC number	249-440-7
ECHA InfoCard	100.044.931
PubChem	72853
Wikidata	Q77250128
properties
Molar mass	280.45 g mol −1
Physical state	firmly
Melting point	69 ° C
boiling point	247-248 ° C (2.7 kPa)
solubility	soluble in diethyl ether and chloroform ; almost insoluble in water;
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Toxicological data	> 500 mg kg −1 ( LD , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chaulmoogric acid , also ( S ) -13- (2-cyclopentenyl) tridecanoic acid, is a fatty acid from the group of cyclopentenyl fatty acids . Its glycerol esters are found in particular in the eponymous Chaulmoogra oil , the seed oil of Hydnocarpus kurzii , as well as in the oils of Hydnocarpus wightianus and some related species from which it is also obtained. Chaulmoogric acid has an antimicrobial effect, but is also toxic to mammals.

Because of the double bond in the cyclopentene ring, chaulmoogric acid is to be regarded as a monounsaturated fatty acid.

history

It was first discovered by John Moss in 1879 and incorrectly referred to as gynocardic acid (after Gynocardia odorata ) because the plant seeds examined were incorrectly labeled. This error was discovered in 1901 and the name was corrected. The exact structure was only determined in later work.

Occurrence

Cyclopentenyl fatty acids such as chaulmoogric acid are found in some species of the Flacourtiaceae family (now considered obsolete) , including not only the Hydnocarpus species but also species of Caloncoba . But they can also be found in some representatives of the passion flower family and saffron mallow family .

properties

The acid is one of the unsaturated, branched and mono- cyclic , more specifically the alicyclic fatty acids and remains one of the aliphatic monocarboxylic acids . It contains a cyclopent- 2-ene ring at position 13 as a functional group . The abbreviated form of chaulmoogric acid is 18: 1cy. It belongs to the cyclopentenyl fatty acids like hydnocarpic acid (16: 1cy) or gorlic acid (18: 2cy-delta-6c). These three acids are optically active fatty acids, they have a clockwise rotation.

Chaulmoogric acid forms lamellar crystals and is not soluble in water, but easily soluble in ether or chloroform .

Biological importance

Similar to the related hydnocarpic acid, chaulmoogric acid has an antimicrobial effect and inhibits the growth of mycobacteria such as the tuberculosis pathogen Mycobacterium tuberculosis . When the cyclopentenyl ring is saturated, the inhibitory activity ceases. The addition of biotin also inhibits the antimicrobial effect. Accordingly, a disruption of the action of biotin by the cyclopentenic acids is discussed as the mechanism of action.

During studies in which mouse paws were infected in vivo with the leprosy pathogen Mycobacterium leprae , the addition of chaulmoogric acid prevented bacterial growth. In Indian folk medicine , Chaulmoogra or Hydnocarpus oils are used as a drug against leprosy and a number of other diseases. Although tests on mice may indicate a leprosy-inhibiting effect when using hydnocarpus oil, there are no valid studies to date that would prove effectiveness in humans, in particular therapeutic success.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on chaulmoogric acid. In: Römpp Online . Georg Thieme Verlag, accessed on August 30, 2017.
↑ ^a ^b ^c Chaulmoograsäure in the Lexikon der Chemie of the Spektrum-Verlag, accessed on August 30, 2017.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Entry on chaulmoogric acid in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on August 30, 2017.
↑ W. Heubner, J. Schüller (Ed.): Handbuch der Experimental Pharmakologie. 5th volume, Springer, 1937, ISBN 978-3-642-47286-2 (reprint), pp. 4, 10.
^ S. Coffey: Rodd's Chemistry of Carbon Compounds. Vol. II, Part A, Second Edition, Elsevier, 1967, p. 196.
↑ Markus Fischer, Marcus A. Glomb: Modern food chemistry . Behr's Verlag, 2015, ISBN 978-3-89947-864-8 , pp. 89 f . ( limited preview in Google Book search).
^ Adolf Grün : Analysis of fats and waxes. Volume 1: Methods , Springer, 1925, ISBN 978-3-642-89780-1 (reprint), p. 133.
↑ ^a ^b Hydnocarpus . In: Wolfgang Blaschek, Rudolf Hänsel, Konstantin Keller, Jürgen Reichling, Horst Rimpler, Georg Schneider (eds.): Hager's Handbook of Pharmaceutical Practice . 5th edition. Sequence Volume 2: Drug A-K . Springer, 1998, ISBN 978-3-642-63794-0 , pp. 863 ff . ( limited preview in Google Book search).

[Römpp-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on chaulmoogric acid. In: Römpp Online . Georg Thieme Verlag, accessed on August 30, 2017.

[Spek_Chem-2] Chaulmoograsäure in the Lexikon der Chemie of the Spektrum-Verlag, accessed on August 30, 2017.

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Entry on chaulmoogric acid in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on August 30, 2017.

[5] W. Heubner, J. Schüller (Ed.): Handbuch der Experimental Pharmakologie. 5th volume, Springer, 1937, ISBN 978-3-642-47286-2 (reprint), pp. 4, 10.

[6] S. Coffey: Rodd's Chemistry of Carbon Compounds. Vol. II, Part A, Second Edition, Elsevier, 1967, p. 196.

[7] Markus Fischer, Marcus A. Glomb: Modern food chemistry . Behr's Verlag, 2015, ISBN 978-3-89947-864-8 , pp. 89 f . ( limited preview in Google Book search).

[8] Adolf Grün : Analysis of fats and waxes. Volume 1: Methods , Springer, 1925, ISBN 978-3-642-89780-1 (reprint), p. 133.

[Hagers-9] Hydnocarpus . In: Wolfgang Blaschek, Rudolf Hänsel, Konstantin Keller, Jürgen Reichling, Horst Rimpler, Georg Schneider (eds.): Hager's Handbook of Pharmaceutical Practice . 5th edition. Sequence Volume 2: Drug A-K . Springer, 1998, ISBN 978-3-642-63794-0 , pp. 863 ff . ( limited preview in Google Book search).