(S)-(−)-Perillyl alcohol
Based on 1 Customer Validation
(S)-(-)-Perillyl alcohol, a monoterpene, is an orally active farnesyl transferase and geranylgeranyl transferase inhibitor. (S)-(-)-Perillyl alcohol up-regulates the mannose-6-phosphate receptor, facilitating TGF-β1 activation and cytostasis,. (S)-(-)-Perillyl alcohol induces apoptosis in cancer cells, modulates cyclin D1 and AP-1 activity. (S)-(-)-Perillyl alcohol exhibits antitumor activity against sarcoma tumors in mice. (S)-(-)-Perillyl alcohol can be used for the research of squamous cell carcinoma of the esophagus and sarcoma 180.
For research use only. We do not sell to patients.
- Purity : 97.0%
- CAS No.: 18457-55-1
- Formula: C10H16O
- Molecular Weight:152.24
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Storage:
4°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Protocols
- Purity & Documentation
- References
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Help & FAQs
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All Endogenous Metabolite Isoforms
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Biological Activity
Description
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| A549 | IC50 |
>1000 μM
Compound: POH
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Cytotoxicity against human A549 cells after 72 hrs by MTT assay
Cytotoxicity against human A549 cells after 72 hrs by MTT assay
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[PMID: 23474907] |
| A549 | IC50 |
350 μM
Compound: POH, (S)-Perillyl alcohol
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Cytotoxicity against human A549 cells after 48 hrs by alamar blue assay
Cytotoxicity against human A549 cells after 48 hrs by alamar blue assay
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[PMID: 25121720] |
| Hs 683 | IC50 |
>1000 μM
Compound: POH
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Cytotoxicity against human Hs683 cells after 72 hrs by MTT assay
Cytotoxicity against human Hs683 cells after 72 hrs by MTT assay
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[PMID: 23474907] |
| MCF7 | IC50 |
>1000 μM
Compound: POH
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Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay
Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay
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[PMID: 23474907] |
| PC-3 | IC50 |
>1000 μM
Compound: POH
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Cytotoxicity against human PC3 cells after 72 hrs by MTT assay
Cytotoxicity against human PC3 cells after 72 hrs by MTT assay
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[PMID: 23474907] |
| PC-3 | IC50 |
380 μM
Compound: POH, (S)-Perillyl alcohol
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Cytotoxicity against human PC3 cells after 48 hrs by alamar blue assay
Cytotoxicity against human PC3 cells after 48 hrs by alamar blue assay
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[PMID: 25121720] |
| SK-MEL-28 | IC50 |
>1000 μM
Compound: POH
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Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay
Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay
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[PMID: 23474907] |
| U-373MG ATCC | IC50 |
>1000 μM
Compound: POH
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Cytotoxicity against human U373 cells after 72 hrs by MTT assay
Cytotoxicity against human U373 cells after 72 hrs by MTT assay
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[PMID: 23474907] |
In Vitro
(S)-(-)-Perillyl alcohol exerts in vitro cytotoxic activity against human ovarian adenocarcinoma, colon carcinoma, and glioblastoma tumor cell lines[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
In Vivo
Dietary 1.0% (S)-(-)-Perillyl alcohol (POH) (1.0% dietary; ad libitum; daily for ~25 weeks) causes transient food aversion and reduced body weight gain but no esophageal tumors or gross abnormalities in healthy male Fischer 344 rats over 25 weeks[1].
(S)-(-)-Perillyl alcohol (100-200 mg/kg/day; i.p.; daily; 7 days) exhibits in vivo antitumor activity against Sarcoma 180 in Swiss mice, with tumor growth inhibition rates of 35.3% at 100 mg/kg/day and 45.4% at 200 mg/kg/day following 7 days of intraperitoneal administration[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Swiss mice (female, 25-30 g) injected with Sarcoma 18 cells[2]
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Dosage:100 mg/kg/day; 200 mg/kg/day
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Administration:i.p.; daily; 7 days
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Result:Reduced mean tumor mass to 0.76 g, corresponding to a tumor growth inhibition rate of 35.3% (100 mg/kg/day dose).
Reduced mean tumor mass to 0.70 g, corresponding to a tumor growth inhibition rate of 45.4% (200 mg/kg/day dose).
Induced statistically significant tumor mass reductions compared to the negative control group at both doses.
Chemical Information
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CAS No. 18457-55-1
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Appearance Liquid (Density: 0.96 g/cm3)
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Molecular Weight 152.24
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Formula C10H16O
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Color Colorless to light yellow
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SMILES
OCC1=CC[C@@H](C(C)=C)CC1
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Structure Classification
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
4°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Solvent & Solubility
In Vitro:
DMSO : ≥ 200 mg/mL (1313.72 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
* "≥" means soluble, but saturation unknown.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 5 mg/mL (32.84 mM); Clear solution
This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 5 mg/mL (32.84 mM); Clear solution
This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocols
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Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
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TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
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Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
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Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
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Subcutaneous Cell-Line-Derived Xenograft
Subcutaneous cell-line-derived xenograft (CDX) models are established by implanting cultured human cancer cell lines into immunodeficient mice, where the injected cells form localized tumors that can be monitored in vivo as a measure of tumorigenic potential, growth kinetics, and treatment response. These models are widely used in oncology research because they allow reproducible tumor formation and enable comparative assessment of tumor growth between different cell lines or genetic manipulations in a controlled in vivo microenvironment. Subcutaneous implantation of cancer cells in immunodeficient mice is a standard approach for evaluating tumor growth behavior and therapeutic response across multiple cancer types, including prostate, esophageal, pancreatic, and colon cancer models.
Purity & Documentation
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Data Sheet (272 KB)
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SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
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Handling Instructions (2659 KB)
References
[1]. Liston BW, et al. Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis. Cancer Res. 2003 May 15;63(10):2399-403. [Content Brief]
[2]. Andrade LN, et al. In Vivo Anti-Tumor Activity and Toxicological Evaluations of Perillaldehyde 8,9-Epoxide, a Derivative of Perillyl Alcohol. Int J Mol Sci. 2016;17(1):32. Published 2016 Jan 4. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 6.5686 mL | 32.8429 mL | 65.6858 mL | 164.2144 mL |
| 5 mM | 1.3137 mL | 6.5686 mL | 13.1372 mL | 32.8429 mL | |
| 10 mM | 0.6569 mL | 3.2843 mL | 6.5686 mL | 16.4214 mL | |
| 15 mM | 0.4379 mL | 2.1895 mL | 4.3791 mL | 10.9476 mL | |
| 20 mM | 0.3284 mL | 1.6421 mL | 3.2843 mL | 8.2107 mL | |
| 25 mM | 0.2627 mL | 1.3137 mL | 2.6274 mL | 6.5686 mL | |
| 30 mM | 0.2190 mL | 1.0948 mL | 2.1895 mL | 5.4738 mL | |
| 40 mM | 0.1642 mL | 0.8211 mL | 1.6421 mL | 4.1054 mL | |
| 50 mM | 0.1314 mL | 0.6569 mL | 1.3137 mL | 3.2843 mL | |
| 60 mM | 0.1095 mL | 0.5474 mL | 1.0948 mL | 2.7369 mL | |
| 80 mM | 0.0821 mL | 0.4105 mL | 0.8211 mL | 2.0527 mL | |
| 100 mM | 0.0657 mL | 0.3284 mL | 0.6569 mL | 1.6421 mL |
(S)-(−)-Perillyl alcohol Related Classifications
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