Oct-1-en-3-one

Last updated
Oct-1-en-3-one
Oct-1-en-3-one.svg
Oct-1-en-3-one molecule spacefill.png
Names
Preferred IUPAC name
Oct-1-en-3-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.116 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3 Yes check.svgY
    Key: KLTVSWGXIAYTHO-UHFFFAOYSA-N Yes check.svgY
  • 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
  • O=C(C=C)CCCCC
Properties
C8H14O
Molar mass 126.20 g/mol
Boiling point 56–60 °C (133–140 °F; 329–333 K)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 35 °C (95 °F; 308 K)
Safety data sheet (SDS) Fisher Scientific
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [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.

Contents

Natural occurrences

It is also produced by Uncinula necator , a fungus that causes powdery mildew of grape. [3]

See also

Related Research Articles

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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.{{cite journal}}: 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.