Oct-1-en-3-one
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Preferred IUPAC name Oct-1-en-3-one | |
Identifiers | |
CAS Number |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.022.116 |
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | C8H14O |
Molar mass | 126.20 g/mol |
Boiling point | 56–60 °C (133–140 °F; 329–333 K) |
Hazards | |
GHS labelling: | |
Pictograms | |
NFPA 704 (fire diamond) | 2 2 0 |
Flash point | 35 °C (95 °F; 308 K) |
Safety data sheet (SDS) | Fisher Scientific |
Related compounds | |
Related enones | Methyl vinyl ketone |
Related compounds | 1-Octene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references |
Oct-1-en-3-one (CH2=CHC(=O)(CH2)4CH3), also known as 1-octen-3-one or amyl vinyl ketone, is the odorant that is responsible for the typical "metallic" smell of metals and blood coming into contact with skin.[1] Oct-1-en-3-one has a strong metallic mushroom-like odor with an odor detection threshold of 0.03–1.12 μg/m3 and it is the main compound responsible for the "smell of metal", followed by decanal (smell: orange skin, flowery) and nonanal (smell: tallowy, fruity).[2] Oct-1-en-3-one is the degradative reduction product of the chemical reaction of skin lipid peroxides and Fe2+. Skin lipid peroxides are formed from skin lipid by oxidation, either enzymatically by lipoxygenases or by air oxygen. Oct-1-en-3-one is a ketone analog of the alkene 1-octene.
Natural occurrences
It is also produced by Uncinula necator, a fungus that causes powdery mildew of grape.[3]
See also
- Odorant
- 1-Octen-3-ol, the alcohol analog that is used by mosquitoes as an odor cue[citation needed]
References
- ^ D. Glindemann, A. Dietrich, H. Staerk, P. Kuschk (2006). "The Two Odors of Iron when Touched or Pickled: (Skin) Carbonyl Compounds and Organophosphines". Angewandte Chemie International Edition. 45 (42): 7006–7009. doi:10.1002/anie.200602100. PMID 17009284.
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: CS1 maint: multiple names: authors list (link) - ^ Supporting information for the Glindemann article
- ^ Darriet P, Pons M, Henry R, et al. (May 2002). "Impact odorants contributing to the fungus type aroma from grape berries contaminated by powdery mildew (Uncinula necator); incidence of enzymatic activities of the yeast Saccharomyces cerevisiae". J. Agric. Food Chem. 50 (11): 3277–82. doi:10.1021/jf011527d. PMID 12009998.