胡薄荷酮

胡薄荷酮
	IUPAC名; (5R)-5-Methyl-2-(propan-2-ylidene)cyclohexan-1-one
别名	p-Menth-4(8)-en-3-one; ; δ-4(8)-p-Menthen-3-one; ; (R)-2-Isopropylidene-5-methylcyclohexanone; ; (R)-p-Menth-4(8)-en-3-one; ; (R)-(+)-Pulegone
识别
CAS号	89-82-7
PubChem	442495
ChemSpider	390923
SMILES	O=C1/C(=C(/C)C)CC[C@@H](C)C1;
InChI	1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1;
InChIKey	NZGWDASTMWDZIW-MRVPVSSYBS
ChEBI	35596
性质
化学式	C10H16O
摩尔质量	152.23 g·mol−1
外观	无色油状物
密度	0.9346 g/cm3
沸点	224 °C（497 K）
溶解性（水）	不溶
溶解性（乙醇; 醚; 氯仿）	混溶
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

胡薄荷酮（英语：Pulegone），也叫长叶薄荷酮或蒲勒酮，是一种天然存在的有机化合物，从多种植物的精油中提取，例如猫薄荷、辣薄荷和唇萼薄荷。^[2]^[3]它被归类为单萜。

事实速览 胡薄荷酮[1], 识别 ...

关闭

胡薄荷酮是一种透明无色油状液体，具有类似于薄荷和樟脑的宜人气味。它用于调味剂、香水和芳香疗法。

据报道，如果大量食用该化学物质，会对老鼠产生毒性。^[4]^[5]

胡薄荷酮也是一种杀虫剂，是许多薄荷物种中天然存在的三种杀虫剂中最强大的一种。^[6]

截至2018年10月，美国食品药品监督管理局撤销了将胡薄荷酮用作食品中合成调味物质的授权，但天然存在的胡薄荷酮可以继续使用。^[7]

薄荷呋喃（英语：Menthofuran）
薄荷醇

[1]
Merck Index, 11th Edition, 7955.
[2]
Grundschober, F. Literature review of pulegone. Perfum. Flavorist. 1979, 4: 15–17.
[3]
Sullivan, J.B., Rumack, B.H., Thomas, H., Peterson, R.G. & Brysch, P. Pennyroyal oil poisoning and hepatotoxicity. J. Am. Med. Assoc. 1979, 242 (26): 2873–2874. PMID 513258. doi:10.1001/jama.1979.03300260043027.
[4]
Thorup, I.; Würtzen, G; Carstensen, J; Olsen, P; et al. Short term toxicity study in rats dosed with pulegone and menthol. Toxicology Letters. 1983, 19 (3): 207–210. PMID 6658833. doi:10.1016/0378-4274(83)90120-0.
[5]
Asekun, O.T.; Grierson, D; Afolayan, A; et al. Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. Capensis. Food Chemistry. 2006, 101 (3): 995–998. doi:10.1016/j.foodchem.2006.02.052.
[6]
Franzios, G; Mirotsou M; Hatziapostolou E; Kral J; Scouras ZG; Mavragani-Tsipidou P. Insecticidal and genotoxic activities of mint essential oils. Journal of Agricultural and Food Chemistry. 16 July 1997, 45 (7): 2690–2694 [19 October 2012]. doi:10.1021/jf960685f. （原始内容存档于23 December 2012）.
[7]
83 FR 50490
[8]
Božović M, Pirolli A, Ragno R. Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry. Molecules (Basel, Switzerland). May 2015, 20 (5): 8605–33. PMC 6272761 . PMID 25985361. doi:10.3390/molecules20058605 .
[9]
Gordon, W. Perry; Valerie Howland; et al. Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicology and Applied Pharmacology. 1982, 65 (3): 413–424. PMID 7157374. doi:10.1016/0041-008X(82)90387-8.
[10]
Farley, Derek R.; Valerie Howland. The natural variation of the pulegone content in various oils of peppermint. Journal of the Science of Food and Agriculture. 2006, 31 (11): 1143–1151. doi:10.1002/jsfa.2740311104.

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[1] [1]
Merck Index, 11th Edition, 7955.

[2] [2]
Grundschober, F. Literature review of pulegone. Perfum. Flavorist. 1979, 4: 15–17.

[3] [3]
Sullivan, J.B., Rumack, B.H., Thomas, H., Peterson, R.G. & Brysch, P. Pennyroyal oil poisoning and hepatotoxicity. J. Am. Med. Assoc. 1979, 242 (26): 2873–2874. PMID 513258. doi:10.1001/jama.1979.03300260043027.

[stts-4] [4]
Thorup, I.; Würtzen, G; Carstensen, J; Olsen, P; et al. Short term toxicity study in rats dosed with pulegone and menthol. Toxicology Letters. 1983, 19 (3): 207–210. PMID 6658833. doi:10.1016/0378-4274(83)90120-0.

[edmq-5] [5]
Asekun, O.T.; Grierson, D; Afolayan, A; et al. Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. Capensis. Food Chemistry. 2006, 101 (3): 995–998. doi:10.1016/j.foodchem.2006.02.052.

[6] [6]
Franzios, G; Mirotsou M; Hatziapostolou E; Kral J; Scouras ZG; Mavragani-Tsipidou P. Insecticidal and genotoxic activities of mint essential oils. Journal of Agricultural and Food Chemistry. 16 July 1997, 45 (7): 2690–2694 [19 October 2012]. doi:10.1021/jf960685f. （原始内容存档于23 December 2012）.

[7] [7]
83 FR 50490

[pmid25985361-8] [8]
Božović M, Pirolli A, Ragno R. Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry. Molecules (Basel, Switzerland). May 2015, 20 (5): 8605–33. PMC 6272761 . PMID 25985361. doi:10.3390/molecules20058605 .

[hptp-9] [9]
Gordon, W. Perry; Valerie Howland; et al. Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicology and Applied Pharmacology. 1982, 65 (3): 413–424. PMID 7157374. doi:10.1016/0041-008X(82)90387-8.

[nvpc-10] [10]
Farley, Derek R.; Valerie Howland. The natural variation of the pulegone content in various oils of peppermint. Journal of the Science of Food and Agriculture. 2006, 31 (11): 1143–1151. doi:10.1002/jsfa.2740311104.

[2]

[3]

[1]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

胡薄荷酮

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胡薄荷酮

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毒理学

来源

参见

参考资料

胡薄荷酮^[1]

IUPAC名 (5R)-5-Methyl-2-(propan-2-ylidene)cyclohexan-1-one
别名	p-Menth-4(8)-en-3-one; δ-4(8)-p-Menthen-3-one; (R)-2-Isopropylidene-5-methylcyclohexanone; (R)-p-Menth-4(8)-en-3-one; (R)-(+)-Pulegone
识别
CAS号	89-82-7 ^Y
PubChem	442495
ChemSpider	390923
SMILES	O=C1/C(=C(/C)C)CC[C@@H](C)C1
InChI	1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1
InChIKey	NZGWDASTMWDZIW-MRVPVSSYBS
ChEBI	35596
性质
化学式	C₁₀H₁₆O
摩尔质量	152.23 g·mol⁻¹
外观	无色油状物
密度	0.9346 g/cm³
沸点	224 °C（497 K）
溶解性（水）	不溶
溶解性（乙醇醚氯仿）	混溶
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。