Identification

Nameperilla alcohol
IUPAC(4-prop-1-en-2-yl-1-cyclohexenyl)methanol
CAS Number536-59-4
EINECS208-639-9
FDA UNII319R5C7293
Molecular FormulaC10 H16 O
Molecular Weight152.23672000
Nikkaji NumberJ11.581I
CoE Number2024

Regulatory

JECFA Food Flavoring974 p-mentha-1,8-dien-7-ol
DG SANTE Food Flavourings02.060 p-mentha-1,8-dien-7-ol
FEMA Number2664
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)536-59-4 ; P-MENTHA-1,8-DIEN-7-OL
FDA RegulationFDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION

Physical Properties

Appearance colorless to pale yellow clear liquid (est)
Assay 96.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 0.95600 to 0.96300 @ 25.00 °C.
Pounds per Gallon - (est). 7.955 to 8.013
Refractive Index 1.49500 to 1.50500 @ 20.00 °C.
Boiling Point 119.00 to 121.00 °C. @ 11.00 mm Hg, 92.00 to 93.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.006000 mmHg @ 25.00 °C. (est)
Flash Point > 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w) 3.170
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesantimicrobial agents

Organoleptic Properties

Odor Strength medium
Substantivity 269 hour(s) at 100.00 %
Odor Description
at 100.00 %.
at 1.00 %.
Odor sample from CA Aromatics Company Inc.
Taste Description
woody aromatic cumin spicy green cardamom waxy floral oily earthy
at 25.00 ppm.

Safety Information

European informationMost important hazard(s):
Human Experience4 % solution: no irritation or sensitization.
Oral/Parenteral Toxicityoral-rat LD50 2100 mg/kg
Dermal Toxicityskin-rabbit LD50 > 5000 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic, flavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
maximum skin levels for fine fragrances0.1700 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey). (IFRA, 2006)
Recommendation for perilla alcohol usage levels up to4.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics0.0200 %
Dermal Systemic Exposure in Cosmetic Products0.0005 mg/kg/day (IFRA, 2006)
Maximised Survey-derived Daily Intakes (MSDI-EU)0.34 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA)1.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)1500 (μg/person/day)
Threshold of Concern1800 (μg/person/day)
Structure ClassI
baked goods10.00000
beverages(nonalcoholic)0.50000
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy0.50000
fruit ices0.50000
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
imitation dairy-
instant coffee / tea-
jams / jellies-
meat products-
milk products-
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy-
soups-
sugar substitutes-
sweet sauces-
Dairy products, excluding products of category 02.0 (01.0)5.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0)-
Edible ices, including sherbet and sorbet (03.0)5.00000
Processed fruit (04.1)5.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)5.00000
Chewing gum (05.3)-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)5.00000
Bakery wares (07.0)8.00000
Meat and meat products, including poultry and game (08.0)-
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)-
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)-
Foodstuffs intended for particular nutritional uses (13.0)-
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)1.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)0.50000
Ready-to-eat savouries (15.0)-
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)2.00000

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Foreverest Resources Ltd.

Leading pine based chemicals supplier

Supplying turpentine based and natural/extracted flavor & fragrance ingredients.

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Indukern, S.A. F&F Ingredients Division

Commitment to quality

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View All Website +34 93 506 91 00 info@indukern.es

Jiangyin Healthway International Trade Co., Ltd

Independent Ingredients Supplier

We provide custom synthesis and contract manufacturing from milligrams to metric tonnes.

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Lluch Essence S.L.

A family company dedicated to sales and distribution

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Penta International Corporation

Chemistry innovation

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Synerzine, Inc.

Innovation. Customization. Aroma Ingredients.

Synerzine is a leading supplier of flavor and fragrance ingredients.

View All Website (404) 524-6744 info@synerzine.com

Potential Uses

FR bergamot FL/FR caraway seed FR cardamom oil replacer FR cranberry FR cumin oil replacer FR gingergrass FR hop FR huckleberry FR lavandin FR root beer FR spearmint FR vanilla

Natural Occurrence

amomum testaceum ridl. fruit oil malaysia @ 1.70% Data angelica root oil @ 0.10% Data bay laurel leaf bergamot plant wild caraway oil caraway plant caraway seed oil @ 0.10% Data chamomile sweet false chamomile plant ginger rhizome gingergrass lavandin PMC mandarin oil uruguay @ 0.02-0.03% Data orange peel oil bitter china @ 0.01% Data perilla rose oil otto bulgaria @ 0.05% Data savin savory winter savory plant spearmint leaf spearmint oil turmeric root oil hydrodistilled @ 0.17% Data wormseed oil spain @ 0.15% Data

Synonyms

cyclohex-1-ene-1-methanol, 4-(1-methylethenyl)- 1- cyclohexene-1-methanol, 4-(1-methylethenyl) dihydro cuminyl alcohol hydrocumin alcohol 1- hydroxymethyl-4-isopropenyl-1-cyclohexene p- mentha-1,8-dien-7-ol para- mentha-1,8-dien-7-ol menthadien-7-carbinol 1,8-p- menthadien-7-ol 4-(1- methyl ethenyl)-1-cyclohexene-1-methanol [4-(1- methylethenyl)-1-cyclohexen-1-yl]methanol 4-(1- methylethenyl)-1-cyclohexene-1-methanol perillic alcohol perillol (4- prop-1-en-2-yl-1-cyclohexenyl)methanol [4-( prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol 4-iso propenyl cyclohex-1-en-1-yl methanol 4-iso propenyl cyclohex-1-ene-1-methanol 4-iso propenyl cyclohex-1-enyl methanol (4-iso propenyl-1-cyclohexen-1-yl)methanol 4-iso propenyl-1-cyclohexene carbinol 4-iso propenyl-1-cyclohexenecarbinol 4-iso propenyl-1-cyclohexenyl methanol 4-iso propenyl-cyclohex-1-ene-1-methanol 4-iso propenyl-cyclohex-1-enylmethanol 4-iso propenylcyclohex-1-en-1-ylmethanol 4-iso propenylcyclohex-1-enyl methanol 4-iso propenylcyclohex-1-enylmethanol US Patents: 3,993,604 - Alicyclic compounds, their use and process for preparing same PubMed: Synthesis and antiproliferative effects of amino-modified perillyl alcohol derivatives. PubMed: Gene discovery for enzymes involved in limonene modification or utilization by the mountain pine beetle-associated pathogen Grosmannia clavigera. PubMed: Influence of culture conditions on the biotransformation of (+)-limonene by Aspergillus niger. PubMed: A Novel Temozolomide-Perillyl Alcohol Conjugate Exhibits Superior Activity against Breast Cancer Cells In Vitro and Intracranial Triple-Negative Tumor Growth In Vivo. PubMed: A systematic review of inhaled intranasal therapy for central nervous system neoplasms: an emerging therapeutic option. PubMed: Long-term outcome in patients with recurrent malignant glioma treated with Perillyl alcohol inhalation. PubMed: Perillyl alcohol suppresses antigen-induced immune responses in the lung. PubMed: Chemical composition and mosquito repellency of essential oil of Conyza newii propagated in different geographical locations of Kenya. PubMed: Intranasal administration of perillyl alcohol activates peripheral and bronchus-associated immune system in vivo. PubMed: Chemoprevention gene therapy (CGT) of pancreatic cancer using perillyl alcohol and a novel chimeric serotype cancer terminator virus. PubMed: Skin repair properties of d-Limonene and perillyl alcohol in murine models. PubMed: Anti-stress effects of d-limonene and its metabolite perillyl alcohol. PubMed: Influence of GSTM1 and GSTT1 polymorphisms on the survival rate of patients with malignant glioma under perillyl alcohol-based therapy. PubMed: eIF4E-Overexpression imparts perillyl alcohol and rapamycin-mediated regulation of telomerase reverse transcriptase. PubMed: Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production. PubMed: Perillyl alcohol as a protective modulator against rat hepatocarcinogenesis via amelioration of oxidative damage and cell proliferation. PubMed: Double reduction of cyclic aromatic sulfonamides: synthesis of (+)-mesembrine and (+)-mesembranol. PubMed: 4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K(+)-ATPase and Ras oncogene activity in cancer cells. PubMed: Disruption of an hTERT-mTOR-RAPTOR protein complex by a phytochemical perillyl alcohol and rapamycin. PubMed: Whole-cell-based CYP153A6-catalyzed (S)-limonene hydroxylation efficiency depends on host background and profits from monoterpene uptake via AlkL. PubMed: Perillyl alcohol causes G1 arrest through p15(INK4b) and p21(WAF1/Cip1) induction. PubMed: Perillyl alcohol for the treatment of temozolomide-resistant gliomas. PubMed: The isoprenoid perillyl alcohol inhibits telomerase activity in prostate cancer cells. PubMed: Chemoprevention of hepatocarcinogenesis with dietary isoprenic derivatives: cellular and molecular aspects. PubMed: Growth-inhibiting effects of Paeonia lactiflora root steam distillate constituents and structurally related compounds on human intestinal bacteria. PubMed: Analysis of EGF+61A>G polymorphism and EGF serum levels in Brazilian glioma patients treated with perillyl alcohol-based therapy. PubMed: Microbial hydroxylation of S-(-)-perillyl alcohol by Fusarium heterosporium. PubMed: Calcium blockers decrease the bortezomib resistance in mantle cell lymphoma via manipulation of tissue transglutaminase activities. PubMed: Geraniol and geranial dehydrogenases induced in anaerobic monoterpene degradation by Castellaniella defragrans. PubMed: Anticancer efficacy of perillyl alcohol-bearing PLGA microparticles. PubMed: Influence of the active compounds of Perilla frutescens leaves on lipid membranes. PubMed: Nonmelanoma skin cancer chemoprevention. PubMed: An efficient route to selective bio-oxidation catalysts: an iterative approach comprising modeling, diversification, and screening, based on CYP102A1. PubMed: Cell physiology rather than enzyme kinetics can determine the efficiency of cytochrome P450-catalyzed C-H-oxyfunctionalization. PubMed: Evaluation of the antioxidant and antiproliferative potential of bioflavors. PubMed: Prevention of transplant coronary artery disease by prenylation inhibitors. PubMed: Mechanism of statin-induced contractile dysfunction in rat cultured skeletal myofibers. PubMed: Perillyl alcohol protects against ethanol induced acute liver injury in Wistar rats by inhibiting oxidative stress, NFκ-B activation and proinflammatory cytokine production. PubMed: Chemo-resistant protein expression pattern of glioblastoma cells (A172) to perillyl alcohol. PubMed: Nonsurgical innovations in the treatment of nonmelanoma skin cancer. PubMed: The anticancer drug perillyl alcohol is a Na/K-ATPase inhibitor. PubMed: Efficacy of monoterpene perillyl alcohol upon survival rate of patients with recurrent glioblastoma. PubMed: Design and Synthesis of Potential New Apoptosis Agents: Hybrid Compounds Containing Perillyl Alcohol and New Constrained Retinoids. PubMed: The promise of natural products for blocking early events in skin carcinogenesis. PubMed: A phase 2a study of topical perillyl alcohol cream for chemoprevention of skin cancer. PubMed: Dynamic proteomic overview of glioblastoma cells (A172) exposed to perillyl alcohol. PubMed: (1S,2R,4S)-1-[(Benzyl-amino)-meth-yl]-4-(prop-1-en-2-yl)cyclo-hexane-1,2-diol. PubMed: Pharmacotherapy of actinic keratosis. PubMed: Protective effects of mastic oil from Pistacia lentiscus variation chia against experimental growth of lewis lung carcinoma. PubMed: Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin. PubMed: Tricistronic overexpression of cytochrome P450cam, putidaredoxin, and putidaredoxin reductase provides a useful cell-based catalytic system. PubMed: Possible contribution of beta-glycosidases and caspases in the cytotoxicity of novel glycoconjugates in colon cancer cells. PubMed: [Natural compounds in chemoprevention of esophageal squamous cell tumors--experimental studies]. PubMed: Components of lemon essential oil attenuate dementia induced by scopolamine. PubMed: GO Explorer: A gene-ontology tool to aid in the interpretation of shotgun proteomics data. PubMed: Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol. PubMed: Perillyl alcohol attenuates Ras-ERK signaling to inhibit murine skin inflammation and tumorigenesis. PubMed: Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol. PubMed: Gateways to clinical trials. PubMed: High-performance liquid chromatographic and pharmacokinetic analyses of an intravenous submicron emulsion of perillyl alcohol in rats. PubMed: Sensitive determination of monoterpene alcohols in urine by HPLC-FLD combined with ESI-MS detection after online-solid phase extraction of the monoterpene-coumarincarbamate derivates. PubMed: Mechanism of in vitro pancreatic cancer cell growth inhibition by melanoma differentiation-associated gene-7/interleukin-24 and perillyl alcohol. PubMed: Ras pathway activation in gliomas: a strategic target for intranasal administration of perillyl alcohol. PubMed: Chemoprevention by perillyl alcohol coupled with viral gene therapy reduces pancreatic cancer pathogenesis. PubMed: Fragrance material review on p-mentha-1,8-dien-7-ol. PubMed: Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds. PubMed: Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells. PubMed: Biphenylalkylacetylhydroquinone ethers suppress the proliferation of murine B16 melanoma cells. PubMed: A pilot study of perillyl alcohol in pancreatic cancer. PubMed: Prevalence of bortezomib-resistant constitutive NF-kappaB activity in mantle cell lymphoma. PubMed: Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer. PubMed: Anti-inflammatory senescence actives 5203-L molecule to promote healthy aging and prolongation of lifespan. PubMed: Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas. PubMed: Perillyl Alcohol Protects Against Fe-NTA-Induced Nephrotoxicity and Early Tumor Promotional Events in Rat Experimental Model. PubMed: Cloning of four genes involved in limonene hydroxylation from Enterobacter cowanii 6L. PubMed: Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. PubMed: Phase II trial of daily oral perillyl alcohol (NSC 641066) in treatment-refractory metastatic breast cancer. PubMed: Rab-small GTPases are involved in fluvastatin and pravastatin-induced vacuolation in rat skeletal myofibers. PubMed: Perillyl alcohol and genistein differentially regulate PKB/Akt and 4E-BP1 phosphorylation as well as eIF4E/eIF4G interactions in human tumor cells. PubMed: Anaplastic oligodendroglioma responding favorably to intranasal delivery of perillyl alcohol: a case report and literature review. PubMed: Cell cycle arrest by the isoprenoids perillyl alcohol, geraniol, and farnesol is mediated by p21(Cip1) and p27(Kip1) in human pancreatic adenocarcinoma cells. PubMed: Effects of perillyl alcohol and heat shock treatment in gene expression of human lung adenocarcinoma cell line A549. PubMed: In vitro induction of apoptosis in U937 cells by perillyl alcohol with sensitization by pentoxifylline: increased BCL-2 and BAX protein expression. PubMed: Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis. PubMed: Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil. PubMed: Terpenoids as plant antioxidants. PubMed: Perillyl alcohol induces c-Myc-dependent apoptosis in Bcr/Abl-transformed leukemia cells. PubMed: Recent advances in the molecular genetics of malignant gliomas disclose targets for antitumor agent perillyl alcohol. PubMed: Polycyclic aromatic hydrocarbon-induced CYP1B1 activity is suppressed by perillyl alcohol in MCF-7 cells. PubMed: Perillyl alcohol inhibits a calcium-dependent constitutive nuclear factor-kappaB pathway. PubMed: Gateways to clinical trials. PubMed: Regio- and stereoselective fungal oxyfunctionalisation of limonenes. PubMed: Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells. PubMed: Protein and m-RNA expression of farnesyl-transferases, RhoA and RhoB in rat liver hepatocytes: action of perillyl alcohol and vitamin A in vivo. PubMed: CaaX-prenyltransferases are essential for expression of genes involvedin the early stages of monoterpenoid biosynthetic pathway in Catharanthus roseus cells. PubMed: Fumigant toxicity of the essential oils of some African plants against Anopheles gambiae sensu stricto. PubMed: Biocatalytic production of perillyl alcohol from limonene by using a novel Mycobacterium sp. cytochrome P450 alkane hydroxylase expressed in Pseudomonas putida. PubMed: Perillyl alcohol induces apoptosis in human glioblastoma multiforme cells. PubMed: Cancer preventive role of selected dietary factors. PubMed: Effect of D-limonene on immune response in BALB/c mice with lymphoma. PubMed: An HPLC method for quantitation of perillyl alcohol in a topical pharmaceutical cream formulation. PubMed: A novel psychrotrophic fungus, Mortierella minutissima, for D-limonene biotransformation. PubMed: Sle1ab mediates the aberrant activation of STAT3 and Ras-ERK signaling pathways in B lymphocytes. PubMed: Species differences in the metabolism of (+)- and (-)-limonenes and their metabolites, carveols and carvones, by cytochrome P450 enzymes in liver microsomes of mice, rats, guinea pigs, rabbits, dogs, monkeys, and humans. PubMed: Clinical trials in cancer prevention: current results and perspectives for the future. PubMed: A pilot surrogate end point biomarker trial of perillyl alcohol in breast neoplasia. PubMed: R-(+)-perillyl alcohol-induced cell cycle changes, altered actin cytoskeleton, and decreased ras and p34(cdc2) expression in colonic adenocarcinoma SW480 cells. PubMed: Monoterpenes enhanced the sensitivity of head and neck cancer cells to radiation treatment in vitro. PubMed: Repellency of essential oils of some Kenyan plants against Anopheles gambiae. PubMed: Studies of the isoprenoid-mediated inhibition of mevalonate synthesis applied to cancer chemotherapy and chemoprevention. PubMed: Perillyl alcohol is an angiogenesis inhibitor. PubMed: A phase I trial of perillyl alcohol administered four times daily for 14 days out of 28 days. PubMed: Effects of POH in combination with STI571 on the proliferation and apoptosis of K562 cells. PubMed: Antinociceptive effects of the essential oil of Dracocephalum kotschyi in the mouse writhing test. PubMed: Gateways to clinical trials. PubMed: Using patients as their own controls for cost evaluation of phase I clinical trials. PubMed: Perillyl alcohol inhibits human breast cancer cell growth in vitro and in vivo. PubMed: Perillyl alcohol-mediated inhibition of lung cancer cell line proliferation: potential mechanisms for its chemotherapeutic effects. PubMed: Transformation of terpenes using a Picea abies suspension culture. PubMed: Development of a perillyl alcohol topical cream formulation. PubMed: Effect of antiproliferative agents on vascular function in normal and in vitro balloon-injured porcine coronary arteries. PubMed: Phase II trial of perillyl alcohol (NSC 641066) administered daily in patients with metastatic androgen independent prostate cancer. PubMed: Gateways to clinical trials. PubMed: Anti-leukemia effect of perillyl alcohol in Bcr/Abl-transformed cells indirectly inhibits signaling through Mek in a Ras- and Raf-independent fashion. PubMed: Cytotoxicity of perillyl alcohol against cancer cells is potentiated by hyperthermia. PubMed: Studies with cytotoxic agents suggest that apoptosis is not a major determinant of clonogenic death in neuroblastoma cells. PubMed: Perillyl alcohol and perillaldehyde induced cell cycle arrest and cell death in BroTo and A549 cells cultured in vitro. PubMed: Phase I trial of perillyl alcohol administered four times daily continuously. PubMed: Skin cancer chemoprevention: strategies to save our skin. PubMed: Perillyl alcohol mediated radiosensitization via augmentation of the Fas pathway in prostate cancer cells. PubMed: In situ detection of neoplastic transformation and chemopreventive effects in rat esophagus epithelium using angle-resolved low-coherence interferometry. PubMed: Perillyl alcohol as a radio-/chemosensitizer in malignant glioma. PubMed: Phase II trial of perillyl alcohol in patients with metastatic colorectal cancer. PubMed: Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis. PubMed: Biotransformation of limonene by bacteria, fungi, yeasts, and plants. PubMed: A phase I trial of perillyl alcohol in patients with advanced solid tumors. PubMed: Monoterpene regulation of Ras and Ras-related protein expression. PubMed: Mechanism-based in vitro screening of potential cancer chemopreventive agents. PubMed: Micronutrients in cancer chemoprevention. PubMed: Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention. PubMed: Plant-derived monoterpenes suppress hamster kidney cell 3-hydroxy-3-methylglutaryl coenzyme a reductase synthesis at the post-transcriptional level. PubMed: Perillyl Alcohol Inhibits Breast Cell Migration without Affecting Cell Adhesion. PubMed: Effects of perillyl alcohol in glial C6 cell line in vitro and anti-metastatic activity in chorioallantoic membrane model. PubMed: Sensitive biomonitoring of monoterpene exposure by gas chromatographic-mass spectrometric measurement of hydroxy terpenes in urine. PubMed: Monoterpenes inhibit proliferation of human colon cancer cells by modulating cell cycle-related protein expression. PubMed: Phase I study of perillyl alcohol in patients with refractory malignancies. PubMed: A phase II trial of daily perillyl alcohol in patients with advanced ovarian cancer: Eastern Cooperative Oncology Group Study E2E96. PubMed: Effects of perillyl alcohol on melanoma in the TPras mouse model. PubMed: Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes. PubMed: Weight-loss drugs and supplements: are there safer alternatives? PubMed: Antileukemia activity of perillyl alcohol (POH): uncoupling apoptosis from G0/G1 arrest suggests that the primary effect of POH on Bcr/Abl-transformed cells is to induce growth arrest. PubMed: Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome p450 enzymes in rat liver microsomes. PubMed: Induction of cytostasis in mammary carcinoma cells treated with the anticancer agent perillyl alcohol. PubMed: Biotransformation of limonene by Pseudomonas putida. PubMed: Chemopreventive efficacy of promising farnesyltransferase inhibitors. PubMed: Failure to demonstrate chemoprevention by the monoterpene perillyl alcohol during early rat hepatocarcinogenesis: a cautionary note. PubMed: Phase I pharmacokinetic trial of perillyl alcohol (NSC 641066) in patients with refractory solid malignancies. PubMed: Cytotoxicity and biotransformation of the anticancer drug perillyl alcohol in PC12 cells and in the rat. PubMed: The state-of-the-art in chemoprevention of skin cancer. PubMed: Cloning and expression of the limonene hydroxylase of Bacillus stearothermophilus BR388 and utilization in two-phase limonene conversions. PubMed: Perillyl alcohol inhibits TCR-mediated [Ca(2+)](i) signaling, alters cell shape and motility, and induces apoptosis in T lymphocytes. PubMed: Prenylation inhibitors to treat proliferative renal disease. PubMed: Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data. PubMed: Progress in cancer chemoprevention: development of diet-derived chemopreventive agents. PubMed: Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day. PubMed: Perillyl alcohol, an inhibitor of geranylgeranyl transferase, induces apoptosis of immortalized human vascular smooth muscle cells in vitro. PubMed: Progress in cancer chemoprevention. PubMed: Drug development in prostate cancer. PubMed: Perillyl alcohol selectively induces G0/G1 arrest and apoptosis in Bcr/Abl-transformed myeloid cell lines. PubMed: Induction of AP-1 activity by perillyl alcohol in breast cancer cells. PubMed: Enhancement of sterol synthesis by the monoterpene perillyl alcohol is unaffected by competitive 3-hydroxy-3-methylglutaryl-CoA reductase inhibition. PubMed: Gas chromatographic-mass spectrometric analysis of perillyl alcohol and metabolites in plasma. PubMed: Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene. PubMed: Novel limonene phosphonate and farnesyl diphosphate analogues: design, synthesis, and evaluation as potential protein-farnesyl transferase inhibitors. PubMed: Activation of the transforming growth factor beta signaling pathway and induction of cytostasis and apoptosis in mammary carcinomas treated with the anticancer agent perillyl alcohol. PubMed: Prevention and therapy of cancer by dietary monoterpenes. PubMed: Inhibition of protein prenylation by metabolites of limonene. PubMed: Insulin promotes phosphorylation and activation of geranylgeranyltransferase II. Studies with geranylgeranylation of rab-3 and rab-4. PubMed: Perillyl alcohol: applications in oncology. PubMed: Monoterpenes inhibit cell growth, cell cycle progression, and cyclin D1 gene expression in human breast cancer cell lines. PubMed: Modulation of small G protein isoprenylation by anticancer monoterpenes in in situ mammary gland epithelial cells. PubMed: Effects of the antitumor agent perillyl alcohol on H-Ras vs. K-Ras farnesylation and signal transduction in pancreatic cells. PubMed: Phase I clinical trial of perillyl alcohol administered daily. PubMed: Monoterpenes in breast cancer chemoprevention. PubMed: Inhibitory effects of perillyl alcohol on UVB-induced murine skin cancer and AP-1 transactivation. PubMed: Quantification of carvone, cineole, perillaldehyde, perillyl alcohol and sobrerol by isocratic high-performance liquid chromatography. PubMed: Clinical trials referral resource. Clinical trials with perillyl alcohol. PubMed: Lysophosphatidic acid stimulates phospholipase D activity and cell proliferation in PC-3 human prostate cancer cells. PubMed: Modulation of RAS expression in human malignant cells by dietary supplements. PubMed: Induction of the apoptosis-promoting protein Bak by perillyl alcohol in pancreatic ductal adenocarcinoma relative to untransformed ductal epithelial cells. PubMed: Inhibition of type I and type II geranylgeranyl-protein transferases by the monoterpene perillyl alcohol in NIH3T3 cells. PubMed: Total Synthesis of the Enantiomer of the Furanocembrane Rubifolide. PubMed: Cancer chemoprevention and therapy by monoterpenes. PubMed: Composition and antimalarial activity in vitro of the essential oil of Tetradenia riparia. PubMed: Isoprenoids suppress the growth of murine B16 melanomas in vitro and in vivo. PubMed: Oral monoterpene therapy (perillyl alcohol) reduces vein graft intimal hyperplasia. PubMed: Production of alpha-terpineol from Escherichia coli cells expressing thermostable limonene hydratase. PubMed: Inhibition of pancreatic cancer growth by the dietary isoprenoids farnesol and geraniol. PubMed: Chemoprevention of colon carcinogenesis by dietary perillyl alcohol. PubMed: Analysis of perillic acid in plasma by reversed-phase high-performance liquid chromatography with ultraviolet detection. PubMed: Chemopreventive effect of perillyl alcohol on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone induced tumorigenesis in (C3H/HeJ X A/J)F1 mouse lung. PubMed: Prevention of mammary preneoplastic transformation by naturally-occurring tumor inhibitors. PubMed: Inhibition of metabolic activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by limonene. PubMed: Inhibition of tumor cell growth by monoterpenes in vitro: evidence of a Ras-independent mechanism of action. PubMed: Chemoprevention of breast cancer. PubMed: Clinical development plan: l-perillyl alcohol. PubMed: Strategy and planning for chemopreventive drug development: clinical development plans II. PubMed: New agents for cancer chemoprevention. PubMed: Monoterpenes as regulators of malignant cell proliferation. PubMed: Antitumorigenic effects of limonene and perillyl alcohol against pancreatic and breast cancer. PubMed: Effects of monoterpenes and mevinolin on murine colon tumor CT-26 in vitro and its hepatic "metastases" in vivo. PubMed: Genetic and cellular changes in colorectal cancer: proposed targets of chemopreventive agents. PubMed: Chemotherapy of pancreatic cancer with the monoterpene perillyl alcohol. PubMed: Induction of differentiation in neuro-2A cells by the monoterpene perillyl alcohol. PubMed: Promoting apoptosis. PubMed: Differential effects of monoterpenes and lovastatin on RAS processing. PubMed: Pharmacokinetics of active drug metabolites after oral administration of perillyl alcohol, an investigational antineoplastic agent, to the dog. PubMed: Isoprenylation of proteins in the protozoan Giardia lamblia. PubMed: The inhibition of protein prenyltransferases by oxygenated metabolites of limonene and perillyl alcohol. PubMed: Induction of apoptosis in liver tumors by the monoterpene perillyl alcohol. PubMed: Prevention and therapy of mammary cancer by monoterpenes. PubMed: The chemoprevention of cancer by mevalonate-derived constituents of fruits and vegetables. PubMed: Structure-activity relationships among monoterpene inhibitors of protein isoprenylation and cell proliferation. PubMed: Growth inhibition of rat liver epithelial tumor cells by monoterpenes does not involve Ras plasma membrane association. 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