1-Octen-3-ol, octenol for short and also known as mushroom alcohol, is a chemical that attracts biting insects such as

mosquito Mosquitoes, the Culicidae, are a Family (biology), family of small Diptera, flies consisting of 3,600 species. The word ''mosquito'' (formed by ''Musca (fly), mosca'' and diminutive ''-ito'') is Spanish and Portuguese for ''little fly''. Mos ...

es. It is contained in human breath and sweat, and it is believed that

insect repellent An insect repellent (also commonly called "bug spray" or "bug deterrent") is a substance applied to the skin, clothing, or other surfaces to discourage insects (and arthropods in general) from landing or climbing on that surface. Insect repellent ...

DEET ''N'',''N''-Diethyl-''meta''-toluamide, also called diethyltoluamide or DEET (, from DET, the initials of di- + ethyl + toluamide), is the oldest, one of the most effective, and most common active ingredients in commercial insect repellents. ...

works by blocking the insects' octenol

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 ...

receptor Receptor may refer to: * Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and respond ...

s. The name "mushroom alcohol" for 1-octen-3-ol comes from it first isolation by S. Murahashi in 1936 and 1938 from crushed

matsutake , ''Tricholoma matsutake'', is a species of choice edible mycorrhizal mushroom that grows in Eurasia and North America. It is prized in Japanese cuisine for its distinct odor. Etymology The common name and specific epithet, ''matsutake'', i ...

mushrooms. A recent study on volatiles of this mushroom has shown this compound is only produced upon tissue disruption. This alcohol is found in many other mushrooms where it may play a role as an

antifeedant Antifeedants are organic compounds produced by plants to repel herbivores through distaste or toxicity. These chemical compounds are typically classified as secondary metabolites in that they are not essential for the metabolism of the plant, but ...

Natural occurrence

Octenol is produced by several plants and fungi, including

edible mushroom Edible mushrooms are the fleshy fruit bodies of numerous species of macrofungi (fungi that bear fruiting structures large enough to be seen with the naked eye). Edibility may be defined by criteria including the absence of poisonous effect ...

s and lemon balm. Octenol is formed during oxidative breakdown of

linoleic acid Linoleic acid (LA) is an organic compound with the formula . Both alkene groups () are ''cis''. It is a fatty acid sometimes denoted 18:2 (n−6) or 18:2 ''cis''-9,12. A linoleate is a salt or ester of this acid. Linoleic acid is a polyunsat ...

. Octenol is responsible for the moldy odor of damp indoor environments. It is also a

wine fault A wine fault is a sensory-associated (organoleptic) characteristic of a wine that is unpleasant, and may include elements of taste, smell, or appearance, elements that may arise from a "chemical or a microbial origin", where particular sensory expe ...

, defined as a

cork taint Cork taint is a broad term referring to an off-odor and off-flavor wine fault arising from the presence of 2,4,6-trichloroanisole (TCA), a chemical compound that represents one of the strongest off-flavors, and one "generated naturally in foods/b ...

, occurring in wines made with bunch rot contaminated grape.

Properties

1-octen-3-ol is a

secondary alcohol In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol ...

derived from 1-octene. It exists in the form of two

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

s, (''R'')-(−)-1-octen-3-ol and (''S'')-(+)-1-octen-3-ol. :

Synthesis

Two possible lab syntheses of 1-octen-3-ol are: * by the Grignard reaction of

acrolein Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat ...

and amyl iodide * by the selective reduction of

1-octen-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 mus ...

Biochemically, 1-octen-3-ol is generated from the peroxidation of

, catalyzed by a

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 ...

, followed by cleavage of the resulting hydroperoxide with the help of a hydroperoxide lyase. This reaction takes place in cheese and is used in biotechnology to produce the ''(R)''-isomer. Octenol-biosynthesis

Uses

Octenol is used, sometimes in combination with

carbon dioxide Carbon dioxide is a chemical compound with the chemical formula . It is made up of molecules that each have one carbon atom covalent bond, covalently double bonded to two oxygen atoms. It is found in a gas state at room temperature and at norma ...

, to attract insects in order to kill them with certain electrical devices. The name 'mushroom alcohol' is used because octenol is the main flavor component of

mushroom A mushroom or toadstool is the fleshy, spore-bearing Sporocarp (fungi), fruiting body of a fungus, typically produced above ground on soil or another food source. ''Toadstool'' generally refers to a poisonous mushroom. The standard for the n ...

Health and safety

Octenol is approved by the

U.S. Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...

as a

food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives, such as vinegar ( pickling), salt ( salting), smoke ( smoking) and sugar ( crystallization), have been used f ...

. It is of moderate

toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...

ity with an LD₅₀ of 340 mg/kg. In an animal study, octenol has been found to disrupt

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

homeostasis In biology, homeostasis (British English, British also homoeostasis; ) is the state of steady internal physics, physical and chemistry, chemical conditions maintained by organism, living systems. This is the condition of optimal functioning fo ...

and may be an environmental agent involved in

parkinsonism Parkinsonism is a clinical syndrome characterized by tremor, bradykinesia (slowed movements), Rigidity (neurology), rigidity, and balance disorder, postural instability. Both hypokinetic features (bradykinesia and akinesia) and hyperkinetic f ...

References