环十五酮

环十五酮是一种环酮，也是大环化合物，化学式C15H28O。它的结构与麝香酮相似，两者只差一个甲基。它存在于大灵猫的臭腺（英语：Scent gland）中。 环十五酮最早由拉沃斯拉夫·鲁日奇卡于1926年通过加热分解十六烷二酸的钍盐合成，产率只有2%。在此之后也有用噻吩或环十二酮开始的合成方法。 环十五酮是有强烈麝香的无色或白色针状晶体，难溶于水。它的晶体结构已用晶体X射线衍射表征，15个碳原子基本共面，羰基中的氧原子则位于此平面外。环十五酮呈单斜晶系，空间群P21/c（No. 14），晶格参数 a = 15.6634 Å、b = 5.5531 Å、c = 17.6928 Å 、β = 116.315°。 环十五酮经过与乙二醇反应生成缩酮，用苯基三甲基三溴化铵溴化，经DBN脱溴，再用酸水解，最终与甲基溴化镁在氯化亚铜存在下反应，生成麝香酮。 环十五酮可用作香水的芳香味化合物和固定剂，也存在于肥皂、洗发精等个人护理产品中。全球每年都会有几十吨的环十五酮应用于此。 环十五酮造成的健康风险非常小。给大鼠口服5 g/kg的环十五酮，以及给小鼠口服10 g/kg的环十五酮都没有出现毒性。环十五酮不刺激皮肤，没有基因毒性和光毒性，在埃姆斯试验中不表现为突变原。 Api, A.M.; Belsito, D.; Botelho, D.; Bruze, M.; Burton, G.A.; Buschmann, J.; Cancellieri, M.A.; Dagli, M.L.; Date, M.; Dekant, W.; Deodhar, C.; Fryer, A.D.; Jones, L.; Joshi, K.; Kumar, M.; Lapczynski, A.; Lavelle, M.; Lee, I.; Liebler, D.C.; Moustakas, H.; Na, M.; Penning, T.M.; Ritacco, G.; Romine, J.; Sadekar, N.; Schultz, T.W.; Selechnik, D.; Siddiqi, F.; Sipes, I.G.; Sullivan, G.; Thakkar, Y.; Tokura, Y. RIFM fragrance ingredient safety assessment, cyclopentadecanone, CAS Registry Number 502-72-7. Food and Chemical Toxicology. 2021, 156: 112474. doi:10.1016/j.fct.2021.112474.  来源：Sigma-Aldrich Co., product no. C111201 . Lide, David R. CRC Handbook of Chemistry and Physics. CRC Press. 1995-03-09: 3-142. ISBN 978-0-8493-0595-5.  McGinty, D.; Letizia, C.s.; Api, A.M. Fragrance material review on cyclopentadecanone. Food and Chemical Toxicology. 2011, 49: S142–S148. doi:10.1016/j.fct.2011.07.041.  Buckingham, John. Dictionary of Natural Products, Supplement 2. London: CRC Press. 1995-12-07: 68. ISBN 978-0-412-60420-1.  Danute Pajaujis Anonis. Civet and civet compounds (PDF). Perfumer & flavorist. 1997 [2024-01-17]. （原始内容存档 (PDF)于2024-01-18）.  Sytniczuk, Adrian; Leszczyńska, Agnieszka; Kajetanowicz, Anna; Grela, Karol. Preparation of Musk‐Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination. ChemSusChem. 2018-09-21, 11 (18): 3157–3166. ISSN 1864-5631. doi:10.1002/cssc.201801463.  Taits, S. Z.; Gol'dfarb, Ya. L. A new synthesis of cyclopentadecanone (exaltone). Bulletin of the Academy of Sciences of the USSR Division of Chemical Science. 1960, 9 (9): 1574–1576. ISSN 0568-5230. doi:10.1007/BF00909832.  Nozaki, H.; Mori, T.; Noyori, R. A novel synthesis of cyclopentadecanone from cyclododecanone. Tetrahedron Letters. 1967, 8 (9): 779–780. doi:10.1016/S0040-4039(00)71561-9.  Noe, Eric A.; Pawar, Diwakar M.; Fronczek, Frank R. Cyclopentadecanone. Acta Crystallographica Section C Crystal Structure Communications. 2008-02-15, 64 (2): o67–o68. ISSN 0108-2701. doi:10.1107/S0108270107066139.  Mookherjee, B. D.; Patel, R. R.; Ledig, W. O. Synthesis of dl-muscone from exaltone (cyclopentadecanone). The Journal of Organic Chemistry. 1971, 36 (26): 4124–4125. ISSN 0022-3263. doi:10.1021/jo00825a024.  Api, A.M.; Belsito, D.; Botelho, D.; Bruze, M.; Burton, G.A.; Buschmann, J.; Cancellieri, M.A.; Dagli, M.L.; Date, M.; Dekant, W.; Deodhar, C.; Fryer, A.D.; Jones, L.; Joshi, K.; Kumar, M.; Lapczynski, A.; Lavelle, M.; Lee, I.; Liebler, D.C.; Moustakas, H.; Na, M.; Penning, T.M.; Ritacco, G.; Romine, J.; Sadekar, N.; Schultz, T.W.; Selechnik, D.; Siddiqi, F.; Sipes, I.G.; Sullivan, G.; Thakkar, Y.; Tokura, Y. RIFM fragrance ingredient safety assessment, cyclopentadecanone, CAS Registry Number 502-72-7. Food and Chemical Toxicology. 2021, 156: 112474. doi:10.1016/j.fct.2021.112474.  Eisenbrand, Gerhard; Schreier, Peter. RÖMPP Lexikon Lebensmittelchemie, 2. Auflage, 2006. Georg Thieme Verlag. 2014-05-28: 386. ISBN 978-3-13-179532-8 （德语）.  Nakata, Haruhiko; Hinosaka, Mari; Yanagimoto, Hayato. Macrocyclic-, polycyclic-, and nitro musks in cosmetics, household commodities and indoor dusts collected from Japan: Implications for their human exposure. Ecotoxicology and Environmental Safety. 2015, 111: 248–255. doi:10.1016/j.ecoenv.2014.09.032.