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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:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
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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:
| | 4-prop-1-en-2-ylcyclohexene-1-carboxylic acid |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 1256 |
| Pubchem (sid): | 135051996 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| 4- | prop-1-en-2-ylcyclohexene-1-carboxylic acid | | 4-iso | propenyl cyclohex-1-ene carboxylic acid | | 4-iso | propenylcyclohex-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. |
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