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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 284.90 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 273.00 °F. TCC ( 134.00 °C. ) (est)
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| 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:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for (-)-perillic acid usage levels up to: | | | not for fragrance use.
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| Recommendation for (-)-perillic acid flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| 1- | cyclohexene-1-carboxylic acid, 4-(1-methylethenyl)-, (4S)- | | (S)-(-)- | perillic acid | | (4S)-4-( | prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid | | (4S)-4- | prop-1-en-2-ylcyclohexene-1-carboxylic acid | | (S)-(-)-4-iso | propenyl-1-cyclohexene-1-carboxylic acid |
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. |
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3D/inchi