| Size | Price | Stock | Qty |
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| 5g |
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| 10g |
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| 25g |
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| Other Sizes |
| Targets |
Multiple targets have been identified for perillyl alcohol. POH inhibits NF-κB and STAT3 signaling pathways. It blocks transmembrane extracellular Ca2+ influx and inhibits protein kinase C (PKC). POH also decreases acetylcholinesterase activity. It has been reported to have anti-inflammatory, antioxidative, anticancer, and neuroprotective properties.
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| ln Vitro |
Perillyl alcohol inhibits the isoprenylation of small G proteins (21-26 kDa) involved in signal transduction, induces cell cycle arrest and apoptosis, and affects differential gene regulation in vitro[1]. In all of the cell lines examined (KPL-1, MCF-7, MKL-F, and MDA-MB-231) perillyl alcohol (POH) inhibits cell proliferation in a dose-dependent manner. POH has a cytostatic effect at a dose of 500 M, wherein growth inhibition is caused by an accumulation of cells in G1 phase. G1 cyclin levels (cyclin D1 and E) drop prior to cell cycle progression, which is then followed by an increase in p21Cip1/Waf1 and a decrease in proliferating cell nuclear antigen levels[2].
Perillyl alcohol demonstrates diverse pharmacological activities. It improves imiquimod-induced psoriasis-like skin inflammation by inhibiting NF-κB and STAT3 signaling pathways. POH induces relaxation of human umbilical vein by blocking transmembrane extracellular Ca2+ influx and inhibiting PKC, with less involvement of K+ channels and NOS and GC enzymes. POH has neuroprotective effects, significantly decreasing acetylcholinesterase activity and improving spatial memory processing. It has hepatoprotective effects in models of acute liver injury by modulating NF-κB and NLRP3 signaling pathways. |
| ln Vivo |
In a nude mouse system, orthotopically transplanted KPL-1 tumor cell growth and regional lymph node metastasis are suppressed by perillyl alcohol (POH) at a dose of 75mg/kg given intraperitoneally three times a week for the entire 6-week experimental period. POH suppresses growth and metastasis in vivo and inhibits the growth of ER-positive and ER-negative human breast cancer cells in vitro[2].
In vivo, perillyl alcohol has demonstrated hepatoprotective effects in experimental models of acute liver injury. It has neuroprotective effects in sporadic Alzheimer's disease models in rats, significantly decreasing acetylcholinesterase activity and improving spatial memory processing. POH has been investigated for intranasal administration for glioblastoma. It has anti-inflammatory effects in models of psoriasis. |
| Enzyme Assay |
In vitro enzyme assays for perillyl alcohol involve measuring acetylcholinesterase inhibition using Ellman's method or other colorimetric assays. The enzyme is incubated with acetylthiocholine substrate and various concentrations of POH, and the production of thiocholine is measured spectrophotometrically. These assays confirm the acetylcholinesterase inhibitory activity of POH.
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| Cell Assay |
Colony formation assay is used to gauge the toxicity of the compounds on treated cells. 6-well plates are used for cell plating (200 cells/well). Cells are exposed to perillyl alcohol (POH) or perillaldehyde (PALD) for 12 or 24 hours after the culture medium is replaced with medium containing varying concentrations of the chemicals. The cells are then washed twice with sterile PBS and once with the proper medium after the treatment medium has been removed and the cells have been exposed. The cells are incubated for a further 12–14 days at 37 °C with the addition of fresh medium to each well. Every other day, microscope views of plates are performed. The culture medium is removed from the cells at the end, and PBS is then rinsed through them. Following the fixation and crystal violet staining step, the dye is gently rinsed off the cells for 5 minutes. In order to count colonies, they must have at least 50 cells.
Cellular assays for perillyl alcohol involve treating cells with the compound and measuring various endpoints including cell proliferation, inflammation, oxidative stress, or calcium signaling. POH blocks transmembrane extracellular Ca2+ influx and inhibits PKC in human umbilical vein endothelial cells. It inhibits NF-κB and STAT3 signaling in models of inflammation. |
| Animal Protocol |
In vivo animal studies for perillyl alcohol typically involve administration to rodent models of disease. In models of acute liver injury, POH demonstrates hepatoprotective effects by modulating NF-κB and NLRP3 signaling. In sporadic Alzheimer's disease models, POH decreases acetylcholinesterase activity and improves spatial memory. In models of psoriasis, POH improves skin inflammation by inhibiting NF-κB and STAT3.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Perillyl alcohol is a known human metabolite of (-)-limonene. Pharmacokinetic studies of perillyl alcohol have investigated its bioavailability and distribution, particularly following intranasal administration for central nervous system delivery. POH is a small lipophilic molecule that can cross the blood-brain barrier. The compound is metabolized in the liver and excreted in urine. Its pharmacokinetic profile supports its investigation for various therapeutic applications. |
| Toxicity/Toxicokinetics |
Preclinical toxicity studies of perillyl alcohol have established its safety profile. As a natural monoterpene found in many foods and essential oils, POH is generally recognized as safe at low concentrations. At therapeutic doses, POH has demonstrated protective effects against various forms of tissue injury rather than toxicity. High doses may cause gastrointestinal irritation or other adverse effects.
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| References | |
| Additional Infomation |
(S)-(-)-Perillyl alcohol is a perillyl alcohol with an S-configuration at its chiral center. It is the enantiomer of (R)-(+)-perillyl alcohol. (-)-Perillyl alcohol has been reported to be found in perilla (Perilla frutescens), citrus (Citrus iyo), and other organisms with relevant data. See also: Root (part) of peony (Paeonia lactiflora).
Perillyl alcohol is a naturally occurring monoterpene with diverse pharmacological activities including anticancer, anti-inflammatory, neuroprotective, and hepatoprotective effects. It has been investigated for intranasal administration for glioblastoma and other central nervous system conditions. POH's mechanism of action involves inhibition of NF-κB, STAT3, PKC, and acetylcholinesterase, among other targets. The compound shows promise as a therapeutic agent for various diseases and is the subject of ongoing research. |
| Molecular Formula |
C10H16O
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| Molecular Weight |
152.237
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| Exact Mass |
152.12
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| Elemental Analysis |
C, 78.90; H, 10.59; O, 10.51
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| CAS # |
18457-55-1
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| Related CAS # |
Perillyl alcohol;536-59-4
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| PubChem CID |
369312
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| Appearance |
Colorless to Pale 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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| 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 |
1
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| SMILES |
C=C(C)[C@@H]1CC=C(CC1)CO
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| InChi Key |
NDTYTMIUWGWIMO-SNVBAGLBSA-N
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| InChi Code |
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3/t10-/m1/s1
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| Chemical Name |
[(4S)-4-prop-1-en-2-ylcyclohexen-1-yl]methanol
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| Synonyms |
Perillyl alcohol; perillic alcohol; Perilla alcohol; POH; perillol; Perycorolle
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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: ≥250 mg/mL (~1642.3 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (13.66 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 20.8 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: ≥ 2.08 mg/mL (13.66 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 20.8 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: ≥ 2.08 mg/mL (13.66 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 | 6.5686 mL | 32.8429 mL | 65.6858 mL | |
| 5 mM | 1.3137 mL | 6.5686 mL | 13.1372 mL | |
| 10 mM | 0.6569 mL | 3.2843 mL | 6.5686 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02704858 | Recruiting | Drug: Perillyl alcohol | Glioblastoma Multiforme | Neonc Technologies, Inc. | April 8, 2016 | Phase 1 Phase 2 |
| NCT00003238 | Completed | Drug: perillyl alcohol | Prostate Cancer | University of Wisconsin, Madison | February 1998 | Phase 2 |
| NCT00003219 | Completed | Drug: perillyl alcohol | Breast Cancer | University of Wisconsin, Madison | May 1998 | Phase 2 |
| NCT00608634 | Completed | Other: placebo Drug: perillyl alcohol |
Precancerous Condition | University of Arizona | May 2004 | Phase 2 |
| NCT00003769 | Completed | Drug: perillyl alcohol Procedure: surgical procedure |
Pancreatic Cancer | Indiana University School of Medicine | February 1999 | Phase 2 |
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