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18457-55-1,MFCD00062995
Catalog No.:AA00AOQA

18457-55-1 | (-)-PERILLYL ALCOHOL

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Purity
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Price(USD)
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250mg
95% mix TBC as stabilizer
in stock  
$12.00   $8.00
- +
1g
95% mix TBC as stabilizer
in stock  
$23.00   $16.00
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10g
≥85%
in stock  
$99.00   $69.00
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50g
≥85%
in stock  
$197.00   $138.00
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100g
≥85%
in stock  
$307.00   $215.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00AOQA
Chemical Name:
(-)-PERILLYL ALCOHOL
CAS Number:
18457-55-1
Molecular Formula:
C10H16O
Molecular Weight:
152.2334
MDL Number:
MFCD00062995
SMILES:
OCC1=CC[C@H](CC1)C(=C)C
NSC Number:
641066
Properties
Properties
 
BP:
241.2 °C at 760 mmHg  
Form:
Liquid  
Storage:
2-8℃;Keep in dry area;  

Computed Properties
 
Complexity:
179  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
2.1  

Downstream Synthesis Route

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18457-55-1    108-24-7   
(S)-(4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methylacetate 

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

Journal: Molecular and cellular biochemistry 20101201

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

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

Journal: Cancer letters 20071118

Title: Modifications of the chemical structure of terpenes in antiplasmodial and antifungal drug research.

Journal: Bioorganic & medicinal chemistry letters 20071115

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: 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: 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: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

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

Journal: Breast cancer research and treatment 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: Development of a perillyl alcohol topical cream formulation.

Journal: International journal of pharmaceutics 20040128

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

Journal: Investigational new drugs 20030801

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

Journal: International journal of gastrointestinal cancer 20020101

Title: Liston BW, et al. Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis. Cancer Res. 2003 May 15;63(10):2399-403.

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Tags:18457-55-1 Molecular Formula|18457-55-1 MDL|18457-55-1 SMILES|18457-55-1 (-)-PERILLYL ALCOHOL