104840-02-0

Upstream product

• 197149-64-7 isopropyl 10,11-epoxyundecanoate 
• 197149-65-8 isopropyl 10-hydroxy-11-phenylthioundecanoate 
• 197149-67-0 isopropyl 10-oxo-11-phenylsulfinylundecanoate 
• 197149-66-9 isopropyl 10-hydroxy-11-phenylsulfinylundecanoate 
• 60-33-3 linoleic acid 
• 197149-68-1 isopropyl 13-hydroxy-10-oxooctadec-11-enoate 
• 111-71-7 heptanal 

Relevant academic research and scientific papers

Linolenate 9R-dioxygenase and allene oxide synthase activities of lasiodiplodia theobromae

Jasmonic acid (JA) is synthesized from linolenic acid (18:3n-3) by sequential action of 13-lipoxygenase, allene oxide synthase (AOS), and allene oxide cyclase. The fungus Lasiodiplodia theobromae can produce large amounts of JA and was recently reported to form the JA precursor 12-oxophytodienoic acid. The objective of our study was to characterize the fatty acid dioxygenase activities of this fungus. Two strains of L. theobromae with low JA secretion (～0.2 mg/L medium) oxygenated 18:3n- 3 to 5,8-dihydroxy-9Z,12Z,15Z- octadecatrienoic acid as well as 9R-hydroperoxy-10E,12Z,15Z-octadecatrienoic acid, which was metabolized by an AOS activity into 9-hydroxy-10-oxo-12Z,15Z- octadecadienoic acid. Analogous conversions were observed with linoleic acid (18:2n-6). Studies using [11S-2H]18:2n-6 revealed that the putative 9R-dioxygenase catalyzed stereospecific removal of the 11R hydrogen followed by suprafacial attack of dioxygen at C-9. Mycelia from these strains of L. theobromae contained 18:2n-6 as the major polyunsaturated acid but lacked 18:3n-3. A third strain with a high secretion of JA (～200 mg/L) contained 18:3n-3 as a major fatty acid and produced 5,8-dihydroxy-9Z,12Z,15Z- octadecatrienoic acid from added 18:3n-3. This strain also lacked the JA biosynthetic enzymes present in higher plants.

Convenient formation of 4-hydroxyalk-2-en-1-one functionality via a Knoevenagel-type carbon chain elongation reaction of aldehyde with 1-arylsulfinylalkan-2-one

A highly functionalized four-carbon unit, 4-hydroxyalk-2-en-1-one functionality [R2CH(OH)CH= CHCOR1], was conveniently prepared by a reaction of an aldehyde (R2CH2CHO) with a 1-(arylsulfinyl)alkan-2-one [ArS(O)CH2COR1] in the presence of diethylamine (Knoevenagel condition). Other functional groups, such as carbonyl and hydroxy groups, in both of the alkyl chains (R1, R2) did not prevent this reaction. This reaction was used to conveniently prepare (±)-(11E)-13-hydroxy-10-oxooctadec-11-enoic acid (14), having cytotoxic activity, and its analogues from undec-10-enoic acid in good yield.