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Reagents and instruments for immunology, cell biology and molecular biology.

(S)-(−)-Perillyl alcohol [18457-55-1]

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Cat# HY-116514-100mg

Size : 100mg

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Brand : MedChemExpress

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Description

(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^[1]^[2].

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	>1000 μM Compound: POH	Cytotoxicity against human A549 cells after 72 hrs by MTT assay Cytotoxicity against human A549 cells after 72 hrs by MTT assay	[PMID: 23474907]
A549	IC₅₀	>1 mM Compound: POH	Cytotoxicity against human A549 cells after 72 hrs by MTT assay Cytotoxicity against human A549 cells after 72 hrs by MTT assay	[PMID: 23474907]
A549	IC₅₀	350 μM Compound: POH, (S)-Perillyl alcohol	Cytotoxicity against human A549 cells after 48 hrs by alamar blue assay Cytotoxicity against human A549 cells after 48 hrs by alamar blue assay	[PMID: 25121720]
Hs 683	IC₅₀	>1000 μM Compound: POH	Cytotoxicity against human Hs683 cells after 72 hrs by MTT assay Cytotoxicity against human Hs683 cells after 72 hrs by MTT assay	[PMID: 23474907]
Hs 683	IC₅₀	>1 mM Compound: POH	Cytotoxicity against human Hs683 cells after 72 hrs by MTT assay Cytotoxicity against human Hs683 cells after 72 hrs by MTT assay	[PMID: 23474907]
MCF7	IC₅₀	>1000 μM Compound: POH	Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay	[PMID: 23474907]
MCF7	IC₅₀	>1 mM Compound: POH	Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay	[PMID: 23474907]
PC-3	IC₅₀	>1000 μM Compound: POH	Cytotoxicity against human PC3 cells after 72 hrs by MTT assay Cytotoxicity against human PC3 cells after 72 hrs by MTT assay	[PMID: 23474907]
PC-3	IC₅₀	>1 mM Compound: POH	Cytotoxicity against human PC3 cells after 72 hrs by MTT assay Cytotoxicity against human PC3 cells after 72 hrs by MTT assay	[PMID: 23474907]
PC-3	IC₅₀	380 μM Compound: POH, (S)-Perillyl alcohol	Cytotoxicity against human PC3 cells after 48 hrs by alamar blue assay Cytotoxicity against human PC3 cells after 48 hrs by alamar blue assay	[PMID: 25121720]
SK-MEL-28	IC₅₀	>1000 μM Compound: POH	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	[PMID: 23474907]
SK-MEL-28	IC₅₀	>1 mM Compound: POH	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	[PMID: 23474907]
U-373MG ATCC	IC₅₀	>1000 μM Compound: POH	Cytotoxicity against human U373 cells after 72 hrs by MTT assay Cytotoxicity against human U373 cells after 72 hrs by MTT assay	[PMID: 23474907]
U-373MG ATCC	IC₅₀	>1 mM Compound: POH	Cytotoxicity against human U373 cells after 72 hrs by MTT assay Cytotoxicity against human U373 cells after 72 hrs by MTT assay	[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.

In Vivo

Dietary (S)-(-)-Perillyl alcohol (POH) (0.5-1.0% dietary; ad libitum; daily for ~23 weeks) weakly promotes early esophageal tumorigenesis in N-nitrosomethylbenzylamine-treated male Fischer 344 rats, as shown by a significant increase in dysplastic lesions, while 1.0% (S)-(-)-Perillyl alcohol also causes a significant reduction in average tumor size without altering Ras membrane localization^[1].
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.

Animal Model:	Swiss mice (female, 25-30 g) injected with Sarcoma 18 cells^[2]
Dosage:	100 mg/kg/day; 200 mg/kg/day
Administration:	i.p.; daily; 7 days
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.

Molecular Weight

152.24

Formula

C₁₀H₁₆O

CAS No.

18457-55-1

Appearance

Liquid (Density: 0.96 g/cm³)

Color

Colorless to light yellow

SMILES

OCC1=CC[C@@H](C(C)=C)CC1

Structure Classification

Initial Source

Endogenous metabolite

Shipping

Room temperature in continental US; may vary elsewhere.

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.

Preparing
Stock Solutions

Concentration Solvent Mass	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

View the 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.

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.

Protocol 1

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.
Protocol 2

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.
Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 5 mg/mL (32.84 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL Corn oil, and mix evenly.

Purity & Documentation

Purity: 97.0%

Data Sheet (272 KB) SDS (394 KB)

COA (243 KB) HNMR (247 KB) MS (229 KB)

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.

(S)-(−)-Perillyl alcohol [18457-55-1]

Cat# HY-116514-100mg

Contact local distributor :

Brand : MedChemExpress

Contact local distributor :

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