Oct-1-en-3-one
Names | |
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Preferred IUPAC name
Oct-1-en-3-one | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.022.116 |
PubChemCID
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UNII | |
CompTox Dashboard(EPA)
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Properties | |
C8H14O | |
Molar mass | 126.20 g/mol |
Boiling point | 56–60 °C (133–140 °F; 329–333 K) at 16 mm Hg[1] |
Hazards | |
GHSlabelling: | |
NFPA 704(fire diamond) | |
Flash point | 35 °C (95 °F; 308 K) |
Safety data sheet(SDS) | Fisher Scientific |
Related compounds | |
Relatedenones
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Methyl vinyl ketone |
Related compounds
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1-Octene |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Oct-1-en-3-one(CH2=CHC(=O)(CH2)4CH3), also known as1-octen-3-oneoramyl vinyl ketone,is theodorantthat is responsible for the typical "metallic" smell ofmetalsandbloodcoming into contact withskin.[2]Oct-1-en-3-one has a strong metallic mushroom-like odor with anodor detection thresholdof 0.03–1.12 μg/m3and it is the main compound responsible for the "smell of metal", followed bydecanal(smell: orange skin, flowery) andnonanal(smell: tallowy, fruity).[3]Oct-1-en-3-one is the degradativereductionproduct of thechemical reactionof skinlipid peroxidesand Fe2+.Skinlipidperoxidesare formed from skin lipid byoxidation,eitherenzymaticallybylipoxygenasesor byairoxygen.Oct-1-en-3-one is aketoneanalog of thealkene1-octene.
Natural occurrences
[edit]It is also produced byUncinula necator,a fungus that causes powdery mildew of grape.[4]
See also
[edit]- Odorant
- 1-Octen-3-ol,the alcohol analog that is used by mosquitoes as an odor cue[citation needed]
References
[edit]- ^"Human Metabolome Database: Showing metabocard for 1-Octen-3-one (HMDB0031309)".hmdb.ca.Retrieved5 October2024.
- ^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.PMID17009284.
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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 yeastSaccharomyces cerevisiae".J. Agric. Food Chem.50(11): 3277–82.doi:10.1021/jf011527d.PMID12009998.