Petroselinic acid oils

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. 

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. 

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). 

Caraway (Camm carvii). This is one of a group of plants whose seed oils contain petroselinic acid (6-18 1). This acid reaches levels of 35 3% in caraway, 66-73% in carrot, 31-75% in coriander, and 80% in parsley. This isomer of oleic acid has some potential use as a source of lauric and adipic acids, produced by oxidative cleavage. The latter, an important component of many polyamides (nylons), is usually made from cyclohexane by a reaction that is reported to be environmentally unfriendly (90). 

Figure 22.2 [A] General triglyceride structure and fatty acid percentage composition of common plant oil. [B] Fatty acids commonly used in polymer chemistry [a] oleic acid, [b] linoleic acid, (c) linolenic acid, [d] erucic acid, [e] petroselinic acid, [f] ricinoleic acid, [g] vernolic acid, [h] 10-undecenoic acid (reprinted with permission of Montero de Espinosa et al., 2011, Elsevier [10]].

Decyl ketene dimer Tetradecyl ketene dimer Octadecyl ketene dimer Docosyl ketene dimer Phenyl ketene dimer Cyclohexyl ketene dimer Naphthenic acid ketene dimer 10-Dodecylenic acid ketene dimer Oleic acid ketene dimer Petroselinic acid ketene dimer Linoleic acid ketene dimer Eleostearic acid ketene dimer Parinaric acid ketene dimer Gadoleic acid ketene dimer Cetoleic acid ketene dimer Selacholeic acid ketene dimer Babassu oil ketene dimer Palm oil ketene dimer Peanut oil ketene dimer Beef tallow ketene dimer... 

Petroselinic acid (18 1 6c) is an isomer of oleic acid which occurs widely in seed oils of the order Umbel-liferae (35-85%) usually along with oleic acid and other saturated and unsaturated acids. The co-occurrence of petroselinic and oleic acids complicates the analysis of these seed oils and the two isomers are usually distinguished after ozonolysis. Kleiman and Spencer (1982) analysed over 200 petroselinic acid-containing oils and designated 14 which were especially rich sources of this acid. The seeds contained 32-50% of oil and the oil had 52-87% of petroselinic acid. 

Petroselinic acid (18 1 6c) can be isolated from parsley seed oil by methanolysis followed by crystallization from acetone at — 30°C and urea fractionation. 

Gunstone, F. D. (1993b) The C-NMR spectra of six oils containing petroselinic acid and of aquilegia oil and meadowfoam oil which contain A5 acids. Chemistry and Physics of Lipids, 58, 159-67. 

This genus formerly know as Umbelliferae contain petroselinate (cis-6-octadecenoate) esters in their seed oil. Most interest has focused on the possible oxidation of petroselinic acid at its double bond to produce adipic and lauric acids for industrial purposes (Kleiman, 1990 Knapp, 1990). Several of the Apiaceae are food plants, notably carrots and coriander. Although humans have not usually consumed much petroselinate in their diets, there is no reason to assume that petroselinate-rich oils would not be acceptable food oils. The Apiaceae produce seed with 20-50% oil and 15-30% protein. The petroselinate content of the oil varies from about 30 to 80%. Experiments are underway to transfer the genes for making petroselinate into other oilseed crops. 

Various positional isomers exist in nature and c/s-6-octadecenoic acid (petroselinic acid) is found in seed oils of the Umbelliferae, for example, while c/s-11-octadecenoic acid is the major unsaturated fatty acid... 

Parsley seed oil contains mainly apiole, myristicin, tetrametboxyallybenzene, and a-pinene. It also contains petroselinic acid and other volatile fatty acids (see also celery seed oil) ... 

Unsaturated fatty compounds such as oleic acid, petroselinic acid, erucic acid, ricinoleic acid, linoleic and linolenic acid, andlO-undecenoic acid and also the respective esters, alcohols and native oils are alkenes, and contain an electron-rich C—C double bond that can be functionalized in many different ways by reactions with electrophilic reagents [287]. 

Coriander (Coriandrum sativum L.) is an herbaceous crop widely grown for the herb cilantro and for coriander seed, a common spice (Evangelista et al., 2015). The seed contains oil consisting of 57-75% petroselinic acid (Fig. 11.11.1), 6-cw-octadecenoic acid (Isbell, 2009). Ozonolysis of petrosele-nic acid would produce lauric acid (C12 0) for use in surfactants and adipic acid for Nylon 6,6 (Millam et al., 1997). The seed produces 12.8-30.2% oil with yields averaging 900-1120 up to 2800 kg/ha but has yet to achieve success as an oilseed crop (Isbell, 2009). Attempts to engineer petroselinic acid production in transgenic crops have also proven problematic (Suh et al., 2002). 

The dried fruits are an important ingredient of spices, such as curry powder, seasonings, confectionery and flavoring spirits. The fruits contain a volatile oil, which is used for flavoring and also in pharmacy. Besides the - essential oil, c. seeds also contain a fatty oil at about 20% of the - seed weight, where the major fatty acid component is - petroselinic acid at about 80%. 

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%). 

The list of natural fatty acids exceeds 1000, but commercial interest is limited to a smaller number— perhaps around 20. Ignoring the lipid membrane, rich in ot-lino-lenic acid and present in all green tissue, the three dominant acids in the plant kingdom are palmitic, oleic, and linoleic, sometimes accompanied by stearic acid and by linolenic acid. Others, occuring in specialty oils, include myristic, lauric, erucic, hexadecenoic, petroselinic, y-linolenic acid, eleostearic and isomers, ricinoleic, and vemolic (Table 1). 

Rapeseed oils still higher in lauric acid, high in erucic, palmitic, oleic, or linoleic acid, or containing Cg and Cjo acids, myristic, stearic, petroselinic, ricinoleic, vernolic, or y-linolenic acid, and wax esters in place of the normal triacylglycerols (Table 11). 

Petroselinic add (Z)-6-octadecenoic acid]. H3C-(CH2),o-CH=CH-(CH2)4-COOH, C,gH3402, Mr 282.47, mp. 32-33°C, bp. 215-217°C (0.2-0.3 kPa) soluble in organic solvents. P. was first found as the glycerol ester in the seed oil of parsley (Petro-selinum crispum), it is a characteristic component of the seed oils of umbelliferous and ivy plants. The fatty acids of these seed oils contain up to 87% P. (e.g. fat coriander oil, 75-80%). P. is also used as a starting material in oleochemistry. For nutritional-physiological aspects, see Lit.. ... 

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