Oct-1-en-3-one

Oct-1-en-3-one
Space-filling model of the oct-1-en-3-one molecule
Identifiers
4312-99-6 YesY
3D model (Jmol) Interactive image
ChemSpider 55282 YesY
ECHA InfoCard 100.022.116
PubChem 61346
UNII 7LT7Z4Q9XR YesY
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

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 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.

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.
  2. ↑ Supporting information for the Glindemann article
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