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Perillyl alcohol

Alias: Perillyl alcohol; perillic alcohol; Perilla alcohol; POH; perillol; Perycorolle
Cat No.:V17541 Purity: ≥98%
Perillyl alcohol (POH) is a natural monocyclic terpenefound in lavender with anti-cancer activity.
Perillyl alcohol
Perillyl alcohol Chemical Structure CAS No.: 18457-55-1
Product category: Apoptosis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
10g
25g
Other Sizes

Other Forms of Perillyl alcohol:

  • Perillyl alcohol
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description

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.

Biological Activity I Assay Protocols (From Reference)
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].
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].
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.
References

[1]. Life Sci . 2003 Oct 17;73(22):2831-40.

[2]. Breast Cancer Res Treat . 2004 Apr;84(3):251-60.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H16O
Molecular Weight
152.237
Exact Mass
152.1201
Elemental Analysis
C, 78.90; H, 10.59; O, 10.51
CAS #
18457-55-1
Related CAS #
Perillyl alcohol;536-59-4
Appearance
Colorless to Pale Yellow liquid
SMILES
CC(=C)[C@H]1CCC(=CC1)CO
InChi Key
NDTYTMIUWGWIMO-SNVBAGLBSA-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/t10-/m1/s1
Chemical Name
[(4S)-4-prop-1-en-2-ylcyclohexen-1-yl]methanol
Synonyms
Perillyl alcohol; perillic alcohol; Perilla alcohol; POH; perillol; Perycorolle
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO: ≥250 mg/mL (~1642.3 mM)
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.

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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.
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 corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

Clinical Trial Information
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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