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( R e d i r e c t e d f r o m O c t e n o l )
1-Octen-3-ol
Names
Preferred IUPAC name
Other names
Amyl vinyl carbinol; 1-Vinylhexanol; Matsutake alcohol; Vinyl amyl carbinol; Vinyl hexanol; Matsuica alcohol; Mushroom alcohol; 3-Hydroxy-1-octene; Octenol
Identifiers
CAS Number
3687-48-7 (R )-(−) Y
24587-53-9 (S )-(+) Y
3D model (JSmol )
Interactive image
ChEBI
ChemSpider
ECHA InfoCard
100.020.206
KEGG
PubChem CID
UNII
BYV0MEV7V1 (R )-(−) Y
07D31239FH (S )-(+) Y
CompTox Dashboard (EPA )
InChI=1S/C8H16O/c1-3-5-6-7-8(9 )4-2/h4,8-9H,2-3,5-7H2,1H3 Y
Key: VSMOENVRRABVKN-UHFFFAOYSA-N Y
InChI=1/C8H16O/c1-3-5-6-7-8(9 )4-2/h4,8-9H,2-3,5-7H2,1H3
Key: VSMOENVRRABVKN-UHFFFAOYAB
CCCCCC(C=C)O
OC(C=C)CCCCC
Properties
Chemical formula
C 8 H 16 O
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 :
Pictograms
Signal word
Warning
NFPA 704 (fire diamond)
Flash point
68 ºC
Autoignition temperature
245 ºC
Explosive limits
0.9% (low) to 8% (high)
Lethal dose or concentration (LD, LC):
LD 50 (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).
Infobox references
Chemical compound
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]
Natural occurrence
[ edit ]
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
[ edit ]
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
Synthesis
[ edit ]
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 ) (8 E ,12Z )-10-hydroperoxyoctadecadienoic acid, 3 ) (R )-1-octen-3-ol, 4 ) (8 E )-10-oxodecenoic acid, 5 ) lipoxygenase, 6 ) hydroperoxide lyase.
Uses
[ edit ]
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
[ edit ]
Octenol is approved by the U.S. Food and Drug Administration as a food additive .[17] It is of moderate toxicity with an LD 50 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
[ edit ]
References
[ edit ]
^ 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 .
^ 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 .
^ Murahashi S. "Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 34, 155". Chemical Absracts . 31 : 21617.
^ Murahashi S. "Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 30, 263". Chemical Absracts . 32 : 27078.
^ Wood W. F., Lefevre C. K. (2007). "Changing volatile compounds from mycelium and sporocarp of American matsutake mushroom, Tricholoma magnivelare ". Biochemical Systematics and Ecology . 35 (9 ): 634–636. Bibcode :2007BioSE..35..634W . doi :10.1016/j.bse.2007.03.001 .
^ 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 .
^ "Chemical properties of attractants" . Archived from the original on 2009-04-27. Retrieved 2010-06-08 .
^ Bennett JW, Inamdar AA (2015). "Are Some Fungal Volatile Organic Compounds (VOCs) Mycotoxins?" . Toxins . 7 (9 ): 3785–3804. doi :10.3390/toxins7093785 . PMC 4591661 . PMID 26402705 .
^ Steel CC, Blackman JW, Schmidtke LM (June 2013). "Grapevine bunch rots: Impacts on wine composition, quality, and potential procedures for the removal of wine faults". Journal of Agricultural and Food Chemistry . 61 (22 ): 5189–206. doi :10.1021/jf400641r . PMID 23675852 .
^ Wnuk S, Kinastowski S, Kamiński E (1983). "Synthesis and analysis of 1-octen-3-ol, the main flavour component of mushrooms" . Die Nahrung . 27 (5 ): 479–486. doi :10.1002/food.19830270523 . ISSN 0027-769X . PMID 6684212 .
^ 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 .
^ Min Kuo T, Gardner HW (2002). Lipid biotechnology . New York: Marcel Dekker. ISBN 0-585-40371-6 . OCLC 48691412 .
^ a b "Biopesticides Fact Sheet for Octenol" (PDF) . EPA fact sheet . 2007-07-05. Retrieved 2022-06-28 .
^ "1-octen-3-ol" . thegoodscentscompany.com . Retrieved 2015-05-31 .
^ US FDAs Center for Food Safety and Applied Nutrition. "US FDA/CFSAN – EAFUS List" . Archived from the original on 2008-02-21. Retrieved 2008-03-16 .
^ Inamdar AA, Hossain MM, Bernstein AI, Miller GW, Richardson JR, Bennett JW (November 2013). "Fungal-derived semiochemical 1-octen-3-ol disrupts dopamine packaging and causes neurodegeneration" . Proceedings of the National Academy of Sciences of the United States of America . 110 (48 ): 19561–6. Bibcode :2013PNAS..11019561I . doi :10.1073/pnas.1318830110 . PMC 3845153 . PMID 24218591 .
^ Glindemann D, Dietrich A, Staerk HJ, Kuschk P (October 2006). "The two odors of iron when touched or pickled: (skin) carbonyl compounds and organophosphines". Angewandte Chemie . 45 (42 ): 7006–9. doi :10.1002/anie.200602100 . PMID 17009284 . S2CID 45055136 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=1-Octen-3-ol&oldid=1234012613 "
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