Oct-1-en-3-one (CH₂=CHC(=O)(CH₂)₄CH₃), also known as 1-octen-3-one or amyl vinyl ketone, is the

odorant An aroma compound, also known as an odorant, aroma, fragrance, flavoring or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficien ...

that is responsible for the typical "metallic" smell of

metal A metal () is a material that, when polished or fractured, shows a lustrous appearance, and conducts electrical resistivity and conductivity, electricity and thermal conductivity, heat relatively well. These properties are all associated wit ...

s and

blood Blood is a body fluid in the circulatory system of humans and other vertebrates that delivers necessary substances such as nutrients and oxygen to the cells, and transports metabolic waste products away from those same cells. Blood is com ...

coming into contact with

skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other animal coverings, such as the arthropod exoskeleton, have different ...

. Oct-1-en-3-one has a strong metallic mushroom-like odor with an

odor detection threshold The odor detection threshold is the lowest concentration of a certain odor compound that is perceivable by the human sense of smell. The threshold of a chemical compound is determined in part by its shape, polarity, partial charges, and mole ...

of 0.03–1.12 μg/m³ and it is the main compound responsible for the "smell of metal", followed by

decanal Decanal is an organic compound with the chemical formula . A colorless oil, it is classified as an aldehyde. Occurrence Decanal occurs naturally in citrus, along with octanal, citral, and sinensal, in buckwheat, and in coriander essential oil ...

(smell: orange skin, flowery) and

nonanal Nonanal is an organic compound with the chemical formula . It is one of several isomers, all are colorless oil. The nonanals are classified as aldehydes. The linear nonanal is produced commercially by the hydroformylation of 1-octene. It is ...

(smell: tallowy, fruity). Oct-1-en-3-one is the degradative reduction product of the

chemical reaction A chemical reaction is a process that leads to the chemistry, chemical transformation of one set of chemical substances to another. When chemical reactions occur, the atoms are rearranged and the reaction is accompanied by an Gibbs free energy, ...

of skin lipid peroxides and Fe²⁺. Skin

lipid Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing ...

peroxide In chemistry, peroxides are a group of Chemical compound, compounds with the structure , where the R's represent a radical (a portion of a complete molecule; not necessarily a free radical) and O's are single oxygen atoms. Oxygen atoms are joined ...

s are formed from skin lipid by

oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

, either

enzymatically An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as produc ...

lipoxygenase Lipoxygenases () (LOX) are a family of (non- heme) iron-containing enzymes, more specifically oxidative enzymes, most of which catalyze the dioxygenation of polyunsaturated fatty acids in lipids containing a cis,cis-1,4- pentadiene into ce ...

s or by

air An atmosphere () is a layer of gases that envelop an astronomical object, held in place by the gravity of the object. A planet retains an atmosphere when the gravity is great and the temperature of the atmosphere is low. A stellar atmosph ...

oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...

. Oct-1-en-3-one is a

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

analog of the

alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

1-octene.

Natural occurrences

It is also produced by ''

Uncinula necator ''Uncinula necator'' (syn. ''Erysiphe necator'') is a fungus that causes powdery mildew of grape. It is a common pathogen of Vitis species, including the wine grape, ''Vitis vinifera''. The fungus is believed to have originated in North Americ ...

'', a fungus that causes powdery mildew of grape.

References

{{DEFAULTSORT:Octen-3-one, 1- Flavors Enones

Natural occurrences

See also

References