| Size | Price | |
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| Other Sizes |
| Targets |
Perillyl alcohol targets several pathways. It inhibits the mevalonate pathway, reducing protein prenylation (Ras, Rho), which leads to cell cycle arrest. It also induces apoptosis via upregulation of Bax and downregulation of Bcl-2. Additionally, it modulates the NF-κB and PI3K/Akt pathways, reducing inflammation and promoting apoptosis in cancer cells. It also inhibits the growth of glioblastoma cells by inducing autophagy.
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| ln Vitro |
In vitro, perillyl alcohol inhibits the proliferation of various cancer cell lines, including glioma (IC50 ~ 100 µM), breast (IC50 ~ 150 µM), and lung (IC50 ~ 120 µM) after 72 h. It also reduces LPS-induced NO and TNF-α in macrophages at 50-200 µM. It shows moderate antioxidant activity (DPPH IC50 ~ 150 µM).
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| ln Vivo |
In vivo, perillyl alcohol has shown efficacy in animal models of cancer. In rats with chemically-induced mammary tumors, dietary perillyl alcohol (2% in diet) reduced tumor incidence and multiplicity. In a mouse glioma xenograft model, intranasal administration of 50 mg/kg daily reduced tumor growth by 50%. It also has anti-inflammatory effects in a mouse model of colitis at 100 mg/kg (p.o.).
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| Enzyme Assay |
The in vitro cell proliferation assay is performed using the MTT method. Cancer cells are seeded in 96-well plates and treated with perillyl alcohol (10-500 µM) for 48-72 h. Cell viability is measured. Apoptosis is assessed by annexin V/PI and caspase-3 activity. The mevalonate pathway inhibition is evaluated by measuring protein prenylation via Western blotting.
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| Cell Assay |
For in vitro cell-based assays, glioma cells (U87MG) are cultured in DMEM and treated with perillyl alcohol (50-200 µM) for 24-48 h. Cell cycle analysis is performed by propidium iodide staining. Autophagy is monitored by LC3-II conversion and p62 degradation. Inflammatory responses are studied in RAW 264.7 macrophages stimulated with LPS.
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| Animal Protocol |
In vivo anti-tumor studies in rats: female Sprague-Dawley rats are given a single dose of DMBA (50 mg) to induce mammary tumors. After tumors develop, rats are fed a diet containing 2% perillyl alcohol for 12 weeks. Tumor size and multiplicity are recorded. For glioma xenografts, athymic mice are implanted subcutaneously with U87MG cells and treated intranasally with perillyl alcohol (20-50 mg/kg) daily for 3 weeks.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Limonene-10-ol is known to have human metabolites including (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[(4-prop-1-en-2-ylcyclohexen-1-yl)methoxy]oxacyclohexane-2-carboxylic acid. Limonene-10-ol is a known human metabolite of (+)-limonene. Pharmacokinetics in humans: perillyl alcohol is rapidly absorbed and metabolized to perillic acid and other metabolites. After oral administration, Tmax is 1-2 h, and half-life is about 2-3 h. Bioavailability is low (~10%) due to extensive first-pass metabolism. It is distributed to tissues and crosses the blood-brain barrier. Plasma protein binding is moderate (60%). |
| Toxicity/Toxicokinetics |
Perillyl alcohol has a good safety profile. The oral LD50 in rats is >2000 mg/kg. In clinical trials, doses up to 2 g/m²/day were tolerated with mild gastrointestinal side effects. No significant hepatotoxicity or nephrotoxicity was observed. It is not mutagenic. However, it may cause mild fatigue and nausea at high doses.
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| References | |
| Additional Infomation |
Perillyl alcohol is a limonene monoterpene composed of a cyclohexene ring with hydroxymethyl and prop-1-en-2-yl substitutions at positions 1 and 4, respectively. It is a component of many essential oils, including lavender oil. It is both a plant metabolite and a volatile oil component. Perillyl alcohol is currently under investigation in the clinical trial NCT02704858 (Safety and Efficacy Study in Recurrent Grade IV Gliomas). It has been reported to exist in Tetradenia riparia, Magnolia officinalis, and several other organisms with relevant data. Perillyl alcohol is a naturally occurring monoterpene associated with limonene and possesses antitumor activity. Perillyl alcohol inhibits farnesyltransferase and geraniylgeraniyltransferase, thereby preventing post-translational farnesylation and isopreneation of proteins, and inhibiting the activation of oncoproteins such as p21-ras, causing tumor cells to arrest in the G1 phase of the cell cycle. (NCI04)
Perillyl alcohol has been investigated in phase I/II clinical trials for glioma, breast cancer, and prostate cancer. It showed some efficacy in stabilizing disease and prolonging survival in glioblastoma patients when administered intranasally. However, it has not received regulatory approval. Its mechanism as a Ras inhibitor and chemopreventive agent is of ongoing interest. It is available as a dietary supplement. |
| Molecular Formula |
C10H16O
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|---|---|
| Molecular Weight |
152.2334
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| Exact Mass |
152.12
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| CAS # |
536-59-4
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| Related CAS # |
(S)-(−)-Perillyl alcohol;18457-55-1
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| PubChem CID |
10819
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
241.2±19.0 °C at 760 mmHg
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| Melting Point |
244 °C
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| Flash Point |
99.6±17.8 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.491
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| LogP |
3.3
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
179
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C([H])([H])C1=C([H])C([H])([H])C([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])C1([H])[H]
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| InChi Key |
NDTYTMIUWGWIMO-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
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| Chemical Name |
(4-prop-1-en-2-ylcyclohexen-1-yl)methanol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~656.90 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.5690 mL | 32.8450 mL | 65.6901 mL | |
| 5 mM | 1.3138 mL | 6.5690 mL | 13.1380 mL | |
| 10 mM | 0.6569 mL | 3.2845 mL | 6.5690 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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