oleyl acetate
cis-9-octadecenyl acetate
Identification
| Name | oleyl acetate |
| CAS Number | 693-80-1 |
| EINECS | 211-759-4 |
| FDA UNII | EU1ETP025C |
| Molecular Formula | C20 H38 O2 |
| Molecular Weight | 310.52126000 |
| MDL Number | MFCD00056326 |
| Nikkaji Number | J206.011F |
| XlogP3 | 7.90 (est) |
Regulatory
| JECFA Food Flavoring | 1638 cis-9-octadecenyl acetate |
| FEMA Number | 4359 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 693-80-1 ; CIS-9-OCTADECENYL ACETATE |
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 92.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.86500 to 0.87400 @ 20.00 °C. |
| Pounds per Gallon - (est). | 7.206 to 7.281 |
| Refractive Index | 1.44600 to 1.45300 @ 20.00 °C. |
| Boiling Point | 205.00 to 207.00 °C. @ 13.00 mm Hg, 395.00 to 396.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.000001 mmHg @ 25.00 °C. (est) |
| Flash Point | 207.00 °F. TCC ( 97.40 °C. ) (est) |
| logP (o/w) | 8.692 (est) |
| Shelf Life | 12.00 month(s) or longer if stored properly. |
| Storage | refrigerate in tightly sealed containers. |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | skin conditioning - emollient |
Organoleptic Properties
| Odor Description | at 100.00 %. |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic agents |
| Recommendation for oleyl acetate usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.012 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 3900 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| baked goods | 50.00000 |
| beverages(nonalcoholic) | 3.00000 |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | 50.00000 |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | 20.00000 |
| fish products | - |
| frozen dairy | 10.00000 |
| fruit ices | - |
| gelatins / puddings | 5.00000 |
| granulated sugar | - |
| gravies | - |
| hard candy | 2.00000 |
| 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 | 10.00000 |
| sugar substitutes | - |
| sweet sauces | - |
| Dairy products, excluding products of category 02.0 (01.0) | 7.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 5.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 10.00000 |
| Processed fruit (04.1) | 7.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 10.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 5.00000 |
| Bakery wares (07.0) | 10.00000 |
| Meat and meat products, including poultry and game (08.0) | 2.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 2.00000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 5.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 10.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 5.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 10.00000 |
| Ready-to-eat savouries (15.0) | 20.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 5.00000 |
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Potential Uses
Natural Occurrence
Synonyms
acetic acid 9-octadecenyl ester
acetic acid oleyl ester
acetic acid, oleyl ester
(9Z)-
octadec-9-en-1-yl acetate
(9Z)-
octadec-9-en-1-ylacetate
[(Z)-
octadec-9-enyl] acetate
(9Z)-9-
octadecen-1-ol acetate
9-
octadecen-1-ol, acetate, (9Z)-
9-
octadecen-1-ol, acetate, (Z)-
9-
octadecen-1-ol,1-acetate, (9Z)-
(9Z)-9-
octadecen-1-yl acetate
9-
octadecen-1-yl acetate
(Z)-9-
octadecenyl acetate
cis-9-
octadecenyl acetate
oleylacetate
PubMed:
Loss of Drosophila pheromone reverses its role in sexual communication in Drosophila suzukii.
PubMed:
Intra- and interspecific activities of semiochemicals from the sex pheromone gland of the Welsh Clearwing, Synanthedon scoliaeformis.
PubMed:
In situ extractive fermentation for the production of hexanoic acid from galactitol by Clostridium sp. BS-1.
PubMed:
Ligands for pheromone-sensing neurons are not conformationally activated odorant binding proteins.
PubMed:
Chelating DTPA amphiphiles: ion-tunable self-assembly structures and gadolinium complexes.
PubMed:
Synthesis of silver-iron oxide nanocomposites by thermal decomposition.
PubMed:
Identification and field evaluation of the sex pheromone of Synanthedon bicingulata (Staudinger).
PubMed:
Suppression of leopard moth (Lepidoptera: Cossidae) populations in olive trees in Egypt through mating disruption.
PubMed:
Protein kinase C-dependent phosphorylation of transient receptor potential canonical 6 (TRPC6) on serine 448 causes channel inhibition.
PubMed:
Hydroxytyrosol acyl esters: biosynthesis and activities.
PubMed:
Development of an LC-MS/MS assay to determine plasma pharmacokinetics of the radioprotectant octadecenyl thiophosphate (OTP) in monkeys.
PubMed:
Quantification of hydrophilic ethoxylates in polysorbate surfactants using diffusion H1 NMR spectroscopy.
PubMed:
Identification and field bioassays of the sex pheromone of Synanthedon haitangvora.
PubMed:
Chemistry of the cephalic labial gland secretions of male Bombus morrisoni and B. rufocinctus, two North American bumblebee males with perching behavior.
PubMed:
Development and biopharmaceutical evaluation of quinupramine-EVA matrix containing penetration enhancer for the enhanced transdermal absorption in rats.
PubMed:
An essential role for a CD36-related receptor in pheromone detection in Drosophila.
PubMed:
Generalization of courtship learning in Drosophila is mediated by cis-vaccenyl acetate.
PubMed:
Enhanced efficacy of triprolidine by transdermal application of the EVA matrix system in rabbits and rats.
PubMed:
Co-solvent effects on drag reduction, rheological properties and micelle microstructures of cationic surfactants.
PubMed:
[Interaction of acyl derivatives of 3beta-hydroxy-5alpha-cholest-8(14)-en-15-one and 3alpha-hydroxy-5alpha-cholest-8(14)-en-15-one with hepatoma hep G2 cells].
PubMed:
Enhanced transdermal delivery of atenolol from the ethylene-vinyl acetate matrix.
PubMed:
Purification and characterization of a PMA-stimulated kinase and identification of PMA-induced phosphorylation of a polypeptide that is dephosphorylated by low temperature in Brassica juncea.
PubMed:
A Ca(2+)-dependent protein kinase with characteristics of protein kinase C in leaves and mesophyll cell protoplasts from Digitaria sanguinalis: possible involvement in the C(4)-phosphoenolpyruvate carboxylase phosphorylation cascade.
PubMed:
Enhanced bioavailability of atenolol by transdermal administration of the ethylene-vinyl acetate matrix in rabbits.
PubMed:
Enhanced transdermal delivery of triprolidine from the ethylene-vinyl acetate matrix.
PubMed:
Determination of iodine values using 1,3-dibromo-5,5-dimethylhydantoin (DBH) without the employment of chlorinated hydrocarbons. Analytical methods of pharmacopoeias with DBH in respect to environmental and economical concern. Part 17.
PubMed:
A dynamic mechanical method for determining the silicone elastomer solubility of drugs and pharmaceutical excipients in silicone intravaginal drug delivery rings.
PubMed:
Functional and expression pattern analysis of chemosensory proteins expressed in antennae and pheromonal gland of Mamestra brassicae.
PubMed:
Inhibition of cardiac L-type calcium channels by protein kinase C phosphorylation of two sites in the N-terminal domain.
PubMed:
Purification and characterization of a novel extracellular lipase catalyzing hydrolysis of oleyl benzoate from Acinetobacter nov. sp. strain KM109.
PubMed:
ZmcPKC70, a protein kinase C-type enzyme from maize. Biochemical characterization, regulation by phorbol 12-myristate 13-acetate and its possible involvement in nitrate reductase gene expression.
PubMed:
Single step thin-layer chromatographic method for quantitation of enzymatic formation of fatty acid anilides.
PubMed:
Activation of protein kinase C induces cortical granule exocytosis in a Ca(2+)-independent manner, but not the resumption of cell cycle in porcine eggs.
PubMed:
Differential Effects of Protein Kinase C Activators and Inhibitors on alpha- and beta-Adrenoceptor-mediated Positive Inotropic Effect in Isolated Rabbit Papillary Muscle.
PubMed:
Effects of protein kinase C activators and staurosporine on protein kinase activity, cell survival, and proliferation in Tetrahymena thermophila.
PubMed:
Bisindolylmaleimide inhibits the PMA-induced down-regulation of collagen synthesis in fibroblasts.
PubMed:
Sphingosine derivatives inhibit depolarization-evoked calcium entry in rat GH4C1 cells.
PubMed:
Crystal structure of a mixed chain diacylglycerol, 1-stearoyl-3-oleyl-glycerol.
PubMed:
Transforming growth factor-beta 1 potentiated alpha 1-adrenergic and stretch-induced c-fos mRNA expression in rat myocardial cells.
PubMed:
The renal basolateral transport system for organic anions: properties of the regulation mechanism.
PubMed:
Preconditioning protects ischemic rabbit heart by protein kinase C activation.
PubMed:
Receptor- and phorbol ester-mediated phospholipase D activation in rat parotid involves two different pathways.
PubMed:
Protein kinase C regulates IL-8 and fMLP induced cytoplasmic Ca2+ increase in human granulocytes by receptor modulation measurements by flow cytometry.
PubMed:
Leukotriene B4 and C4 production in isolated rat gastric mucosal cells.
PubMed:
Modulation of endothelial autacoid release by protein kinase C: feedback inhibition or non-specific attenuation of receptor-dependent cell activation?
PubMed:
Intracellular mediation of GnRH action on GTH release in tilapia.
PubMed:
Comparison of the action of two protein kinase C activators on dihydropyridine-sensitive Ca2+ channels in neonatal rat ventricular myocytes.
PubMed:
Neurohormonal regulation of histamine release from isolated rabbit fundic mucosal cells.
PubMed:
Agonist-induced activation of phospholipase D in bovine pulmonary artery endothelial cells: regulation by protein kinase C and calcium.
PubMed:
A rise and fall in 1,2-diacylglycerol content signal hexamethylene bisacetamide-induced erythropoiesis.
PubMed:
Inhibition of apical Na+ channels in rabbit cortical collecting tubules by basolateral prostaglandin E2 is modulated by protein kinase C.
PubMed:
Modulation of luteinizing hormone-stimulated inositol phosphate accumulation by phorbol esters in bovine luteal cells.
PubMed:
Purification and properties of extracellular lipase from Pseudomonas aeruginosa EF2.
PubMed:
Effects of protein kinase A and calcium/phospholipid-dependent kinase modulators in the process of HL-60 cell differentiation: their opposite effects between HL-60 cell and K-562 cell differentiation.
PubMed:
Signal transduction and the regulation of actin conformation during myeloid maturation: studies in HL60 cells.
PubMed:
Lipid trafficking between high density lipoproteins and Babesia divergens-infected human erythrocytes.
PubMed:
Membrane stabilizing effect of vitamin E: existence of a hydrogen bond between alpha-tocopherol and phospholipids in bilayer liposomes.
PubMed:
Direct and cytokine-mediated activation of protein kinase C induces human immunodeficiency virus expression in chronically infected promonocytic cells.
PubMed:
Development of pheromone lure for monitoring field populations ofEoreuma loftini (Lepidoptera: Pyralidae).
PubMed:
Protein kinase-c activation inhibits tyrosine phosphorylation of the c-met protein.
PubMed:
Ultraviolet stimulated melanogenesis by human melanocytes is augmented by di-acyl glycerol but not TPA.
PubMed:
Activators of protein kinase C enhance accumulation of interferon-beta mRNA in murine cell lines.
PubMed:
Effects of protein kinase C stimulation and free Ca2+ rise in mammalian egg activation.
PubMed:
Dufour gland contents of three species ofMyrmecia (Hymenoptera: Formicidae), primitive ants of australia.
PubMed:
Effects of luminal Na+ on single Na+ channels in A6 cells, a regulatory role for protein kinase C.
PubMed:
Protein kinase C modulates neurotransmitter responses in Xenopus oocytes injected with rat brain RNA.
PubMed:
Aggregation pheromone ofDrosophila mauritiana, Drosophila yakuba, andDrosophila rajasekari.
PubMed:
Aggregation pheromone characterization and comparison inDrosophila ananassae andDrosophila bipectinata.
PubMed:
(Z)-11-Eicosenyl acetate, an aggregation pheromone inDrosophila malerkotliana.
PubMed:
Response of aequorin-loaded platelets to activators of protein kinase C.
PubMed:
Protein kinase C modulates actin conformation in human T lymphocytes.
PubMed:
In vitro alterations of L-asparaginase activity of Tetrahymena pyriformis by lipids.
PubMed:
The multifunctional Ca2+/calmodulin-dependent protein kinase mediates Ca2+-dependent phosphorylation of tyrosine hydroxylase.
PubMed:
Tumor necrosis factor receptors and cytocidal activity are down-regulated by activators of protein kinase C.
PubMed:
Effect of diterpene esters on actin cytoskeleton of SV40-transformed keratinocytes is not reproduced by diacylglycerols.
PubMed:
Components of female sex pheromone ofEoreuma loftini Dyar.
PubMed:
Phorbol esters inhibit adenylate cyclase activity in cultured collecting tubular cells.
PubMed:
[Regulation of glucose metabolism by insulin: dual role of protein kinase C].
PubMed:
1,2-Diacylglycerols but not phorbol esters stimulate sphingomyelin hydrolysis in GH3 pituitary cells.
PubMed:
Ca2+-stimulated catecholamine release from alpha-toxin-permeabilized PC12 cells: biochemical evidence for exocytosis and its modulation by protein kinase C and G proteins.
PubMed:
Alpha-adrenoceptor stimulation, but not muscarinic stimulation, increases cyclic AMP accumulation in brain slices due to protein kinase C mediated enhancement of adenosine receptor effects.
PubMed:
Downregulation of tumor necrosis factor (TNF) sensitivity via modulation of TNF binding capacity by protein kinase C activators.
PubMed:
Parathyroid hormone induction of creatine kinase activity and DNA synthesis is mimicked by phospholipase C, diacylglycerol and phorbol ester.
PubMed:
Inhibition of insect juvenile hormone synthesis by phorbol 12-myristate 13-acetate.
PubMed:
[Calcium, phospholipase C and protein kinase C stimulate prostaglandin secretion of isolated gastric mucosa cells of the human].
PubMed:
(Z)-11-octadecenyl acetate, an aggregation pheromone inDrosophila simulans.
PubMed:
Parallel changes in amino acid transport and protein kinase C localization in LLC-PK1 cells treated with TPA or diradylglycerols.
PubMed:
Regulation of calcium channels in aortic muscle cells by protein kinase C activators (diacylglycerol and phorbol esters) and by peptides (vasopressin and bombesin) that stimulate phosphoinositide breakdown.
PubMed:
Effects of phorbol esters and a diacylglycerol on the mouse sperm acrosome reaction induced by the zona pellucida.
PubMed:
Rapid modulation of tumor necrosis factor membrane receptors by activators of protein kinase C.
PubMed:
[Phorbol ester or diacylglycerol modulates somatostatin binding to its receptors on rat pancreatic acinar cell membranes].
PubMed:
Insulin stimulation of glucose metabolism in rat adipocytes: possible implication of protein kinase C.
PubMed:
Synergy between phorbol esters, 1-oleyl-2-acetylglycerol, urushiol, and calcium ionophore in eliciting aggregation of marine sponge cells.
PubMed:
Biosynthesis of paf-acether: VIII: Impairment of paf-acether production in activated macrophages does not depend upon acetyltransferase activity.
PubMed:
Phorbol ester or diacylglycerol modulates somatostatin binding to its receptors on rat pancreatic acinar cell membranes.
PubMed:
cis-Vaccenyl acetate as an aggregation pheromone inDrosophila melanogaster.
PubMed:
Phorbol ester- and diacylglycerol-mediated desensitization of cardiac beta-adrenergic receptors.
PubMed:
Effect of various excitatory agonists on the secretion of 5-hydroxytryptamine from permeabilised human platelets induced by Ca2+ in the presence or absence of GTP.
PubMed:
Activation of protein kinase C in neutrophil cytoplasts. Localization of protein substrates and possible relationship with stimulus-response coupling.
PubMed:
Diacylglycerol modulates binding and phosphorylation of the epidermal growth factor receptor.
PubMed:
Thrombin and activators of protein kinase C modulate secretory responses of permeabilised human platelets induced by Ca2+.
PubMed:
Cyclic nucleotides control a system which regulates Ca2+ sensitivity of platelet secretion.
PubMed:
Fat Metabolism in Higher Plants: LVII. A Comparison of Fatty Acid-Synthesizing Enzymes in Chloroplasts Isolated from Mature and Immature Leaves of Spinach.
PubMed:
Studies on acetyl-coenzyme A synthetase of yeast: inhibition by long-chain acyl-coenzyme A esters.