環十五酮

環十五酮
識別
CAS號	502-72-7
PubChem	10409
SMILES	C1CCCCCCCCCCCCCC1=O;
EC編號	207-951-2
性質
化學式	C15H28O
摩爾質量	224.38 g·mol−1
外觀	無色或白色針狀晶體
氣味	強烈麝香
密度	0.897 g·cm−3
熔點	63—65 °C（336—338 K）
沸點	120 °C（393 K）（0.3 mmHg）
溶解性（水）	0.5989 mg/L
溶解性	與乙醇、苯混溶，可溶於丙酮
危險性
	致死量或濃度：
LD50（中位劑量）	>5000 mg·kg−1（兔子，經皮給藥（英語：Transdermal））
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

環十五酮是一種環酮，也是大環化合物，化學式C₁₅H₂₈O。它的結構與麝香酮相似，兩者只差一個甲基。它存在於大靈貓的臭腺（英語：Scent gland）中。^[5]^[6]

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製備

環十五酮最早由拉沃斯拉夫·魯日奇卡於1926年通過加熱分解十六烷二酸的釷鹽合成，產率只有2%。^[7]在此之後也有用噻吩^[8]或環十二酮^[9]開始的合成方法。

性質

環十五酮是有強烈麝香的無色或白色針狀晶體，難溶於水。^[1]它的晶體結構已用晶體X射線繞射表徵，15個碳原子基本共面，羰基中的氧原子則位於此平面外。環十五酮呈單斜晶系，空間群P2₁/c（No. 14），晶格參數 a = 15.6634 Å、b = 5.5531 Å、c = 17.6928 Å 、β = 116.315°。^[10]

反應

環十五酮經過與乙二醇反應生成縮酮，用苯基三甲基三溴化銨溴化，經DBN 脫溴，再用酸水解，最終與甲基溴化鎂在氯化亞銅存在下反應，生成麝香酮。^[11]

用處

環十五酮可用作香水的芳香味化合物和固定劑，^[12]^[13]也存在於肥皂、洗髮精等個人護理產品中。^[14]全球每年都會有幾十噸的環十五酮應用於此。^[12]

毒性

環十五酮造成的健康風險非常小。給大鼠口服5 g/kg的環十五酮，以及給小鼠口服10 g/kg的環十五酮都沒有出現毒性。^[4]環十五酮不刺激皮膚^[4]，沒有基因毒性和光毒性，在埃姆斯試驗中不表現為突變原。^[12]

參考資料

[1]
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.
[2]
來源：Sigma-Aldrich Co., product no. C111201 .
[3]
Lide, David R. CRC Handbook of Chemistry and Physics. CRC Press. 1995-03-09: 3-142. ISBN 978-0-8493-0595-5.
[4]
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.
[5]
Buckingham, John. Dictionary of Natural Products, Supplement 2. London: CRC Press. 1995-12-07: 68. ISBN 978-0-412-60420-1.
[6]
Danute Pajaujis Anonis. Civet and civet compounds (PDF). Perfumer & flavorist. 1997 [2024-01-17]. （原始內容存檔 (PDF)於2024-01-18）.
[7]
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.
[8]
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.
[9]
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.
[10]
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.
[11]
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.
[12]
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.
[13]
Eisenbrand, Gerhard; Schreier, Peter. RÖMPP Lexikon Lebensmittelchemie, 2. Auflage, 2006. Georg Thieme Verlag. 2014-05-28: 386. ISBN 978-3-13-179532-8 （德語）.
[14]
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.

[:2-1] [1]
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.

[Sigma-2] [2]
來源：Sigma-Aldrich Co., product no. C111201 .

[David_R._Lide-3] [3]
Lide, David R. CRC Handbook of Chemistry and Physics. CRC Press. 1995-03-09: 3-142. ISBN 978-0-8493-0595-5.

[:3-4] [4]
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.

[Dict-5] [5]
Buckingham, John. Dictionary of Natural Products, Supplement 2. London: CRC Press. 1995-12-07: 68. ISBN 978-0-412-60420-1.

[:1-6] [6]
Danute Pajaujis Anonis. Civet and civet compounds (PDF). Perfumer & flavorist. 1997 [2024-01-17]. （原始內容存檔 (PDF)於2024-01-18）.

[7] [7]
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.

[8] [8]
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.

[9] [9]
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.

[10] [10]
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.

[11] [11]
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.

[:0-12] [12]
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.

[Alfred_Hagen_Meyer-13] [13]
Eisenbrand, Gerhard; Schreier, Peter. RÖMPP Lexikon Lebensmittelchemie, 2. Auflage, 2006. Georg Thieme Verlag. 2014-05-28: 386. ISBN 978-3-13-179532-8 （德語）.

[14] [14]
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.

[5]

[6]

[1]

[2]

[3]

[4]

[7]

[8]

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