Names | |
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Preferred IUPAC name Oct-1-en-3-ol | |
Other names Amyl vinyl carbinol; 1-Vinylhexanol; Matsutake alcohol; Vinyl amyl carbinol; Vinyl hexanol; Matsuica alcohol; Mushroom alcohol; 3-Hydroxy-1-octene; Octenol | |
Identifiers | |
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3D model (JSmol) |
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ChEBI |
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ChEMBL |
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ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.020.206 |
EC Number |
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648361 | |
KEGG | |
PubChem CID | |
UNII |
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CompTox Dashboard (EPA) | |
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Properties | |
C8H16O | |
Molar mass | 128.215 g·mol−1 |
Density | 0.837 g/mL |
Boiling point | 174 ºC at 1 atm |
Vapor pressure | 0.3 kPa (at 50 °C) |
Hazards | |
GHS labelling: | |
Warning | |
NFPA 704 (fire diamond) | |
Flash point | 68 ºC |
245 ºC | |
Explosive limits | 0.9% (low) to 8% (high) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 340 mg/kg (rat) |
Safety data sheet (SDS) | Fisher Scientific |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
1-Octen-3-ol, octenol for short and also known as mushroom alcohol, [1] is a chemical that attracts biting insects such as mosquitoes. It is contained in human breath and sweat, and it is believed that insect repellent DEET works by blocking the insects' octenol odorant receptors. [2] [3] [4]
The name “mushroom Alcohol” for 1-octen-3-ol comes from it first isolation by Murahashi in 1936 and 1938 from crushed matsutake mushrooms. [5] [6] A recent study on volatiles of this mushroom has shown this compound is only produced upon tissue disruption. [7] This alcohol is found in many other mushrooms where it may play a role as an antifeedant. [8]
Octenol is produced by several plants and fungi, including edible mushrooms and lemon balm. Octenol is formed during oxidative breakdown of linoleic acid. [9] Octenol is responsible for the moldy odor of damp indoor environments. [10]
It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape. [11]
1-octen-3-ol is a secondary alcohol derived from 1-octene. It exists in the form of two enantiomers, (R)-(−)-1-octen-3-ol and (S)-(+)-1-octen-3-ol.
Two possible lab syntheses of 1-octen-3-ol are: [12]
Biochemically, 1-octen-3-ol is generated from the peroxidation of linoleic acid, catalyzed by a lipoxygenase, 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. [13] [14]
Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electrical devices. [15]
The name 'mushroom alcohol' is used because octenol is the main flavor component of mushrooms. [16]
Octenol is approved by the U.S. Food and Drug Administration as a food additive. [17] It is of moderate toxicity with an LD50 of 340 mg/kg. [15]
In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism. [18]
N,N-Diethyl-meta-toluamide, also called diethyltoluamide or DEET, is the oldest, one of the most effective and most common active ingredient in commercial insect repellents. It is a slightly yellow oil intended to be applied to the skin or to clothing and provides protection against mosquitoes, flies, ticks, fleas, chiggers, leeches, and many other biting insects.
Tansy is a perennial, herbaceous flowering plant in the genus Tanacetum in the aster family, native to temperate Europe and Asia. It has been introduced to other parts of the world, including North America, and in some areas has become invasive. It is also known as common tansy, bitter buttons, cow bitter, or golden buttons. The Latin word vulgare means "common".
In organic chemistry, an allyl group is a substituent with the structural formula −CH2−HC=CH2. It consists of a methylene bridge attached to a vinyl group. The name is derived from the scientific name for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride.
Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. 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.
An insect repellent is a substance applied to the skin, clothing, or other surfaces to discourage insects from landing or climbing on that surface. Insect repellents help prevent and control the outbreak of insect-borne diseases such as malaria, Lyme disease, dengue fever, bubonic plague, river blindness, and West Nile fever. Pest animals commonly serving as vectors for disease include insects such as flea, fly, and mosquito; and ticks (arachnids).
cis-3-Hexenal, also known as (Z)-3-hexenal and leaf aldehyde, is an organic compound with the formula CH3CH2CH=CHCH2CHO. It is classified as an unsaturated aldehyde. It is a colorless liquid and an aroma compound with an intense odor of freshly cut grass and leaves.
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 experiences might arise from more than one wine fault. Wine faults may result from poor winemaking practices or storage conditions that lead to wine spoilage.
Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.
Icaridin, also known as picaridin, is an insect repellent which can be used directly on skin or clothing. It has broad efficacy against various arthropods such as mosquitos, ticks, gnats, flies and fleas, and is almost colorless and odorless. A study performed in 2010 showed that picaridin spray and cream at the 20% concentration provided 12 hours of protection against ticks. Unlike DEET, icaridin does not dissolve plastics, synthetics or sealants, is odorless and non-greasy and presents a lower risk of toxicity when used with sunscreen, as it may reduce skin absorption of both compounds.
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.
Tricholoma magnivelare, commonly known as the matsutake, white matsutake, ponderosa mushroom, pine mushroom, or American matsutake, is a gilled mushroom found East of the Rocky Mountains in North America growing in coniferous woodland. These ectomycorrhizal fungi are typically edible species that exist in a symbiotic relationship with various species of pine, commonly jack pine. They belong to the genus Tricholoma, which includes the closely related East Asian songi or matsutake as well as the Western matsutake (T. murrillianum) and Meso-American matsutake (T. mesoamericanum).
Clitopilus prunulus, commonly known as the miller or the sweetbread mushroom, is an edible pink-spored basidiomycete mushroom found in grasslands in Europe and North America. Growing solitary to gregarious in open areas of conifer/hardwood forests; common under Bishop pine along the coast north of San Francisco; fruiting shortly after the fall rains. It has a grey to white cap and decurrent gills.
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful.
6-Nonenal is an organic compound with the formula C2H5CH=CH(CH2)4CHO. Other isomeric nonenal compounds are also known to exist naturally, e.g. 2-nonenal. The cis-isomer of 6-nonenal is often listed as the principal component in the aromas of muskmelon fruits. The trans-isomer is listed as an off-flavor aroma of milk foams, and thought to be a possible polypropylene odorant.
Anthranilate-based insect repellents include methyl anthranilate, N,N-dimethylanthranilic acid (DMA), ethyl anthranilate (EA), and butyl anthranilate (BA). Chemically, they are esters of anthranilic acid. While the United States Food and Drug Administration (FDA) has approved some of these compounds for use as food additives, cinnamyl anthranilate is banned by the FDA. The compounds repel both fruit flies and mosquitos, and target the same neurons that respond to DEET. The receptors are located on part of the antennae known as the sacculus.
Divinylether fatty acids contain a fatty acid chemically combined with a doubly unsaturated carbon chain linked by an oxygen atom (ether).
Insect olfaction refers to the function of chemical receptors that enable insects to detect and identify volatile compounds for foraging, predator avoidance, finding mating partners and locating oviposition habitats. Thus, it is the most important sensation for insects. Most important insect behaviors must be timed perfectly which is dependent on what they smell and when they smell it. For example, olfaction is essential for locating host plants and hunting prey in many species of insects, such as the moth Deilephila elpenor and the wasp Polybia sericea, respectively.
Hydroperoxide lyases are enzymes that catalyze the cleavage of C-C bonds in the hydroperoxides of fatty acids. They belong to the cytochrome P450 enzyme family.
The smell of freshly cut grass is an odour caused by green leaf volatiles (GLVs) released when it is damaged. Mechanical damage to grass from activities such as lawnmowing results in the release of cis-3-hexenal and other compounds that contribute to a grassy or "green" smell. cis-3-Hexenal has a low odour detection threshold that humans can perceive at concentrations as low as 0.25 parts per billion.
(3Z)-Nonenal is an unsaturated aldehyde that occurs naturally in various plants.