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perillic acid
1-cyclohexene-1-carboxylic acid, 4-(1-methylethenyl)-

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Name:4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
CAS Number: 7694-45-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:231-709-5
FDA UNII: PKS69DU4ZQ
Nikkaji Web:J13.588G
XlogP3-AA:2.70 (est)
Molecular Weight:166.21998000
Formula:C10 H14 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 284.90 °C. @ 760.00 mm Hg (est)
Flash Point: 273.00 °F. TCC ( 134.00 °C. ) (est)
logP (o/w): 2.960 (est)
Soluble in:
 water, 136.5 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
(-)-Perillic acid 95%
 
Safety Information:
 
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:
natural substances and extractives
Recommendation for perillic acid usage levels up to:
 not for fragrance use.
 
Recommendation for perillic acid flavor usage levels up to:
 not for flavor use.
 
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 :1256
National Institute of Allergy and Infectious Diseases:Data
4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
Chemidplus:0007694453
 
References:
 4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):1256
Pubchem (sid):135051996
 
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
Golm Metabolome Database:Search
UM BBD:Search
KEGG (GenomeNet):C11924
HMDB (The Human Metabolome Database):HMDB04586
FooDB:FDB013215
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
 cardamom fruit
Search Trop Picture
 
Synonyms:
4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
4-isopropenyl cyclohex-1-ene carboxylic acid
4-isopropenylcyclohex-1-enecarboxylic acid
1-cyclohexene-1-carboxylic acid, 4-(1-methylethenyl)-
 

Articles:

PubMed:The oxygen-independent metabolism of cyclic monoterpenes in Castellaniella defragrans 65Phen.
PubMed:A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study.
PubMed:Bioconversion of R-(+)-limonene to perillic acid by the yeast Yarrowia lipolytica.
PubMed:Radical-scavenging compounds from olive tree (Olea europaea L.) wood.
PubMed:Human breast tissue disposition and bioactivity of limonene in women with early-stage breast cancer.
PubMed:Whole-cell-based CYP153A6-catalyzed (S)-limonene hydroxylation efficiency depends on host background and profits from monoterpene uptake via AlkL.
PubMed:D-Limonene modulates T lymphocyte activity and viability.
PubMed:Influence of the active compounds of Perilla frutescens leaves on lipid membranes.
PubMed:Inhibition of tumor progression by naturally occurring terpenoids.
PubMed:Protective role of perillic acid against radiation-induced oxidative stress, cytokine profile, DNA damage, and intestinal toxicity in mice.
PubMed:Interaction of salicylate and a terpenoid plant extract with model membranes: reconciling experiments and simulations.
PubMed:Rosuvastatin induces delayed preconditioning against oxygen-glucose deprivation in cultured cortical neurons.
PubMed:Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells.
PubMed:Activation of calcium-dependent kinases and epidermal growth factor receptor regulate muscarinic acetylcholine receptor-mediated MAPK/ERK activation in thyroid epithelial cells.
PubMed:P2Y receptors activate MAPK/ERK through a pathway involving PI3K/PDK1/PKC-zeta in human vein endothelial cells.
PubMed:Modulatory effect of interleukin-1beta on rat isolated basilar artery contraction.
PubMed:Effect of D-limonene on immune response in BALB/c mice with lymphoma.
PubMed:A novel psychrotrophic fungus, Mortierella minutissima, for D-limonene biotransformation.
PubMed:Monoterpenes enhanced the sensitivity of head and neck cancer cells to radiation treatment in vitro.
PubMed:A phase I trial of perillyl alcohol administered four times daily for 14 days out of 28 days.
PubMed:Farnesyl transferase inhibitors enhance death receptor signals and induce apoptosis in multiple myeloma cells.
PubMed:Effect of naturally occurring monoterpenes carvone, limonene and perillic acid in the inhibition of experimental lung metastasis induced by B16F-10 melanoma cells.
PubMed:Pharmacological modulation of fatty acid desaturation and of cholesterol biosynthesis in THP-1 cells.
PubMed:Immunomodulatory activity of naturally occurring monoterpenes carvone, limonene, and perillic acid.
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:Fluvastatin induces apoptosis in rat neonatal cardiac myocytes: a possible mechanism of statin-attenuated cardiac hypertrophy.
PubMed:Pharmacokinetics of perillic acid in humans after a single dose administration of a citrus preparation rich in d-limonene content.
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:ATP-inhibition of M current in frog sympathetic neurons involves phospholipase C but not Ins P(3), Ca(2+), PKC, or Ras.
PubMed:Role of mitogen-activated protein kinase pathway in acetylcholine-mediated in vitro relaxation of rat pulmonary artery.
PubMed:Effect of S(-) perillic acid on protein prenylation and arterial smooth muscle cell proliferation.
PubMed:Bioconversion of limonene to increased concentrations of perillic acid by Pseudomonas putida GS1 in a fed-batch reactor.
PubMed:Effect of perillic acid, a putative isoprenylation inhibitor, on the cultured rat lens.
PubMed:Biotransformation of (+)- and (-)-Limonene by the Larvae of Common Cutworm (Spodoptera litura).
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:Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day.
PubMed:Gas chromatographic-mass spectrometric analysis of perillyl alcohol and metabolites in plasma.
PubMed:Inhibition of protein prenylation by metabolites of limonene.
PubMed:Blocking signaling through the Gp130 receptor chain by interleukin-6 and oncostatin M inhibits PC-3 cell growth and sensitizes the tumor cells to etoposide and cisplatin-mediated cytotoxicity.
PubMed:Monoterpenes inhibit cell growth, cell cycle progression, and cyclin D1 gene expression in human breast cancer cell lines.
PubMed:Involvement of Ras/MAP kinase in the regulation of Ca2+ channels in adult bullfrog sympathetic neurons by nerve growth factor.
PubMed:3-Hydroxy-3-methylglutaryl coenzyme a reductase and isoprenylation inhibitors induce apoptosis of vascular smooth muscle cells in culture.
PubMed:Phase I and pharmacokinetic study of D-limonene in patients with advanced cancer. Cancer Research Campaign Phase I/II Clinical Trials Committee.
PubMed:Phase I clinical trial of perillyl alcohol administered daily.
PubMed:Perillic acid inhibits Ras/MAP kinase-driven IL-2 production in human T lymphocytes.
PubMed:HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture.
PubMed:Analysis of perillic acid in plasma by reversed-phase high-performance liquid chromatography with ultraviolet detection.
PubMed:Inhibition of tumor cell growth by monoterpenes in vitro: evidence of a Ras-independent mechanism of action.
PubMed:Mechanical strain induces constitutive and regulated secretion of glycosaminoglycans and proteoglycans in fetal lung cells.
PubMed:Identification and characterization of limonene metabolites in patients with advanced cancer by liquid chromatography/mass spectrometry.
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: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:Human metabolism of the experimental cancer therapeutic agent d-limonene.
PubMed:Modulation of insulin secretion from normal rat islets by inhibitors of the post-translational modifications of GTP-binding proteins.
PubMed:Multiple signal transduction pathways mediate c-Jun protein phosphorylation.
PubMed:Identification of metabolites of the antitumor agent d-limonene capable of inhibiting protein isoprenylation and cell growth.
PubMed:Selective inhibition of isoprenylation of 21-26-kDa proteins by the anticarcinogen d-limonene and its metabolites.
PubMed:Metabolism of alpha-terpineol by Pseudomonas incognita.
PubMed:Studies on the metabolism of d-limonene (p-mentha-1,8-diene). IV. Isolation and characterization of new metabolites and species differences in metabolism.
 
Notes:
d-limonene metabolite. Perillic acid is an intermediate in the Limonene and pinene degradation pathway. (KEGG); Its measurement in urine is used to monitor cancer patients receiving oral Limonene (a farnesyl transferase inhibitor that has shown antitumor properties)(PubMed ID 8723738 )
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