Oct-1-en-3-one

Oct-1-en-3-one
Identifiers
CAS Number	4312-99-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	55282 ;
ECHA InfoCard	100.022.116
PubChem CID	61346;
UNII	7LT7Z4Q9XR ;
CompTox Dashboard (EPA)	DTXSID5047162 ;
	InChI InChI=1S/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3 Key: KLTVSWGXIAYTHO-UHFFFAOYSA-N ; 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;
	SMILES O=C(C=C)CCCCC;
Properties
Chemical formula	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.[3]

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References

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.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 yeast Saccharomyces cerevisiae". J. Agric. Food Chem. 50 (11): 3277–82. doi:10.1021/jf011527d. PMID 12009998.

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[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.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.

Oct-1-en-3-one

Natural occurrences

See also

References