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Oct-1-en-3-one

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Oct-1-en-3-one

Oct-1-en-3-one
Skeletal formula of oct-1-en-3-one
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
UNII  YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H14O
Molar mass 126.20 g/mol
Related compounds
Related enones Methyl vinyl ketone
Related compounds 1-Octene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)

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 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".  
  2. ^ Supporting information for the Glindemann article

External links

  • Science Daily: The Smell of Money
  • The smell of iron
  • PubChem 61346
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