Oct-1-en-3-one

1-Octen-3-one
Identifiers
CAS number	[4312-99-6]
SMILES	C=CC(=O)CCCCC
InChI	InChI=1/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3
Properties
Molecular formula	C8H14O
Molar mass	126.20 g/mol
Related compounds
Related alkanes	Octane
Related compounds	1-Octene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) 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.

See also

• Odorant
• 1-Octen-3-ol, the hydroxy analog that is used by mosquitoes as an odor cue

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. 
2. ^ Supporting information for the Glindemann article

External links

• Science Daily: The Smell of Money
• PubChem 61346