4-Oxodecanoic acid

This acid chloride is prepared from oxalyl chloride and 6-oxodecanoic acid.127d The reaction procedure is applicable to a range of unsubstituted and substituted aliphatic and aromatic acid chlorides. 

Oxodecanoic acid, 0-00237 9-Oxodecanoic acid, 0-00238 9-Oxo-2,4,5,7-decatetraenoic acid, 0-00239... 

Oxodecanoic acid. Dissolve 4.0 g of 3-carboxy-3,4-dibromodecanoic acid in 60 ml of 2m sodium hydroxide solution and heat the solution at 80-90 °C for 2 hours. Cool to room temperature and acidify with dilute sulphuric acid carbon dioxide is evolved and a white precipitate is formed. Filter the precipitated keto acid from the cold solution and recrystallise from light petroleum (b.p. 40-60 °C). 4-Oxodecanoic acid, m.p. 68-69 °C, is obtained the yield is 1.6 g (80%). The infrared spectrum shows absorptions at 3400-2400 cm-1 (OH stretch of COzH) and 1700 cm-1 (0=0). 

Acid hydrolysis by concentrated hydrochloric acid at 100°C of 113 and 115 yielded histamine hydrochloride and 4-oxodecanoic acid, respectively. In contrast, 114 proved to be stable to this acidic condition. The relative instability of glochidine (113) in strong acid was attributed to the N-C-N system, which is not present in the isomeric glochidicine (114). 

Fig. 10. Structures of nonribosomally synthesized peptides of bacterial origin (1-6) and fungal origin (7-9). Me, N-methylated peptide boni Orn, ornithine 4-MHA, 4-methyl-3-hydroxyanthranilic acid Aad, aminoadipic acid Aeo, 2-amino-9,10-epoxy-8-oxodecanoic acid D-Hiv, D-hydroxyisovaleric acid Bmt, (4i )-4-[( )-2-butenyl]-4-methyl-L-threonine Abu, a-aminoisobutyric acid Sar, sarcosine. The boxes signify gene products for peptide synthetases composed of modules which activate and process the indicated amino acids...

The terminal double bond of 9-decenoic acid (i), prepared from commercially available 10-undecenoic acid, is oxidized with PdCl2/CuCl2 to give 9-oxodecanoic acid (2), which is converted to 3-(6-methoxycarbonylhexyl) cyclopentane-1,2,4-trione (3). This is an important intermediate in the prostaglandin synthesis5 (Scheme 2). 

Oxodecanoic acid is reduced by baker s yeast immobilized in carrageenan to the (S)-config-urated alcohol with 96% ee168. 

---