Decanoic acid, sources

The most abundant fatty acids in vegetable oils and fats are palmitic acid (hexa-decanoic acid or 16 0), oleic acid ([9Z]-octadec-9-enoic acid or 18 1 cis-9), and lino-leic acid (cis, cis-9,12-octadccadicnoic acid or 18 2 cis-9 cis-12) [21], Other fatty acids are found in special oils (e.g. 80% 87% ricinoleic acid in castor oil) [23], but these oils are quite rare. Castor oil, for example, has a production rate of 610,000 tons/year compared to the top four palm oil (46 million tons/year), soya oil (40 million tons/year), rapeseed oil (24 million tons/year), and sunflower oil (12 million tons/ year) [24]. Further sources of fatty acids are tall oils (2 million tons/year) [25] and to a lesser degree synthetic fatty acids derived by mainly hydroformylation and hy-drocarboxylation of olefins [23], The summed fatty acid production is estimated to be 8 million tons/year (2006) [23],... 

Cuphea. Cuphea plants furnish seeds with oils that may be rich in Cg, Cjo, C12, or Ci4 acids. They generally contain >30% of oil and are expected to produce a commercial crop in the period 2005-2010. Problems of seed dormancy and seed shattering have already been solved. As markets for lauric oils already exist, there should be no difficulty in substituting cuphea oUs. More recently, it has been reported that cuphea will be used as a commercial source of lauric acid from 2003 onward (30, 102, 103). Pandey et al. (104) have described the oil (17-29%) from Cupea procumbens containing 89-95% of decanoic acid. See also Section 9.2. 

Farbood and Willis(68) in a recent patent application disclosed a process for production of optically active alpha-hydroxy decanoic acid (gamma-decalactone) by growing Yarrowia lipolytica on castor oil as a sole source of carbon. This is a good example of a commercial application of a volatile chemical produced by a microorganism. Yields of up to 6 grams per liter culture media were obtained making this a promising industrial fermentation. 

The origin of fatty acids and civetone in panda is unknown. Based on four samples of bladder urine obtained between 1999 and 2003, which were not from the days of peak excretion, decanoic acid and traces of octanoic and dodecanoic acid were also detectable in bladder urine. In addition, civeton was also demonstrated in bladder urine. Those findings might rule out the possibility of an extra-renal source from acessory glands of the reproductive tract. Octanoic and decanoic acid were also detected in a cotton wool swab from the female s anal gland three days after urinary peak excretion. 

A number of prodrugs in clinical use are esters of fatty acids. For example, haloperidol decanoate is of interest in slow-release preparations. This compound was hydrolyzed by such hydrolases as purified carboxylesterase but was reported to be stable in human blood or plasma and in a variety of rat tissue homogenates [107], The source of this apparent lack of reactivity was competitive binding to blood and tissue proteins. In other words, protein binding sequesters this very lipophilic prodrug and prevents enzymatic hydrolysis, thereby slowing its activation and prolonging its in vivo effects. 

Knothe, G., Cermak, S.C., Evangelista, R.L., 2009. Cuphea oil as source of biodiesel with improved fuel properties caused by high content of methyl decanoate. Energ. Euel 23,1743—1747. Miller, R.W., Earle, E.R., Woflf, I.A., 1964. Search for new industrial oils. IX. Cuphea, a versatile source of fatty acids. J. Am. Oil Chem. Soc. 41, 279—280. 

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