蒎烯

蒎烯
	IUPAC名; (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene ; (1S,5S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane
識別
CAS號	80-56-8（(±)-α） ; 7785-70-8（1R,5R-α） ; 7785-26-4（1S,5S-α） ; 2437-95-8（來源未指明） ; 127-91-3（(±)-β） ; 18172-67-3（1S,5S-β）
性質
化學式	C10H16
莫耳質量	136.24 g·mol⁻¹
外觀	液體
密度	0.86 g·cm−3 (α, 15 °C)
熔點	-62 ~ -55 °C
沸點	155 ~ 156 °C
溶解性（水）	幾乎不溶於水
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

蒎烯（Pinene）是一類具有相同骨架結構的天然有機化合物，屬於雙環單萜，分子式C₁₀H₁₆。^[1]

自然界存在α-蒎烯和β-蒎烯，它們之間屬雙鍵的位置異構。這兩種蒎烯是松節油的主要成分（蒎烯英文名即出自松樹），也存在於其它松柏門植物中。在針葉植物以外的種類中也發現其存在，比如一種菊科植物Heterotheca（英語：Heterotheca）^[3]以及大鼠尾草（三齒蒿（英語：Artemisia tridentata））。

異構體

鍵線式
透視圖	X		X
球棒模型	X		X
名稱	(1R)-(+)-α-蒎烯	(1S)-(−)-α-蒎烯	(1R)-(+)-β-蒎烯	(1S)-(−)-β-蒎烯
CAS號	7785-70-8	7785-26-4	19902-08-0	18172-67-3

生物合成

生物體內，α-蒎烯和β-蒎烯都是由香葉基焦磷酸酯轉化生成的。反應機理經過酯基異構化，首先得芳樟醇焦磷酸酯，接著環化重排，然後從碳正離子失去一個質子得到產物。

Biosynthesis of pinene from geranyl pyrophosphate

分布

α-蒎烯是自然界中最廣泛分布的萜烯之一，^[4]具有強烈的驅蟲性。^[5]

α-蒎烯主要存在於針葉樹等植物。^[6]也是毒馬草屬和鼠尾草屬植物精油的主要成分。^[7]^[8]大麻屬也含α-蒎烯。^[6] 圓柄黃連木的樹脂富含蒎烯。松子中也存在。^[6]

箭葉橙的果皮精油主要成分為檸烯和β-蒎烯。^[9]

應用

化學工業上，蒎烯的催化氧化得到各種人工香料，如馬鞭烯酮等。^[10]

Pinene left verbenone right

參考資料

^ Record of alpha-Pinen in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）, accessed on 07-January-2016
^ Record of beta-Pinen in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）, accessed on 07-January-2016
^ Lincoln, D.E., B.M. Lawrence. 1984. The volatile constituents of camphorweed, Heterotheca subaxillaris. Phytochemistry 23(4):933-934
^ Noma Y, Asakawa Y (2010). Biotransformation of monoterpenoids by microorganisms, insects, and mammals. In: Baser KHC, Buchbauer G (eds). Handbook of Essential Oils: Science, Technology, and Applications. CRC Press: Boca Raton, FL, pp. 585–736.
^ Nerio LS, Olivero-Verbel J, Stashenko E. Repellent activity of essential oils: a review. Bioresour Technol. 2010, 101 (1): 372–378. PMID 19729299. doi:10.1016/j.biortech.2009.07.048.
^ ^6.0 ^6.1 ^6.2 Russo, E. B. Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. British Journal of Pharmacology. 2011, 163 (7): 1344–1364 [2017-05-12]. PMC 3165946  . PMID 21749363. doi:10.1111/j.1476-5381.2011.01238.x. （原始內容存檔於2018-02-22）.
^ Kose EO, Deniz IG, Sarikurkcu C, Aktas O, Yavuz M (2010). Chemical composition, antimicrobial and antioxidant activities of the essential oils of Sideritis erythrantha Boiss. and Heldr. (var. erythrantha and var. cedretorum P.H. Davis) endemic in Turkey. Food Chem Toxicol 48: 2960–2965.
^ Ozek G, Demirci F, Ozek T, Tabanca N, Wedge DE, Khan SI et al. (2010). Gas chromatographic-mass spectrometric analysis of volatiles obtained by four different techniques from Salvia rosifolia Sm., and evaluation for biological activity. J Chromatog 1217: 741–748.
^ Kasuan, Nurhani. Extraction of Citrus hystrix D.C. (Kaffir Lime) Essential Oil Using Automated Steam Distillation Process: Analysis of Volatile Compounds (PDF). Malyasian Journal of Analytical Sciences. 2013, 17 (3): 359–369 [2017-05-12]. （原始內容存檔 (PDF)於2020-08-06）.
^ U. Neuenschwander, Mechanism of the Aerobic Oxidation of α-Pinene, ChemSusChem. 2010, 3 (1): pp. 75–84,
doi:10.1002/cssc.200900228
（德文）

Mann, J.; Davidson, R. S.; Hobbs, J. B.; Banthorpe, D. V.; Harborne, J. B. Natural Products. Harlow, UK: Addison Wesley Longman Ltd. 1994: 309–311. ISBN 0-582-06009-5.

[GESTIS-1] Record of alpha-Pinen in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）, accessed on 07-January-2016

[GESTIS_beta-2] Record of beta-Pinen in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）, accessed on 07-January-2016

[3] Lincoln, D.E., B.M. Lawrence. 1984. The volatile constituents of camphorweed, Heterotheca subaxillaris. Phytochemistry 23(4):933-934

[noma2010-4] Noma Y, Asakawa Y (2010). Biotransformation of monoterpenoids by microorganisms, insects, and mammals. In: Baser KHC, Buchbauer G (eds). Handbook of Essential Oils: Science, Technology, and Applications. CRC Press: Boca Raton, FL, pp. 585–736.

[nerio2010-5] Nerio LS, Olivero-Verbel J, Stashenko E. Repellent activity of essential oils: a review. Bioresour Technol. 2010, 101 (1): 372–378. PMID 19729299. doi:10.1016/j.biortech.2009.07.048.

[russo2011-6] 6.0 ^6.1 ^6.2 Russo, E. B. Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. British Journal of Pharmacology. 2011, 163 (7): 1344–1364 [2017-05-12]. PMC 3165946  . PMID 21749363. doi:10.1111/j.1476-5381.2011.01238.x. （原始內容存檔於2018-02-22）.

[7] Kose EO, Deniz IG, Sarikurkcu C, Aktas O, Yavuz M (2010). Chemical composition, antimicrobial and antioxidant activities of the essential oils of Sideritis erythrantha Boiss. and Heldr. (var. erythrantha and var. cedretorum P.H. Davis) endemic in Turkey. Food Chem Toxicol 48: 2960–2965.

[8] Ozek G, Demirci F, Ozek T, Tabanca N, Wedge DE, Khan SI et al. (2010). Gas chromatographic-mass spectrometric analysis of volatiles obtained by four different techniques from Salvia rosifolia Sm., and evaluation for biological activity. J Chromatog 1217: 741–748.

[kasuan-9] Kasuan, Nurhani. Extraction of Citrus hystrix D.C. (Kaffir Lime) Essential Oil Using Automated Steam Distillation Process: Analysis of Volatile Compounds (PDF). Malyasian Journal of Analytical Sciences. 2013, 17 (3): 359–369 [2017-05-12]. （原始內容存檔 (PDF)於2020-08-06）.

[10] U. Neuenschwander, Mechanism of the Aerobic Oxidation of α-Pinene, ChemSusChem. 2010, 3 (1): pp. 75–84,
doi:10.1002/cssc.200900228
（德文）

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蒎烯

IUPAC名 (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene (1S,5S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane
識別
CAS號	80-56-8（(±)-α） ^Y 7785-70-8（1R,5R-α） ^Y 7785-26-4（1S,5S-α） ^Y 2437-95-8（來源未指明） ^Y 127-91-3（(±)-β） ^Y 18172-67-3（1S,5S-β） ^Y
性質
化學式	C₁₀H₁₆
莫耳質量	136.24 g·mol⁻¹
外觀	液體
密度	0.86 g·cm⁻³ (α, 15 °C)^[1]^[2]
熔點	-62 ~ -55 °C
沸點	155 ~ 156 °C
溶解性（水）	幾乎不溶於水
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。