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Linalyl acetate

Linalyl acetate structure

Linalyl acetate 

structure
  • CAS No:

    115-95-7

  • Formula:

    C12H20O2

  • Chemical Name:

    Linalyl acetate

  • Synonyms:

    1,6-Octadien-3-ol,3,7-dimethyl-,3-acetate;1,6-Octadien-3-ol,3,7-dimethyl-,acetate;Linalool acetate;Acetic acid linalool ester;Bergamiol;Bergamol;Linalyl acetate;3,7-Dimethyl-1,6-octadien-3-yl acetate;Bergamot mint oil;3-Acetoxy-3,7-dimethyl-1,6-octadiene;(±)-Linaloyl acetate;dl-Linalool acetate;(±)-Linalyl acetate;1,5-Dimethyl-1-vinyl-4-hexenyl acetate;NSC 2138;8022-85-3;16509-66-3;40135-38-4

  • Categories:

    Cosmetic Ingredient  >  Fragrance Ingredient

Description

Linalyl Acetate occurs as its isomer as the main component of lavender oil (30–60%, depending on the origin of the oil), of lavandin oil (25–50%, depending on the species), and of bergamot oil (30–45%). It has also been found in clary sage oil (up to 75%) and in a small amount in many other essential oils. Racemic linalyl acetate is a colorless liquid with a distinct bergamot–lavender odor. Linalyl acetate is used extensively in perfumery.


Liquid|Solid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|colourless liquid with a floral, fruity odour


3,7-dimethylocta-1,6-dien-3-yl acetate is a monoterpenoid that is the acetate ester of linalool. It forms a principal component of the essential oils from bergamot and lavender. It is an acetate ester and a monoterpenoid. It derives from a linalool.

Linalyl acetate Basic Attributes

196.29

196.29

204-116-4

1716

2138

DTXSID7026946

Clear, colorless, oily liquid

29153900

Characteristics

26.3

3.9

Clear colorless Liquid

0.8997 g/cm3 @ Temp: 15 °C

<25 °C

220 °C

194 °F

n 20/D 1.453(lit.)

Solubility in water: poor

2-8°C

0.1 mm Hg ( 20 °C)

6.8 (vs air)

LD50 orally in Rabbit: 13934 mg/kg

Angular rotation: -1 to +1 deg

vol% in air: 0.7.3

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

Persistent sweet, acrid taste

Henry's Law constant = 1.7X10-3 atm-cu m/mole at 25 °C (est)

Acid value: 1 max|Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.|Hydroxyl radical reaction rate constant = 1.16X10-10 cu cm/molec-sec at 25 °C (est)

225 °C

Safety Information

NA 1993 / PGIII

1

36/37/38-38

26-36-37-24/25

RG5910000

Xi

Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. Ventilation along the floor.

Stable under recommended storage conditions.

P261-P305 + P351 + P338

H315-H319-H335

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.

Incompatible materials: Strong oxidizing agents

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/]

Combustible. Above 85 °C explosive vapour/air mixtures may be formed.

|Warning|H315 (98.83%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 2347 companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|H227: Combustible liquid [Warning Flammable liquids]|P210, P261, P264, P271, P272, P280, P302+P352, P304+P340, P312, P321, P332+P313, P333+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Combustible liquid.|Combustible.

Explosive limits , vol% in air: 0.7-4.3

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: 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.

A severe skin irritant.|Linalyl acetate (100%) appeared to be severely irritating to rabbit skin and moderately irritating to the skin of the guinea pig. In a test with miniature swines, application of 0.05 g linalyl acetate under a patch for 48 hours /caused/ no irritation ... .

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.

Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. Ventilation along the floor.

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.

The substance is mildly irritating to the eyes.

NO open flames. Above 85 °C use a closed system and ventilation.

Use ventilation.

Protective gloves.

Wear safety spectacles.

| 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.

Linalyl acetate is an ingredient in personal and pet care products(1). Linalyl acetate was identified as a volatile organic compound emitted by ten household products used for cleaning and/or conservation (eight waxes or polishes and two detergents)(2). Linalyl acetate was detected at a maximum of 96 ug/cu m after air freshener was sprayed in a closed room(3). The mean concentration of linalyl acetate in 63 snus packets (smokeless tobacco product) was 150.1 ug/pouch, after use, the mean was 121.0 ug/pouch; a mean of 19.2% was extracted during use; experiment was run Aug to Oct 2008 in Sweden(4).

Toxicity

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.

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. ...

LD50 Rat oral 14,550 mg/kg|LD50 Rat ip 2864 mg/kg (95% C.I. 2414- 3399 mg/kg)|LD50 Rat (female) ip 2984 mg/kg (95% C.I. 2293-3884 mg/kg)|LD50 Rat (male) ip 2778 mg/kg (95% C.I. 2246-3435 mg/kg)|For more Non-Human Toxicity Values (Complete) data for LINALYL ACETATE (6 total), please visit the HSDB record page.

/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 is a frequently encountered component of plant oils including lavender and citrus leaf oils(1). It is also a primary constituent of oils of orange flower (neroli), lavender and lavandin, bergamot, petitgrain bigarade, and sage (clary)(2). Linalyl acetate is 43.6, 26.8 and 45% of essential oil concentrations of Lavandula angustifolia, Salvia desoleana Atzei and Bergamot, respectively(3).|Linalyl acetate is reported to be found in the essential oils of bergamot, lavender, clary sage and lavandin(1). It is also found in essential oils of Salvia officinalis, petitgrain, sassafras, neroli, lemon, Italian lime, jasmine, Mentha citrata, Mentha aquatica, Thymus mastichina. It is found in abundant quantities in the essential oils 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. It is also found in citrus peel oils and juices, berries, celery, tomato, cinnamon, clove, nutmeg, pepper, thymus, grape wines, avocado, mushroom, marjoram, mongo, cardamon, coriander, gin, origanum, lovage, laurel, myrtle leaf, rosemary, sage and mastic gum oil(1).

Linalyl acetate's production and use in extracts, perfumery, as a flavoring agent, and as a substitute for petitgrain oil(1) may result in its release to the environment through various waste streams(SRC).

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).

The rate constant for the vapor-phase reaction of linalyl acetate with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of linalyl acetate with ozone has been estimated as 4.3X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 38 minutes at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Linalyl acetate may also react with nitrate radicals in the atmosphere(3).The hydrolysis half-life is <24 hours at 20 °C, with expected end products of linalool and acetic acid(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).

An estimated BCF of 180 was calculated in fish for linalyl acetate(SRC), using a log Kow of 3.93(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of linalyl acetate can be estimated to be 430(SRC). According to a classification scheme(2), this estimated Koc value suggests that linalyl acetate is expected to have moderate mobility in soil.

The Henry's Law constant for linalyl acetate is estimated as 1.7X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that linalyl acetate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 4.8 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5.8 days(SRC). Linalyl acetate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 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).

SURFACE WATER: Linalyl acetate was identified at an unreported concentration in water samples taken from Stockacher Aach, an industrially polluted river in southwest Germany(1).

Linalyl acetate was detected in 90 tea samples purchased in 10 European Union member states; loose leaf tea contained the highest amount at 66%(1).

According to the 2012 TSCA Inventory Update Reporting data, 9 reporting facilities estimate the number of persons reasonably likely to be exposed in the manufacturing, processing, or use of linalyl acetate in the United States may be as low as <10 workers up to the range of 100-499 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 155,492 workers (85,069 of these are female) were potentially exposed to linalyl acetate in the US(1). Occupational exposure to linalyl acetate may occur through inhalation and dermal contact with this compound at workplaces where linalyl acetate is produced or used. Monitoring data indicate that the general population may be exposed to linalyl acetate via inhalation of ambient air, ingestion of food, and dermal contact with consumer products containing linalyl acetate(SRC).

Drug Information

... 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.

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 ...

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 ...

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.

Dihydrolinalool, dehydrolinalool, tetrahydrolinalylacetate, linalool.

Fresh air, rest.


Rinse and then wash skin with water and soap.


Rinse with plenty of water (remove contact lenses if easily possible).

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ A 48-hr closed patch test on the lower back with 20% linalyl acetate (in petrolatum or unguentum hydrophilicum) in 40 male and female volunteers produced no irritation, nor did a 24-72 hr closed patch test on the inner arm with 2% linalyl acetate (in unguentum simplex or in unguentum hydrophilicum) in 30 male and female volunteers. Irritation was observed in 1 subject, when 0.2% linalyl acetate (in ethanol or in a non-irritative cream base) was tested on 82 male and female patients with dermatoses in a 24-48 hr closed patch test on the inner arm.|/HUMAN EXPOSURE STUDIES/ Olfactory stimuli are used in aromatherapy to enhance mood, well-being and work efficiency. Nevertheless, the impact of fragrances on cognitive performance in humans is not well understood. The present investigation aimed to evaluate the effects of 1,8-cineol, jasmine absolute ether, linalyl acetate and peppermint essential oil on human vigilance performance. The odorants were administered by means of inhalation and, except for peppermint essential oil, were tested at 2 different dosages. Performance in a standard visual vigilance task was measured in terms of speed and accuracy and subjective ratings of the odorants were assessed in terms of pleasantness, intensity, arousal and stress. We hypothesized that 1,8-cineol, jasmine absolute ether and peppermint essential oil would improve vigilance performance, whereas linalyl acetate would impair such performance. Comparison of the performances of the seven independent experimental groups with that of a control group did not show any of the expected effects. In contrast, inhalation of linalyl acetate decreased reaction times. Within-group analyses, however, revealed significant interactions between subjective ratings of the odorants and task performance. The results of the present investigation emphasize the high impact of subjective factors on the modulation of attentional functions by olfactory stimuli in humans.|/HUMAN EXPOSURE STUDIES/ ... The aim of this study was to investigate if the autoxidation observed for the single synthetic terpenes, resulting in strong contact allergens, will take place also in lavender oil. Lavender oil was exposed to air and the autoxidation was followed by chemical analysis. The sensitizing potency before and after air exposure was investigated in mice using the local lymph node assay. Patients with patch test reactions to oxidized linalool were tested to investigate if air-exposed lavender oil could elicit dermatitis in these individuals. The terpenes oxidized in air-exposed lavender oil at the same rates as the pure compounds exposed to air, and the same oxidation products were identified. The sensitizing potency of lavender oil increased accordingly on air exposure. Patch testing showed positive reactions to air-exposed lavender oil and also to oxidized linalyl acetate in patients with contact allergy to oxidized linalool. This study shows that lavender oil lacks natural protection against autoxidation, and that air-exposed lavender oil can be an important source of exposure to allergenic hydroperoxides.|/HUMAN EXPOSURE STUDIES/ Linalyl acetate is a fragrance chemical that is prone to autoxidation. Exposure to linalyl acetate occurs through cosmetic products and essential oils, but is difficult to assess, as linalyl acetate is not labelled in the EU. The objective /of this study was/ to investigate the frequencies of contact allergy to oxidized linalyl acetate among dermatitis patients, and to investigate the autoxidation of linalyl acetate in terms of hydroperoxide formation and sensitization potency. Hydroperoxide formation in air-exposed linalyl acetate was determined with high-performance liquid chromatography. The sensitization potencies of hydroperoxides were determined with the local lymph node assay. One thousand seven hundred and seventeen patients were patch tested with oxidized linalyl acetate at 6.0% in petrolatum. Of the patients, 2.2% showed positive reactions to oxidized linalyl acetate. Forty-three per cent of the positive patients also had positive patch test reactions to other fragrance markers. Linalyl acetate hydroperoxides were detected early in the autoxidation process, and accumulated to a concentration of 37% after 42 weeks of air exposure. The linalyl acetate hydroperoxides were classified as moderate sensitizers. The frequency of positive reactions to oxidized linalyl acetate is comparable to that of previously studied oxidized fragrance terpenes. Oxidized linalyl acetate could thus be a common fragrance contact allergen.|For more Human Toxicity Excerpts (Complete) data for LINALYL ACETATE (13 total), please visit the HSDB record page.

linalyl acetate

Redness.

Linalyl acetate Use and Manufacturing

Methods of Manufacturing

Linalyl acetate is present in essential oils such as natural bergamot, orange leaf, orange blossom, lavender, linal and so on. Therefore, linalyl acetate can be isolated from natural essential oil by vacuum distillation. But industry is generally prepared by the reaction of acetic anhydride and linalool. Adding linalool (phosphoric acid and acetic anhydride to form a composite catalyst) to the mixture of acetic anhydride and phosphoric acid can perform the reaction at a lower temperature. After the esterification is completed, it is washed with water and saturated saline until neutral. After adding anhydrous sodium carbonate for dehydration and drying, the product was fractionally distilled under reduced pressure with a purity of >95%.

Uses

In perfumery.


Odor agents


Air care products

Production

1,000,000 - 10,000,000 lb|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1851]|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.

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

All other chemical product and preparation 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.

Linalyl acetate was found in sage oil by TLC.|Gas chromatography determination of linalyl acetate in 4 toilet water prepn.|Linalyl acetate was determined by titrimetry. Results showed that gas chromatography was superior to the other methods for quality evaluation of oils & from distinguishing artificial from genuine oils.

EPA Safer Chemical Functional Use Classes -> Fragrances|Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues|Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Masking

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:196.29
XLogP3:3.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:196.146329876
Monoisotopic Mass:196.146329876
Topological Polar Surface Area:26.3
Heavy Atom Count:14
Complexity:237
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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