10-hydroxy-decanoate

Lipase CA also polymerized hydrophobic oxyacids efficiently. The DP value was beyond 100 in the polymerization of 16-hydroxyhexadecanoic acid, 12-hydroxy dodecanoic acid, or 10-hydroxy decanoic acid under vacuum at high temperature (90°C) for 24 h, whereas the polyester with lower molecular weight was formed from 6-hydroxyhexanoic acid under similar reaction conditions. This difference may be due to the lipase-substrate interachon. 

Heating methyl ricinoleate with two saponifying equivalents of sodium hydroxide in the presence of 1-octanol or 2-octanol at 185-195 C leads to production of 10-hydroxy decanoate and methyl hexyl ketone (Hargreaves and Owen, 1947 Diamond and Applewhite, 1967). The 10-hydroxy-decanoate can be polymerized by heating with catalyst for ester formation, or by hpase action to condense the monomers into polyesters (Mahapatro et al., 2004). The enzymatic approach eliminates possible side reactions caused by heating. The ketone co-product is used in flavorings and perfumes. 

Sulfonation yields turkey red oil (- sulfated fats and oils), which is used in - textile auxiliaries. Alkali fusion of c. dissolved in octane at 180-200 °C yields methyl hexyl ketone and 10-hydroxy decanoic acid. At 250-275 °C, octanol-2 and - sebacic acid are obtained. 

Figure 15.7 Cliromatographic separation of cliiral hydroxy acids from Pseudomonas aeruginosa without (a) and with (h) co-injection of racemic standards. Peak identification is as follows 1, 3-hydroxy decanoic acid, methyl ester 2, 3-hydroxy dodecanoic acid, methyl ester 3, 2-hydroxy dodecanoic acid, methyl ester. Adapted from Journal of High Resolution Chromatography, 18, A. Kaunzinger et al., Stereo differentiation and simultaneous analysis of 2- and 3-hydroxyalkanoic acids from hiomemhranes hy multidimensional gas cliromatog-raphy , pp. 191 -193, 1995, with permission from Wiley-VCH. (continuedp. 419)...

Two different PHA biosynthesis gene loci were recently cloned [95]. The PHA negative mutant of R. eutropha harboring the Pseudomonas sp. PHA biosynthesis locus produced PHA consisting of 3HB, 3HHx, 3HO, and 3-hydroxy-decanoate (3HD), 3-hydroxydodecanoate (3HDD) with the PHA content of up to 14 wt % of CDW. 

Fig. 4.7 Infarct sizes of beta-adrenergic preconditioned hearts effects of 5-hydroxy-decanoate (1 x 10-4M) or adenosine deaminase (0.3U/ml) pretreatment. The drugs were given for 5 min before and during the administration of isoproterenol (lx 10-7 M).

Candida strains convert ricinoleic acid into If-decalactone, which displays the fatty, fruity aroma typical of peaches. Ricinoleic acid (12-hydroxy octadec-9-enoic acid) is the major fatty acid in castor oil (approx. 80 %). The yeast can lipolyze castor oil glycerides and the liberated ricinoleic acid is subsequently metabolized via d-oxidation and eventually converted to 4-hydroxy-decanoic acid (Figure 5). Recently a European patent has been filed (20) essentially covering the same procedure. Shake culture fermentations were carried out on 100 ml scale for one week. The 4-hydroxydecanoic acid formed was converted to )f-decalactone by boiling the crude, acidified (pH 1.5) fermentation broth for a period of 10 minutes. The lactone was isolated via solvent extraction and a yield of some 5 g/1 was obtained. The same lactone was detected as the major volatile component formed when the yeast, Sporobolomyces odorus was grown in standard culture medium (21). Although the culture medium displayed an intense fruity, typical peach-like odor, the concentration of y-decalactone amounted to no more than 0.5 mg/1. 

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. 

Microginins, a main class of cyanobacte-rial peptides from Microcystis, Planktothrix, and Nostoc. The linear peptides vary in length from four to six amino acids, contain a C-terminal 3-amino-2-hydroxy-decanoic acid moiety (Ahda), and two tyrosine units at the C-terminus. The first member was isolated from the freshwater blue-green alga Microcystis aeruginosa (NIES-100), and is an inhibitor of angiotensin-converting enzyme [T. Okino et al.. Tetrahedron Lett. 

Farbood, M. and Willis, B. (1985) Optically active gamma-hydroxy decanoic acid preparation by cultivating microorganism to hydrolyse castor oil and subjecting to /J-oxidation. Patent US 4,560,656. 

The FT-IR spectra of pure PHA containing short-chain-length monomers, such as hydroxybutyrate (HB), medium-chain-length hydroxyalkanoate (mclHA) monomers including hydroxyoctanoate (HO) and hydroxy-decanoate (HD), or both HB and mclHA monomers, show their strong characteristic band at 1728, 1740, and 1732 cm respectively. Other accompanying bands near 1280 and 1165 cm help identify the types of PHA. The intensity of the methylene band near 2925 cm" provides additional information for PHA characterization. In comparison, bacterial... 

A (1 — SO-coupled compound between methyl (3/ )-3-[(3 / )-3 -hydroxy-decanoyloxy]decanoate and 2-0-a-L-rhamnopyranosyl-o -L-rhamnopyra-nose, a rhamnolipid from Pseudomonas aeruginosa, expected to have various biological activities, was prepared by double couplings using 3,4-di-0-benzyl-2-0-chloroacetyl-a-L-rhamnopyranosyl fluoride (by the BFj- OEtj method). 

Another process patented by Givaudan uses Mucor circinelloides as a biocatalyst for the production of 4-decanolide [228]. Here the natural substrate is the ethyl ester of decanoic acid which is isolated from coconut oil. The key microbial activity harnessed in this process is the stereoselective and regioselective hydroxylation of the fatty acid in the y-position, which is followed by spontaneous lactonisation of the hydroxy fatty acid under acidic conditions and results in yields of up to 10.5 g 4-decanolide after 60 h. 

Decanoic Acid HepUideeafluoro-2-hydroxy-2H- E10b2. 44 [Oxiran -> C(OH) —COOH]... 

Decanoic Acid 9-Fluoro-l 0-hydroxy-ElOb,. 593 (Educt)... 

D-Phenyl propionates of methyl esters of racemic hydroxy acids were prepared by Hammarstrom and Hamberg [190] and used for the separation of enantiomers of these compounds on QF-1. The separation was successful with methyl 3-, 15-, 16- and-17-hydroxyoctadecanoates, whereas diastereoisomers of methyl 4-, 7- and 13-hydroxyocta-decanoic acids were not separated. The derivatives were prepared at room temperature reaction of the ester of the hydroxy acid with D-2-phenylpropionyl chloride in the presence of pyridine for 2 h. 

The objective of grafting absorbable lipases such as esterastin or tetrahydroestrastin onto a non-absorbable biocompatible substrate is to rendere the product non-absorbable. The non-absorbable lipase (2S,3S,5S)-5-[(S)-2-formamido-4-methyl-valeryloxy]-2-hexyl-3-hydroxy-hexa decanoic 1,3 acid lactone is described (1). 

Disposition in the Body. The hydrochloride is well absorbed after oral administration the decanoate and enanthate are slowly absorbed from sites of injection. Fluphenazine is metabolised by sulphoxidation, hydroxylation, and conjugation with glucuronic acid or sulphate. Fluphenazine sulphoxide and 7-hydroxy-fluphenazine have been detected in urine and faeces. After an oral dose of the hydrochloride, 20% is excreted in the urine and 60% is eliminated in the faeces in 7 days after an intramuscular dose of the enanthate, 26% is eliminated in the faeces and 14% excreted in the urine in 14 days after an intramuscular dose of the decanoate, 17% is eliminated in the faeces and 6% excreted in the urine in 30 days. 

The major use of sesame oil in pharmaceutical formulations is as a solvent in the preparation of sustained-release intramuscular injections of steroids, such as estradiol valerate, hydroxy-progesterone caproate, testosterone enanthate, and nandrolone decanoate, or other oil-soluble drug substances, such as, the decanoates or enanthate esters of fluphenazine. The disappearance of sesame oil from the injection site, following subcutaneous or intramuscular administration to pigs, has been reported to have a half-life of about 23 days. ... 

Ikndrolone Decanoate, USP, and Nandroione Phen-pnptonate, USP. Nandrolone decanoate, 17/9-hydroxy-t ti-4-en-3-onc 17-dccanoate. has been used in the man-i menl of certain anemias, but the availability of tryihropoictin has greatly reduced this use. Nandrolone fiienpropionale is 17p-hydroxycstr-4-en-3-one 17- 3 - hcny I propionate. 

A comparison of biotransformation patterns in patients receiving oral fluphenazine versus intramuscularly injected fluphenazine decanoate revealed a significant first pass effect (422,427). Thus, plasma ratios of fluphenazine sulfoxide and 7-hydroxy-fluphenazine to fluphenazine were much higher after oral administration compared with intramuscular administration of fluphenazine decanoate. The plasma ratios of fluphenazine-N-oxide to fluphenazine did not differ between the two dosage forms. In a study measuring fluphenazine serum levels during reduced dose fluphenazine decanoate maintenance therapy at two dose levels, it was determined that serum levels could be monitored at maintenance doses (429,430). 

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