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536-59-4,MFCD00001567
Catalog No.:AA0038L5

536-59-4 | Perillyl Alcohol

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5g
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$99.00   $69.00
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10g
90%
in stock  
$131.00   $92.00
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25g
90%
in stock  
$193.00   $135.00
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100g
90%
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$497.00   $348.00
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0038L5
Chemical Name:
Perillyl Alcohol
CAS Number:
536-59-4
Molecular Formula:
C10H16O
Molecular Weight:
152.2334
MDL Number:
MFCD00001567
SMILES:
OCC1=CCC(CC1)C(=C)C
FEMA Number:
2664
Properties
Computed Properties
 
Complexity:
179  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
Undefined Atom Stereocenter Count:
1  
XLogP3:
2.1  

Literature

Title: The isoprenoid perillyl alcohol inhibits telomerase activity in prostate cancer cells.

Journal: Biochimie 20121201

Title: Analysis of EGF+61A>G polymorphism and EGF serum levels in Brazilian glioma patients treated with perillyl alcohol-based therapy.

Journal: Journal of cancer research and clinical oncology 20120801

Title: Calcium blockers decrease the bortezomib resistance in mantle cell lymphoma via manipulation of tissue transglutaminase activities.

Journal: Blood 20120315

Title: Influence of the active compounds of Perilla frutescens leaves on lipid membranes.

Journal: Journal of natural products 20120224

Title: Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: A therapeutic approach for wound healing by using essential oils of cupressus and juniperus species growing in Turkey.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: The role of nutraceuticals in chemoprevention and chemotherapy and their clinical outcomes.

Journal: Journal of oncology 20120101

Title: Anticancer efficacy of perillyl alcohol-bearing PLGA microparticles.

Journal: International journal of nanomedicine 20120101

Title: Microbial hydroxylation of S-(-)-perillyl alcohol by Fusarium heterosporium.

Journal: Natural product communications 20111201

Title: Nonmelanoma skin cancer chemoprevention.

Journal: Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.] 20111101

Title: Cell physiology rather than enzyme kinetics can determine the efficiency of cytochrome P450-catalyzed C-H-oxyfunctionalization.

Journal: Journal of industrial microbiology & biotechnology 20110901

Title: Prevention of transplant coronary artery disease by prenylation inhibitors.

Journal: The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20110701

Title: Evaluation of the antioxidant and antiproliferative potential of bioflavors.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110701

Title: An efficient route to selective bio-oxidation catalysts: an iterative approach comprising modeling, diversification, and screening, based on CYP102A1.

Journal: Chembiochem : a European journal of chemical biology 20110614

Title: Efficacy of monoterpene perillyl alcohol upon survival rate of patients with recurrent glioblastoma.

Journal: Journal of cancer research and clinical oncology 20110201

Title: Perillyl alcohol protects against ethanol induced acute liver injury in Wistar rats by inhibiting oxidative stress, NFκ-B activation and proinflammatory cytokine production.

Journal: Toxicology 20110111

Title: Chemo-resistant protein expression pattern of glioblastoma cells (A172) to perillyl alcohol.

Journal: Journal of proteome research 20110107

Title: (1S,2R,4S)-1-[(Benzyl-amino)-meth-yl]-4-(prop-1-en-2-yl)cyclo-hexane-1,2-diol.

Journal: Acta crystallographica. Section E, Structure reports online 20110101

Title: NNK-Induced Lung Tumors: A Review of Animal Model.

Journal: Journal of oncology 20110101

Title: Hydroxyl radical and its scavengers in health and disease.

Journal: Oxidative medicine and cellular longevity 20110101

Title: Chemical composition and antigenotoxic properties of Lippia alba essential oils.

Journal: Genetics and molecular biology 20110101

Title: Pentoxifylline sensitizes human cervical tumor cells to cisplatin-induced apoptosis by suppressing NF-kappa B and decreased cell senescence.

Journal: BMC cancer 20110101

Title: Chamomile (Matricaria chamomilla L.): An overview.

Journal: Pharmacognosy reviews 20110101

Title: The anticancer drug perillyl alcohol is a Na/K-ATPase inhibitor.

Journal: Molecular and cellular biochemistry 20101201

Title: Nonsurgical innovations in the treatment of nonmelanoma skin cancer.

Journal: The Journal of clinical and aesthetic dermatology 20100601

Title: Dynamic proteomic overview of glioblastoma cells (A172) exposed to perillyl alcohol.

Journal: Journal of proteomics 20100310

Title: A phase 2a study of topical perillyl alcohol cream for chemoprevention of skin cancer.

Journal: Cancer prevention research (Philadelphia, Pa.) 20100201

Title: The promise of natural products for blocking early events in skin carcinogenesis.

Journal: Cancer prevention research (Philadelphia, Pa.) 20100201

Title: Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin.

Journal: Anti-cancer drugs 20100101

Title: Tumour-specific HMG-CoAR is an independent predictor of recurrence free survival in epithelial ovarian cancer.

Journal: BMC cancer 20100101

Title: Sensitization of cervix cancer cells to Adriamycin by Pentoxifylline induces an increase in apoptosis and decrease senescence.

Journal: Molecular cancer 20100101

Title: Expressed sequence tags from cephalic chemosensory organs of the northern walnut husk fly, Rhagoletis suavis, including a putative canonical odorant receptor.

Journal: Journal of insect science (Online) 20100101

Title: Antineoplastic activities of MT81 and its structural analogue in Ehrlich ascites carcinoma-bearing Swiss Albino mice.

Journal: Oxidative medicine and cellular longevity 20100101

Title: Mechanism of statin-induced contractile dysfunction in rat cultured skeletal myofibers.

Journal: Journal of pharmacological sciences 20100101

Title: Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol.

Journal: Investigational new drugs 20091201

Title: Pharmacotherapy of actinic keratosis.

Journal: Expert opinion on pharmacotherapy 20091201

Title: Statin-induced muscle damage and atrogin-1 induction is the result of a geranylgeranylation defect.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20090901

Title: Tricistronic overexpression of cytochrome P450cam, putidaredoxin, and putidaredoxin reductase provides a useful cell-based catalytic system.

Journal: Biotechnology letters 20090901

Title: Perillyl alcohol attenuates Ras-ERK signaling to inhibit murine skin inflammation and tumorigenesis.

Journal: Chemico-biological interactions 20090515

Title: Components of lemon essential oil attenuate dementia induced by scopolamine.

Journal: Nutritional neuroscience 20090401

Title: [Natural compounds in chemoprevention of esophageal squamous cell tumors--experimental studies].

Journal: Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego 20090201

Title: GO Explorer: A gene-ontology tool to aid in the interpretation of shotgun proteomics data.

Journal: Proteome science 20090101

Title: Protective effects of mastic oil from Pistacia lentiscus variation chia against experimental growth of lewis lung carcinoma.

Journal: Nutrition and cancer 20090101

Title: A transcriptomic computational analysis of mastic oil-treated Lewis lung carcinomas reveals molecular mechanisms targeting tumor cell growth and survival.

Journal: BMC medical genomics 20090101

Title: Targeted therapy in the treatment of malignant gliomas.

Journal: OncoTargets and therapy 20090101

Title: High-performance liquid chromatographic and pharmacokinetic analyses of an intravenous submicron emulsion of perillyl alcohol in rats.

Journal: Journal of pharmaceutical and biomedical analysis 20081201

Title: 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.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20081115

Title: Fragrance material review on p-mentha-1,8-dien-7-ol.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20081101

Title: Mechanism of in vitro pancreatic cancer cell growth inhibition by melanoma differentiation-associated gene-7/interleukin-24 and perillyl alcohol.

Journal: Cancer research 20080915

Title: Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas.

Journal: Surgical neurology 20080901

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20080901

Title: Ras pathway activation in gliomas: a strategic target for intranasal administration of perillyl alcohol.

Journal: Archivum immunologiae et therapiae experimentalis 20080801

Title: Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells.

Journal: Bioorganic & medicinal chemistry letters 20080715

Title: Chemoprevention by perillyl alcohol coupled with viral gene therapy reduces pancreatic cancer pathogenesis.

Journal: Molecular cancer therapeutics 20080701

Title: A pilot study of perillyl alcohol in pancreatic cancer.

Journal: The Journal of surgical research 20080615

Title: Phase II trial of daily oral perillyl alcohol (NSC 641066) in treatment-refractory metastatic breast cancer.

Journal: Cancer chemotherapy and pharmacology 20080601

Title: Anti-inflammatory senescence actives 5203-L molecule to promote healthy aging and prolongation of lifespan.

Journal: Rejuvenation research 20080401

Title: Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer.

Journal: Nutrition and cancer 20080101

Title: Prevalence of bortezomib-resistant constitutive NF-kappaB activity in mantle cell lymphoma.

Journal: Molecular cancer 20080101

Title: Biphenylalkylacetylhydroquinone ethers suppress the proliferation of murine B16 melanoma cells.

Journal: Anticancer research 20080101

Title: Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20080101

Title: PatternLab for proteomics: a tool for differential shotgun proteomics.

Journal: BMC bioinformatics 20080101

Title: Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol.

Journal: Journal of experimental therapeutics & oncology 20080101

Title: Rab-small GTPases are involved in fluvastatin and pravastatin-induced vacuolation in rat skeletal myofibers.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20071201

Title: Perillyl Alcohol Protects Against Fe-NTA-Induced Nephrotoxicity and Early Tumor Promotional Events in Rat Experimental Model.

Journal: Evidence-based complementary and alternative medicine : eCAM 20071201

Title: Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells.

Journal: Cancer letters 20071118

Title: Perillyl alcohol and genistein differentially regulate PKB/Akt and 4E-BP1 phosphorylation as well as eIF4E/eIF4G interactions in human tumor cells.

Journal: Archives of biochemistry and biophysics 20070901

Title: Cloning of four genes involved in limonene hydroxylation from Enterobacter cowanii 6L.

Journal: Journal of microbiology and biotechnology 20070701

Title: Cell cycle arrest by the isoprenoids perillyl alcohol, geraniol, and farnesol is mediated by p21(Cip1) and p27(Kip1) in human pancreatic adenocarcinoma cells.

Journal: The Journal of pharmacology and experimental therapeutics 20070301

Title: Anaplastic oligodendroglioma responding favorably to intranasal delivery of perillyl alcohol: a case report and literature review.

Journal: Surgical neurology 20061201

Title: Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil.

Journal: Bioscience, biotechnology, and biochemistry 20060801

Title: Polycyclic aromatic hydrocarbon-induced CYP1B1 activity is suppressed by perillyl alcohol in MCF-7 cells.

Journal: Toxicology and applied pharmacology 20060601

Title: Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells.

Journal: Cancer letters 20060518

Title: Recent advances in the molecular genetics of malignant gliomas disclose targets for antitumor agent perillyl alcohol.

Journal: Surgical neurology 20060101

Title: Perillyl alcohol induces c-Myc-dependent apoptosis in Bcr/Abl-transformed leukemia cells.

Journal: Oncology 20060101

Title: Apocynin derivatives interrupt intracellular signaling resulting in decreased migration in breast cancer cells.

Journal: Journal of biomedicine & biotechnology 20060101

Title: Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis.

Journal: Nutrition and cancer 20060101

Title: In vitro induction of apoptosis in U937 cells by perillyl alcohol with sensitization by pentoxifylline: increased BCL-2 and BAX protein expression.

Journal: Chemotherapy 20060101

Title: Effects of perillyl alcohol and heat shock treatment in gene expression of human lung adenocarcinoma cell line A549.

Journal: Journal of experimental therapeutics & oncology 20060101

Title: Perillyl alcohol inhibits a calcium-dependent constitutive nuclear factor-kappaB pathway.

Journal: Cancer research 20050915

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20050601

Title: Effect of D-limonene on immune response in BALB/c mice with lymphoma.

Journal: International immunopharmacology 20050501

Title: Perillyl alcohol induces apoptosis in human glioblastoma multiforme cells.

Journal: Oncology reports 20050501

Title: CaaX-prenyltransferases are essential for expression of genes involvedin the early stages of monoterpenoid biosynthetic pathway in Catharanthus roseus cells.

Journal: Plant molecular biology 20050401

Title: An HPLC method for quantitation of perillyl alcohol in a topical pharmaceutical cream formulation.

Journal: Journal of pharmaceutical and biomedical analysis 20050309

Title: Fumigant toxicity of the essential oils of some African plants against Anopheles gambiae sensu stricto.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20050301

Title: Sle1ab mediates the aberrant activation of STAT3 and Ras-ERK signaling pathways in B lymphocytes.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20050201

Title: The number of functional olfactory receptor genes and the relative size of olfactory brain structures are poor predictors of olfactory discrimination performance with enantiomers.

Journal: Chemical senses 20050201

Title: A novel psychrotrophic fungus, Mortierella minutissima, for D-limonene biotransformation.

Journal: Biotechnology letters 20050201

Title: Cancer preventive role of selected dietary factors.

Journal: Indian journal of cancer 20050101

Title: Protein and m-RNA expression of farnesyl-transferases, RhoA and RhoB in rat liver hepatocytes: action of perillyl alcohol and vitamin A in vivo.

Journal: Journal of biomedical science 20050101

Title: Regio- and stereoselective fungal oxyfunctionalisation of limonenes.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101

Title: Terpenoids as plant antioxidants.

Journal: Vitamins and hormones 20050101

Title: Inherent growth advantage of (pre)malignant hepatocytes associated with nuclear translocation of pro-transforming growth factor alpha.

Journal: British journal of cancer 20041129

Title: A pilot surrogate end point biomarker trial of perillyl alcohol in breast neoplasia.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041115

Title: Perillyl alcohol is an angiogenesis inhibitor.

Journal: The Journal of pharmacology and experimental therapeutics 20041101

Title: A phase I trial of perillyl alcohol administered four times daily for 14 days out of 28 days.

Journal: Cancer chemotherapy and pharmacology 20041001

Title: Repellency of essential oils of some Kenyan plants against Anopheles gambiae.

Journal: Phytochemistry 20041001

Title: Studies of the isoprenoid-mediated inhibition of mevalonate synthesis applied to cancer chemotherapy and chemoprevention.

Journal: Experimental biology and medicine (Maywood, N.J.) 20040701

Title: Antinociceptive effects of the essential oil of Dracocephalum kotschyi in the mouse writhing test.

Journal: Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques 20040420

Title: Perillyl alcohol inhibits human breast cancer cell growth in vitro and in vivo.

Journal: Breast cancer research and treatment 20040401

Title: Using patients as their own controls for cost evaluation of phase I clinical trials.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20040401

Title: Perillyl alcohol-mediated inhibition of lung cancer cell line proliferation: potential mechanisms for its chemotherapeutic effects.

Journal: Toxicology and applied pharmacology 20040301

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20040301

Title: Olfactory discrimination ability of human subjects for enantiomers with an isopropenyl group at the chiral center.

Journal: Chemical senses 20040201

Title: Development of a perillyl alcohol topical cream formulation.

Journal: International journal of pharmaceutics 20040128

Title: Transformation of terpenes using a Picea abies suspension culture.

Journal: Journal of biotechnology 20040122

Title: Effects of POH in combination with STI571 on the proliferation and apoptosis of K562 cells.

Journal: Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20040101

Title: BAK overexpression mediates p53-independent apoptosis inducing effects on human gastric cancer cells.

Journal: BMC cancer 20040101

Title: Monoterpenes enhanced the sensitivity of head and neck cancer cells to radiation treatment in vitro.

Journal: Anticancer research 20040101

Title: Effect of antiproliferative agents on vascular function in normal and in vitro balloon-injured porcine coronary arteries.

Journal: European journal of pharmacology 20031114

Title: Phase I trial of perillyl alcohol administered four times daily continuously.

Journal: Cancer chemotherapy and pharmacology 20031101

Title: Cytotoxicity of perillyl alcohol against cancer cells is potentiated by hyperthermia.

Journal: International journal of radiation oncology, biology, physics 20031101

Title: Perillyl alcohol and perillaldehyde induced cell cycle arrest and cell death in BroTo and A549 cells cultured in vitro.

Journal: Life sciences 20031017

Title: Studies with cytotoxic agents suggest that apoptosis is not a major determinant of clonogenic death in neuroblastoma cells.

Journal: European journal of cancer (Oxford, England : 1990) 20031001

Title: Anti-leukemia effect of perillyl alcohol in Bcr/Abl-transformed cells indirectly inhibits signaling through Mek in a Ras- and Raf-independent fashion.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20031001

Title: Perillyl alcohol as a radio-/chemosensitizer in malignant glioma.

Journal: The Journal of biological chemistry 20030919

Title: Perillyl alcohol mediated radiosensitization via augmentation of the Fas pathway in prostate cancer cells.

Journal: The Prostate 20030915

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20030901

Title: Phase II trial of perillyl alcohol (NSC 641066) administered daily in patients with metastatic androgen independent prostate cancer.

Journal: Investigational new drugs 20030801

Title: In situ detection of neoplastic transformation and chemopreventive effects in rat esophagus epithelium using angle-resolved low-coherence interferometry.

Journal: Cancer research 20030701

Title: Monoterpene regulation of Ras and Ras-related protein expression.

Journal: Journal of lipid research 20030601

Title: A phase I trial of perillyl alcohol in patients with advanced solid tumors.

Journal: Cancer chemotherapy and pharmacology 20030601

Title: Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis.

Journal: Cancer research 20030515

Title: Mechanism-based in vitro screening of potential cancer chemopreventive agents.

Journal: Mutation research 20030101

Title: Skin cancer chemoprevention: strategies to save our skin.

Journal: Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer 20030101

Title: Effects of perillyl alcohol in glial C6 cell line in vitro and anti-metastatic activity in chorioallantoic membrane model.

Journal: International journal of molecular medicine 20021201

Title: Sensitive biomonitoring of monoterpene exposure by gas chromatographic-mass spectrometric measurement of hydroxy terpenes in urine.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20021125

Title: Monoterpenes inhibit proliferation of human colon cancer cells by modulating cell cycle-related protein expression.

Journal: Cancer letters 20020726

Title: Effects of perillyl alcohol on melanoma in the TPras mouse model.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20020601

Title: A phase II trial of daily perillyl alcohol in patients with advanced ovarian cancer: Eastern Cooperative Oncology Group Study E2E96.

Journal: Gynecologic oncology 20020601

Title: Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20020501

Title: 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.

Journal: Leukemia 20020201

Title: Induction of cytostasis in mammary carcinoma cells treated with the anticancer agent perillyl alcohol.

Journal: Carcinogenesis 20020101

Title: Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome p450 enzymes in rat liver microsomes.

Journal: Chemical research in toxicology 20020101

Title: Weight-loss drugs and supplements: are there safer alternatives?

Journal: Medical hypotheses 20020101

Title: Phase I study of perillyl alcohol in patients with refractory malignancies.

Journal: Cancer biology & therapy 20020101

Title: Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention.

Journal: Anticancer research 20020101

Title: Micronutrients in cancer chemoprevention.

Journal: Cancer metastasis reviews 20020101

Title: Phase II trial of perillyl alcohol in patients with metastatic colorectal cancer.

Journal: International journal of gastrointestinal cancer 20020101

Title: 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.

Journal: Drug metabolism and pharmacokinetics 20020101

Title: Biotransformation of limonene by Pseudomonas putida.

Journal: Applied microbiology and biotechnology 20010501

Title: Breast cancer chemoprevention: beyond tamoxifen.

Journal: Breast cancer research : BCR 20010101

Title: Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.

Journal: Anticancer research 20000101

Title: Perillyl alcohol dehydrogenase from a soil pseudomonad.

Journal: Biochemical and biophysical research communications 19660525

Title: Belanger JT. Perillyl alcohol: applications in oncology. Altern Med Rev. 1998 Dec;3(6):448-57.

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Tags:536-59-4 Molecular Formula|536-59-4 MDL|536-59-4 SMILES|536-59-4 Perillyl Alcohol