13552-96-0

Usage

Occurrence

Reported found in cooked chicken.

InChI:InChI=1/C13H20O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14/h6-7,9-13H,2-5,8H2,1H3/b7-6-,10-9-,12-11+

Upstream product

• 85514-73-4 (2E,4Z,7Z)-2,4,7-tridecatrienol 
• 74454-36-7 (E)-2-tridecene-4,7-diyn-1-ol 
• 20739-58-6 2-octyn-1-ol 
• 18495-27-7 1-bromooct-2-yne 
• 477724-14-4 2,2-Dimethyl-4-((Z)-oct-2-enyl)-[1,3]dioxolane 
• 89616-41-1 (2RS,4Z)-4-decen-1,2-diol 
• 66-25-1 hexanal 

Downstream Products

• 477724-13-3 (9E,11Z,14Z)-8-(tert-Butyl-diphenyl-silanyloxy)-5-diazo-6-oxo-icosa-9,11,14-trienoic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of the eight enantiomerically pure diastereomers of the 12-F2-isoprostanes

Syntheses of the eight enantiomerically pure diastereomers of the 12-F2-isoprostanes (4-11) are described. The key steps included rhodium-mediated intramolecular cyclopropanation and enzymatic resolution of the racemic diol 12.

Identification of potent odorants formed by autoxidation of arachidonic acid: Structure elucidation and synthesis of (E,Z,Z)-2,4,7-tridecatrienal

The aroma composition of autoxidized arachidonic acid was characterized by aroma extract dilution analysis. The most potent odorant was trans-4,5-epoxy-(E)-2-decenal followed by 1-octen-3-one, (E,Z)-2,4-decadienal, (E,Z,Z)-2,4,7-tridecatrienal, (E,E)-2,4-decadienal, and hexanal. (E,Z,Z)-2,4,7-Tridecatrienal was unequivocally identified by mass spectrometry and nuclear magnetic resonance (NMR) data. The stereochemistry of its extended double-bond system was elucidated on the basis of NMR measurements. The target compound was synthesized in four steps starting with bromination of 2-octyn-1-ol, followed by copper-catalyzed coupling of the bromide with ethyl-magnesium bromide and (E)-2-penten-4-yn-1-ol. Partial hydrogenation of the resulting C13-compound with triple bonds in the positions C-4 and C-7 gave rise to (E,Z,Z)-2,4,7-tridecatrien-1,ol, which was finally oxidized to the target compound. It exhibits a typical egg-white-like, marine-like odor at low concentrations, and an intense orange-citrus, animal-like odor at higher concentrations. Its odor threshold was estimated by gas chromatography-olfactometry to be 0.07 ng/L air, Which is of the same order of magnitude as that reported for 1-octen-3-one and (E,E)-2,4-decadienal.