99640-09-2

Basic information

• Product Name: trans-11-oxooctadec-9-enoic acid
• Synonyms: trans-11-oxooctadec-9-enoic acid
• CAS NO: 99640-09-2
• Molecular Weight: 296.45
• Mol File: 99640-09-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: trans-11-oxooctadec-9-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-11-oxooctadec-9-enoic acid(99640-09-2)
• EPA Substance Registry System: trans-11-oxooctadec-9-enoic acid(99640-09-2)

Safety Data

• Hazardous Substances Data: 99640-09-2(Hazardous Substances Data)

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 112-79-8 Elaidic acid 
• 110551-46-7 trans-9-hydroperoxyoctadec-10-enoic acid 

Downstream Products

• 1282617-41-7 (E)-N-[2-(3,4-dihydroxyphenyl)ethyl]-11-oxo-octadec-9-enamide 

Relevant articles and documents

Anti-inflammatory constituents of the Red Alga Gracilaria verrucosa and their synthetic analogues

A chemical study on the anti-inflammatory components of the red alga Gracilaria verrucosa led to the isolation of new 11-deoxyprostaglandins (1-4), a ceramide (5), and a C16 keto fatty acid (6), along with known oxygenated fatty acids (7-14). Their structures were elucidated on the basis of NMR and MS data. The absolute configurations of compounds 1-5 were determined by Mosher's method. The anti-inflammatory activity of the isolated compounds (1-14) was evaluated by determining their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-α) in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 9 and 10 exhibited the most potent activity. In the evaluation of these two compounds and derivatized analogues (15-40), the anti-inflammatory activity was enhanced in some synthetic analogues. These enone fatty acids were investigated as potential anti-inflammatory leads for the first time.

Allylic Hydroperoxide Rearrangement: β-Scission or Concerted Pathway?

The rearrangements of the allylic hydroperoxides derived from oleic acid have been studied.Two hydroperoxides are formed by singlet-oxygen oxidation of oleic acid trans-9-hydroperoxyoctadec-10-enoic acid (5) and trans-10-hydroperoxyoctadec-8-enoic acid (6).These hydroperoxides can be separated by reverse-phase chromatography.Rearrangement of 18O-labeled hydroperoxides (5 or 6) under a 32O2 atmosphere led to no incorporation of 16O into the rearrangement products.Similarly, rearrangement of 16O-labeled hydroperoxides (5 or 6) under a 36O2 atmosphere led to no incorporation of 18O into the rearrangement products.The hydroperoxide 5 rearranges to a mixture of 5 and trans-11-hydroperoxyoctadec-9-enoic acid and alcohols and ketones resulting from Russell termination steps.The results are discussed in terms of a concerted rearrangement of allylic peroxyl radicals proceeding through a five-membered-ring transition state.