Oct-1-en-3-one

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.

Oct-1-en-3-one
Skeletal formula of oct-1-en-3-one
Space-filling model of the oct-1-en-3-one molecule
Names
Preferred IUPAC name
Oct-1-en-3-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.116
UNII
  • InChI=1S/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3 checkY
    Key: KLTVSWGXIAYTHO-UHFFFAOYSA-N checkY
  • InChI=1/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3
  • InChI=1/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3
    Key: KLTVSWGXIAYTHO-UHFFFAOYAV
  • O=C(C=C)CCCCC
Properties
C8H14O
Molar mass 126.20 g/mol
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).
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Infobox references

Natural occurrences

It is also produced by Uncinula necator, a fungus that causes powdery mildew of grape.[3]

See also

References
  1. 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}}: CS1 maint: multiple names: authors list (link)
  2. Supporting information for the Glindemann article
  3. 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.
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