Perillyl alcohol is a monoterpene that can cause apoptosis in tumor cells without affecting normal cells.

Physicochemical Properties

Molecular Formula	C10H16O
Molecular Weight	152.2334
Exact Mass	152.12
CAS #	536-59-4
Related CAS #	(S)-(−)-Perillyl alcohol;18457-55-1
PubChem CID	10819
Appearance	Colorless to light yellow liquid
Density	0.9±0.1 g/cm3
Boiling Point	241.2±19.0 °C at 760 mmHg
Melting Point	244 °C
Flash Point	99.6±17.8 °C
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.491
LogP	3.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Heavy Atom Count	11
Complexity	179
Defined Atom Stereocenter Count	0
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]
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
Chemical Name	(4-prop-1-en-2-ylcyclohexen-1-yl)methanol
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
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ADME/Pharmacokinetics	Metabolism / Metabolites Limonen-10-ol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[(4-prop-1-en-2-ylcyclohexen-1-yl)methoxy]oxane-2-carboxylic acid. Limonen-10-ol is a known human metabolite of (+)-limonene.
References	[1]. Belanger JT. Perillyl alcohol: applications in oncology. Altern Med Rev. 1998 Dec;3(6):448-57.
Additional Infomation	Perillyl alcohol is a limonene monoterpenoid consists of a cyclohexene ring substituted by a hydroxymethyl and a prop-1-en-2-yl group at positions 1 and 4 respectively. It is a constituent of a variety of essential oils including lavender. It has a role as a plant metabolite and a volatile oil component. Perillyl alcohol is under investigation in clinical trial NCT02704858 (Safety and Efficacy Study in Recurrent Grade IV Glioma). Perillyl alcohol has been reported in Tetradenia riparia, Magnolia officinalis, and other organisms with data available. Perillyl Alcohol is a naturally occurring monoterpene related to limonene with antineoplastic activity. Perillyl alcohol inhibits farnesyl transferase and geranylgeranyl transferase, thereby preventing post-translational protein farnesylation and isoprenylation and activation of oncoproteins such as p21-ras, and arresting tumor cells in the G1 phase of the cell cycle. (NCI04)

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~656.90 mM)

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. 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. 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 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	6.5690 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.