Oct-1-en-3-one
Encyclopedia
Oct-1-en-3-one also known as 1-octen-3-one, is the odorant
that is responsible for the typical metallic smell of metal
s 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
peroxide
s and Fe2+. Skin lipid peroxides are formed from skin lipid by oxidation
, either enzymatically
by lipoxygenase
s or by air oxygen
. Oct-1-en-3-one is a ketone
analog of the alkene
1-octene
.
Aroma compound
An aroma compound, also known as odorant, aroma, fragrance or flavor, is a chemical compound that has a smell or odor...
that is responsible for the typical metallic smell of metal
Metal
A metal , is an element, compound, or alloy that is a good conductor of both electricity and heat. Metals are usually malleable and shiny, that is they reflect most of incident light...
s and blood
Blood
Blood is a specialized bodily fluid in animals that delivers necessary substances such as nutrients and oxygen to the cells and transports metabolic waste products away from those same cells....
coming into contact with skin
Skin
-Dermis:The dermis is the layer of skin beneath the epidermis that consists of connective tissue and cushions the body from stress and strain. The dermis is tightly connected to the epidermis by a basement membrane. It also harbors many Mechanoreceptors that provide the sense of touch and heat...
. Oct-1-en-3-one has a strong metallic mushroom-like odor with an odor detection threshold
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 thresholds of a chemical compound is determined in part by its shape, polarity, partial charges and molecular mass...
of 0.03 - 1.12 µg/m³ and it is the main compound responsible for the "smell of metal", followed by decanal
Decanal
Decanal is an organic compound with the chemical formula C9H19CHO. It is the simplest ten-carbon aldehyde. Decanal occurs naturally and is used in fragrances and flavoring. Decanal occurs in nature and is an important component in citrus along with octanal, citral, and sinensal...
(smell: orange skin, flowery) and nonanal
Nonanal
Nonanal, also called nonanaldehyde or pelargonaldehyde, is an alkyl aldehyde. It has a strong fruity or floral odor and is used in flavors and perfume. It is also produced by the human body.- Mosquitoes :...
(smell: tallowy, fruity). Oct-1-en-3-one is the degradative reduction
Redox
Redox reactions describe all chemical reactions in which atoms have their oxidation state changed....
product of the chemical reaction
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...
of skin lipid
Lipid
Lipids constitute a broad group of naturally occurring molecules that include fats, waxes, sterols, fat-soluble vitamins , monoglycerides, diglycerides, triglycerides, phospholipids, and others...
peroxide
Peroxide
A peroxide is a compound containing an oxygen–oxygen single bond or the peroxide anion .The O−O group is called the peroxide group or peroxo group. In contrast to oxide ions, the oxygen atoms in the peroxide ion have an oxidation state of −1.The simplest stable peroxide is hydrogen peroxide...
s and Fe2+. Skin lipid peroxides are formed from skin lipid by oxidation
Redox
Redox reactions describe all chemical reactions in which atoms have their oxidation state changed....
, either enzymatically
Enzyme
Enzymes are proteins that catalyze chemical reactions. In enzymatic reactions, the molecules at the beginning of the process, called substrates, are converted into different molecules, called products. Almost all chemical reactions in a biological cell need enzymes in order to occur at rates...
by lipoxygenase
Lipoxygenase
Lipoxygenases are a family of iron-containing enzymes that catalyse the dioxygenation of polyunsaturated fatty acids in lipids containing a cis,cis-1,4- pentadiene structure. It catalyses the following reaction:...
s or by air oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
. Oct-1-en-3-one is a ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
analog of the alkene
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...
1-octene
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 position, endowing this compound with higher reactivity and thus useful chemical properties. 1-Octene is one of the...
.
See also
- OdorantAroma compoundAn aroma compound, also known as odorant, aroma, fragrance or flavor, is a chemical compound that has a smell or odor...
- 1-Octen-3-ol1-Octen-3-ol1-Octen-3-ol, octenol for short , is a chemical that attracts biting insects such as mosquitos. It is contained in human breath and sweat, and it was once believed that insect repellent DEET works by blocking the insects' octenol odorant receptors.Octenol is used in combination with carbon dioxide...
, the hydroxyl analog that is used by mosquitoes as an odor cue