Malvalic acid

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Structural formula
Structure of malvalic acid
General
Surname Malvalic acid
other names
  • 7- (2-octylcyclopropen-1-yl) heptanoic acid ( IUPAC )
  • Malvalic acid
  • Malvalic acid
Molecular formula C 18 H 32 O 2
External identifiers / databases
CAS number 503-05-9
PubChem 10416
ChemSpider 9987
Wikidata Q412814
properties
Molar mass 280.45 g mol −1
Physical state

liquid

Melting point

10.3-10.5 ° C

safety instructions
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 .

Malvalic acid (engl. Malvalic acid ), scientific 7- (2-Octylcyclopropen-1-yl) heptanoic acid, is a cyclic fatty acid which like the cyclopropane fatty acid to the Cyclopropensäuren counts. It is an aliphatic monocarboxylic acid with a cyclopropene ring in the carbon chain. The terms malvalic acid or malvalic acid are also used. The salts are called malvalates. The connection has been demonstrated in many mallow plants ( Malvaceae ). A few other occurrences are known, but overall malvalic acid occurs only rarely in the fatty acid spectrum of living beings.

Name and history

Malvalic acid was isolated from the mallow species Malva verticillata and Malva parviflora in 1956 . A little later, the (English) name malvalic acid was suggested, replacing the now outdated term halphen acid , which was derived from the halphen reaction .

The German translation of the English term malvalic acid is inconsistent. The name variants malvalic acid , malvalic acid and malvalic acid occur with comparable frequency. The term mallow acid is quite subordinate .

Occurrence

Within the mallow family (Malvaceae), malvalic acid is widespread as a component of the glycerides of seeds and leaves. A few examples of more well-known species are representative. This is how malvalic acid is found

Occurrences outside of the mallow family are rare. The two genera Welwitschia and Gnetum , which belong to the Nacktsamern and are closely related to one another, are such an exception - cyclopropenoid compounds also occur in their seed capsules, including malvalic acid. The liana Gnetum gnemon , which is used for human consumption, contains 38.6% malvalic acid in the fat content of its seeds (but with a relatively low total fat content of 4% in the dried seeds).

Malvalic acid is usually associated with sterculic acid, which is chemically very similar .

Biological importance

There is evidence that malvalic acid inhibits enzymatic dehydration processes in the liver , albeit less strongly than sterculic acid.

Analytics

Just like sterculic acid, malvalic acid also shows the Halphen reaction due to the cyclopropene ring . For example, an admixture of cottonseed oil to more expensive oils such as corn oil can be detected without a great deal of equipment; a content of 10 ppm or more of malvalic acid is sufficient for the color reaction.

Individual evidence

  1. ↑ a b F.S. Shenstone, JR Vickery: A biologically active fatty acid in Malvaceae. In: Nature. 177, p. 94, PMID 13288607 , doi : 10.1038 / 177094a0 .
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ JJ Mac Farlane, FS Shenstone, JR Vickery: Malvalic Acid and Its Structure. In: Nature . 179; 1957: pp. 830-831, PMID 13430715 , doi : 10.1038 / 179830a0 .
  4. ↑ a b c d e R. Hegnauer: Chemotaxonomy of plants. Volume 5. Birkhäuser Verlag, Basel 1969, ISBN 3-7643-0168-6 , p. 31 f.
  5. ^ S. Krist, G. Buchbauer, C. Klausberger: Lexicon of vegetable fats and oils. Springer-Verlag, Vienna 2008, ISBN 978-3-211-75606-5 , p. 36.
  6. ↑ R. Hegnauer: Chemotaxonomy of plants. Volume 6. Birkhäuser Verlag, Basel 1973, ISBN 3-7643-0667-X , p. 522.
  7. ↑ K. Aitzetmüller, K. Vosmann: Cyclopropenoic fatty acids in gymnosperms: The seed oil of Welwitschia. In: Journal of the American Oil Chemists' Society . 75 (12); 1998: pp. 1761-1765, doi : 10.1007 / s11746-998-0329-8 .
  8. ↑ W. Ternes, A. Täufel, L. Tunger, M. Zobel (eds.): Food Lexicon. 4th edition, Behr's Verlag, Hamburg 2005, ISBN 3-89947-165-2 , p. 672 f.
  9. ↑ E. Allen et al .: Inhibition by cyclopropene fatty acids of the desaturation of stearic acid in hen liver. In: Lipids. 2 (5), 1967, pp. 419-23, PMID 17805703 .
  10. ↑ J. Cao, JP Blond, J. Bezard: Inhibition of fatty acid delta 6- and delta 5-desaturation by cyclopropene fatty acids in rat liver microsomes. In: Biochim. Biophys. Acta . 1210 (1), 1993, pp. 27-34. PMID 7903050 .
  11. ↑ R. Hansel, O. Sticher: Pharmakognosie - Phytopharmazie. 9th edition, Springer Verlag, Heidelberg 2010, ISBN 978-3-642-00962-4 , p. 707.