(-)-Limonene
(Synonyms: (-)-柠檬烯,(S)-(-)-Limonene) 目录号 : GC38316
A monoterpene with diverse biological activities
Cas No.:5989-54-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(+)-Limonene is a monoterpene that has been found in citrus oils and Cannabis and has diverse biological activities, including anticancer, antimicrobial, antioxidant, anti-inflammatory, and chemoprotective properties.1,2,3,4 It inhibits the growth of bacteria including S. aureus, B. cereus, E. faecalis, E. coli, P. aeruginosa, K. pneumoniae, M. catarrhalis, and C. neoformans with MIC values ranging from 3 to 27 mg/ml.1 In a human BGC-823 gastric cancer nude mouse orthotopic transplantation model, (+)-limonene inhibits tumor growth by 47.6% compared to controls and reduces the number of metastases in the liver, peritoneum, and other organs when administered by gastric perfusion at a dose of 15 ml/kg of a 1% emulsion.5 Dietary administration of (+)-limonene (5 and 10% in chow) reverses doxorubicin-induced decreases in glutathione (GSH) levels in rat kidney.3 Formulations containing (+)-limonene have been used as flavoring and fragrance agents and in the treatment of gallstones, heartburn, and gastroesophageal reflux disorder.
1.van Vuuren, S.F., and Viljoen, A.M.Antimicrobial activity of limonene enantiomers and 1,8-cineole alone and in combinationFlavor and Frag. J.22(6)540-544(2007) 2.Sun, J.D-Limonene: Safety and clinical applicationsAltern. Med. Rev.12(3)259-264(2007) 3.Rehman, M.U., Tahir, M., Khan, A.Q., et al.D-limonene suppresses doxorubicin-induced oxidative stress and inflammation via repression of COX-2, iNOS, and NFκB in kidneys of Wistar ratsExp. Biol. Med. (Maywood)239(4)465-476(2014) 4.Handbook of Cannabis therapeutics from bench to bedside(2010) 5.Lu, X.-G., Zhan, L.-B., Feng, B.-A., et al.Inhibition of growth and metastasis of human gastric cancer implanted in nude mice by d-limoneneWorld J. Gastroenterol.10(14)2140-2144(2004)
| Cas No. | 5989-54-8 | SDF | |
| 别名 | (-)-柠檬烯,(S)-(-)-Limonene | ||
| Canonical SMILES | CC1=CC[C@@H](C(C)=C)CC1 | ||
| 分子式 | C10H16 | 分子量 | 136.23 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 20 mg/ml,Ethanol: 20 mg/ml,Ethanol:PBS (pH 7.2)(1:2): 0.33 mg/ml | 储存条件 | 4°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 | 7.3405 mL | 36.7026 mL | 73.4053 mL |
| 5 mM | 1.4681 mL | 7.3405 mL | 14.6811 mL |
| 10 mM | 0.7341 mL | 3.6703 mL | 7.3405 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。
Conversion of Limonene over Heterogeneous Catalysis: An Overview
Curr Org Synth 2022;19(3):414-425.PMID:34429049DOI:10.2174/1570179418666210824101837.
The natural terpene limonene is widely found in nature. The (R)-Limonene (the most abundant enantiomer) is present in the essential oils of lemon, orange, and other citrus fruits, while the (S)- limonene is found in peppermint and the racemate in turpentine oil. Limonene is a low-cost, low toxicity biodegradable terpene present in agricultural wastes derived from citrus peels. The products obtained from the conversion of limonene are valuable compounds widely used as additives for food, cosmetics, or pharmaceuticals. The conversion of limonene to produce different products has been the subject of intense research, mainly with the objective of improving catalytic systems. This review focused on the application of heterogeneous catalysts in the catalytic conversion of limonene.
Effect of d-limonene and its derivatives on breast cancer in human trials: a scoping review and narrative synthesis
BMC Cancer 2021 Aug 6;21(1):902.PMID:34362338DOI:10.1186/s12885-021-08639-1.
Background: D-limonene and its derivatives have demonstrated potential chemopreventive and anticancer activity in preclinical and clinical studies. The aim of this scoping review was to assess and critically appraise current literature on the effect of these bioactive citrus peel compounds on breast cancer in human trials and to identify knowledge gaps for exploration in future studies. Methods: This study followed a scoping review framework. Peer-reviewed journal articles were included if they reported the effect of d-limonene or its derivatives on breast cancer in human subjects. Articles were retrieved from academic databases - PubMed, EMBASE, CINAHL, Web of Science, and Cochrane reviews - and iteratively through review of bibliographies of relevant manuscripts. Titles and abstracts were appraised against the aforementioned inclusion criteria in a first round of screening. Through consensus meetings and full article review by authors, a final set of studies were selected. Results were reported according to the PRISMA extension for scoping reviews. Results: Our search strategy yielded 367 records. Following screening and adjudication, five articles reporting on phase 1(n = 2), phase 2 (n = 2) and both trial phases (n = 1) were included as the final dataset for this review. Trials evaluating the effect of d-limonene (n = 2) showed it was well tolerated in subjects. One study (n = 43 participants) showed d-limonene concentrated in breast tissue (mean 41.3 μg/g tissue) and reduction in tumor cyclin D1 expression, which is associated with tumor proliferation arrest. This study did not show meaningful change in serum biomarkers associated with breast cancer, except for a statistically significant increase in insulin-like growth factor-1 (IGF-I) levels. While elevation of IGF-I is associated with increased cancer risk, the clinical implication of this study remains uncertain given its short duration. Trials with perillyl alcohol (n = 3) showed low tolerance and no effect on breast cancer. Conclusion: This review demonstrated a dearth of clinical studies exploring the effect of d-limonene and its derivatives on breast cancer. Limited literature suggests d-limonene is safe and tolerable in human subjects compared to its derivative, perillyl alcohol. Our review demonstrates the need for additional well-powered placebo-controlled trials that assess d-limonene's efficacy on breast cancer compared to other therapies.
Use of Limonene Epoxides and Derivatives as Promising Monomers for Biobased Polymers
Chempluschem 2022 Aug;87(8):e202200190.PMID:35957544DOI:10.1002/cplu.202200190.
(R)-Limonene, a renewable terpene, and its epoxidized derivatives, i. e. limonene epoxides, have prompted growing attention over the last decade as building blocks for the synthesis of biobased monomers and polymers. With the goal of replacing petroleum-based polymers several polymerization techniques have been applied on limonene oxide and limonene dioxide monomers. This paper aims to contribute to the literature by presenting a review dedicated to limonene oxide and dioxide as raw monomers of renewable origin for the development of biobased polymers. The polymerization techniques described are namely the homopolymerization, the copolymerization with carbon dioxide and anhydrides, and the copolymerization of limonene epoxide-based monomers. Limonene oxide polymerizations will be investigated first, followed by limonene dioxide polymerizations.
Review of toxicological assessment of d-limonene, a food and cosmetics additive
Food Chem Toxicol 2018 Oct;120:668-680.PMID:30075315DOI:10.1016/j.fct.2018.07.052.
R-(+)-Limonene (d-limonene) is a commonly used flavor additive in food, beverages and fragrances for its pleasant lemon-like odor. Considering its increasing applications, it's necessary to understand toxicological effects and risk associated with its use. R-(+)-Limonene is rapidly absorbed in experimental animals and human beings following oral administration. In humans, it gets distributed to liver, kidney, and blood resulting in the formation of metabolites like perillic acid, dihydroperillic acid, limonene-1,8-diol and limonene-1,2 diol. Important toxic effects primarily reported in rodents are severe hyaline droplet nephrotoxicity (only in male rats due to specific protein α2u-globulin; however, this effect isn't valid for humans), hepatotoxicity and neurotoxicity. R-(+)-Limonene does not show genotoxic, immunotoxic and carcinogenic effects. Substantial data is available about limonene's stability after treatment with thermal and non-thermal food processing techniques; however, information about toxicity of metabolites formed and their safe scientific limits is not available. In addition, toxicity of limonene degradation products formed during storage of citrus juices isn't known. Based on all available toxicological considerations, R-(+)-Limonene can be categorized as low toxic additive. More detailed studies are required to better understand interaction of limonene with modern food processing techniques as well as degradation products generated and toxicity arising from such products.
Identification of Fungal Limonene-3-Hydroxylase for Biotechnological Menthol Production
Appl Environ Microbiol 2021 Apr 27;87(10):e02873-20.PMID:33637576DOI:10.1128/AEM.02873-20.
More than 30,000 tons of menthol are produced every year as a flavor and fragrance compound or as a medical component. So far, only extraction from plant material and chemical synthesis are possible. An alternative approach for menthol production could be a biotechnological-chemical process with ideally only two conversion steps, starting from (+)-Limonene, which is a side product of the citrus processing industry. The first step requires a limonene-3-hydroxylase (L3H) activity that specifically catalyzes hydroxylation of limonene at carbon atom 3. Several protein engineering strategies have already attempted to create limonene-3-hydroxylases from bacterial cytochrome P450 monooxygenases (CYPs, or P450s), which can be efficiently expressed in bacterial hosts. However, their regiospecificity is rather low compared to that of the highly selective L3H enzymes from the biosynthetic pathway for menthol in Mentha species. The only naturally occurring limonene-3-hydroxylase activity identified in microorganisms so far was reported for a strain of the black yeast-like fungus Hormonema sp. in South Africa. We have discovered additional fungi that can catalyze the intended reaction and identified potential CYP-encoding genes within the genome sequence of one of the strains. Using heterologous gene expression and biotransformation experiments in yeasts, we were able to identify limonene-3-hydroxylases from Aureobasidium pullulans and Hormonema carpetanum Further characterization of the A. pullulans enzyme demonstrated its high stereospecificity and regioselectivity, its potential for limonene-based menthol production, and its additional ability to convert α- and β-pinene to verbenol and pinocarveol, respectively.IMPORTANCE (-)-Menthol is an important flavor and fragrance compound and furthermore has medicinal uses. To realize a two-step synthesis starting from renewable (+)-Limonene, a regioselective limonene-3-hydroxylase enzyme is necessary. We identified enzymes from two different fungi which catalyze this hydroxylation reaction and represent an important module for the development of a biotechnological process for (-)-menthol production from renewable (+)-Limonene.