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(S)-(-)-perillyl alcohol
1-cyclohexene-1-methanol, 4-(1-methylethenyl)-, (4S)-

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Name:[(4S)-4-prop-1-en-2-yl-1-cyclohexenyl]methanol
CAS Number: 18457-55-1Picture of molecule3D/inchi
FDA UNII: 3UL4QIY642
Nikkaji Web:J86.014J
MDL:MFCD00062995
XlogP3-AA:2.10 (est)
Molecular Weight:152.23672000
Formula:C10 H16 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:colorless to yellow clear liquid (est)
Assay: 96.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 119.00 to 121.00 °C. @ 11.00 mm Hg
Boiling Point: 241.00 to 242.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.006000 mmHg @ 25.00 °C. (est)
Flash Point: 230.00 °F. TCC ( 110.00 °C. )
logP (o/w): 3.077 (est)
Soluble in:
 alcohol
 water, 471 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Perillyl Alcohol >98%
Odor: characteristic
Use: Perillyl Alcohol, or POH, a monoterpene derived from the mevalonate pathway in plants, induces apoptosis in colon tumor cells.
ExtraSynthese
For experimental / research use only.
(-)-Perillylalcohol
Glentham Life Sciences
(-)-Perillyl alcohol
Penta International
S-(-)-PERILLA ALCOHOL
Santa Cruz Biotechnology
For experimental / research use only.
(-)-Perillyl Alcohol ≥90%
Sigma-Aldrich
(S)-(-)-Perillyl alcohol, ≥95%, FG
sds
Odor: green; fatty
Certified Food Grade Products
Synerzine
(S)-(-)-PERILLYL ALCOHOL
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
 
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :369312
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
[(4S)-4-prop-1-en-2-yl-1-cyclohexenyl]methanol
Chemidplus:0018457551
 
References:
 [(4S)-4-prop-1-en-2-yl-1-cyclohexenyl]methanol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):369312
Pubchem (sid):500472
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
KEGG (GenomeNet):C02452
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 citrus sudachi
Search Trop Picture
 
Synonyms:
(S)-(-)-dihydrocuminic alcohol
(-)-perillyl alcohol
(S)-perillyl alcohol
(S)-(-)-perillyl alcohol
1-cyclohexene-1-methanol, 4-(1-methylethenyl)-, (4S)-
 

Articles:

PubMed:Synthesis and antiproliferative effects of amino-modified perillyl alcohol derivatives.
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: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: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: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: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:Anticancer efficacy of perillyl alcohol-bearing PLGA microparticles.
PubMed:Influence of the active compounds of Perilla frutescens leaves on lipid membranes.
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: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: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: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: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:Components of lemon essential oil attenuate dementia induced by scopolamine.
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:Mechanism of in vitro pancreatic cancer cell growth inhibition by melanoma differentiation-associated gene-7/interleukin-24 and 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:Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells.
PubMed:Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas.
PubMed:Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer 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:Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis.
PubMed:Perillyl alcohol induces c-Myc-dependent apoptosis in Bcr/Abl-transformed leukemia cells.
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: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: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: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 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: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: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: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: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: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:Perillyl alcohol mediated radiosensitization via augmentation of the Fas pathway in prostate cancer cells.
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:A phase I trial of perillyl alcohol in patients with advanced solid tumors.
PubMed:Monoterpene regulation of Ras and Ras-related protein expression.
PubMed:Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention.
PubMed:Effects of perillyl alcohol in glial C6 cell line in vitro and anti-metastatic activity in chorioallantoic membrane model.
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: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: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:Perillyl alcohol inhibits TCR-mediated [Ca(2+)](i) signaling, alters cell shape and motility, and induces apoptosis in T lymphocytes.
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: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: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:Monoterpenes inhibit cell growth, cell cycle progression, and cyclin D1 gene expression in human breast cancer cell lines.
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: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: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:Oral monoterpene therapy (perillyl alcohol) reduces vein graft intimal hyperplasia.
PubMed:Inhibition of pancreatic cancer growth by the dietary isoprenoids farnesol and geraniol.
PubMed:Chemoprevention of colon carcinogenesis by dietary perillyl alcohol.
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:Inhibition of tumor cell growth by monoterpenes in vitro: evidence of a Ras-independent mechanism of action.
PubMed:Effects of monoterpenes and mevinolin on murine colon tumor CT-26 in vitro and its hepatic "metastases" in vivo.
PubMed:Chemotherapy of pancreatic cancer with the monoterpene perillyl alcohol.
PubMed:Induction of differentiation in neuro-2A cells by the monoterpene perillyl alcohol.
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:Inhibition of ubiquinone and cholesterol synthesis by the monoterpene perillyl alcohol.
PubMed:Mammary carcinoma regression induced by perillyl alcohol, a hydroxylated analog of limonene.
 
Notes:
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