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Oct-1-en-3-one

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Oct-1-en-3-one
Skeletal formula of oct-1-en-3-one
Space-filling model of the oct-1-en-3-one molecule
Names
Preferred IUPAC name Oct-1-en-3-one
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.116 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3Key: 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,2-3,5-7H2,1H3Key: KLTVSWGXIAYTHO-UHFFFAOYAV
SMILES
  • O=C(C=C)CCCCC
Properties
Chemical formula C8H14O
Molar mass 126.20 g/mol
Boiling point 56–60 °C (133–140 °F; 329–333 K) at 16 mm Hg
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation mark
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. Oct-1-en-3-one has a strong metallic mushroom-like odor with an odor detection threshold of 0.03–1.12 μg/m 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 Fe. 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.

See also

References

  1. "Human Metabolome Database: Showing metabocard for 1-Octen-3-one (HMDB0031309)". hmdb.ca. Retrieved 5 October 2024.
  2. 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)
  3. Supporting information for the Glindemann article
  4. 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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