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Linalyl Acetate
1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate · FEMA 2636 · LINALOOL ACETATE · LINALYL ACETATE NATURAL · Bergamol · Bergamot mint oil · linalyl · Lynalyl acetate
Identifikatoren & physikalische Daten
| CAS No. | 115-95-7 |
|---|---|
| Summenformel | C12H20O2 |
| Durchschnittliche Molmasse | 196,29 g/mol |
| Monoisotopische Masse | 196,14632988 g/mol |
| SMILES | C=CC(C)(CCC=C(C)C)OC(C)=O |
| InChIKey | UWKAYLJWKGQEPM-UHFFFAOYSA-N |
| PubChem CID | 8294 |
| ChEMBL | CHEMBL502773 |
| ChEBI | CHEBI:78333 |
| EC No. | 204-116-4 |
| DTXSID | DTXSID7026946 |
Chemische & physikalische Eigenschaften
| XLogP | 3,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 237 |
| Stoffklassen | Biological Agents -> Plant Oils and Extracts |
| Kosmetika | Cosmetics ingredient -> FlavorFragranceMasking |
| Duftstoffe | Fragrance Ingredient (Linalyl acetate) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | log Kow = 3.93 |
| Geruch | ...floral-fruity odor, reminiscent of bergamot and it also has some pear characterBergamot-lavender odorSweet, floral-fruity odor recalling Bergamot and Pear. |
| Geschmack | Persistent sweet, acrid tasteSweet, fruity, pear-like with a faintly floral note |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.895 g/cu cm at 20 °CRelative density (water = 1): 0.90.895-0.9140.901 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Viscosity | 2.4 mm²/s at 23 °C |
| Color/Form | Clear, colorless, oily liquid |
| Löslichkeit | Insoluble in waterMiscible with ethanol, etherSoluble in alcohol, ether, diethyl phthalate, benzyl benzoate, mineral oil, fixed oilsslightly soluble in propylene glycolinsoluble in glycerol.Solubility in water: poorinsoluble in glycerol and watermiscible with alcohol and fixed oils1 ml in 5 ml 70% alcohol (in ethanol)Chloroform (Slightly), Methanol (Slightly)499.8mg/L(25 ºC) |
| Schmelzpunkt | 85°C |
| Siedepunkt | 220 °C(lit.) |
| Dampfdichte | 6.8 (vs air) |
| Dampfdruck | 0.1 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.453(lit.) |
| FEMA | 2636 | LINALYL ACETATE |
| Flammpunkt | 194 °F |
| Lagerbedingungen | -20°C |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| Geruch | at 100.00 %. sweet green citrus bergamot lavender woody |
| Geruchsart | herbal |
| Biologische Quelle | synthetic |
| JECFA Number | 359 |
| Merck | 14,5496 |
| BRN | 1724500 |
| Henry-Konstante | 1.8×10-2 mol/(m3Pa) at 25℃, Dupeux et al. (2022) |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCE |
| InChI | 1S/C12H20O2/c1-6-12(5,14-11(4)13)9-7-8-10(2)3/h6,8H,1,7,9H2,2-5H3 |
| InChIKey | UWKAYLJWKGQEPM-LBPRGKRZSA-N |
| SMILES | C\C(C)=C\CCC(C)(OC(C)=O)C=C |
| LogP (Verteilungskoeffizient) | 3.9 at 25℃ |
| CAS Datenbank | 115-95-7(CAS DataBase Reference) |
| NIST chemische Informationen | 1,6-Octadien-3-ol, 3,7-dimethyl-, acetate(115-95-7) |
| EPA chemische Informationen | Linalyl acetate (115-95-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 13.5% (316 of 2347) of reports.WarningH315 (85.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2347 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1,6-Octadien-3-ol, 3,7-dimethyl-, acetateHazard Traits - Fragrance Allergen1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 11-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14484Linalyl acetate: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Simple esters of linalool: Human health tier II assessment |
| Brandgefahren | Combustible. Above 85 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Combustible liquid.Combustible. |
| Gefahrenübersicht | Emergency treatment: Linalool[HSDB] Included in list of established contact allergens in humans[EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] Causes somnolence and ataxia and acts as a general anesthetic in lethal dose studies of rats[RTECS] Safe when used as a flavoring agent in food[JECFA] Hydrolyzed in the GI tract into linalool and acetic acidNot a mutagenNot likely to be a sensitizerLinalool, a hydrolysis product, caused hepatocellular cytoplasmic vacuolisation in 28-day feeding studies of rats[Reference #1] See Linalool. |
| FDA-Anforderungen | Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Linalyl acetate is included on this list.Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Linalyl acetate is included on this list. |
| Special Reports | Organization for Economic Cooperation and DevelopmentScreening Information Data Set for Linalyl Acetate (115-95-7) 57 pp. (March 2002). This OECD Initial Assessment of HPV Chemicals is part of a series of OECD SIDS documents published by UNEP Chemicals to facilitate the access to information needed for health and environmental risk assessments of chemicals.[Available from, as of November 9, 2015: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html]Letizia CS, Cocchiara J, Lalko J, Api AMFragrance material review on linalyl acetate. Food Chem Toxicol 41 (7): 965-76 (2003) presents a toxicologic and dermatologic review of linalyl acetate when used as a fragrance ingredient.European Chemicals BureauIUCLID Dataset, Linalool (78-70-6), 55 pp. (2000 CD-ROM edition).[Available from, as of August 5, 2008: http://esis.jrc.ec.europa.eu/] |
| Chemical Dangers | Decomposes on burning. This produces irritating fumes. |
| NFPA Hazard Classification | 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides |
| Hazard Classes and Categories | Skin Irrit. 2 (85.5%)Skin irritation - category 2Flammable liquids - Category 4 |
| Explosive Limits and Potential | Explosive limits , vol% in air: 0.7-4.3 |
| Brandbekämpfung | Use powder, alcohol-resistant foam, water spray, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Rinse and then wash skin with water and soap.Rinse with plenty of water (remove contact lenses if easily possible).Rinse mouth. |
| Sichere Lagerung | Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. Ventilation along the floor. |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.Extinguishing method: Alcohol foam. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature 2-8 °C. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas.Environmental precautions Do not let product enter drains., Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal. |
| Entsorgungsverfahren | SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product. |
| Verschüttetes entsorgen | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. Above 85 °C use a closed system and ventilation. |
| Inhalation Risk | No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C. |
| Wechselwirkungen | In Swiss mice (ICR/Ha) dermal coapplication of linalyl acetate (3 mg in 0.1 mL acetone) with /5 ug/ benzo(a)pyrene /3 times weekly for 67 wk/ did slightly increase the number of skin papillomas and carcinomas compared to benzo(a)pyrene controls ... .The sedative properties of the essential oil of Lavender (Lavandula angustifolia Miller) and of its main constituents--linalool and linalyl acetate--were investigated in mice followed up in a series of experimental procedures. The significant decrease in the mobility of female and male laboratory animals under standardized experimental conditions is found to be closely dependent on the exposure time to the drugs. Nevertheless after an injection of caffeine into mice a hyperactivity was observed which was reduced to nearly a normal mobility only by inhalation of these fragrance drugs. ... |
| Ökotoxizitätswerte | LC50Species: Cyprinus carpio (carp) length 28.8 + or - 1.5 mmConditions: flow-through, 21-22 deg.C, water hardness 250 mg/L CaCO3, pH 8.0-8.1Concentration: 11 mg/L for 96 hr /Purity 97.6%/EC50Species: Daphnia magna (water flea) < or = 24 hr oldConditions: static, 20 + or - 1 °C, water hardness 240 mg/L (CaCO3), pH 7.7-8.0Concentration: 15 mg/L for 48 hrEffect: immobility /Purity 97.1%/Species: Scenedesmus subspicatus (green alga)Conditions: pH 7.7-9.0temperature 23 + or - 1 °CConcentration: 4.4 mg/L for 72 hrEffect: reduction of biomass /Purity 97.1%/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 430(SRC), determined from a structure estimation method(2), indicates that linalyl acetate is expected to have moderate mobility in soil(SRC). Volatilization of linalyl acetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Linalyl acetate has a reported vapor pressure of 0.111 mm Hg(3) and exists as a liquid under environmental conditionstherefore, linalyl acetate may volatilize from dry soil(SRC). A 75% of Theoretical BOD using activated sludge in the Japanese MITI test(4) suggests that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 430(SRC), determined from a structure estimation method(2), indicates that linalyl acetate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.7X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.8 hours and 5.8 days, respectively(SRC). The hydrolysis half-life is <24 hours at 20 °C, with expected end products of linalool and acetic acid(4). According to a classification scheme(5), an estimated BCF of 180(SRC), from its log Kow of 3.93(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). A 75% of Theoretical BOD using activated sludge in the Japanese MITI test(4) suggests that biodegradation is an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), linalyl acetate, which has a vapor pressure of 0.111 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase linalyl acetate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC)the half-lives for these reactions in air are estimated to be 200 and 38 minutes, respectively(SRC), calculated from respective rate constants of 1.2X10-10 and 4.3X10-16 cu cm/molecule-sec at 25 °C(SRC) that were derived using structure estimation methods(3). Linalyl acetate may also react with nitrate radicals in the atmosphere(4). Linalyl acetate does not contain chromophores that absorb at wavelengths >290 nm(5) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Lebensmitteluntersuchungswerte | Linalyl acetate was detected in 90 tea samples purchased in 10 European Union member statesloose leaf tea contained the highest amount at 66%(1). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Linalyl acetate is a clear, colorless, oily liquid. It is an excellent fragrance material. It can also be employed in soaps and detergents and as a food additive. It is a component of oil paint. It is used in extracts and as a substitute for petitgrain oil. HUMAN EXPOSURE AND TOXICITY: Application of linalyl acetate in acetone (33%) to the back of male volunteers without known allergies during 48 hours under occlusion did not induce signs of irritation up to 120 hours after removal of the patch. Linalyl acetate is identified as one of the constituents of lavender oil that may cause allergic reactions. Oxidized linalyl acetate could be a common fragrance contact allergen. The potential genotoxicity of linalyl acetate, was evaluated in vitro by the micronucleus test on peripheral human lymphocytes. In the range of non-toxic concentrations (0.5-100 ug/mL), linalyl acetate increased the frequency of micronuclei significantly and in concentration-dependent manner. In a chromosome aberration test with human lymphocytes, linalyl acetate did not induce aberrations, both with and without S-9 mix. ANIMAL STUDIES: Inhalation exposure of mice to 2.74 mg linalyl acetate/L air during 90 minutes led to reduced motor activity compared to untreated controls. The effect was more severe in mice aged 6-8 weeks (up to 100% reduction) than in mice of 6 months (up to 81% reduction). In mice dermal coapplication of linalyl acetate (3 mg in 0.1 mL acetone) with benzo(a)pyrene did slightly increase the number of skin papillomas and carcinomas compared to benzo(a)pyrene controls. An Ames test was performed with linalyl acetate in Salmonella typhimurium strains TA97, TA98, TA100, TA1535 and TA102 with and without metabolic activation. Linalyl acetate was found to be not mutagenic in this assay. An in vitro unscheduled DNA synthesis (UDS) assay was negative in primary rat hepatocytes at doses up to 300 nL/mL. ECOTOXICITY STUDIES: In a 96-hour flow-through test with carps (Cyprinus carpio), fish were exposed to 10, 18, 32, 56 and 100 mg/L (nominal concentrations). Mean measured concentrations were 7.9, 12.3, 20.1, 27.3 and 27.2 mg/L. At the highest concentrations (32 mg/L and above) all fish died. At all concentrations hypoactive swimming behavior, loss of equilibrium and/or immobility was observed. |
| Average Daily Intake | Annual consumption /of linalyl acetate/ is 3550.00 lb. Individual consumption is 0.003008 mg/kg/day. |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ In a 96-hour flow-through test with carps (Cyprinus carpio), fish were exposed to 10, 18, 32, 56 and 100 mg/L (nominal concentrations). Mean measured concentrations were 7.9, 12.3, 20.1, 27.3 and 27.2 mg/L. At the highest concentrations (32 mg/L and above) all fish died ... At all concentrations hypoactive swimming behavior, loss of equilibrium and/or immobility was observed. ... /Purity 97.6%/ |
| Plant Concentrations | Linalyl acetate was qualitatively identified as a component of the twig and needle oils of the Balkan pine (Pinus peuce)(1). Linalyl acetate is 33% of essential oil of Skimmia laureola growing wild in Jammu and Kashmir, India(2). Linalyl acetate is 4.8% of essential oil of Cuminum cyminum L collected from Alborz Mountain, Iran(3). Lavandula angustifolia essential oil, grown in southeast Spain, contained 21-36% linalyl acetate(4). Linalyl acetate is 50.5% of essential oil of Skimmia laureola leaves collected in Patrak, Pakistan(5). Lemon peels (Citrus limon), collected from Akure main market, Nigeria contained 1.48% linalyl acetate(6). The essential oil from Thymus praecox ssp. arcticus, grown in Iceland contained 70% linalyl acetate(7). Linalyl acetate is 43.6, 26.8 and 45% of essential oil concentrations of Lavandula angustifolia, Salvia desoleana Atzei and Bergamot, respectively(8).Linalyl acetate plant concentrations(1).[Table#1848] |
| Signs and Symptoms | Redness. |
| Ongoing Test Status | EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assaysClick on the "Chemical Explorer" button on the tool bar to see the data./[USEPAICSS Dashboard ApplicationAvailable from, as of October 14, 2015: http://actor.epa.gov/dashboard/] |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. It is strongly advised not to let the chemical enter into the environment. |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | NA 1993 / PGIII |
| Zollcode | 29153900 |
| RTECS-Nr. | RG5910000 |
| R-Sätze (R) | 36/37/38-38 |
| Toxizität | LD50 orally in Rabbit: 13934 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-37-24/25 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 115-95-7(Hazardous Substances Data) |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2Skin Sens. 1B |
Anwendungen & Verwendung
Occurrence
Reported found in the essential oils of bergamot, lavender, clary sage and lavandin; also identified among the constituents of the essential oils of Salvia officinalis, petitgrain, sassafras, neroli, lemon, Italian lime, jasmine, Mentha citrata, Mentha aquatica, Thymus mastichina, etc; also reported in abundant quantities in the essential oil from flowers, leaves and stems of Tagetes patula, in the distillate from leaves of Citrus aurantifolia from India, and in the essential oil of Mentha arvensis. Also reported found in citrus peel oils and juices, berries, peach, celery, tomato, cinnamon, clove, nutmeg, pepper, thymus, grape wines, avocado, mushroom, marjoram, mango, cardamom, coriander, gin, origanum, lovage, laurel, myrtle leaf, rosemary, sage and mastic gum oil.
Verwenden
Linalyl Acetate ermentative production of medium or short chain length alcohol, esters and/or glucosides by metabolically engineered microorganism.
Herstellung & Synthese
synthetische
Linalyl acetate is synthesized by two methods: 1) Esterification of linalool requires special reaction conditions since it tends to undergo dehydration and cyclization as it is an unsaturated tertiary alcohol. These reactions can be avoided as follows: esterification with ketene in the presence of an acidic esterification catalyst below 30 °C results in the formation of linalyl acetate without any by-products. Esterification can be achieved in good yield, with boiling acetic anhydride, whereby the acetic acid is distilled off as it is formed; a large excess of acetic anhydride must be maintained by continuous addition of anhydride to the still vessel. Highly pure linalyl acetate can be obtained by transesterification of tert-butyl acetate with linalool in the presence of sodium methylate and by continuous removal of the tert-butanol formed in the process. 2) Dehydrolinalool, obtained by ethynylation of 6-methyl-5-hepten-2-one, can be converted into dehydrolinalyl acetatewith acetic anhydride in the presence of an acidic esterification catalyst. Partial hydrogenation of the triple bond to linalyl acetate can be carried out with, for example, palladium catalysts deactivated with lead.