Oct-1-en-3-one (original) (raw)
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Oct-1-en-3-one
 Skeletal formula of oct-1-en-3-one |
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| Names | |
| Preferred IUPAC name Oct-1-en-3-one | |
| Identifiers | |
| CAS Number | 4312-99-6  Y |
| 3D model (JSmol) | Interactive image |
| ChemSpider | 55282 Y |
| ECHA InfoCard | 100.022.116  |
| PubChem CID | 61346 |
| UNII | 7LT7Z4Q9XR Y |
| CompTox Dashboard (EPA) | DTXSID5047162 |
| InChI InChI=1S/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3 YKey: KLTVSWGXIAYTHO-UHFFFAOYSA-N YInChI=1/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3InChI=1/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3Key: KLTVSWGXIAYTHO-UHFFFAOYAV |
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| SMILES O=C(C=C)CCCCC | |
| Properties | |
| Chemical formula | C8H14O |
| Molar mass | 126.20 g/mol |
| Boiling point | 56–60 °C (133–140 °F; 329–333 K) at 16 mm Hg[1] |
| 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 Y N ?) Infobox references |
Chemical compound
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.[2] 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).[3] 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
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It is also produced by Uncinula necator, a fungus that causes powdery mildew of grape.[4]
- Odorant
- 1-Octen-3-ol, the alcohol analog that is used by mosquitoes as an odor cue[_citation needed_]
- ^ "Human Metabolome Database: Showing metabocard for 1-Octen-3-one (HMDB0031309)". hmdb.ca. Retrieved 5 October 2024.
- ^ 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.
{{[cite journal](/wiki/Template:Cite%5Fjournal "Template:Cite journal")}}: 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.