Piperitone
(Synonyms: 胡椒酮) 目录号 : GC48955
A monoterpenoid with diverse biological activities
Cas No.:89-81-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Piperitone is a monoterpenoid that has been found in Mentha and has diverse biological activities.1,2,3,4 It is active against E. coli, P. aeruginosa, S. typhimurium, S. aureus, R. leguminosarum, and B. subtilis in agar diffusion assays.1 Piperitone enhances the antibacterial activity of nitrofurantoin against several nitrofurantoin-resistant species of Enterobacteriaceae, including C. freundii, E. coli, and S. marcescens, by 3- to 20-fold.2 It exhibits feeding deterrent and repellent activities against ants (Crematogaster) with 80% deterrence index (D80) and 80% repellent index (R80) values of 0.13 µg/µl and 8.9 µg/cm2, respectively.3 Piperitone is insecticidal against C. maculatus eggs, larvae, and adults.4
1.Sivropoulou, A., Kokkini, S., Lanaras, T., et al.Antimicrobial activity of mint essential oilsJ. Agric. Food Chem.43(9)2384-2388(1995) 2.Shahverdi, A.R., Rafii, F., Tavassoli, F., et al.Piperitone from Mentha longifolia var. chorodictya Rech F. reduces the nitrofurantoin resistance of strains of EnterobacteriaceaePhytother. Res.18(11)911-914(2004) 3.Bowers, W.S., Ortego, F., You, X., et al.Insect repellents from the Chinese prickly ash Zanthoxylum bungeanumJ. Nat. Prod.56(6)935-938(1993) 4.Ketoh, G.K., Koumaglo, H.K., Glitho, I.A., et al.Comparative effects of Cymbopogon schoenanthus essential oil and piperitone on Callosobruchus maculatus developmentFitoterapia77(7-8)506-510(2006)
| Cas No. | 89-81-6 | SDF | |
| 别名 | 胡椒酮 | ||
| Canonical SMILES | O=C1C=C(CCC1C(C)C)C | ||
| 分子式 | C10H16O | 分子量 | 152.2 |
| 溶解度 | Ethanol: 30 mg/ml,Ethanol:PBS (pH 7.2) (1:6): 0.14 mg/ml | 储存条件 | Store at -20°C,protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.5703 mL | 32.8515 mL | 65.703 mL |
| 5 mM | 1.3141 mL | 6.5703 mL | 13.1406 mL |
| 10 mM | 0.657 mL | 3.2852 mL | 6.5703 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Identification and analysis of Piperitone in red wines
Food Chem 2016 Sep 1;206:191-6.PMID:27041315DOI:10.1016/j.foodchem.2016.03.064.
The present study concerns the search for new aroma compounds associated with the flavor of aged and prematurely aged red wines. Sensory descriptive analysis associated with gas chromatography-olfactometry was first performed to find specific odoriferous zones. One of the zones, reminiscent of mint, was found in red wines with a prune flavor. Thanks to several analytical approaches including preparative gas chromatography, p-menth-1-en-3-one (Piperitone), has been identified in red wines. The olfactory detection threshold of this terpene reminiscent of mint was 0.9μg/L in model hydroalcoholic solution and 70μg/L in red wines. Chiral multidimensional GC-MS was used to show that Piperitone was present mainly in the (R) form in red wines. The concentration of Piperitone in aged red wines ranged from a few ng/L to 435ng/L, but the level was not linked to the age of the wine nor to its premature evolution.
Piperitone-derived saturated lactones: synthesis and aphid behavior-modifying activity
J Agric Food Chem 2013 Apr 10;61(14):3364-72.PMID:23477664DOI:10.1021/jf3052219.
Two racemic and two enantiomeric pairs of new saturated lactones with the p-menthane system were obtained. The lactones were synthesized from racemic and enantiomerically enriched cis- and trans-piperitols, which were obtained from Piperitone. The structures of the compounds were confirmed by spectroscopic data. The antifeedant activity of Piperitone to Myzus persicae was studied, and the biological consequences of structural modifications of Piperitone, that is, lactonization and chiral center configuration, were examined as well. The behavioral responses of M. persicae to Piperitone and piperitone-derived saturated lactones were investigated to reveal the biological background of their deterrent activity. Piperitone appeared rather neutral or weakly deterrent to aphids. The introduction of a lactone moiety into a Piperitone molecule dramatically changed its biological activity. All piperitone-derived lactones evoked negative aphid responses. However, the deterrent activity of individual compounds varied in potency, the time of expression, and the duration of the effect, depending on the spatial structure of the lactone. Lactones (1R,3S,6R)-3-isopropyl-6-methyl-9-oxabicyclo[4.3.0]nonan-8-one and trans-3-isopropyl-6-methyl-9-oxabicyclo[4.3.0]nonan-8-one showed the broadest ranges and the highest potencies and durabilities of deterrent activity to M. persicae: they acted immediately after application, caused a cessation of probing before aphids reached phloem elements, and decreased the quality of phloem sap.
Structural and antitrypanosomal data of different carbasones of Piperitone
Data Brief 2016 Nov 18;9:1039-1043.PMID:27900358DOI:10.1016/j.dib.2016.11.044.
This article reports data on four carbazones of Piperitone: semicarbazone 1, thiosemicarbazone 2, 4-phenyl semicarbazone 3 and 4-phenyl thiosemicarbazone 4 prepared directly in situ from essential oil of Cymbopogon schoenantus, whose GC-FID and GC-MS analysis revealed Piperitone as major component (68.20%). The structures of hemi-synthesized compounds were confirmed by high throughput IR, MS, 1H and 13C NMR based spectrometric analysis. Their antiparasitic activities were evaluated in vitro on Trypanosoma brucei brucei (Tbb). The compound 3 (IC50=8.63±0.81 µM) and 4 (IC50=10.90±2.52 µM) exhibited antitrypanosomal activity, 2 had a moderate activity (IC50=74.58±4.44 µM) but 1 was void of significant activity (IC50=478.47 µM). The in vitro tests showed that all compounds were less cytotoxic against the human non cancer fibroblast cell line (WI38) (IC50>80 µM) while only 2 (IC50=21.16±1.37 μM) and 4 (IC50=32.22±1.66 µM) were cytotoxic against the Chinese Hamster Ovary (CHO) cells and toxic on Artemia salina (Leach) larvae. Piperitone 4-phenyl semicarbazone 3, the best antitrypanosomal compound, showed also a selectivity index (SI) higher than 7 on the larvae and the tested cells and therefore might be further studied as antitrypanosomal agent. Also, all compounds except 3 showed selectivity between the two tested cell lines (SI>2). This data reveals for the first time the antitrypinosomal properties of thiosemicarbazones, their cytotoxicity on mammalian cells as well as their activities against Tbb and A. salina Leach.
Piperitone from Mentha longifolia var. chorodictya Rech F. reduces the nitrofurantoin resistance of strains of enterobacteriaceae
Phytother Res 2004 Nov;18(11):911-4.PMID:15597306DOI:10.1002/ptr.1566.
The diluted essential oil of Mentha longifolia (L.) var. chlorodictya Rech F. foliage enhanced the bactericidal activity of nitrofurantoin decreasing the minimum inhibitory concentration (MIC) of nitrofurantoin for nitrofurantoin-resistant strains of Enterobacteriaceae. Thin-layer chromatography (TLC) analysis of the essential oil detected a fraction (R(f) = 0.35, UV lambda(max) of 232.5), which was the most effective in enhancement of nitrofurantoin activity. Using gas liquid chromatography and known standards, the active fraction was identified as Piperitone. 1 microl of the Piperitone fraction decreased the MIC of nitrofurantoin 3-20 fold for the different strains of Enterobacteriaceae tested.
Enantioselectivity of hydroxylation of racemic Piperitone by fungi
Chirality 2010 Nov;22(10):929-35.PMID:20872669DOI:10.1002/chir.20862.
The biotransformation of racemic Piperitone ((±)-1) was investigated using four strains of fungi selected in the screening procedure. The substrate was transformed by Botrytis cinerea AM235, Absidia cylindrospora AM336, Absidia coerulea AM93, and Absidia glauca AM177 into more polar metabolites. The transformation of racemic Piperitone ((±)-1) catalyzed by B. cinerea AM235 gave 7-hydroxypiperitone (2) as the only product. The biotransformation of (±)-1 by A. cylindrospora AM336 afforded mixture of three products: (-)-(R)-7-hydroxypiperitone ((-)-2), (+)-(4S,6R)-trans-6-hydroxypiperitone ((+)-3), and (+)-(4R,6R)-cis-6-hydroxypiperitone ((+)-4). The transformation of this substrate ((±)-1) by A. coerulea AM93 gave (±)-7-hydroxypiperitone ((±)-2), (-)-(4R,6S)-trans-6-hydroxypiperitone (-)-3), and (-)-(4S,6S)-cis-6-hydroxypiperitone ((-)-4). The last strain studied, A. glauca AM177, converted racemic Piperitone ((±)-1) to four products: (+)-(S)-7-hydroxypiperitone (2), (+)-(4S,6R)-trans-6-hydroxypiperitone ((+)-3), (±)-cis-6-hydroxypiperitone ((±)-4), and 8-hydroxypiperitone (5).