Cucurbic acid

Structural formula
General
Surname	Cucurbic acid
other names	(+) - cucurbic acid; (1 R , 2 S , 3 S ) -3-Hydroxy-2- (2- ( Z ) -pentenyl) cyclopentane-1-acetic acid;
Molecular formula	C 12 H 20 O 3
External identifiers / databases
PubChem	5281159
ChemSpider	4444599
Wikidata	Q1143102
properties
Molar mass	212.29 g mol −1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cucurbic acid is a natural product that belongs to the jasmonate group.

Occurrence

Garden pumpkin

Cucurbic acid is found in garden pumpkins . Furthermore, (+) - cucurbic acid and its epimers in addition to jasmonic acid from Juglans regia (walnut blossom) and the spores of Anemia phyllitidis could be isolated and detected by means of mass spectrometry .

presentation

The representation of cucurbic possible, for example by the reduction of jasmonic acid :

With achiral reducing agents , only a low diastereoselectivity is achieved. However, the mixture of diastereomers can be separated by chromatography .

properties

(+) - Cucurbic acid is a chiral compound. It has a specific angle of rotation of + 9.6 ° ( c = 4 g / l, 26.0 ° C).

Biological effects

In Cymbidium orchids, like jasmonic acid, cucurbic acid leads to the formation of sprouts from the rhizome. It can therefore also be called a phytohormone .

Web links

Cucurbic acid Compound - C08482 in the Kyoto Encyclopedia of Genes and Genomes

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b ^c W. Dathe, C. Schindler, G. Schneider, J. Schmidt, A. Porzel, E. Jensen, I. Yamaguchi: Cucurbic acid and its 6,7-stereoisomers . In: Phytochemistry . tape 30 , no. 6 , 1991, pp. 1909-1914 , doi : 10.1016 / 0031-9422 (91) 85038-2 .
↑ Kerstin Weil: 3- (R) -hydroxy acids as products of selective fatty acid degradation: studies on β-oxidation in Stenotrophomonas maltophilia . Würzburg 2001, DNB 964105012 , urn : nbn: de: bvb: 20-1181440 (dissertation).
↑ Kazuhiko Shimasaki, Jiro Tsuneisi, Yasufumi Fukumoto: The Effects of Jasmonic Acid, Methyl-Jasmonate, and Cucurbic Acid on Organogenesis in Rhizome Segments of Cymbidium kanran Makino . In: Journal of Society of High Technology in Agriculture . tape 14 , no. 2 , 2002, p. 100-103 , doi : 10.2525 / jshita.14.100 .

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[dathe-2] W. Dathe, C. Schindler, G. Schneider, J. Schmidt, A. Porzel, E. Jensen, I. Yamaguchi: Cucurbic acid and its 6,7-stereoisomers . In: Phytochemistry . tape 30 , no. 6 , 1991, pp. 1909-1914 , doi : 10.1016 / 0031-9422 (91) 85038-2 .

[3] Kerstin Weil: 3- (R) -hydroxy acids as products of selective fatty acid degradation: studies on β-oxidation in Stenotrophomonas maltophilia . Würzburg 2001, DNB 964105012 , urn : nbn: de: bvb: 20-1181440 (dissertation).

[4] Kazuhiko Shimasaki, Jiro Tsuneisi, Yasufumi Fukumoto: The Effects of Jasmonic Acid, Methyl-Jasmonate, and Cucurbic Acid on Organogenesis in Rhizome Segments of Cymbidium kanran Makino . In: Journal of Society of High Technology in Agriculture . tape 14 , no. 2 , 2002, p. 100-103 , doi : 10.2525 / jshita.14.100 .