1-Octen-3-ol

vanc Octenol octanal octanol Octonal (disambiguation)octonal changed 477208406 (RS)-1-Octen-3-ol FormulaV1.svg 200px Oct-1-en-3-ol Amyl vinyl carbinol; 1-Vinylhexanol; Matsutake alcohol; Vinyl amyl carbinol; Vinyl hexanol; Matsuica alcohol; Mushroom alcohol; 3-Hydroxy-1-octene; Octenol correct chemspider correct EBI 34118 39932 46735 3183573 1230177 17778 : 5360388 : 2007013 DB03025 222-226-0 648361 correct kegg C14272 1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 VSMOENVRRABVKN-UHFFFAOYAB VSMOENVRRABVKN-QMMMGPOBSA-N VSMOENVRRABVKN-MRVPVSSYSA-N correct chemspider 1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 correct chemspider VSMOENVRRABVKN-UHFFFAOYSA-N correct CAS 3391-86-4 correct ?? 3687-48-7 (R)-(−) (S)-(+) correct ?? 24587-53-9 18827 6992244 correct FDA WXB511GE38 correct FDA BYV0MEV7V1 correct FDA 07D31239FH CCCCCC(C=C)O CCCCC[C@@H](O)C=C CCCCC[C@H](O)C=C 8 16 1 0.837 g/mL 174 ºC at 1 atm 0.3 kPa (at 50 °C) 68 ºC 245 ºC 0.9% (low) to 8% (high) 07 Warning 2 2 0 340 mg/kg (rat) Fisher Scientific 1-Octen-3-ol, octenol for short and also known as mushroom alcohol, is an organic compound with the formula CH2\dCHCH(OH)(CH2)4CH3. It is a chiral secondary alcohol. It is a colorless liquid that occurs widely in nature. 1-Octen-3-ol, Mushroom alcohol 2019-08-29 https://www.hmdb.ca/metabolites/HMDB0031299Fungal Volatile Organic Compounds: More Than Just a Funky Smell? Annual Review of Microbiology 2020 74 101–116 10.1146/annurev-micro-012420-080428 32905756 Inamdar AA, Morath S, Bennett JW Occurrence The name "mushroom alcohol" for 1-octen-3-ol comes from its first isolation by S. Murahashi in 1936 and 1938 from crushed matsutake mushrooms. Murahashi S. Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 34, 155 Chemical Abstracts 31 21617 Murahashi S. Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 30, 263 Chemical Abstracts 32 27078 A recent study on volatiles of this mushroom has shown this compound is only produced upon tissue disruption. Biochemical Systematics and Ecology 35 2007 Changing volatile compounds from mycelium and sporocarp of American matsutake mushroom, Tricholoma magnivelare Wood W. F. Lefevre C. K. 9 10.1016/j.bse.2007.03.001 634–636 2007BioSE..35..634W This alcohol is found in many other mushrooms where it may play a role as an antifeedant. Wood William F. Archer Cynthia L. Largent David L. 2001 1-Octen-3-ol, a banana slug antifeedant from mushrooms Biochemical Systematics and Ecology 29 5 531–533 10.1016/s0305-1978(00)00076-4 11274773 2001BioSE..29..531W In combination with exhaled CO2 and other volatile compounds secreted from the epidermis, it attracts biting insects such as mosquitoes.Takken W Kline D L 1989-09-01 Carbon dioxide and 1-octen-3-ol as mosquito attractants https://europepmc.org/article/med/2573687 Journal of the American Mosquito Control Association 5 3 311–316 1943-6270 2573687 It is contained in human breath and sweat, and it is believed that the insect repellent DEET works by blocking the insects' octenol odorant receptors.Anna Petherick How DEET jams insects' smell sensors Nature News 2008-03-13 http://www.nature.com/news/2008/080313/full/news.2008.672.html https://web.archive.org/web/20080315162356/http://www.nature.com/news/2008/080313/full/news.2008.672.html 15 March 2008 live 10.1038/news.2008.672 free subscription Ditzen M, Pellegrino M, Vosshall LB Insect odorant receptors are molecular targets of the insect repellent DEET Science 319 5871 1838–42 March 2008 18339904 10.1126/science.1153121 2008Sci...319.1838D 18499590 Leslie B. Vosshall Syed Z, Leal WS 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 September 2008 18711137 2518096 10.1073/pnas.0805312105 free In nature Octenol is produced by several plants and fungi, including edible mushrooms and lemon balm. Octenol is formed during oxidative breakdown of linoleic acid. Chemical properties of attractants 2010-06-08 http://www.nri.org/tsetse/FAQ/chemprop.html https://web.archive.org/web/20090427113618/http://www.nri.org/tsetse/FAQ/chemprop.html 2009-04-27 dead Octenol is responsible for the moldy odor of damp indoor environments. Bennett JW, Inamdar AA Are Some Fungal Volatile Organic Compounds (VOCs) Mycotoxins? Toxins 2015 7 9 3785–3804 10.3390/toxins7093785 free 4591661 26402705 It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape. Steel CC, Blackman JW, Schmidtke LM 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 June 2013 23675852 10.1021/jf400641r 2013JAFC...61.5189S Synthesis It can be prepared by the Grignard reaction of acrolein with the Grignard reagent derived from amyl iodide.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 10.1002/food.19830270523 0027-769X 6684212 It also arises by the selective reduction of 1-octen-3-one Biosynthesis 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.Matsui Kenji Sasahara Satomi Akakabe Yoshihiko Kajiwara Tadahiko 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 10.1271/bbb.67.2280 0916-8451 14586122 46173472 freeMin Kuo Tsung Lipid biotechnology Gardner Harold W. 2002 Marcel Dekker 0-585-40371-6 New York 48691412 thumb|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.|center|399x399px Uses Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electrical devices.2007-07-05 Biopesticides Fact Sheet for Octenol https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_G-126_05-Jul-07.pdf 2022-06-28 EPA fact sheet The enantiopure right-handed isomer known as mushroom alcohol or matsutake alcohol is used in perfumery, because it is the main flavor and odor component of matsutake.https://www.thegoodscentscompany.com/data/rw1024051.html 1-octen-3-ol thegoodscentscompany.com 2015-05-31 Health and safety Octenol is approved by the U.S. Food and Drug Administration as a food additive. US FDAs Center for Food Safety and Applied Nutrition US FDA/CFSAN – EAFUS List 2008-03-16 http://vm.cfsan.fda.gov/~dms/eafus.html https://web.archive.org/web/20080221184706/http://vm.cfsan.fda.gov/~dms/eafus.html 2008-02-21 dead It is of moderate toxicity with an LD50 of 340 mg/kg. In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism. Inamdar AA, Hossain MM, Bernstein AI, Miller GW, Richardson JR, Bennett JW 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 November 2013 24218591 3845153 10.1073/pnas.1318830110 2013PNAS..11019561I free See also Olfactory receptor Oct-1-en-3-one, the ketone analog that gives blood on skin its typical metallic, mushroom-like smell Glindemann D, Dietrich A, Staerk HJ, Kuschk P The two odors of iron when touched or pickled: (skin) carbonyl compounds and organophosphines Angewandte Chemie 45 42 7006–9 October 2006 17009284 10.1002/anie.200602100 2006ACIE...45.7006G 45055136 1-Octen-3-yl acetate, the acetate ester of this compound References Category:Secondary alcohols Category:Alkenols Category:Vinyl compounds