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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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.116Edit this at Wikidata
UNII
  • InChI=1S/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3checkY
    Key: KLTVSWGXIAYTHO-UHFFFAOYSA-NcheckY
  • 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
GHSlabelling:
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
Relatedenones
 Methyl vinyl ketone
Related compounds
 1-Octene
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Oct-1-en-3-one(CH2=CHC(=O)(CH2)4CH3), also known as1-octen-3-oneoramyl vinyl ketone,is theodorantthat is responsible for the typical "metallic" smell ofmetalsandbloodcoming into contact withskin.[1]Oct-1-en-3-one has a strong metallic mushroom-like odor with anodor detection thresholdof 0.03–1.12 μg/m3and it is the main compound responsible for the "smell of metal", followed bydecanal(smell: orange skin, flowery) andnonanal(smell: tallowy, fruity).[2]Oct-1-en-3-one is the degradativereductionproduct of thechemical reactionof skinlipid peroxidesand Fe2+.Skinlipidperoxidesare formed from skin lipid byoxidation,eitherenzymaticallybylipoxygenasesor byairoxygen.Oct-1-en-3-one is aketoneanalog of thealkene1-octene.

Natural occurrences

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

See also

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References

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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.PMID17009284.{{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 yeastSaccharomyces cerevisiae".J. Agric. Food Chem.50(11): 3277–82.doi:10.1021/jf011527d.PMID12009998.
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