Oct-1-en-3-one (CH₂=CHC(=O)(CH₂)₄CH₃), also known as 1-octen-3-one, is the odorant that is responsible for the typical "metallic" smell of

metal A metal (from ancient Greek, Greek μέταλλον ''métallon'', "mine, quarry, metal") is a material that, when freshly prepared, polished, or fractured, shows a lustrous appearance, and conducts electrical resistivity and conductivity, e ...

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 in the cir ...

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 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 classified as an aldehyde with the chemical formula C10H20O. Occurrence Decanal occurs naturally in citrus, along with octanal, citral, and sinensal, in buckwheat, and in coriander essential oil. It is used in ...

(smell: orange skin, flowery) and nonanal (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 chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking ...

of skin

lipid peroxide Lipid peroxidation is the chain of reactions of oxidative degradation of lipids. It is the process in which free radicals "steal" electrons from the lipids in cell membranes, resulting in cell damage. This process proceeds by a free radical chain ...

s and Fe²⁺. Skin

lipid Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids in ...

peroxide In chemistry, peroxides are a group of compounds with the structure , where R = any element. The group in a peroxide is called the peroxide group or peroxo group. The nomenclature is somewhat variable. The most common peroxide is hydrogen p ...

s are formed from skin lipid by

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

, either

enzymatically Enzymes () are proteins that act as biological catalysts 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 products. A ...

by lipoxygenases or by air

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements ...

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

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double b ...

analog of the

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic ...

1-octene 1-Octene is an organic compound with a formula CH2CHC6H13. The alkene is classified as a higher olefin and alpha-olefin, meaning that the double bond is located at the alpha (primary) position, endowing this compound with higher reactivity and thu ...

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 America ...

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

References

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

Natural occurrences

See also

References