胡薄荷酮

化合物

胡薄荷酮(英語:Pulegone),也叫長葉薄荷酮蒲勒酮,是一種天然存在的有機化合物,從多種植物的精油中提取,例如貓薄荷辣薄荷唇萼薄荷[2][3]它被歸類為單萜

胡薄荷酮[1]
IUPAC名
(5R)-5-Methyl-2-(propan-2-ylidene)cyclohexan-1-one
別名 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
識別
CAS號 89-82-7  checkY
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
性質
化學式 C10H16O
摩爾質量 152.23 g·mol−1
外觀 無色油狀物
密度 0.9346 g/cm3
沸點 224 °C(497 K)
溶解性 不溶
溶解性乙醇

氯仿
混溶
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

胡薄荷酮是一種透明無色油狀液體,具有類似於薄荷樟腦的宜人氣味。它用於調味劑、香水芳香療法

毒理學

據報道,如果大量食用該化學物質,會對老鼠產生毒性。[4][5]

胡薄荷酮也是一種殺蟲劑,是許多薄荷物種中天然存在的三種殺蟲劑中最強大的一種。[6]

截至2018年10月,美國食品藥品監督管理局撤銷了將胡薄荷酮用作食品中合成調味物質的授權,但天然存在的胡薄荷酮可以繼續使用。[7]

來源

參見

參考資料

  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. ^ 5.0 5.1 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. (原始內容存檔於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.