Petroselinic

Anodic Syntheses. Part XI. Synthesis of Tariric and Petroselinic Acid. J. Chem. Soc. [London] 1954, 1804. 

Ashraf, M., R. Ahmad, S. Mahood, and M. K. Bhatty. Studies of the essential oils of the Pakistani species of the family Umbelliferae. XLV. Ferula assa-foetida, Linn (Herra Hing) gum oil. Pak J Sci Ind Res 1980 23 68-69. Ashraf, M., R. Ahmad, S. Mahood, and M. K. Bhatty. Studies of the essential oils of the Pakistani species of the family Umbelliferae. Part XXXV. Ferula assafoetida, Linn (Hing) seed oil. Pak J Sci Ind Res 1979 22(6) 308-310. Kleiman, R., and G. E. Spencer. Search for new industrial oils 16. Umbelliflorae-seed oils rich in petroselinic acid. J Amer OU Chem Soc 1982 59 29-32. Rajanikanth, B., B. Ravindranath, and M. L. Shankaranarayana. Volatile polysulphides of asafoetida. Phytochemistry 1984 23(4) 899—900. Shankaranarayana, M. L., B. Raghavan, and C. P. Natarajan. Odorous compounds of asafetida. VII. Isolation and identification. Indian Food Pack 1982 36(5) 65-76. 

Daucus carota L. subsp. sative Hoffm. Nan He Chi (Carrot) (whole plant) Carotenes, lycopene, phytofluere, umbelliferone, alpha-pinene, camphene, myrcene, daucol, alpha-phellandrene, bisabolene, luteolin-7-glucoside, daucine, pyrrolidine, geraniol, citronellol, carotol, citral, caryophyllene, p-cymene, asarone, daucosterol, petroselinic acid.48 For chronic dysentery, worms, carminative, diuretic, emmenagogue, lower blood sugar, prevent cancer, diabetes, dyspepsia and gout. 

N.A. Limonene, coumarins, apiin, oleic, linoleic, palmitic, paliloleic, petroselinic, petroselaidic, stearic, myristic, and myristoleic acids, bergapten.99-102 110 It is carminative and antirheumatic. 

Fig. 11 Separation of phenacyl esters of the isomeric octadecenoic acids, petroselinic acid (6-18 1), oleic acid (9-18 1), and vaccenic acid (11-18 1) by HPLC on silver ion column (Nucleosil 5SA) loaded with silver ion eluted with dichloromethane-dichloroethane-acetonitrile 50 50 0. 25 (vol vol) detection light-scattering detector. (From W.W. Christie, Analusis 26 M38 (1998), reproduced with permission.)...

The metathesis of oleochemicals in the presence of ethylene, also called ethenolysis, provides an efficient way to a-oleftns and 0)-unsaturated esters, which are useful intermediates for the synthesis of polymers, fragrances, surfactants, lubricants, and others [51, 52], The ethenolysis of methyl oleate was demonstrated in 1994 by Grubbs et al. using C3 [32], They could reach productive turnovers of 130-140. In 2001, Warwel et al. carried out the ethenolysis of the methyl esters of oleic, erucic, 5-eicosenoic, and petroselinic acids also in the presence of C3 [53]. The reactions were performed at 50°C and 10 bar using 0.025 mol% of catalyst and gave conversions from 58% to 74%. 

The production of a,m-diesters from fatty esters can be realized via their SM as already explained, but it can also be performed by CM with methyl acrylate. The bulk CM of several unsaturated fatty acid methyl esters containing double bonds in different positions with methyl acrylate was studied by Rybak and Meier (Scheme 6) [43], C4 and C5 displayed very good activities with high conversions and CM selectivities. Among them, C5 showed the best performance for both methyl oleate (97% conversion, 92% selectivity, with 0.2 mol%) and methyl 10-undecenoate (99% conversion, 99% selectivity, with 0.1 mol%). The same conditions were successfully applied to methyl erucate and methyl petroselinate. The reaction conditions were further optimized, also considering the effect of 1,4-benzoquinone as additive for the reduction of double-bond isomerization [39], The CM of methyl 10-undecenoate and methyl acrylate worked with full conversions and high selectivity if five- to tenfold excess of methyl acrylate is used. Furthermore, using a 1 1 ratio between both reactants led, after optimization of the reaction... 

FIGURE 18.10 Increased synthesis of profilaggrin/filaggrin in human axilla skin detected by immunohisto-chemistry following a 3 week application of a 1 % petroselinic acid formulation. 

Watkinson, A. etal. PPAR alpha activators petroselinic acid as a novel skin benefit agent for antiperspirants, in Proceedings Oral Papers, 22nd IFSCC Congress, Podium, 2002, p. 11. 

Petroselinic acid, an isomer of oleic acid, is found in many seed oils of the Um-belliferae family (ranging from 50-90% of oil composition). It can be oxidised to adipic and lauric acids, and may have pharmaceutical and cosmetic applications. Coriander is being evaluated as a potential source of this fatty acid in Europe. 

The saponifiable portion of the fatty oil accounts for about 90% of the total fixed oil and is characterized by a very high content of octadecenoic acids. Petroselinic and oleic acid occur at similar levels and jointly comprise 74-85%, linoleic 7-16% and palmitic 4-8%, of the constituent fatty acids. During prolonged storage of the spice, the free fatty acid content gradually increases and this is a good indicator of the age of the material. The contents of fatty acids, sterols and total tocopherols in a deodorized oil derived from coriander seeds (yield up to 28%) are compared with those in sunflower oil and tests on the biological effects of coriander oil are reported by Mironova et al. (1991). Of the fatty acids present, total C18 1 acids (petroselinic acid + oleinic acids) constituted 80—82% and petroselinic acid alone 50—60%, and the food value was lower than that of sunflower oif. Kim et al. (1996) found the production of petroselinic acid from cell suspension cultures of C. Sativum. 

Stoyanova et al. (2003) reported an oil yield of 0.8% by C02 extraction, which is lower than that of conventional extraction methods. The major volatile compounds were petroselinic + oleic acids (C18 1, 66.9%) and palmitic acid (C16 0, 8.6%). 

Mekhedov, S., Cahoon, E.B. and Ohlrogge, J. (2001) An unusual seed-specific 3-ketoacyl ACP synthase associated with the biosynthesis of petroselinic acid in coriander. Plant Molecular Biology 47(4), 507-518. 

The yield and composition of the volatile fraction of the pentane extracts of leaves, stems and seeds of F. vulgare Mill, have been studied by Guillen and Manzanos (1996). The yield obtained from seeds was much higher than that obtained from leaves and stems. The volatile fraction of the pentane extract of the latter two has a higher concentration of terpene hydrocarbons and a smaller concentration of oxygenated terpene hydrocarbons than that of the seeds. Sesquiterpenes and the antioxidant vitamin E have been detected in the leaves and petroselinic acid in the seeds. Saturated aliphatic hydrocarbons with 25 or more carbon atoms have been found in all the plant parts. 

Of the fatty acid in the fixed oil, most of which is contained in the polygonal cells in the seed endosperm, total monounsaturated acids account for 10% and total polyunsaturated fatty acids 2%. The main components of an expressed oil are petroselinic acid (up to 75%), oleic acid (up to 25%), linoleic acid (up to 15%) and palmitic acid (up to 5%) (Weiss, 2002). 

Guiet et al. (2003) demonstrated that deuterium (2H) distribution in fatty acids was non-statistical and could be related to isotopic discrimination during chain extension and desaturation. Petroselinic acid (C18 1A6) (Fig. 21.4), a fatty acid characteristic of the seeds of the Apiaceae, has been shown to be biosynthesized from palmitoyl-ACP (C16 0) by two steps, catalysed by a dedicated A4-desaturase and an elongase. The isotopic profile resulting from this pathway is similar to the classical plant fatty acid pathway, but the isotopic fingerprint from both the desaturase and elongase steps shows important differences relative to oleic and linoleic acid biosynthesis. 

Guiet, S., Robins, R.J., Lees, M. and BillauIt, I. (2003) Quantitative 2H NMR analysis of deuterium distribution in petroselinic acid isolated from parsley seed. Phytochemistry 64(1), 227-233. 

Hughes and Rideal1 found that oleic and petroselinic acids are very 1 Proo. Boy. Soc. A, 140, 253 (1933). 

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