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Perillyl Alcohol

CAS No.:
536-59-4
Catalog Number:
AG0038NX
Molecular Formula:
C10H16O
Molecular Weight:
152.2334
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Purity
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Product Description
Catalog Number:
AG0038NX
Chemical Name:
Perillyl Alcohol
CAS Number:
536-59-4
Molecular Formula:
C10H16O
Molecular Weight:
152.2334
MDL Number:
MFCD00001567
IUPAC Name:
(4-prop-1-en-2-ylcyclohexen-1-yl)methanol
InChI:
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
InChI Key:
NDTYTMIUWGWIMO-UHFFFAOYSA-N
SMILES:
OCC1=CCC(CC1)C(=C)C
EC Number:
208-639-9
FEMA Number:
2664
Properties
Complexity:
179  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
152.12g/mol
Formal Charge:
0
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
152.237g/mol
Monoisotopic Mass:
152.12g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
20.2A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
2.1  
Literature
Title Journal
The isoprenoid perillyl alcohol inhibits telomerase activity in prostate cancer cells. Biochimie 20121201
Analysis of EGF+61A>G polymorphism and EGF serum levels in Brazilian glioma patients treated with perillyl alcohol-based therapy. Journal of cancer research and clinical oncology 20120801
Calcium blockers decrease the bortezomib resistance in mantle cell lymphoma via manipulation of tissue transglutaminase activities. Blood 20120315
Influence of the active compounds of Perilla frutescens leaves on lipid membranes. Journal of natural products 20120224
Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo. Evidence-based complementary and alternative medicine : eCAM 20120101
A therapeutic approach for wound healing by using essential oils of cupressus and juniperus species growing in Turkey. Evidence-based complementary and alternative medicine : eCAM 20120101
The role of nutraceuticals in chemoprevention and chemotherapy and their clinical outcomes. Journal of oncology 20120101
Anticancer efficacy of perillyl alcohol-bearing PLGA microparticles. International journal of nanomedicine 20120101
Microbial hydroxylation of S-(-)-perillyl alcohol by Fusarium heterosporium. Natural product communications 20111201
Nonmelanoma skin cancer chemoprevention. Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.] 20111101
Cell physiology rather than enzyme kinetics can determine the efficiency of cytochrome P450-catalyzed C-H-oxyfunctionalization. Journal of industrial microbiology & biotechnology 20110901
Prevention of transplant coronary artery disease by prenylation inhibitors. The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20110701
Evaluation of the antioxidant and antiproliferative potential of bioflavors. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110701
An efficient route to selective bio-oxidation catalysts: an iterative approach comprising modeling, diversification, and screening, based on CYP102A1. Chembiochem : a European journal of chemical biology 20110614
Efficacy of monoterpene perillyl alcohol upon survival rate of patients with recurrent glioblastoma. Journal of cancer research and clinical oncology 20110201
Perillyl alcohol protects against ethanol induced acute liver injury in Wistar rats by inhibiting oxidative stress, NFκ-B activation and proinflammatory cytokine production. Toxicology 20110111
Chemo-resistant protein expression pattern of glioblastoma cells (A172) to perillyl alcohol. Journal of proteome research 20110107
(1S,2R,4S)-1-[(Benzyl-amino)-meth-yl]-4-(prop-1-en-2-yl)cyclo-hexane-1,2-diol. Acta crystallographica. Section E, Structure reports online 20110101
NNK-Induced Lung Tumors: A Review of Animal Model. Journal of oncology 20110101
Hydroxyl radical and its scavengers in health and disease. Oxidative medicine and cellular longevity 20110101
Chemical composition and antigenotoxic properties of Lippia alba essential oils. Genetics and molecular biology 20110101
Pentoxifylline sensitizes human cervical tumor cells to cisplatin-induced apoptosis by suppressing NF-kappa B and decreased cell senescence. BMC cancer 20110101
Chamomile (Matricaria chamomilla L.): An overview. Pharmacognosy reviews 20110101
The anticancer drug perillyl alcohol is a Na/K-ATPase inhibitor. Molecular and cellular biochemistry 20101201
Nonsurgical innovations in the treatment of nonmelanoma skin cancer. The Journal of clinical and aesthetic dermatology 20100601
Dynamic proteomic overview of glioblastoma cells (A172) exposed to perillyl alcohol. Journal of proteomics 20100310
A phase 2a study of topical perillyl alcohol cream for chemoprevention of skin cancer. Cancer prevention research (Philadelphia, Pa.) 20100201
The promise of natural products for blocking early events in skin carcinogenesis. Cancer prevention research (Philadelphia, Pa.) 20100201
Perillyl alcohol and methyl jasmonate sensitize cancer cells to cisplatin. Anti-cancer drugs 20100101
Tumour-specific HMG-CoAR is an independent predictor of recurrence free survival in epithelial ovarian cancer. BMC cancer 20100101
Sensitization of cervix cancer cells to Adriamycin by Pentoxifylline induces an increase in apoptosis and decrease senescence. Molecular cancer 20100101
Expressed sequence tags from cephalic chemosensory organs of the northern walnut husk fly, Rhagoletis suavis, including a putative canonical odorant receptor. Journal of insect science (Online) 20100101
Antineoplastic activities of MT81 and its structural analogue in Ehrlich ascites carcinoma-bearing Swiss Albino mice. Oxidative medicine and cellular longevity 20100101
Mechanism of statin-induced contractile dysfunction in rat cultured skeletal myofibers. Journal of pharmacological sciences 20100101
Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol. Investigational new drugs 20091201
Pharmacotherapy of actinic keratosis. Expert opinion on pharmacotherapy 20091201
Statin-induced muscle damage and atrogin-1 induction is the result of a geranylgeranylation defect. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20090901
Tricistronic overexpression of cytochrome P450cam, putidaredoxin, and putidaredoxin reductase provides a useful cell-based catalytic system. Biotechnology letters 20090901
Perillyl alcohol attenuates Ras-ERK signaling to inhibit murine skin inflammation and tumorigenesis. Chemico-biological interactions 20090515
Components of lemon essential oil attenuate dementia induced by scopolamine. Nutritional neuroscience 20090401
[Natural compounds in chemoprevention of esophageal squamous cell tumors--experimental studies]. Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego 20090201
GO Explorer: A gene-ontology tool to aid in the interpretation of shotgun proteomics data. Proteome science 20090101
Protective effects of mastic oil from Pistacia lentiscus variation chia against experimental growth of lewis lung carcinoma. Nutrition and cancer 20090101
A transcriptomic computational analysis of mastic oil-treated Lewis lung carcinomas reveals molecular mechanisms targeting tumor cell growth and survival. BMC medical genomics 20090101
Targeted therapy in the treatment of malignant gliomas. OncoTargets and therapy 20090101
High-performance liquid chromatographic and pharmacokinetic analyses of an intravenous submicron emulsion of perillyl alcohol in rats. Journal of pharmaceutical and biomedical analysis 20081201
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 of chromatography. B, Analytical technologies in the biomedical and life sciences 20081115
Fragrance material review on p-mentha-1,8-dien-7-ol. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20081101
Mechanism of in vitro pancreatic cancer cell growth inhibition by melanoma differentiation-associated gene-7/interleukin-24 and perillyl alcohol. Cancer research 20080915
Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas. Surgical neurology 20080901
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20080901
Ras pathway activation in gliomas: a strategic target for intranasal administration of perillyl alcohol. Archivum immunologiae et therapiae experimentalis 20080801
Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells. Bioorganic & medicinal chemistry letters 20080715
Chemoprevention by perillyl alcohol coupled with viral gene therapy reduces pancreatic cancer pathogenesis. Molecular cancer therapeutics 20080701
A pilot study of perillyl alcohol in pancreatic cancer. The Journal of surgical research 20080615
Phase II trial of daily oral perillyl alcohol (NSC 641066) in treatment-refractory metastatic breast cancer. Cancer chemotherapy and pharmacology 20080601
Anti-inflammatory senescence actives 5203-L molecule to promote healthy aging and prolongation of lifespan. Rejuvenation research 20080401
Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer. Nutrition and cancer 20080101
Prevalence of bortezomib-resistant constitutive NF-kappaB activity in mantle cell lymphoma. Molecular cancer 20080101
Biphenylalkylacetylhydroquinone ethers suppress the proliferation of murine B16 melanoma cells. Anticancer research 20080101
Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds. Chemistry (Weinheim an der Bergstrasse, Germany) 20080101
PatternLab for proteomics: a tool for differential shotgun proteomics. BMC bioinformatics 20080101
Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol. Journal of experimental therapeutics & oncology 20080101
Rab-small GTPases are involved in fluvastatin and pravastatin-induced vacuolation in rat skeletal myofibers. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20071201
Perillyl Alcohol Protects Against Fe-NTA-Induced Nephrotoxicity and Early Tumor Promotional Events in Rat Experimental Model. Evidence-based complementary and alternative medicine : eCAM 20071201
Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. Cancer letters 20071118
Perillyl alcohol and genistein differentially regulate PKB/Akt and 4E-BP1 phosphorylation as well as eIF4E/eIF4G interactions in human tumor cells. Archives of biochemistry and biophysics 20070901
Cloning of four genes involved in limonene hydroxylation from Enterobacter cowanii 6L. Journal of microbiology and biotechnology 20070701
Cell cycle arrest by the isoprenoids perillyl alcohol, geraniol, and farnesol is mediated by p21(Cip1) and p27(Kip1) in human pancreatic adenocarcinoma cells. The Journal of pharmacology and experimental therapeutics 20070301
Anaplastic oligodendroglioma responding favorably to intranasal delivery of perillyl alcohol: a case report and literature review. Surgical neurology 20061201
Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil. Bioscience, biotechnology, and biochemistry 20060801
Polycyclic aromatic hydrocarbon-induced CYP1B1 activity is suppressed by perillyl alcohol in MCF-7 cells. Toxicology and applied pharmacology 20060601
Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells. Cancer letters 20060518
Recent advances in the molecular genetics of malignant gliomas disclose targets for antitumor agent perillyl alcohol. Surgical neurology 20060101
Perillyl alcohol induces c-Myc-dependent apoptosis in Bcr/Abl-transformed leukemia cells. Oncology 20060101
Apocynin derivatives interrupt intracellular signaling resulting in decreased migration in breast cancer cells. Journal of biomedicine & biotechnology 20060101
Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis. Nutrition and cancer 20060101
In vitro induction of apoptosis in U937 cells by perillyl alcohol with sensitization by pentoxifylline: increased BCL-2 and BAX protein expression. Chemotherapy 20060101
Effects of perillyl alcohol and heat shock treatment in gene expression of human lung adenocarcinoma cell line A549. Journal of experimental therapeutics & oncology 20060101
Perillyl alcohol inhibits a calcium-dependent constitutive nuclear factor-kappaB pathway. Cancer research 20050915
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20050601
Effect of D-limonene on immune response in BALB/c mice with lymphoma. International immunopharmacology 20050501
Perillyl alcohol induces apoptosis in human glioblastoma multiforme cells. Oncology reports 20050501
CaaX-prenyltransferases are essential for expression of genes involvedin the early stages of monoterpenoid biosynthetic pathway in Catharanthus roseus cells. Plant molecular biology 20050401
An HPLC method for quantitation of perillyl alcohol in a topical pharmaceutical cream formulation. Journal of pharmaceutical and biomedical analysis 20050309
Fumigant toxicity of the essential oils of some African plants against Anopheles gambiae sensu stricto. Phytomedicine : international journal of phytotherapy and phytopharmacology 20050301
Sle1ab mediates the aberrant activation of STAT3 and Ras-ERK signaling pathways in B lymphocytes. Journal of immunology (Baltimore, Md. : 1950) 20050201
The number of functional olfactory receptor genes and the relative size of olfactory brain structures are poor predictors of olfactory discrimination performance with enantiomers. Chemical senses 20050201
A novel psychrotrophic fungus, Mortierella minutissima, for D-limonene biotransformation. Biotechnology letters 20050201
Cancer preventive role of selected dietary factors. Indian journal of cancer 20050101
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 of biomedical science 20050101
Regio- and stereoselective fungal oxyfunctionalisation of limonenes. Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101
Terpenoids as plant antioxidants. Vitamins and hormones 20050101
Inherent growth advantage of (pre)malignant hepatocytes associated with nuclear translocation of pro-transforming growth factor alpha. British journal of cancer 20041129
A pilot surrogate end point biomarker trial of perillyl alcohol in breast neoplasia. Clinical cancer research : an official journal of the American Association for Cancer Research 20041115
Perillyl alcohol is an angiogenesis inhibitor. The Journal of pharmacology and experimental therapeutics 20041101
A phase I trial of perillyl alcohol administered four times daily for 14 days out of 28 days. Cancer chemotherapy and pharmacology 20041001
Repellency of essential oils of some Kenyan plants against Anopheles gambiae. Phytochemistry 20041001
Studies of the isoprenoid-mediated inhibition of mevalonate synthesis applied to cancer chemotherapy and chemoprevention. Experimental biology and medicine (Maywood, N.J.) 20040701
Antinociceptive effects of the essential oil of Dracocephalum kotschyi in the mouse writhing test. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques 20040420
Perillyl alcohol inhibits human breast cancer cell growth in vitro and in vivo. Breast cancer research and treatment 20040401
Using patients as their own controls for cost evaluation of phase I clinical trials. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20040401
Perillyl alcohol-mediated inhibition of lung cancer cell line proliferation: potential mechanisms for its chemotherapeutic effects. Toxicology and applied pharmacology 20040301
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20040301
Olfactory discrimination ability of human subjects for enantiomers with an isopropenyl group at the chiral center. Chemical senses 20040201
Development of a perillyl alcohol topical cream formulation. International journal of pharmaceutics 20040128
Transformation of terpenes using a Picea abies suspension culture. Journal of biotechnology 20040122
Effects of POH in combination with STI571 on the proliferation and apoptosis of K562 cells. 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
BAK overexpression mediates p53-independent apoptosis inducing effects on human gastric cancer cells. BMC cancer 20040101
Monoterpenes enhanced the sensitivity of head and neck cancer cells to radiation treatment in vitro. Anticancer research 20040101
Effect of antiproliferative agents on vascular function in normal and in vitro balloon-injured porcine coronary arteries. European journal of pharmacology 20031114
Phase I trial of perillyl alcohol administered four times daily continuously. Cancer chemotherapy and pharmacology 20031101
Cytotoxicity of perillyl alcohol against cancer cells is potentiated by hyperthermia. International journal of radiation oncology, biology, physics 20031101
Perillyl alcohol and perillaldehyde induced cell cycle arrest and cell death in BroTo and A549 cells cultured in vitro. Life sciences 20031017
Studies with cytotoxic agents suggest that apoptosis is not a major determinant of clonogenic death in neuroblastoma cells. European journal of cancer (Oxford, England : 1990) 20031001
Anti-leukemia effect of perillyl alcohol in Bcr/Abl-transformed cells indirectly inhibits signaling through Mek in a Ras- and Raf-independent fashion. Clinical cancer research : an official journal of the American Association for Cancer Research 20031001
Perillyl alcohol as a radio-/chemosensitizer in malignant glioma. The Journal of biological chemistry 20030919
Perillyl alcohol mediated radiosensitization via augmentation of the Fas pathway in prostate cancer cells. The Prostate 20030915
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20030901
Phase II trial of perillyl alcohol (NSC 641066) administered daily in patients with metastatic androgen independent prostate cancer. Investigational new drugs 20030801
In situ detection of neoplastic transformation and chemopreventive effects in rat esophagus epithelium using angle-resolved low-coherence interferometry. Cancer research 20030701
Monoterpene regulation of Ras and Ras-related protein expression. Journal of lipid research 20030601
A phase I trial of perillyl alcohol in patients with advanced solid tumors. Cancer chemotherapy and pharmacology 20030601
Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis. Cancer research 20030515
Mechanism-based in vitro screening of potential cancer chemopreventive agents. Mutation research 20030101
Skin cancer chemoprevention: strategies to save our skin. Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer 20030101
Effects of perillyl alcohol in glial C6 cell line in vitro and anti-metastatic activity in chorioallantoic membrane model. International journal of molecular medicine 20021201
Sensitive biomonitoring of monoterpene exposure by gas chromatographic-mass spectrometric measurement of hydroxy terpenes in urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20021125
Monoterpenes inhibit proliferation of human colon cancer cells by modulating cell cycle-related protein expression. Cancer letters 20020726
Effects of perillyl alcohol on melanoma in the TPras mouse model. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20020601
A phase II trial of daily perillyl alcohol in patients with advanced ovarian cancer: Eastern Cooperative Oncology Group Study E2E96. Gynecologic oncology 20020601
Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes. Drug metabolism and disposition: the biological fate of chemicals 20020501
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. Leukemia 20020201
Induction of cytostasis in mammary carcinoma cells treated with the anticancer agent perillyl alcohol. Carcinogenesis 20020101
Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome p450 enzymes in rat liver microsomes. Chemical research in toxicology 20020101
Weight-loss drugs and supplements: are there safer alternatives? Medical hypotheses 20020101
Phase I study of perillyl alcohol in patients with refractory malignancies. Cancer biology & therapy 20020101
Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention. Anticancer research 20020101
Micronutrients in cancer chemoprevention. Cancer metastasis reviews 20020101
Phase II trial of perillyl alcohol in patients with metastatic colorectal cancer. International journal of gastrointestinal cancer 20020101
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. Drug metabolism and pharmacokinetics 20020101
Biotransformation of limonene by Pseudomonas putida. Applied microbiology and biotechnology 20010501
Breast cancer chemoprevention: beyond tamoxifen. Breast cancer research : BCR 20010101
Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data. Anticancer research 20000101
Perillyl alcohol dehydrogenase from a soil pseudomonad. Biochemical and biophysical research communications 19660525
Properties