Petroselenic acid

Glehnia littoralis F. Schmidt et Miq. Bei Za Seng (Beech silver-top) (leaf, root) Stigmasterol, beta-sitosterol, imperatorin, psoralen, osthenol-7-o-(3-gentiobioside, petroselenic acid, petroselidinic acid, polyine, polysaccharides, falcalindiol, anthocyanin, furanocoumarin.53 84 477-478,479,480-383- 384 Anthelmintic, for chronic bronchitis, cough and hoarseness, antiproliferative activities, antimycobacterial, immunosuppressive activities. 

Adipic acid for the preparation of nylon is made starting with benzene. It can be made from glucose via catechol, as shown by Frost and co-workers (see Chap. 9). It can also be made by the oxidation of petroselenic acid with ozone (12.1), the companion product lauric acid also being valuable.34... 

Petroselenic acid constitutes 70-80% of the seed oil of many species of Umbelliferae. This requires growing a new crop or putting the appropriate genes into a microorganism or higher plant (such as rapeseed). It may be possi-... 

Ajowan Oil, Ptychotis oil. Obtained by distillation of seeds of Carum copticum (DC.) Benth. Hook. (Ptychotis ajowan DC.), Vmbelliferae. Contains thymol, ft-pinene, p-cymene, dipentene, v-terpinCne fixed oil content includes petroselenic acid, oleic acid, linoleic acid, resin acids, and palmitic acid. Ref Fa rook et at J. Sci. Food Agr. 4, 132 (1953) E. Guenther, The Essential Oils IV, 551-2 (Van Nostrand, New York, 1950). 

When an extract of parsley seed is saponified and acidified, one of the fatty acids isolated is petroselenic acid, formula... 

CigH3402. Hydrogenation of petroselenic acid gives pure stearic acid. When petroselenic acid is treated with warm potassium permanganate followed by acidification, the only organic products are dodecanoic acid and adipic acid. The NM R spectrum shows absorptions of vinyl protons split by coupling constants of 7 Hz and 10 Hz. Propose a structure for petroselenic acid, and show how your structure is consistent with these observations. 

Petroselenic acid is c/s-6-octadecenoic acid. 2530. The sugarlike head is polar and hydrophilic, and the alkane-like tail is nonpolar and hydrophobic. This is a good nonionic surfactant (that is, an uncharged detergent). 

All parts of the plant are aromatic. The leaves are used as a pot-herb. The petioles are used as such for salads or as vegetable. The bulbs of the whole plant as well as the stems are used as vegetable also. The seeds contain, beside the - essential oil, also around 20% of fatty oil, which is composed of about 80% of - petroselenic acid, which may be... 

The only large-scale application is the splitting of - oleic acid into - pelaigonic and - azelaic acid and of - erucic acid into - pelaigonic and - brassylic acid. - Petroselenic acid yields - lau-ric and adipic acid. 

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