1-Octen-3-ol

Last updated

1-Octen-3-ol
Oct-1-en-3-ol.svg
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.020.206 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 222-226-0
648361
KEGG
PubChem CID
UNII
  • InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 Yes check.svgY
    Key: VSMOENVRRABVKN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3
    Key: VSMOENVRRABVKN-UHFFFAOYAB
  • (R)-(−):Key: VSMOENVRRABVKN-QMMMGPOBSA-N
  • (S)-(+):Key: VSMOENVRRABVKN-MRVPVSSYSA-N
  • CCCCCC(C=C)O
  • (R)-(−):CCCCC[C@@H](O)C=C
  • (S)-(+):CCCCC[C@H](O)C=C
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:
GHS-pictogram-exclam.svg
Warning
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 68 ºC
245 ºC
Explosive limits 0.9% (low) to 8% (high)
Lethal dose or concentration (LD, LC):
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

The name "mushroom alcohol" for 1-octen-3-ol comes from it first isolation by S. 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]

Natural occurrence

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]

Properties

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.

The two enantiomers of 1-octen-3-ol (RS)-1-Octen-3-ol FormulaV1.svg
The two enantiomers of 1-octen-3-ol

Synthesis

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]

Biosynthesis of (R)-1-octen-3-ol: 1) linoleic acid, 2) (8E,12Z)-10-hydroperoxyoctadecadienoic acid, 3) (R)-1-octen-3-ol, 4) (8E)-10-oxodecenoic acid, 5) lipoxygenase, 6) hydroperoxide lyase. Octenol-biosynthesis.png
Biosynthesis of (R)-1-octen-3-ol: 1) linoleic acid, 2) (8E,12Z)-10-hydroperoxyoctadecadienoic acid, 3) (R)-1-octen-3-ol, 4) (8E)-10-oxodecenoic acid, 5) lipoxygenase, 6) hydroperoxide lyase.

Uses

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]

Health and safety

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]

See also

Related Research Articles

<span class="mw-page-title-main">DEET</span> Chemical compound

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.

<span class="mw-page-title-main">Allyl group</span> Chemical group (–CH₂–CH=CH₂)

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.

<span class="mw-page-title-main">Aroma compound</span> Chemical compound that has a smell or odor

An aroma compound, also known as an odorant, aroma, fragrance or flavoring, 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 sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds.

<span class="mw-page-title-main">Insect repellent</span> Substance which repels insects

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).

<i>cis</i>-3-Hexenal Chemical compound

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.

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.

<span class="mw-page-title-main">Oct-1-en-3-one</span> Chemical compound

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.

<i>Tricholoma magnivelare</i> Species of fungus

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).

<i>Clitopilus prunulus</i> Species of fungus

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.

<span class="mw-page-title-main">VUAA1</span> Chemical compound

VUAA1 is a chemical compound that works by over activating an insect's olfactory senses causing a repellent effect. It is considered to be an Orco allosteric agonist. It was discovered at Vanderbilt University with research being partially funded by the Bill and Melinda Gates Foundation.

<span class="mw-page-title-main">6-Nonenal</span> Chemical compound

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.

<span class="mw-page-title-main">Divinylether fatty acids</span>

Divinylether fatty acids contain a fatty acid chemically combined with a doubly unsaturated carbon chain linked by an oxygen atom (ether).

<span class="mw-page-title-main">Insect olfaction</span> Function of chemical receptors

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.

trans,cis-2,6-Nonadienal is an organic compound that is classified as a doubly unsaturated derivative of nonanal. The molecule consists of a α,β-unsaturated aldehyde with an isolated alkene group. The compound has attracted attention as the essence of cucumbers, but it is also found in bread crust and freshly cut watermelon.

<span class="mw-page-title-main">Hydroperoxide lyase</span>

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.

<span class="mw-page-title-main">Smell of freshly cut grass</span> Odour released when grass is damaged

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.

(3<i>Z</i>)-Nonenal Organic compound in various plants

(3Z)-Nonenal is an unsaturated aldehyde that occurs naturally in various plants.

References

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  2. Petherick A (2008-03-13). "How DEET jams insects' smell sensors". Nature News. doi: 10.1038/news.2008.672 . Archived from the original on 15 March 2008.
  3. Ditzen M, Pellegrino M, Vosshall LB (March 2008). "Insect odorant receptors are molecular targets of the insect repellent DEET". Science. 319 (5871): 1838–42. Bibcode:2008Sci...319.1838D. doi:10.1126/science.1153121. PMID   18339904. S2CID   18499590.
  4. Syed Z, Leal WS (September 2008). "Mosquitoes smell and avoid the insect repellent DEET". Proceedings of the National Academy of Sciences of the United States of America. 105 (36): 13598–603. doi: 10.1073/pnas.0805312105 . PMC   2518096 . PMID   18711137.
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  6. Murahashi S. "Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 30, 263". Chemical Absracts. 32: 27078.
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  8. Wood WF, Archer CL, Largent DL (2001). "1-Octen-3-ol, a banana slug antifeedant from mushrooms". Biochemical Systematics and Ecology. 29 (5): 531–533. Bibcode:2001BioSE..29..531W. doi:10.1016/s0305-1978(00)00076-4. PMID   11274773.
  9. "Chemical properties of attractants". Archived from the original on 2009-04-27. Retrieved 2010-06-08.
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  13. Matsui K, Sasahara S, Akakabe Y, Kajiwara T (2003). "Linoleic acid 10-hydroperoxide as an intermediate during formation of 1-octen-3-ol from linoleic acid in Lentinus decadetes". Bioscience, Biotechnology, and Biochemistry. 67 (10): 2280–2282. doi: 10.1271/bbb.67.2280 . ISSN   0916-8451. PMID   14586122. S2CID   46173472.
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  15. 1 2 "Biopesticides Fact Sheet for Octenol" (PDF). EPA fact sheet. 2007-07-05. Retrieved 2022-06-28.
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