Vernolic acid

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Structural formula
Structure of vernolic acid
Structural formula of the (12 R , 13 S ) isomer
General
Surname Vernolic acid
other names
  • (12 R , 13 S ) -12,13-epoxy-9- cis -octadecenoic acid ( IUPAC )
  • cis -12,13-epoxy oleic acid
  • Leukotoxin B
Molecular formula C 18 H 32 O 3
External identifiers / databases
CAS number
  • 503-07-1 [(+) - form]
  • 32381-42-3 [(-) - form]
  • 17966-13-1 [(±) - (racemate)]
PubChem 5281128
ChemSpider 4444572
Wikidata Q7922031
properties
Molar mass 296.45 g mol −1
Physical state

liquid

Melting point
  • 32.5 ° C [(+) - shape]
  • 30–31 ° C [(-) - form]
  • 35-36 ° C [(±) - (racemate)]
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 .

Vernolic acid is a naturally occurring, unsaturated, epoxidized fatty acid . It was first detected in 1954 in Vernonia oil, the seed oil of Baccharoides anthelmintica (Syn .: Vernonia anthelmintica ).

One isomer is coronaric acid (9 R , 10 S ) or (9 S , 10 R ) -9,10-epoxy-12- cis -octadecenoic acid. Vernolic acid and coronaric acid are the most common naturally occurring epoxied fatty acids.

Occurrence

Vernolic acid is the main component of vernonia oil. This is preferably extracted from the seeds ( achenes ) of the daisy family (Asteraceae) Centrapalus pauciflorus (Syn .: Vernonia galamensis ) and Baccharoides anthelmintica (Syn .: Vernonia anthelmintica ). It occurs in just as high concentrations in Acilepis aspera (Syn .: Vernonia roxburghii ), Vernonia volkameriifolia , Vernonia lasiopus and in Shorea laevis . The seeds contain up to 43% oil, which in turn consists of 54 to 80% vernolic acid. It is also found in larger amounts of over 50% in Euphorbia lagascae and in the cornflower aster ( Stokesia laevis ), in the Cephalocroton cordofanus and in Crepis species. Most of the time, the (+) isomer occurs in the Asteraceae. It also occurs in other species in lower concentrations and also as a (-) isomer.

use

Oils containing vernolic acid are suitable for the production of epoxy resins . It is comparable to epoxidized linseed oil in its application .

Individual evidence

  1. ↑ a b c d Frank D. Gunstone, John L. Harwood, Fred B. Padley: The Lipid Handbook. Second Edition, Chapmen & Hall, 1994, ISBN 0-412-43320-6 , pp. 50 f, 106, 120.
  2. ↑ JM Osbond: 1043. Essential fatty acids. Part II. Synthesis of (±) -vernolic, linoleic, and γ-linolenic acid. J. Chem. Soc. 1961; P. 5270 ff. Doi : 10.1039 / jr9610005270
  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. ↑ FD Gunstone: Fatty acids. Part II. The nature of the oxygenated acid present in Vernonia anthelmintica (Willd.) Seed oil. In: Journal of the Chemical Society (Resumed). 1954, p. 1611, doi : 10.1039 / JR9540001611 .
  5. ↑ Frank D. Gunstone, Fred B. Padley: Lipid Technologies and Applications. Marcel Dekker, 1997, ISBN 0-8247-9838-4 , p. 760.
  6. ↑ Denis J. Murphy: Plant Lipids. Blackwell, 2005, ISBN 1-4051-1904-7 , pp. 90 f.
  7. ↑ Ursula Biermann, Uwe Bornscheuer, Michael AR Meier, Jürgen O. Metzger, Hans J. Schäfer: Fats and oils as renewable raw materials in chemistry. In: Angewandte Chemie. 123, 2011, pp. 3938-3956, doi : 10.1002 / anie.201002767 .