13552-96-0

Basic information

• Product Name: (E,Z,Z)-trideca-2,4,7-trienal
• Synonyms: (E,Z,Z)-trideca-2,4,7-trienal;2,4,7-Tridecatrienal, (2E,4Z,7Z)-;2-TRANS,4-CIS,7-CIS-TRIDECATRIENAL;TRIDECA-2,4,7-TRIENAL;(E,Z,Z)-2,4,7-Tridecatrienal;(2E,4Z,7Z)-2,4,7-Tridecatrienal
• CAS NO: 13552-96-0
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.2973
• EINECS: 236-936-3
• Mol File: 13552-96-0.mol

Chemical Properties

• Boiling Point: 309.5 °C at 760 mmHg
• Flash Point: 149 °C
• Appearance: /
• Density: 0.869 g/cm³
• Vapor Pressure: 0.000637mmHg at 25°C
• Refractive Index: 1.477
• CAS DataBase Reference: (E,Z,Z)-trideca-2,4,7-trienal(CAS DataBase Reference)
• NIST Chemistry Reference: (E,Z,Z)-trideca-2,4,7-trienal(13552-96-0)
• EPA Substance Registry System: (E,Z,Z)-trideca-2,4,7-trienal(13552-96-0)

Safety Data

• Hazardous Substances Data: 13552-96-0(Hazardous Substances Data)

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

• 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 
• 85514-73-4 (2E,4Z,7Z)-2,4,7-tridecatrienol 

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 articles and documents

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.