(S)-(-)-Perillic acid is a terpenoid plant extract with antibacterial and anti-cancer activity. (S)-(-)-Perillic acid causes apoptosis and cell cycle arrest, and increases intracellular protein levels of Bax, Bcl2, p21 and caspase-3. (S)-(-)-Perillic acid may be used in cancer and infection research.

Physicochemical Properties

Molecular Formula	C10H14O2
Molecular Weight	165.20902
Exact Mass	166.099
CAS #	23635-14-5
Related CAS #	Perillic acid;7694-45-3
PubChem CID	2724160
Appearance	White to off-white solid powder
Density	1.068g/cm3
Boiling Point	284.9ºC at 760mmHg
Melting Point	129-131ºC(lit.)
Flash Point	134ºC
Vapour Pressure	0.000746mmHg at 25°C
LogP	2.373
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Heavy Atom Count	12
Complexity	238
Defined Atom Stereocenter Count	1
SMILES	C=C(C)[C@@H]1CC=C(CC1)C(=O)O
InChi Key	CDSMSBUVCWHORP-MRVPVSSYSA-N
InChi Code	InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)/t8-/m1/s1
Chemical Name	(4S)-4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
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

ln Vitro	Arterial smooth muscle cell (SMC) proliferation is time- and dose-dependently inhibited by (S)-(-)-Perillic acid (1.0-3.5 mM; 24, 48, and 72 hours) [1]. In rat arterial smooth muscle cells (SMC), (S)-(-)-Perillic acid (1.0-3.5 mM; 20 hours) dose-dependently inhibits intranuclear thymine binding [1]. In arterial smooth muscle cells, (S)-(-)-Perillic acid (2.5 mM; 24 hours) causes apoptosis and inhibits cell cycle progression in the G0/G1 phase [1]. Certain low molecular weight proteins are resistant to the incorporation of [3H]FOH and [3H]GGOH when exposed to (S)-(-)-Perillic acid (1.0-3.5 mM; 20 hours) in a dose-dependent manner [1]. In H520 cells, (S)-(-)-Perillic acid (0.5 mM; 24 hours) raises the levels of the proteins Bax, Bcl2, p21, and caspase-3 [2].
Cell Assay	Cell Viability Assay[2] Cell Types: Human lung cancer A549 cell line Tested Concentrations: 0-5 mM Incubation Duration: 24 hour Experimental Results: Inhibited long-term proliferation of A549 cells with an IC50 value of 3.6 mM.
References	[1]. Ferri N, et al. Effect of S(-) perillic acid on protein prenylation and arterial smooth muscle cell proliferation. Biochem Pharmacol. 2001 Dec 15;62(12):1637-45. [2]. Yeruva L, et al. Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. Cancer Lett. 2007 Nov 18;257(2):216-26. [3]. Khandelia H, et al. Interaction of salicylate and a terpenoid plant extract with model membranes: reconciling experiments and simulations. Biophys J. 2010 Dec 15;99(12):3887-94.
Additional Infomation	4-Isopropenylcyclohexene-1-carboxylic acid has been reported in Perilla frutescens and Spodoptera litura with data available.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	6.0529 mL	30.2645 mL	60.5290 mL
	5 mM	1.2106 mL	6.0529 mL	12.1058 mL
	10 mM	0.6053 mL	3.0265 mL	6.0529 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.