perilla alcohol
p-mentha-1,8-dien-7-ol
 
Notes:
inhibits geranylgeranyl transferase. Perillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID: 9855569) [HMDB] Occurs in a variety of essential oils, e.g. lavender
  • CTC Organics
    • CTC Organics
      For More Than 40 Year
      Your source for rare aroma chemicals for the flavor and fragrance industy.
      “The world is run by middle men.” The number of times I have heard Dr. Liu utter those words are innumerable. He loved reciting and recording famous quotes and had many of his own. Among his many talents, Dr. Liu had a unique genius in the area of chemistry. He had an uncanny understanding of the pulse of the chemical industry and was a superb salesman.
      US Email: Customer Service
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      Product(s):
      W1684 perillyl alcohol
       
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  • Lluch Essence
    • Lluch Essence S.L.
      A family company dedicated to sales and distribution
      Flexibility, availability, price and quality.
      Flexibility, availability, price and quality make LLUCH ESSENCE S.L. one of Europe’s references when it comes to essential oils and aroma chemicals, and it is now well known all around the world.
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      PERILLA ALCOHOL
       
  • Penta International
    • Penta International Corporation
      Chemistry innovation
      At Penta, our products and services help businesses do business better.
      For over 30 years, Penta Manufacturing Company has played a growing role in worldwide chemistry innovations and applications. As an industry leader, Penta continues to pioneer chemistry-based solutions for practically every area of commerce. Our products and expertise have helped fuel technical advances in dozens of commercial applications including flavoring, coloring, fragrances and chemical processes.
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      Product(s):
      16-14700 PERILLA ALCOHOL, Kosher
       
Synonyms   Articles   Notes   Search
(4-prop-1-en-2-yl-1-cyclohexenyl)methanol (Click)
CAS Number: 536-59-4Picture of molecule
ECHA EINECS - REACH Pre-Reg: 208-639-9
FDA UNII: 319R5C7293
Nikkaji Web: J11.581I
CoE Number: 2024
XlogP3-AA: 2.10 (est)
Molecular Weight: 152.23672000
Formula: C10 H16 O
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic, flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
JECFA Food Flavoring: 974  p-mentha-1,8-dien-7-ol
Flavis Number: 02.060 (Old)
DG SANTE Food Flavourings: 02.060  p-mentha-1,8-dien-7-ol
FEMA Number: 2664  p-mentha-1,8-dien-7-ol
FDA Mainterm: P-MENTHA-1,8-DIEN-7-OL
FDA Regulation:
FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION
Subpart F--Flavoring Agents and Related Substances
Sec. 172.515 Synthetic flavoring substances and adjuvants.
Synonyms   Articles   Notes   Search   Top
Physical Properties:
Appearance: colorless to pale yellow clear liquid (est)
Assay: 96.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.95000 to 0.96500 @  25.00 °C.
Pounds per Gallon - (est).: 7.905 to  8.030
Refractive Index: 1.48800 to 1.50500 @  20.00 °C.
Boiling Point: 119.00 to  121.00 °C. @ 11.00 mm Hg
Boiling Point: 92.00 to  93.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.006000 mm/Hg @ 25.00 °C. (est)
Flash Point: > 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w): 3.170
Soluble in:
 alcohol
 water, 471 mg/L @ 25 °C (est)
Insoluble in:
 water
Synonyms   Articles   Notes   Search   Top
Organoleptic Properties:
Odor Type: green
Odor Strength: medium
 green  bois de rose  lilac  fatty  
Odor Description:
at 100.00 %. 
green linalool terpineol fatty
 sweet  woody  aromatic  spicy  cardamom  green  cumin  orange peel  green  waxy  floral  
Odor Description:
at 1.00 %.  
sweet , woody, aromatic spicy cardamom and green cumin like with dried orange peel and green waxy floral nuances
Mosciano, Gerard, (2009)
 sweet  woody  aromatic  spicy  cardamom  green  cumin  orange peel  green  waxy  floral  
Taste Description:
at 25.00 ppm.  
sweet , woody, aromatic spicy cardamom and green cumin like with dried orange peel and green waxy floral nuances
Mosciano, Gerard, (2009)
  
Synonyms   Articles   Notes   Search   Top
Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antimicrobial agents
antioxidants
masking agents
perfuming agents
skin protecting agents
Synonyms   Articles   Notes   Search   Top
Suppliers:
Citrus and Allied Essences
Perilla Alcohol
Market Report
CTC Organics
perillyl alcohol
De Monchy Aromatics
dihydro cuminyl alcohol
Indukern F&F
PERILLA ALCOHOL
Odor: GREEN, HERBAL
CROP CALENDAR
Lluch Essence
PERILLA ALCOHOL
Nippon Terpene Chemicals
l-Perillyl alcohol 85% up
Penta International
PERILLA ALCOHOL, Kosher
Reincke & Fichtner
p-Mentha-1,8-dien-7-ol
Synonyms   Articles   Notes   Search   Top
Safety Information:
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
 
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.
Human Experience:
4 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50  2100 mg/kg
Food and Cosmetics Toxicology. Vol. 19, Pg. 253, 1981.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 19, Pg. 253, 1981.

Inhalation Toxicity:
Not determined
Synonyms   Articles   Notes   Search   Top
Safety in Use Information:
Category: cosmetic, flavor and fragrance agents
maximum skin levels for fine fragrances:
  0.1700 %  and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey). (IFRA, 2006)
Recommendation for perilla alcohol usage levels up to:
  4.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
  0.0200 %
Dermal Systemic Exposure in Cosmetic Products:
 0.0005 mg/kg/day (IFRA, 2006)
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 1.60 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 1.00 (μg/capita/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
 average usual ppmaverage maximum ppm
baked goods: 10.0000050.00000
beverages(nonalcoholic): 0.500001.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 0.500001.00000
fruit ices: 0.500001.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -20.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --
Synonyms   Articles   Notes   Search   Top
Safety References:
Flavor & Extract Manufacturers Association (FEMA) reference(s):
The FEMA GRAS assessment of alicyclic substances used as flavor ingredients.View pdf
European Food Safety Athority(efsa): Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
European Food Safety Authority (EFSA) reference(s):
Scientific Opinion on Flavouring Group Evaluation 208 Revision 1 (FGE.208Rev1): Consideration of genotoxicity data on representatives for 10 alicyclic aldehydes with the a,▀-unsaturation in ring / side-chain and precursors from chemical subgroup 2.2 of
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 208 Revision 2 (FGE.208Rev2): Consideration of genotoxicity data on alicyclic aldehydes with a,▀-unsaturation in ring/side-chain and precursors from chemical subgroup 2.2 of FGE.19
View page or View pdf
EPI System: View
ClinicalTrials.gov: search
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 536-59-4
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10819
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 (4-prop-1-en-2-yl-1-cyclohexenyl)methanol
Chemidplus: 0000536594
RTECS: OS8395000 for cas# 536-59-4
Synonyms   Articles   Notes   Search   Top
References:
 (4-prop-1-en-2-yl-1-cyclohexenyl)methanol
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 536-59-4
Pubchem (cid): 10819
Pubchem (sid): 134977617
Pherobase: View
Synonyms   Articles   Notes   Search   Top
Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS): View
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
UM BBD: Search
KEGG (GenomeNet): C02452
HMDB (The Human Metabolome Database): HMDB03634
FooDB: FDB014925
Export Tariff Code: 2906.10
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Read: Under the conditions of intended use - New developments in the FEMA GRAS program and the safety assessment of flavor ingredients
Read: A GRAS assessment program for flavor ingredients
Read: Sensory testing for flavorings with modifying properties. Food Technology
Read: Criteria for the safety evaluation of flavoring substances
Read: A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils
Read: FEMA Expert Panel: 30 Years of safety evaluation for the flavor industry
Read: Consumption ratio and food predominance of flavoring materials
Synonyms   Articles   Notes   Search   Top
Potential Blenders and core components note
 
For Odor
aldehydic
 citronellyl oxyacetaldehydeFL/FR
 lily pentanalFR
 muguet undecadienalFR
 nonanal (aldehyde C-9)FL/FR
animal
para-cresyl isobutyrateFL/FR
para-cresyl phenyl acetateFL/FR
balsamic
 linalyl cinnamateFL/FR
citrus
 benzyl anthranilateFR
 citrus ocimenolFR
(Z)-4-decenalFL/FR
 myrmac aldehydeFR
 tetrahydromyrcenolFR
earthy
 octyl phenyl acetateFL/FR
floral
alpha-amyl cinnamaldehyde dimethyl acetalFL/FR
 bois de rose oil brazilFL/FR
alpha-butyl cinnamaldehydeFL/FR
 citronellyl ethoxalateFR
 coranol (Firmenich)FR
 cumin carbinolFR
 cyclamen aldehyde / methyl anthranilate schiff's baseFR
 cyclamen homoaldehydeFR
 cyclohexyl ethyl alcoholFL/FR
 cyclohexyl propanolFR
2-decalinolFR
 dihydrolinaloolFL/FR
3,6-dimethyl-3-octanolFL/FR
 ethyl linaloolFR
 ethyl linalyl acetalFR
 ethyl linalyl acetateFR
 ethyl linalyl etherFL/FR
(E,E)-farnesolFL/FR
 floral butanalFR
 floral pyranolFR
 freesia acetateFR
 gardenia decaloneFR
 hawthorn ethanolFR
 ho leaf oilFR
 ho wood oilFR
 hydroxycitronellalFL/FR
 hydroxycitronellal / methyl anthranilate schiff's baseFR
 hydroxycitronellal diethyl acetalFL/FR
 hydroxycitronellal dimethyl acetalFL/FR
 hydroxycitronellolFL/FR
 jasimiaFR
 leerallFR
 leerall / methyl anthranilate schiff's baseFR
 lily propanolFR
 lilyallFR
 lilyall / methyl anthranilate schiff's baseFR
laevo-linaloolFL/FR
dextro-linaloolFL/FR
 linaloolFL/FR
 linalool oxideFL/FR
 linalyl anthranilateFL/FR
 linalyl benzoateFL/FR
 linalyl propionateFL/FR
 magnolia cyclohexanolFR
 magnolia decadienalFR
 methoxycitronellalFR
2-methyl octanalFL/FR
 muguet butanalFR
 muguet butanolFR
 muguet carbaldehydeFR
 muguet carbinolFL/FR
 muguet carboxaldehydeFR
 muguet ethanolFR
 muguet nitrileFR
 muguet octadienolFR
 muguet propanolFR
 muguet shiseolFL/FR
 phenyl glycol diacetateFR
alpha-terpinyl anthranilateFL/FR
 tetrahydrolinaloolFL/FR
 ylang ylang flower oilFL/FR
 ylang ylang flower oil CO2 extractFL/FR
 ylang ylang flower oil IFL/FR
 ylang ylang flower oil IIFL/FR
 ylang ylang flower oil IIIFL/FR
herbal
 dimethyl benzyl carbinyl formateFL/FR
marine
 ozone propanalFR
spicy
 cubeb oilFL/FR
 
For Flavor
 
No flavor group found for these
alpha-amyl cinnamaldehyde dimethyl acetalFL/FR
 dimethyl benzyl carbinyl formateFL/FR
 ethyl linalyl etherFL/FR
(E,E)-farnesolFL/FR
 hydroxycitronellal dimethyl acetalFL/FR
laevo-linaloolFL/FR
dextro-linaloolFL/FR
 linalyl cinnamateFL/FR
2-methyl octanalFL/FR
 octyl phenyl acetateFL/FR
alpha-terpinyl anthranilateFL/FR
aldehydic
 nonanal (aldehyde C-9)FL/FR
aromatic
para-cresyl isobutyrateFL/FR
para-cresyl phenyl acetateFL/FR
citrus
 citronellyl oxyacetaldehydeFL/FR
(Z)-4-decenalFL/FR
 linaloolFL/FR
floral
 bois de rose oil brazilFL/FR
 dihydrolinaloolFL/FR
 hydroxycitronellolFL/FR
 linalyl anthranilateFL/FR
 linalyl benzoateFL/FR
 linalyl propionateFL/FR
 muguet carbinolFL/FR
 muguet shiseolFL/FR
 tetrahydrolinaloolFL/FR
 ylang ylang flower oilFL/FR
 ylang ylang flower oil CO2 extractFL/FR
 ylang ylang flower oil IFL/FR
 ylang ylang flower oil IIFL/FR
 ylang ylang flower oil IIIFL/FR
green
alpha-butyl cinnamaldehydeFL/FR
 cyclohexyl ethyl alcoholFL/FR
 linalool oxideFL/FR
herbal
3,6-dimethyl-3-octanolFL/FR
melon
 hydroxycitronellal diethyl acetalFL/FR
spicy
 cubeb oilFL/FR
waxy
 hydroxycitronellalFL/FR
 
Synonyms   Articles   Notes   Search   Top
Potential Uses:
 bergamotFR
 carawayFL/FR
 cardamomFL/FR
 cranberryFR
 cuminFL/FR
 gingergrassFR
 hops houblonFL/FR
 huckleberry bilberryFR
 lavandinFL/FR
 root beerFR
 spearmintFR
 vanillaFR
Synonyms   Articles   Notes   Search   Top
Occurrence (nature, food, other): note
 amomum testaceum ridl. fruit oil malaysia @ 1.70%
Data  GC  Search Trop  Picture
 angelica root oil @ 0.10%
Data  GC  Search Trop  Picture
 bay laurel leaf
Search Trop  Picture
 bergamot plant wild
Search Trop  Picture
 caraway oil
Search Trop  Picture
 caraway plant
Search Trop  Picture
 caraway seed oil @ 0.10%
Data  GC  Search Trop  Picture
 chamomile sweet false chamomile plant
Search Trop  Picture
 ginger rhizome
Search Trop  Picture
 gingergrass
Search Trop  Picture
 lavandin
Search  Picture
 mandarin oil uruguay @ 0.02-0.03%
Data  GC  Search Trop  Picture
 orange peel oil bitter china @ 0.01%
Data  GC  Search Trop  Picture
 perilla
Search  Picture
 rose oil otto bulgaria @ 0.05%
Data  GC  Search Trop  Picture
 savin
Search Trop  Picture
 savory winter savory plant
Search Trop  Picture
 spearmint leaf
Search Trop  Picture
 spearmint oil
Search Trop  Picture
 turmeric root oil hydrodistilled @ 0.17%
Data  GC  Search Trop  Picture
 wormseed oil spain @ 0.15%
Data  GC  Search Trop  Picture
Synonyms   Articles   Notes   Search   Top
Synonyms:
 cyclohex-1-ene-1-methanol, 4-(1-methylethenyl)-
1-cyclohexene-1-methanol, 4-(1-methylethenyl)
 dihydro cuminyl alcohol
 hydrocumin alcohol
1-hydroxymethyl-4-isopropenyl-1-cyclohexene
p-mentha-1,8-dien-7-ol
para-mentha-1,8-dien-7-ol
 menthadien-7-carbinol
1,8-p-menthadien-7-ol
4-(1-methyl ethenyl)-1-cyclohexene-1-methanol
[4-(1-methylethenyl)-1-cyclohexen-1-yl]methanol
4-(1-methylethenyl)-1-cyclohexene-1-methanol
 perillic alcohol
 perillol
(4-prop-1-en-2-yl-1-cyclohexenyl)methanol
[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
4-isopropenyl cyclohex-1-en-1-yl methanol
4-isopropenyl cyclohex-1-ene-1-methanol
4-isopropenyl cyclohex-1-enyl methanol
(4-isopropenyl-1-cyclohexen-1-yl)methanol
4-isopropenyl-1-cyclohexene carbinol
4-isopropenyl-1-cyclohexenecarbinol
4-isopropenyl-1-cyclohexenyl methanol
4-isopropenyl-cyclohex-1-ene-1-methanol
4-isopropenyl-cyclohex-1-enylmethanol
4-isopropenylcyclohex-1-en-1-ylmethanol
4-isopropenylcyclohex-1-enyl methanol
4-isopropenylcyclohex-1-enylmethanol
Synonyms   Articles   Notes   Search   Top
Articles:
US Patents: 3,993,604 - Alicyclic compounds, their use and process for preparing same
PubMed: Synthesis and antiproliferative effects of amino-modified perillyl alcohol derivatives.
PubMed: Gene discovery for enzymes involved in limonene modification or utilization by the mountain pine beetle-associated pathogen Grosmannia clavigera.
PubMed: Influence of culture conditions on the biotransformation of (+)-limonene by Aspergillus niger.
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: A systematic review of inhaled intranasal therapy for central nervous system neoplasms: an emerging therapeutic option.
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: eIF4E-Overexpression imparts perillyl alcohol and rapamycin-mediated regulation of telomerase reverse transcriptase.
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: 4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K(+)-ATPase and Ras oncogene activity in cancer cells.
PubMed: Disruption of an hTERT-mTOR-RAPTOR protein complex by a phytochemical perillyl alcohol and rapamycin.
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: Chemoprevention of hepatocarcinogenesis with dietary isoprenic derivatives: cellular and molecular aspects.
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: Geraniol and geranial dehydrogenases induced in anaerobic monoterpene degradation by Castellaniella defragrans.
PubMed: Anticancer efficacy of perillyl alcohol-bearing PLGA microparticles.
PubMed: Influence of the active compounds of Perilla frutescens leaves on lipid membranes.
PubMed: Nonmelanoma skin cancer chemoprevention.
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: Prevention of transplant coronary artery disease by prenylation inhibitors.
PubMed: Mechanism of statin-induced contractile dysfunction in rat cultured skeletal myofibers.
PubMed: Perillyl alcohol protects against ethanol induced acute liver injury in Wistar rats by inhibiting oxidative stress, NF╬║-B activation and proinflammatory cytokine production.
PubMed: Chemo-resistant protein expression pattern of glioblastoma cells (A172) to perillyl alcohol.
PubMed: Nonsurgical innovations in the treatment of nonmelanoma skin cancer.
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: Design and Synthesis of Potential New Apoptosis Agents: Hybrid Compounds Containing Perillyl Alcohol and New Constrained Retinoids.
PubMed: The promise of natural products for blocking early events in skin carcinogenesis.
PubMed: A phase 2a study of topical perillyl alcohol cream for chemoprevention of skin cancer.
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: Pharmacotherapy of actinic keratosis.
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: Possible contribution of beta-glycosidases and caspases in the cytotoxicity of novel glycoconjugates in colon cancer cells.
PubMed: [Natural compounds in chemoprevention of esophageal squamous cell tumors--experimental studies].
PubMed: Components of lemon essential oil attenuate dementia induced by scopolamine.
PubMed: GO Explorer: A gene-ontology tool to aid in the interpretation of shotgun proteomics data.
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: Correlation of tumor topography and peritumoral edema of recurrent malignant gliomas with therapeutic response to intranasal administration of perillyl alcohol.
PubMed: Gateways to clinical trials.
PubMed: High-performance liquid chromatographic and pharmacokinetic analyses of an intravenous submicron emulsion of perillyl alcohol in rats.
PubMed: 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.
PubMed: Mechanism of in vitro pancreatic cancer cell growth inhibition by melanoma differentiation-associated gene-7/interleukin-24 and perillyl alcohol.
PubMed: Ras pathway activation in gliomas: a strategic target for intranasal administration of 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: Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds.
PubMed: Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells.
PubMed: Biphenylalkylacetylhydroquinone ethers suppress the proliferation of murine B16 melanoma cells.
PubMed: A pilot study of perillyl alcohol in pancreatic cancer.
PubMed: Prevalence of bortezomib-resistant constitutive NF-kappaB activity in mantle cell lymphoma.
PubMed: Phase 1 study of topical perillyl alcohol cream for chemoprevention of skin cancer.
PubMed: Anti-inflammatory senescence actives 5203-L molecule to promote healthy aging and prolongation of lifespan.
PubMed: Preliminary results from a phase I/II study of perillyl alcohol intranasal administration in adults with recurrent malignant gliomas.
PubMed: Perillyl Alcohol Protects Against Fe-NTA-Induced Nephrotoxicity and Early Tumor Promotional Events in Rat Experimental Model.
PubMed: Cloning of four genes involved in limonene hydroxylation from Enterobacter cowanii 6L.
PubMed: Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells.
PubMed: Phase II trial of daily oral perillyl alcohol (NSC 641066) in treatment-refractory metastatic breast cancer.
PubMed: Rab-small GTPases are involved in fluvastatin and pravastatin-induced vacuolation in rat skeletal myofibers.
PubMed: Perillyl alcohol and genistein differentially regulate PKB/Akt and 4E-BP1 phosphorylation as well as eIF4E/eIF4G interactions in human tumor 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: In vitro induction of apoptosis in U937 cells by perillyl alcohol with sensitization by pentoxifylline: increased BCL-2 and BAX protein expression.
PubMed: Mastic oil from Pistacia lentiscus var. chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis.
PubMed: Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil.
PubMed: Terpenoids as plant antioxidants.
PubMed: Perillyl alcohol induces c-Myc-dependent apoptosis in Bcr/Abl-transformed leukemia cells.
PubMed: Recent advances in the molecular genetics of malignant gliomas disclose targets for antitumor agent perillyl alcohol.
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: Gateways to clinical trials.
PubMed: Regio- and stereoselective fungal oxyfunctionalisation of limonenes.
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: Fumigant toxicity of the essential oils of some African plants against Anopheles gambiae sensu stricto.
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: Cancer preventive role of selected dietary factors.
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 novel psychrotrophic fungus, Mortierella minutissima, for D-limonene biotransformation.
PubMed: Sle1ab mediates the aberrant activation of STAT3 and Ras-ERK signaling pathways in B lymphocytes.
PubMed: 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.
PubMed: Clinical trials in cancer prevention: current results and perspectives for the future.
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: Repellency of essential oils of some Kenyan plants against Anopheles gambiae.
PubMed: Studies of the isoprenoid-mediated inhibition of mevalonate synthesis applied to cancer chemotherapy and chemoprevention.
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: Effects of POH in combination with STI571 on the proliferation and apoptosis of K562 cells.
PubMed: Antinociceptive effects of the essential oil of Dracocephalum kotschyi in the mouse writhing test.
PubMed: Gateways to clinical trials.
PubMed: Using patients as their own controls for cost evaluation of phase I clinical trials.
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: Transformation of terpenes using a Picea abies suspension culture.
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: Gateways to clinical trials.
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: Studies with cytotoxic agents suggest that apoptosis is not a major determinant of clonogenic death in neuroblastoma cells.
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: Skin cancer chemoprevention: strategies to save our skin.
PubMed: Perillyl alcohol mediated radiosensitization via augmentation of the Fas pathway in prostate cancer cells.
PubMed: In situ detection of neoplastic transformation and chemopreventive effects in rat esophagus epithelium using angle-resolved low-coherence interferometry.
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: Biotransformation of limonene by bacteria, fungi, yeasts, and plants.
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: Mechanism-based in vitro screening of potential cancer chemopreventive agents.
PubMed: Micronutrients in cancer chemoprevention.
PubMed: Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention.
PubMed: Plant-derived monoterpenes suppress hamster kidney cell 3-hydroxy-3-methylglutaryl coenzyme a reductase synthesis at the post-transcriptional level.
PubMed: Perillyl Alcohol Inhibits Breast Cell Migration without Affecting Cell Adhesion.
PubMed: Effects of perillyl alcohol in glial C6 cell line in vitro and anti-metastatic activity in chorioallantoic membrane model.
PubMed: Sensitive biomonitoring of monoterpene exposure by gas chromatographic-mass spectrometric measurement of hydroxy terpenes in urine.
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: Weight-loss drugs and supplements: are there safer alternatives?
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: Biotransformation of limonene by Pseudomonas putida.
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: The state-of-the-art in chemoprevention of skin cancer.
PubMed: Cloning and expression of the limonene hydroxylase of Bacillus stearothermophilus BR388 and utilization in two-phase limonene conversions.
PubMed: Perillyl alcohol inhibits TCR-mediated [Ca(2+)](i) signaling, alters cell shape and motility, and induces apoptosis in T lymphocytes.
PubMed: Prenylation inhibitors to treat proliferative renal disease.
PubMed: Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.
PubMed: Progress in cancer chemoprevention: development of diet-derived chemopreventive agents.
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: Progress in cancer chemoprevention.
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: Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene.
PubMed: Novel limonene phosphonate and farnesyl diphosphate analogues: design, synthesis, and evaluation as potential protein-farnesyl transferase inhibitors.
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: Prevention and therapy of cancer by dietary monoterpenes.
PubMed: Inhibition of protein prenylation by metabolites of limonene.
PubMed: Insulin promotes phosphorylation and activation of geranylgeranyltransferase II. Studies with geranylgeranylation of rab-3 and rab-4.
PubMed: Perillyl alcohol: applications in oncology.
PubMed: Monoterpenes inhibit cell growth, cell cycle progression, and cyclin D1 gene expression in human breast cancer cell lines.
PubMed: Modulation of small G protein isoprenylation by anticancer monoterpenes in in situ mammary gland epithelial cells.
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: Monoterpenes in breast cancer chemoprevention.
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: Clinical trials referral resource. Clinical trials with perillyl alcohol.
PubMed: Lysophosphatidic acid stimulates phospholipase D activity and cell proliferation in PC-3 human prostate cancer cells.
PubMed: Modulation of RAS expression in human malignant cells by dietary supplements.
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: Cancer chemoprevention and therapy by monoterpenes.
PubMed: Composition and antimalarial activity in vitro of the essential oil of Tetradenia riparia.
PubMed: Isoprenoids suppress the growth of murine B16 melanomas in vitro and in vivo.
PubMed: Oral monoterpene therapy (perillyl alcohol) reduces vein graft intimal hyperplasia.
PubMed: Production of alpha-terpineol from Escherichia coli cells expressing thermostable limonene hydratase.
PubMed: Inhibition of pancreatic cancer growth by the dietary isoprenoids farnesol and geraniol.
PubMed: Chemoprevention of colon carcinogenesis by dietary perillyl alcohol.
PubMed: Analysis of perillic acid in plasma by reversed-phase high-performance liquid chromatography with ultraviolet detection.
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: Prevention of mammary preneoplastic transformation by naturally-occurring tumor inhibitors.
PubMed: Inhibition of metabolic activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by limonene.
PubMed: Inhibition of tumor cell growth by monoterpenes in vitro: evidence of a Ras-independent mechanism of action.
PubMed: Chemoprevention of breast cancer.
PubMed: Clinical development plan: l-perillyl alcohol.
PubMed: Strategy and planning for chemopreventive drug development: clinical development plans II.
PubMed: New agents for cancer chemoprevention.
PubMed: Monoterpenes as regulators of malignant cell proliferation.
PubMed: Antitumorigenic effects of limonene and perillyl alcohol against pancreatic and breast cancer.
PubMed: Effects of monoterpenes and mevinolin on murine colon tumor CT-26 in vitro and its hepatic "metastases" in vivo.
PubMed: Genetic and cellular changes in colorectal cancer: proposed targets of chemopreventive agents.
PubMed: Chemotherapy of pancreatic cancer with the monoterpene perillyl alcohol.
PubMed: Induction of differentiation in neuro-2A cells by the monoterpene perillyl alcohol.
PubMed: Promoting apoptosis.
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: Prevention and therapy of mammary cancer by monoterpenes.
PubMed: The chemoprevention of cancer by mevalonate-derived constituents of fruits and vegetables.
PubMed: Structure-activity relationships among monoterpene inhibitors of protein isoprenylation and cell proliferation.
PubMed: Growth inhibition of rat liver epithelial tumor cells by monoterpenes does not involve Ras plasma membrane association.
PubMed: Prenylated proteins and lymphocyte proliferation: inhibition by d-limonene related monoterpenes.
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.
PubMed: [Constituents of essential oils from leaves, stems, and fruits of Perilla frutescens (L.) Britt].
PubMed: Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves.
PubMed: Benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase II from Acinetobacter calcoaceticus. Substrate specificities and inhibition studies.
PubMed: Metabolism of alpha-terpineol by Pseudomonas incognita.
PubMed: Monographs on fragrance raw materials.
PubMed: Microbiological transformations of terpenes. XIV. Purification & properties of perillyl alcohol dehydrogenase.
PubMed: Perillyl alcohol dehydrogenase from a soil pseudomonad.
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