93979-14-7Relevant articles and documents
Method of synthesizing 4-decenoic acid
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Paragraph 0027; 0029; 0031, (2017/08/29)
The invention discloses a method of synthesizing 4-decenoic acid, including the following steps: performing heat reflux with 1-octylene-3-ol and ortho-acetate as raw materials in presence of a catalyst, distilling generated ethanol out at the same time, performing reduced pressure distillation to remove excessive ortho-acetate, and finally rectifying the product to obtain pure 4-decenoate; performing heat reflux to the 4-decenoate under an alkaline condition and distilling hydrolyzed alcohol compounds out, regulating the pH to 7, extracting and distilling the liquid, and finally rectifying the liquid to obtain pure 4-decenoic acid. The pure 4-decenoic acid is prepared through a Claisen rearrangement reaction. The synthesis process is simple.
Metabolism of deuterated isomeric 6,7-dihydroxydodecanoic acids in Saccharomyces cerevisiae - Diastereo- and enantioselective formation and characterization of 5-hydroxydecano-4-lactone (=4,5-dihydro-5-(1-hydroxyhexyl)furan-2(3H)-one) isomers
Garbe, Leif-A.,Tressl, Roland
, p. 2349 - 2363 (2007/10/03)
The chemical synthesis of deuterated isomeric 6,7-dihydroxydodecanoic acid methyl esters 1 and the subsequent metabolism of esters 1 and the corresponding acids 1a in liquid cultures of the yeast Saccharomyces cerevisiae was investigated. Incubation experiments with (6R,7R)- or (6S,7S)-6,7-dihydroxy(6,7-2H2)dodecanoic acid methyl ester ((6R,7R)- or (6S,7S)-(6,7-2H2)-1, resp.) and (±)-threo- or (±)-erythro-6,7-dihydroxy(6,7-2H 2)dodecanoic acid ((±)-threo- or (±)-erythro-(6,7- 2H2)-1a, resp.) elucidated their metabolic pathway in yeast (Tables 1-3). The main products were isomeric 2H-labeled 5-hydroxydecano-4-lactones 2. The absolute configuration of the four isomeric lactones 2 was assigned by chemical synthesis via Sharpless asymmetric dihydroxylation and chiral gas chromatography (Lipodex E). The enantiomers of threo-2 were separated without derivatization on Lipodex E; in contrast, the enantiomers of erythro-2 could be separated only after transformation to their 5-O-(trifluoroacetyl) derivatives. Biotransformation of the methyl ester (6R,7R)-(6,7-2H2)-1 led to (4R,5R)- and (4S,5R)-(2,5- 2H2)-2 (ratio ca. 4:1; Table 2). Estimation of the label content and position of (4S,5R)-(2,5-2H2)-2 showed 95% label at C(5), 68% label at C(2), and no 2H at C(4) (Table 2). Therefore, oxidation and subsequent reduction with inversion at C(4) of 4,5-dihydroxydecanoic acid and transfer of 2H from C(4) to C(2) is postulated. The 5-hydroxydecano-4-lactones 2 are of biochemical importance: during the fermentation of Streptomyces griseus, (4S,5R)-2, known as L-factor, occurs temporarily before the antibiotic production, and (-)-muricatacin (=(4R,5R)-5-hydroxy-heptadecano-4-lactone), a homologue of (4R,5R)-2, is an anticancer agent.
FACTORS GOVERNING PRODUCT DISTRIBUTION IN THE OXIDATION OF ALKENES BY MANGANESE(III) ACETATE IN ACETIC ACID AND ACETIC ANHYDRIDE
Midgley, Gary,Thomas, C. Barry
, p. 1537 - 1544 (2007/10/02)
A systematic investigation has been carried out into the effect of different reaction parameters on the oxidation of oct-1-ene by manganese(III) acetate in acetic acid and acetic anhydride.The most important factor in dictating the ratio of products is the composition of the solvent.In the absence of anhydride γ-decanolactone is virtually the sole product.Even small quantitites of anhydride lead to the lactone being replaced by other products derived from cationic intermediates C6H13CH(1+)CH2COX (X = OH or OAc).Further increases in the amount of anhydride encourage the formation of decanoic acid until, in 90percent anhydride, this becomes the predominant product.The results cannot be interpreted simply in terms of competition for the alkene by the radicals (.)CH2CO2H and (.)CH2COOCOCH3.Decanoic acid formation is also favoured by low temperatures, low concentration of oxidants, and by the addition of acetate ions.A comparision is made of the efficiency of addition when the initiating species is manganese(III) or a peroxide.