(-)-Perillyl Alcohol
(Synonyms: 紫苏醇) 目录号 : GC40698
A monoterpene alcohol with diverse biological activities
Cas No.:18457-55-1
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
(-)-Perillyl alcohol is a monoterpene alcohol that has been found in lavender essential oil and has diverse biological activities. It reduces production of hydroperoxidienes and thiobarbituric acid reactive substances (TBARS) in vitro in a concentration-dependent manner. (-)-Perillyl alcohol inhibits PANC-1 pancreatic carcinoma cell and H-Ras-transformed fibroblast growth when used at a concentration of 1 mM. It also inhibits the growth of P. aeruginosa, E. coli, S. aureus, and C. albicans (MICs = 480-2,900 ppm).
| Cas No. | 18457-55-1 | SDF | |
| 别名 | 紫苏醇 | ||
| Canonical SMILES | CC([C@@H]1CC=C(CO)CC1)=C | ||
| 分子式 | C10H16O | 分子量 | 152.2 |
| 溶解度 | DMF: miscible,DMSO: miscible,Ethanol: miscible | 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。
Biosynthesis of ( R)-(+)-Perillyl Alcohol by Escherichia coli expressing neryl pyrophosphate synthase
Eng Life Sci 2022 Feb 13;22(5):407-416.PMID:35573132DOI:10.1002/elsc.202100135.
(R)-(+)-Perillyl Alcohol is widely used in agricultural and anticarcinogenic fields. Microbial production of (R)-(+)-Perillyl Alcohol was investigated in this study. We optimized biosynthesis of (R)-(+)-Perillyl Alcohol in Escherichia coli by using neryl pyrophosphate synthase and NADPH regeneration. Engineering neryl pyrophosphate (NPP)-supplied pathway resulted in a 4-fold improvement of (R)-(+)-Perillyl Alcohol titer. Subsequently, combined engineering of p-cymene monooxygenase (CymA) expression and module for NADPH regeneration exhibited a 15.4-fold increase of titer over the initial strain S02. Finally, 453 mg/L (R)-(+)-Perillyl Alcohol was achieved in fed-batch fermentation, which is the highest (R)-(+)-Perillyl Alcohol titer in E. coli.
Efficient Synthesis of ( R)-(+)-Perillyl Alcohol From ( R)-(+)-Limonene Using Engineered Escherichia coli Whole Cell Biocatalyst
Front Bioeng Biotechnol 2022 Apr 25;10:900800.PMID:35547170DOI:10.3389/fbioe.2022.900800.
(R)-(+)-Perillyl Alcohol is a much valued supplemental compound with a wide range of agricultural and pharmacological characteristics. The aim of this study was to improve (R)-(+)-Perillyl Alcohol production using a whole-cell catalytic formula. In this study, we employed plasmids with varying copy numbers to identify an appropriate strain, strain 03. We demonstrated that low levels of alKL provided maximal biocatalyst stability. Upon determination of the optimal conditions, the (R)-(+)-Perillyl Alcohol yield reached 130 mg/L. For cofactor regeneration, we constructed strain 10, expressing FDH from Candida boidinii, and achieved (R)-(+)-Perillyl Alcohol production of 230 mg/L. As a result, 1.23 g/L (R)-(+)-Perillyl Alcohol was transformed in a 5 L fermenter. Our proposed method facilitates an alternative approach to the economical biosynthesis of (R)-(+)-Perillyl Alcohol.
The Release of Perillyl Alcohol from the Different Kind of Vehicles
Curr Pharm Biotechnol 2018;19(7):573-580.PMID:30062959DOI:10.2174/1389201019666180730165330.
Background: Skin cancers are the most common malignancy in humans, and the number of cases has increased dramatically in the past few decades. Therefore, it is very important to carry out studies concerning new and safer anticancer natural agents (e.g. perillyl alcohol) and modern drug delivery systems, such as nanoformulations, which increase their bioavailability. Objectives: The aim of this work was to obtain different kinds of topical vehicles formulation and compare their efficiency in the release of perillyl alcohol. The release kinetics was determined by using certain selected mathematical models. Method: Formulations of a hydrogel, O/W nanoemulsion, O/W macroemulsion and nanostructured lipid carrier were developed as carriers for perillyl alcohol - one of the promising anticancer natural agents. The release study of the active agents was carried out using the Spectra/Por Standard Regenerated Cellulose membrane, at temperature T=320C. The concentration of active agents in the receptor solution was analyzed by high performance liquid chromatography. The release kinetics was determined by using selected mathematical models. Results: The results of our release studies have shown that the highest and comparable amount of perillyl alcohol was released from hydrogel (35.72 ± 0.21%), NLC (35.54 ± 1.48%) and nanoemulsion (34.87 ± 4.49%). The release was found to follow Fickian diffusion in the case of hydrogel and macroemulsion, while an anomalous mechanism was observed in the case of nanoformulations. Nevertheless, the obtained nanoformulations, as well as a conventional hydrogel, may be considered potential vehicles in topical delivery of perillyl alcohol.
Effectiveness of recombinant Escherichia coli on the production of (R)-(+)-Perillyl Alcohol
BMC Biotechnol 2021 Jan 8;21(1):3.PMID:33419424DOI:10.1186/s12896-020-00662-7.
Background: (R)-(+)-Perillyl Alcohol is a naturally oxygenated monoterpene widely used as the natural flavor additives, insecticides, jet fuels and anti-cancer therapies. It was also readily available monoterpene precursors. However, this natural product is present at low concentrations from plant sources which are not economically viable. Therefore, alternative microbial production methods are rapidly emerging as an attractive alternative to make (R)-(+)-Perillyl Alcohol production more sustainable and environmentally friendly. Results: We engineered Escherichia coli to possess a heterologous mevalonate (MVA) pathway, including limonene synthase, P-cymene monoxygenase hydroxylase and P-cymene monoxygenase reductase for the production of (R)-(+)-Perillyl Alcohol. The concentration of (R)-(+)-limonene (the monoterpene precursor to (R)-(+)-Perillyl Alcohol) reached 45 mg/L from glucose. Enhanced (R)-(+)-Perillyl Alcohol production was therefore achieved. The strain produced (R)-(+)-Perillyl Alcohol at a titer of 87 mg/L and a yield of 1.5 mg/g glucose in a 5 L bioreactor fed batch system. Conclusions: These datas highlight the efficient production of (R)-(+)-Perillyl Alcohol through the mevalonate pathway from glucose. This method serves as a platform for the future production of other monoterpenes.
Orofacial antinociceptive effects of perillyl alcohol associated with codeine and its possible modes of action
Braz Oral Res 2022 Aug 8;36:e109.PMID:35946737DOI:10.1590/1807-3107bor-2022.vol36.0109.
This study evaluated the orofacial antinociceptive effect of (S)-(-)-Perillyl Alcohol (PA) associated with codeine (C) and investigated the possible molecular anchorage mechanisms of PA. Mice (n = 5 per group) were treated with PA alone and associated with codeine and assigned to the following groups: 75.0 mg/kg PA; 75.0 mg/kg PA + C 30 mg/kg; PA 37.5 mg/kg + C 15.0 mg/kg; C 30.0 mg/kg; and control. Nociception was induced by formalin, capsaicin, and glutamate, and was quantified based on the duration (in seconds) of face grooming. The possible mechanisms of action were evaluated by molecular docking study. In the formalin test, PA75/C30 presented an effect in the neurogenic (p < 0.0001) and inflammatory (p < 0.005) phases. Mice treated with PA75 (p < 0.0001) and PA75/C30 (p < 0.0005) showed a reduced nociceptive behavior in the capsaicin test. Glutamate-induced nociception also was blocked by PA75 (p < 0.0005) and C30 (p < 0.0005). The molecular anchorage analysis indicated high negative binding energy values for the evaluated receptors, especially glutamate receptors (AMPA -79.57 Kcal/mol, mGLUR6 -71.25, and NMDA -66.33 Kcal/mol). PA associated with codeine showed orofacial antinociceptive activity, with theoretical evidence of interaction with glutamate receptors.