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Oct-1-en-3-one

| NFPA-H = 2 | NFPA-F = 2 | NFPA-I = 0 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.{{cite journal 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).

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.

References

References

  1. "Human Metabolome Database: Showing metabocard for 1-Octen-3-one (HMDB0031309)".
  2. [http://www.wiley-vch.de/contents/jc_2002/2006/z602100_s.pdf Supporting information for the Glindemann article]
  3. (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..
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