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Perillyl alcohol (POH) is a natural monocyclic terpene found in lavender with anti-cancer activity. Acts by preventing the farnesylation of Ras, stimulating the mannose-6-phosphate receptor, and inducing apoptosis.
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].
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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].
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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.
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References |
Molecular Formula |
C10H16O
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Molecular Weight |
152.237
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Exact Mass |
152.1201
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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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Appearance |
Colorless to Pale Yellow liquid
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SMILES |
CC(=C)[C@H]1CCC(=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 |