Oct-1-en-3-one

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.

Quick Facts Names, Identifiers ...

Oct-1-en-3-one

Names
Preferred IUPAC name Oct-1-en-3-one
Identifiers
CAS Number	4312-99-6 Y
3D model (JSmol)	Interactive image
ChemSpider	55282 Y
ECHA InfoCard	100.022.116
PubChem CID	61346
UNII	7LT7Z4Q9XR Y
CompTox Dashboard (EPA)	DTXSID5047162
InChI InChI=1S/C8H14O/c1-3-5-6-7-8(9)4-2/h4H,2-3,5-7H2,1H3 Y Key: KLTVSWGXIAYTHO-UHFFFAOYSA-N Y 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[1]
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). Y verify (what is YN ?) Infobox references

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