Structure via PubChem · Public domain (PubChem)
1-octen-3-one
Sign in to saveAlso known as FEMA 3515, Octen-3-one, 1, Pentyl vinyl ketone, Amyl vinyl ketone, Oct-1-en-3-one, Vinyl amyl ketone, 1-Octene-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. 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).
Chemical data
- Formula
- C8H14O
- Molecular weight
- 126.2 g/mol
- IUPAC name
- oct-1-en-3-one
- SMILES
- CCCCCC(=O)C=C
- InChIKey
- KLTVSWGXIAYTHO-UHFFFAOYSA-N
- XLogP
- 2.4
- Polar surface area
- 17.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 126.104
Show 4 more facts
- found in taxon
- Matsutake
- chemical formula
- C₈H₁₄O
- canonical SMILES
- CCCCCC(=O)C=C
- Commons category
- Oct-1-en-3-one
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Natural occurrences
- See also
- 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. 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).
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.
Excerpted from Wikipedia’s “1-octen-3-one” article, available under the CC BY-SA 4.0 licence.