Oct-1-en-3-one

Oct-1-en-3-one
Names
	Preferred IUPAC name 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
Boiling point	56–60 °C (133–140 °F; 329–333 K) at 16 mm Hg
Hazards
	GHS labelling:
Pictograms
NFPA 704 (fire diamond)	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). verify (what is ?) Infobox references

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.^[2] 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).^[3] 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.^[4]

References

^ "Human Metabolome Database: Showing metabocard for 1-Octen-3-one (HMDB0031309)". hmdb.ca. Retrieved 5 October 2024.
^ 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)
^ 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.

[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.

[1]

[2]

[3]

[4]

Natural occurrences

See also

References