Euphorbia lagascae

Turley D, Eroment M, Cook S (2000) Development of Euphorbia lagascae as a new industrial oil crop. ADAS, Wolverhampton... 

Epoxidised oils (with isolated double bonds), such as epoxidised soybean are used as plasticisers. The natural occurrence of epoxidised fatty acids could be exploited to reduce processing costs on the pathway to polymerisation. For example, seed oils derived from Vernonia galamensis and Euphorbia lagascae both contain significant proportions (60-80%) of the epoxy acid vemolic acid, with interesting applications in greases and polyurethane applications (Turley et al., 2000). 

Turley, D.B., M.Froment and S. Cook (Eds) Development of Euphorbia Lagascae as a New Industrial Oil Crop, ADAS, Wolverhampton (2000). 

New oilseed crops, currently studied as potential sources of specialty fatty acids, include Crambe abyssinica for erucic acid, Limnanthes alba for very long-chain fatty acids, Dimorphotheca pluvialis for dimor-phecolic acid, Lesquerella fendleri for les-querolic acid, Calendula officinalis for calendic acid, and Euphorbia lagascae and various Vernonia species for vernolic acid.194 The lowest cost sources (inedible fats and oils and palm oil fractions) are likely most likely to be exhausted first as world trade in industrial applications grows. Cornstarch is becoming a major feedstock for plastics production. This may compete with potential oil uses, but also will increase production of com oil. 

Oils containing epoxy acids Several natural epoxy acids are known, but vernolic acid (12,13-epoxyoleic) is the most common and occurs at high levels in several seed oils. Of these, serious attempts are now being made to develop Vernonia galamensis (73-78% vemolic acid) and Euphorbia lagascae (57-62% vernolic acid) as commercial crops (198). Several potential uses of this acid and the seed oils in which it occurs are being explored. 

Seed oils also contain potentially useful fatty acids that have not been introduced into commerce because the plant has not yet been adapted to large-scale planting. Examples of such plants include Vernonia anthelmintica and Euphorbia lagascae,... 

Vernolic (epoxy) Octadeca-9c, 12,13-0-enoic Vernonia, Euphorbia lagascae Coatings, plasticizer... 

Vernolic 18 1 -9c,-epoxy- 12,13c Vernonia galamensis (77-81%) or Euphorbia lagascae (60-65%) oil... 

Gaboon EB, Ripp KG, Hall SE, McGonigle B. (2002) Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed. Plant Physiol 128 615-624. 

C.jHjjO, Mr 296.45, mp. 32.5 °C, [alg +2.03° (hexane), soluble in organic solvents. V. occurs in large amounts (60- 80%) as glycerol esters in the seed oils of Vemonia anthelmintica and V. galamensis (Astera-ceae) as well as Euphorbia lagascae (Euphorbiaceae). V. and other epoxy fatty acids are toxic compounds ... 

Another interesting oilseed crop tiiat has been researched in our laboratories for several years is Euphorbia lagascae (22) (Fig. 3). This oilseed crop contains vemolic acid (12,13 -epoxy-cis-9-octadecenoic acid), with a natural epoxide content of 65% (see Table 2). 

Powder coatings Epoxidized Euphorbia lagascae Epoxidized linseed oil Epoxidized Latterr antia ibcrica... 

The best known and most widely occurring of the natural epoxy acids is vernolic acid (12,13-epoxyoleic) which is present in the seed lipids of several different plant families. Rich sources of the acid include the seed oils of Vernonia anthelmintica (72%) in which it was first discovered, Cephalocroton cor-dofanus (62%) Euphorbia lagascae (57-62%), Er-langea tomentosa (52%), Crepis aurea (52-54%) and Crepis biennis (68%). Crepis oils are of interest in that some contain vernolic acid, others contain cre-penynic acid, and yet others contain both these acids even though there is no accepted biosynthetic relationship between the two. Most samples of vernolic acid are the (-1-) isomer but seed oils of the Malvaceae contain the (—) isomer. 

Dihydroxyoleic acid (30) (Fig. 2.15) is formed from vemolic acid (39) (which, in turn, is formed from linoleic acid) in crushed seeds of Xeranthemum annuum (As-teraceae) and Euphorbia lagascae (Euphorbiaceae). 

Epoxy fatty acids also are found as components of triglycerides of the seed oils (Smith, 1970). This unusual fatty acid type is sporadically distributed in species of several taxo-nomically unrelated plant families. Z-12,13-Epoxyoleic acid (vemolic acid) (39) (Fig. 2.15) is biosynthesized from linoleic acid in the seeds of Xemnthemum anmum and Euphorbia lagascae (Hitchcock and Nichols, 1971). This compound and Z-9,10-epoxy stearate are synthesized by the introduction of oxygen from O2 across the double bonds of linoleic and oleic acids, respectively (Butt and Lamb, 1981 Morris, 1970). The biosynthesis of epoxy fatty acids is related to that of dihydroxy fatty acids, and epoxy fatty acids may serve as precursors for the latter type of compound. 

Bafor, M., Smith, M.A., Jonsson, L., Stobart, K. and Stymne, S. (1993) Biosynthesis of vernoleate (cis-12-epoxyoctadeca-cis-9-enoate) in microsomal preparations from developing endosperm of Euphorbia lagascae, Arch. Biochem. Biophys. 303, 145-151. 

Vernolic (cz>12,13-epoxy-c/5 -9-octadecenoic) acid is an epoxy fatty acid which accumulates in the triglyceride of a few plant species such as Vemonia galamensis and Euphorbia lagascae. Vernolic acid has industrial applications such as in paints, plastic formulations, and protective coatings (1). 

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