:Oct-1-en-3-one
{{chembox
| verifiedrevid = 444032253
| Name = Oct-1-en-3-one
| ImageFile = Oct-1-en-3-one.svg
| ImageSize = 215px
| ImageName = Skeletal formula of oct-1-en-3-one
| ImageFile1 = Oct-1-en-3-one molecule spacefill.png
| ImageAlt1 = Space-filling model of the oct-1-en-3-one molecule
| PIN = Oct-1-en-3-one
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7LT7Z4Q9XR
| SMILES = O=C(C=C)CCCCC
| InChI =1/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 55282
| PubChem = 61346
| InChI1 = 1/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3
| InChIKey1 = KLTVSWGXIAYTHO-UHFFFAOYAV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KLTVSWGXIAYTHO-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 4312-99-6
}}
|Section2={{Chembox Properties
| C=8 | H=14 | O=1
| MolarMass = 126.20 g/mol
| BoilingPtC = 56-60
| BoilingPt_notes = at 16 mm Hg{{cite web |title=Human Metabolome Database: Showing metabocard for 1-Octen-3-one (HMDB0031309) |url=http://www.hmdb.ca/metabolites/HMDB0031309 |website=hmdb.ca |access-date=5 October 2024}}
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS07}}
| NFPA-H = 2
| NFPA-F = 2
| NFPA-I = 0
| FlashPtC = 35
| ExternalSDS = [https://www.fishersci.com/store/msds?partNumber=AAL0718903&productDescription=1-OC10-3-1+97+STAB.+W+.+B+1G&vendorId=VN00024248&countryCode=US&language=en Fisher Scientific]
}}
|Section8={{Chembox Related
| OtherFunction_label = enones
| OtherFunction = Methyl vinyl ketone
| OtherCompounds = 1-Octene
}}
}}
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
| author= D. Glindemann, A. Dietrich, H. Staerk, P. Kuschk
| title = The Two Odors of Iron when Touched or Pickled: (Skin) Carbonyl Compounds and Organophosphines
| journal = Angewandte Chemie International Edition
| year = 2006
| volume = 45
| issue = 42
| pages = 7006–7009
| doi = 10.1002/anie.200602100
| pmid= 17009284| doi-access =
}}
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).[http://www.wiley-vch.de/contents/jc_2002/2006/z602100_s.pdf Supporting information for the Glindemann article] 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.{{cite journal |vauthors=Darriet P, Pons M, Henry R, etal |title=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 |journal=J. Agric. Food Chem. |volume=50 |issue=11 |pages=3277–82 |date=May 2002 |pmid=12009998 |doi=10.1021/jf011527d}}
See also
- Odorant
- 1-Octen-3-ol, the alcohol analog that is used by mosquitoes as an odor cue{{citation needed|date=August 2013}}