Home Other Building Blocks (-)-PERILLYL ALCOHOL

(-)-PERILLYL ALCOHOL

CAS No.:
18457-55-1
Catalog Number:
AG00AOT2
Molecular Formula:
C10H16O
Molecular Weight:
152.2334
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
98%(GC)
In Stock USA
United States
$85
- +
5g
98%(GC)
In Stock USA
United States
$215
- +
25g
98%(GC)
In Stock USA
United States
$607
- +
Product Description
Catalog Number:
AG00AOT2
Chemical Name:
(-)-PERILLYL ALCOHOL
CAS Number:
18457-55-1
Molecular Formula:
C10H16O
Molecular Weight:
152.2334
MDL Number:
MFCD00062995
IUPAC Name:
[(4S)-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/t10-/m1/s1
InChI Key:
NDTYTMIUWGWIMO-SNVBAGLBSA-N
SMILES:
OCC1=CC[C@H](CC1)C(=C)C
UNII:
3UL4QIY642
NSC Number:
641066
Properties
Complexity:
179  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
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:
0
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
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
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
The anticancer drug perillyl alcohol is a Na/K-ATPase inhibitor. Molecular and cellular biochemistry 20101201
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
Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol. Investigational new drugs 20091201
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
Protective effects of mastic oil from Pistacia lentiscus variation chia against experimental growth of lewis lung carcinoma. Nutrition and cancer 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
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
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
Anti-thrombin as a prognostic biomarker candidate for patients with recurrent glioblastoma multiform under treatment with perillyl alcohol. Journal of experimental therapeutics & oncology 20080101
Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. Cancer letters 20071118
Modifications of the chemical structure of terpenes in antiplasmodial and antifungal drug research. Bioorganic & medicinal chemistry letters 20071115
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
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
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
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
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
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
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
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
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
Perillyl alcohol inhibits human breast cancer cell growth in vitro and in vivo. Breast cancer research and treatment 20040401
Perillyl alcohol-mediated inhibition of lung cancer cell line proliferation: potential mechanisms for its chemotherapeutic effects. Toxicology and applied pharmacology 20040301
Development of a perillyl alcohol topical cream formulation. International journal of pharmaceutics 20040128
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
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
Phase II trial of perillyl alcohol (NSC 641066) administered daily in patients with metastatic androgen independent prostate cancer. Investigational new drugs 20030801
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
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
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
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
Phase II trial of perillyl alcohol in patients with metastatic colorectal cancer. International journal of gastrointestinal cancer 20020101
Properties