Oct-1-en-3-one
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| 1-Octen-3-one | |
|---|---|
 |
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| Identifiers | |
| CAS number | [4312-99-6] |
| SMILES | C=CC(=O)CCCCC |
| InChI | InChI=1/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3 |
| Properties | |
| Molecular formula | C8H14O |
| Molar mass | 126.20 g/mol |
| Related compounds | |
| Related alkanes | Octane |
| Related compounds | 1-Octene |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Oct-1-en-3-one (CH2=CHC(=O)(CH2)4CH3), also known as 1-octen-3-one, 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 lipids 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.
[edit] See also
- Odorant
- 1-Octen-3-ol, the hydroxy analog that is used by mosquitoes as an odor cue
[edit] 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:.
- ^ Supporting information for the Glindemann article
