5503-03-7

Basic information

• Product Name: (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid
• CAS NO: 5503-03-7
• Molecular Weight: 312.45
• Mol File: 5503-03-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid(5503-03-7)
• EPA Substance Registry System: (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid(5503-03-7)

Safety Data

• Hazardous Substances Data: 5503-03-7(Hazardous Substances Data)

Upstream product

• 60-33-3 linoleic acid 
• 5502-91-0 9(S)-hydroperoxyoctadeca-10Z,12E-dienoic acid 

Relevant articles and documents

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.

Detection of divinyl ether synthase in Lily-of-the-Valley (Convallaria majalis) roots

Incubations of linoleic acid with cell-free preparations from Lily-of-the-Valley (Convallaria majalis L., Ruscaceae) roots revealed the presence of 13-lipoxygenase and divinyl ether synthase (DES) activities. Exogenous linoleic acid was metabolized predominantly into (9Z,11E,1′E)-12-(1′-hexenyloxy)-9,11-dodecadienoic (etheroleic) acid. Its identification was confirmed by the data of ultraviolet spectroscopy, mass spectra, 1H NMR, COSY, catalytic hydrogenation. The isomeric divinyl ether (8E,1′E,3′Z)-12-(1′,3′-nonadienyloxy)-8-nonenoic (colneleic) acid was detected as a minor product. Incubations with linoleic acid hydroperoxides revealed that 13-hydroperoxide was a preferential substrate, while the 9-hydroperoxide was utilized with lesser efficiency.