1-辛烯-3-醇

1-辛烯-3-醇
	IUPAC名; Oct-1-en-3-ol
别名	蘑菇醇; 松茸醇
识别
CAS号	3391-86-4 ; 3687-48-7（(R)-(–)） ; 24587-53-9（(S)-(+)）
PubChem	18827
ChemSpider	17778
SMILES	CCCCCC(C=C)O;
InChI	1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3;
InChIKey	VSMOENVRRABVKN-UHFFFAOYAB
ChEBI	34118
KEGG	C14272
性质
化学式	C8H16O
摩尔质量	128.21 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1-辛烯-3-醇，也稱為蘑菇醇，^[1]是一種能吸引蚊子等叮咬昆蟲的化學物質，化學式為C₈H₁₆O。它包含在人類的呼吸和汗液中，據信驅蟲劑避蚊胺通過阻斷昆蟲的1-辛烯-3-醇氣味受體發揮作用。^[2]^[3]^[4]

自然發現

1-辛烯-3-醇由多種植物和真菌產生，包括食用菌和香蜂花等。1-辛烯-3-醇在亞油酸氧化分解過程中形成。^[5]

性質

1-辛烯-3-醇是衍生自1-辛烯的二級醇。它以兩種對映體，(R)-(–)-1-辛烯-3-醇和(S)-(+)-1-辛烯-3-醇的形式存在。

合成

1-辛烯-3-酮的兩種可能的實驗室合成為：^[6]

丙烯醛和戊基碘的格氏反應
對1-辛烯-3-酮的選擇性還原

在生物化學中，1-辛烯-3醇是從亞油酸的脂質過氧化，由脂氧合酶催化，然後通過氫過氧化物裂解酶（英语：Hydroperoxide lyase）的幫助下產生。該反應發生在奶酪中，在生物技術中用於產生(R)-異構體。^[7]^[8]

*(R)*-1-辛烯-3-醇的生物合成：（1）亞油酸（2）(8E,12Z)-10-氫過氧基十八烷酸（3）*(R)*-1-辛烯-3-醇（4）(8E)-10-氧代癸烯酸（5）脂氧合酶（6）氫過氧化物裂解酶

用途

1-辛烯-3-醇有時與二氧化碳結合使用來吸引昆蟲，以便用某些設備殺死它們。^[9]

使用「蘑菇醇」這個名稱是因為1-辛烯-3-醇是蘑菇的主要風味成分。^[10]

健康和安全

1-辛烯-3-醇已被美國食品和藥物管理局批准為食品添加劑。^[11]它具有中等毒性，LD₅₀為340 mg/kg。^[9]

在一項動物研究中，已發現1-辛烯-3-醇會破壞多巴胺體內平衡，並且可能是一種與帕金森氏症有關的環境因素。^[12]

參見

參考資料

^ 1-Octen-3-ol, Mushroom alcohol. [2019-08-29]. （原始内容存档于2020-11-24）.
^ Petherick A. How DEET jams insects' smell sensors. Nature News. 2008-03-13. doi:10.1038/news.2008.672. （原始内容存档于15 March 2008）.
^ Ditzen M, Pellegrino M, Vosshall LB. Insect odorant receptors are molecular targets of the insect repellent DEET. Science. March 2008, 319 (5871): 1838–42. Bibcode:2008Sci...319.1838D. PMID 18339904. S2CID 18499590. doi:10.1126/science.1153121.
^ 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. September 2008, 105 (36): 13598–603. PMC 2518096 . PMID 18711137. doi:10.1073/pnas.0805312105 .
^ Chemical properties of attractants. [2010-06-08]. （原始内容存档于2009-04-27）.
^ Wnuk, S.; Kinastowski, S.; Kamiński, E. Synthesis and analysis of 1-octen-3-ol, the main flavour component of mushrooms. Die Nahrung. 1983, 27 (5): 479–486 [2022-12-31]. ISSN 0027-769X. PMID 6684212. doi:10.1002/food.19830270523. （原始内容存档于2022-12-31）.
^ Matsui, Kenji; Sasahara, Satomi; Akakabe, Yoshihiko; Kajiwara, Tadahiko. Linoleic acid 10-hydroperoxide as an intermediate during formation of 1-octen-3-ol from linoleic acid in Lentinus decadetes. Bioscience, Biotechnology, and Biochemistry. 2003, 67 (10): 2280–2282 [2022-12-31]. ISSN 0916-8451. PMID 14586122. S2CID 46173472. doi:10.1271/bbb.67.2280. （原始内容存档于2022-12-31）.
^ Lipid biotechnology. Tsung Min Kuo, Harold W. Gardner. New York: Marcel Dekker. 2002. ISBN 0-585-40371-6. OCLC 48691412.
^ ^9.0 ^9.1 Biopesticides Fact Sheet for Octenol (PDF). EPA fact sheet. 2007-07-05 [2022-06-28]. （原始内容存档 (PDF)于2021-12-17）.
^ 1-octen-3-ol. thegoodscentscompany.com. [2015-05-31]. （原始内容存档于2022-12-26）.
^ US FDAs Center for Food Safety and Applied Nutrition. US FDA/CFSAN – EAFUS List. [2008-03-16]. （原始内容存档于2008-02-21）.
^ 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. November 2013, 110 (48): 19561–6. Bibcode:2013PNAS..11019561I. PMC 3845153 . PMID 24218591. doi:10.1073/pnas.1318830110 .

[1] 1-Octen-3-ol, Mushroom alcohol. [2019-08-29]. （原始内容存档于2020-11-24）.

[petherick-2] Petherick A. How DEET jams insects' smell sensors. Nature News. 2008-03-13. doi:10.1038/news.2008.672. （原始内容存档于15 March 2008）.

[3] Ditzen M, Pellegrino M, Vosshall LB. Insect odorant receptors are molecular targets of the insect repellent DEET. Science. March 2008, 319 (5871): 1838–42. Bibcode:2008Sci...319.1838D. PMID 18339904. S2CID 18499590. doi:10.1126/science.1153121.

[4] 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. September 2008, 105 (36): 13598–603. PMC 2518096 . PMID 18711137. doi:10.1073/pnas.0805312105 .

[5] Chemical properties of attractants. [2010-06-08]. （原始内容存档于2009-04-27）.

[6] Wnuk, S.; Kinastowski, S.; Kamiński, E. Synthesis and analysis of 1-octen-3-ol, the main flavour component of mushrooms. Die Nahrung. 1983, 27 (5): 479–486 [2022-12-31]. ISSN 0027-769X. PMID 6684212. doi:10.1002/food.19830270523. （原始内容存档于2022-12-31）.

[7] Matsui, Kenji; Sasahara, Satomi; Akakabe, Yoshihiko; Kajiwara, Tadahiko. Linoleic acid 10-hydroperoxide as an intermediate during formation of 1-octen-3-ol from linoleic acid in Lentinus decadetes. Bioscience, Biotechnology, and Biochemistry. 2003, 67 (10): 2280–2282 [2022-12-31]. ISSN 0916-8451. PMID 14586122. S2CID 46173472. doi:10.1271/bbb.67.2280. （原始内容存档于2022-12-31）.

[8] Lipid biotechnology. Tsung Min Kuo, Harold W. Gardner. New York: Marcel Dekker. 2002. ISBN 0-585-40371-6. OCLC 48691412.

[epa-9] 9.0 ^9.1 Biopesticides Fact Sheet for Octenol (PDF). EPA fact sheet. 2007-07-05 [2022-06-28]. （原始内容存档 (PDF)于2021-12-17）.

[10] 1-octen-3-ol. thegoodscentscompany.com. [2015-05-31]. （原始内容存档于2022-12-26）.

[11] US FDAs Center for Food Safety and Applied Nutrition. US FDA/CFSAN – EAFUS List. [2008-03-16]. （原始内容存档于2008-02-21）.

[12] 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. November 2013, 110 (48): 19561–6. Bibcode:2013PNAS..11019561I. PMC 3845153 . PMID 24218591. doi:10.1073/pnas.1318830110 .

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