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Cosmetics ingredient -> Flavor; Fragrance

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Fragrance Ingredient (Linalyl acetate) -> IFRA transparency List

Fragrance

log Kow = 3.93

3.93

3.9

3.93

...floral-fruity odor, reminiscent of bergamot and it also has some pear character

Bergamot-lavender odor

Sweet, floral-fruity odor recalling Bergamot and Pear.

Persistent sweet, acrid taste

Sweet, fruity, pear-like with a faintly floral note

0.895 g/cu cm at 20 °C

Relative density (water = 1): 0.9

0.895-0.914

Insoluble in water

Miscible with ethanol, ether

Soluble in alcohol, ether, diethyl phthalate, benzyl benzoate, mineral oil, fixed oils; slightly soluble in propylene glycol; insoluble in glycerol.

Solubility in water: poor

slightly soluble in propylene glycol; insoluble in glycerol and water; miscible with alcohol and fixed oils

1 ml in 5 ml 70% alcohol (in ethanol)

This chemical does not meet GHS hazard criteria for 13.5% (316 of 2347) of reports.

Warning

H315 (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.

Warning

Chemical: 1,6-Octadien-3-ol, 3,7-dimethyl-, acetate

Hazard Traits - Fragrance Allergen

1,6-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/14484

Linalyl acetate: Does not have an individual approval but may be used under an appropriate group standard

Combustible liquid.

Combustible.

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 acid; Not a mutagen; Not likely to be a sensitizer; Linalool, a hydrolysis product, caused hepatocellular cytoplasmic vacuolisation in 28-day feeding studies of rats; [Reference #1] See Linalool.

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.

Organization for Economic Cooperation and Development; Screening 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 AM; Fragrance 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 Bureau; IUCLID Dataset, Linalool (78-70-6), 55 pp. (2000 CD-ROM edition).[Available from, as of August 5, 2008: http://esis.jrc.ec.europa.eu/]

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.

Skin Irrit. 2 (85.5%)

Skin irritation - category 2

Flammable liquids - Category 4

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.

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.

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.

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 quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and 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.

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.

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. ...

LC50; Species: Cyprinus carpio (carp) length 28.8 + or - 1.5 mm; Conditions: flow-through, 21-22 deg.C, water hardness 250 mg/L CaCO3, pH 8.0-8.1; Concentration: 11 mg/L for 96 hr /Purity 97.6%/

EC50; Species: Daphnia magna (water flea) < or = 24 hr old; Conditions: static, 20 + or - 1 °C, water hardness 240 mg/L (CaCO3), pH 7.7-8.0; Concentration: 15 mg/L for 48 hr; Effect: immobility /Purity 97.1%/

EC50; Species: Scenedesmus subspicatus (green alga); Conditions: pH 7.7-9.0; temperature 23 + or - 1 °C; Concentration: 4.4 mg/L for 72 hr; Effect: reduction of biomass /Purity 97.1%/

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 conditions; therefore, 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).

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.

/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%/

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]

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 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of October 14, 2015: http://actor.epa.gov/dashboard/]

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.

In a preliminary experiment, ... lavender essential oil relaxed vascular smooth muscle. Thus, the/se/ ... experiments were designed to investigate the relaxation mechanism of linalyl acetate as the major ingredient of lavender essential oil in rabbit carotid artery specimens. Linalyl acetate produced sustained and progressive relaxation during the contraction caused by phenylephrine. The relaxation effect of linalyl acetate at a concentration near the EC50 was partially but significantly attenuated by nitroarginine as an inhibitor of nitric oxide synthase, 1H-(1,2,4)oxadiazolo(4,3-a)quinoxaline-1-one as an inhibitor of guanylyl cyclase, or by the denudation of endothelial cells. In specimens without endothelium, the phenylephrine-induced contraction and phosphorylation of myosin light chain (MLC) were significantly attenuated after the pretreatment with linalyl acetate. The relaxation caused by linalyl acetate in the endothelium-denuded specimens was clearly inhibited by calyculin A as an inhibitor of MLC phosphatase, although not by ML-9 as an inhibitor of MLC kinase. Furthermore, suppression of the phenylephrine-induced contraction and MLC phosphorylation with linalyl acetate was canceled by the pretreatment with calyculin A. These results suggest that linalyl acetate relaxes the vascular smooth muscle through partially activation of nitric oxide/cyclic guanosine monophosphate pathway, and partially MLC dephosphorylation via activating MLC phosphatase.

Percutaneous absorption ofthe main components of lavender oil were measured in a male human subject. Blood levels of linalool and linalyl acetate were followed for 90 min after the use of a massage oil which contained lavender oil and peanut oil in a 2:98 ratio. The lavender oil contained 24.79% linalool and 29.59% linalyl acetate. A 1500 mg sample of the lavender oil was gently massaged for 10 min into a 376 sq cm area on the abdomen of a 60 kg male volunteer. Blood samples were drawn from the left cubital vein at 0, 5, 10, 15, 20, 30, 45, 60, 75 and 90 min. After adding heparin to the samples, the plasma was centrifuged and the samples were then stored until they were analyzed. Linalyl acetate was absorbed quickly and trace amounts could be detected in the blood 5 min after finishing the massage. The peak plasma concentration was reached at 19 min with a mean plasma concentration of 121 ng/mL. Most of the linalyl acetate disappeared from the blood in 90 min with a biological half-life of 14.3 min.

Linalyl acetate is hydrolysed in gastric and pancreatic fluids with mean half-lives of 5.5 and 52.6 minutes respectively ...

Esters are readily hydrolyzed by carboxylesterases or esterases. Linalyl acetate has been demonstrated to be hydrolyzed in vitro in rat blood and liver preparations. It is expected to be readily hydrolyzed in vivo. Acetate is a normal constituent of the body. The metabolism of linalool is known and is primarily through glucuronic acid conjugation and excretion

In neutral gastric juice, linalyl acetate is slowly (t1/2=121 min) hydrolyzed to a mixture of linalool and the ring closed isomer alpha-terpineol. In acidic artificial gastric juice, linalyl acetate is rapidly hydrolyzed (t1/2<5 min) to yield linalool, which rapidly rearranges into alpha-terpineol. Linalyl acetate was slowly hydrolyzed (t1/2=153-198 min) in intestinal fluid with or without pancreatin. Linalyl acetate also hydrolyzed in homogenates of rat intestinal mucosal, blood, and liver, but at rates much slower than in acidic gastric juice (rate constant for hydrolysis k=0.01-0.0055/min vs. >5/min). Based on these observations it is concluded that linalyl acetate hydrolyzes in gastric juice to yield linalool which, to some extent, is rapidly ring closed to yield alpha-terpineol.

... Hydrolysis occurs more rapidly at the low pH of gastric fluids. The reaction products are linalool and acetic acid (ester hydrolysis). This is supported by the findings of the hydrolysis study ... at pH 4, 7 and 9. Therefore it is expected that linalool is the substance that will enter the systemic circulation after oral uptake of linalyl acetate. Linalool is probably converted to geraniol and its metabolites, 1,5-dimethyl-hexadiene-1,6-dicarboxylic acid and 7-carboxy-5-methylocto-6-enoic acid ...

... Permeation of Salvia desoleana Atzei & Picci essential oil (linalyl acetate, 26.8%) through the porcine buccal mucosa is possible in vitro. /Salvia desoleana Atzei & Picci essential oil (linalyl acetate, 26.8%)/

The percutaneous absorption of a massage oil containing lavender oil was studied following application to the skin of a male subject (age 34 yr). Within 5 min after application, traces of linalool and linalyl acetate, the main constituents of lavender oil, could be detected in the blood. After 20 min, maximum concentrations of 100 ng/mL linalyl acetate and 121 ng/mL linalool were reached. Within 90 min most of the lavender oil was eliminated. It was concluded that lavender oil is rapidly absorbed through the skin and is excreted within 90 minutes.

Present in bergamot, lavender, and other volatile oils; [Merck Index] Used in perfumes, soaps, cleaning products, cosmetics, oil paints, and flavoring extracts; [HSDB]

Painting (Solvents) [Category: Paint]

Extracts, perfumery, flavoring agent, substitute for petitgrain oil.

/In perfumery/ it is widely used as a fresh and sweet blender.

It is an excellent fragrance material for, among others, bergamot, lilac, lavender, linden, neroli, ylang-ylang, and phantasy notes (particularly chypre). Smaller amounts are used in other citrus products. Since linalyl acetate is fairly stable toward alkali, it can also be employed in soaps and detergents.

Reported uses (ppm): (Flavor and Extract Manufacturers' Association, 1994)

2023: 10,000,000 - <25,000,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1849]

1,6-Octadien-3-ol, 3,7-dimethyl-, acetate is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate. National Production Volume: 3,228,892 lb/yr.

Normally prepared by direct acetylation of linalool; another method starts from myrcene hydrochloride, anhydrous sodium acetate and acetate anhydride in the presence of a catalyst; all synthetic methods tend to avoid the simultaneous formation (because of isomerization) of terpenyl and geranyl acetate.

Action of acetic anhydride on linalool in presence of sulfuric acid. May also be obtained from bergamot and other oils. Method of purification: rectification.

Esterification /of linalool/ with ketene in the presence of an acidic esterification catalyst below 30 °C results in formation of linalyl acetate without any byproducts. 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.

Dehydrolinalool, obtained by ethynylation of 2-methyl-2-hepten-6-one, can be converted into dehydrolinalyl acetate with 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.

Grade: Ex bois de rose oil 92%, 96-98%, FCC /Food Chemical Codex/ (natural and synthetic).

Purity >96%

Cosmetics product ingredient: 3,7-Dimethyl octa-1,6-diene-3-yl acetate (Linalyl Acetate)

Information on 273 consumer products that contain Linalyl acetate in the following categories is provided:

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Food, beverage, and tobacco product manufacturing

1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate: ACTIVE

The l-form is a chief constituent of lavender and bergamot oils; also found in essential oils of many other plants.

Bergamot oil is a complex mixture of more than 300 compounds. The most prevalent compounds are linalyl acetate (30 to 60%), linalool (11 to 22%) and other alcohols.