Geranyl acetate

196.29

196.29

203-341-5

3W81YG7P9R

2584

DTXSID0020654|DTXSID8048153|DTXSID1025352

Clear, colorless liquid

26.3

3.5

Geranyl acetate is a clear colorless liquid with an odor of lavender. (NTP, 1992)

0.9174 g/cm³ @ Temp: 15 °C

<25 °C

240 °C

220 °F

1.458

H2O: <0.1 g/100 mL at 20 ºC

2-8°C

0.07 mm Hg ( 20 °C)

6.8 (vs air)

Specific optical rotation: -2 ro +2 degrees

Odor of lavender

Taste threshold values: Taste characteristics at 20 ppm: Green, floral, fruity with a citrus nuance

Henry's Law constant = 2.42X10-3 atm-cu m/mol at 25 °C (est)

ASSAY: 90% MIN; 92% (85% TECHNICAL)|Hydroxyl radical reaction rate constant = 1.78X10-10 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

GERANYL ACETATE should be protected from light. This compound reacts with strong oxidizing agents. (NTP, 1992)

NONH for all modes of transport

3

36/37/38

26-36-24/25

RG5920000

Xi

Irritant

Stable under normal temperatures and pressures.

P261-P305 + P351 + P338

H315-H319-H335

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Synthetic flavoring substances and adjuvants /for human comsumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Geranyl 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. Geranyl acetate is included on this list.

DHHS/NTP; Toxicology & Carcinogenesis Studies of Food Grade Geranyl Acetate (71% Geranyl Acetate, 29% Citronellyl Acetate in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 252 (1987) NIH Publication No. 88-2508

This chemical is probably combustible. (NTP, 1992)

|Warning|H315 (80.06%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P273, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P391, and P501|Aggregated GHS information provided by 2207 companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315 (16.67%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 140 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Not Classified

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it under ambient temperatures. Keep it away from oxidizing materials. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

"ALCOHOL" FOAM.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.

In human patch test, geraniol @ 32% concn was severely irritating & geranyl acetate mildly irritating.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

LD50 Rat oral 6330 mg/kg

Carcinogenesis studies of food-grade geranyl acetate (containing approximately 29% citronellyl acetate) were conducted by administering the test chemical in corn oil by gavage to groups of 50 male and 50 female F344/N rats at doses of 1,000 or 2,000 mg/kg body weight and to groups of 50 male and 50 female B6C3F1 mice at doses of 500 or 1,000 mg/kg. Doses were administered five times per week for 103 weeks. Groups of 50 rats and 50 mice of each sex received corn oil by gavage on the same dosing schedule and served as vehicle controls. The cumulative toxicity of geranyl acetate in the 2-year study was indicated by the significantly shorter survival of high dose male rats (control, 34/50; low dose, 29/50; high dose, 18/50) and of high dose male mice (control, 31/50; low dose, 32/50; high dose, 0/50) and of dosed female mice (38/50; 15/50; 0/50) when compared with controls. Throughout most of the 2-year study, mean body weights of high dose rats and mice of each sex were lower than those of the controls. The occurrence of retinopathy or cataracts in the high dose male rats and low dose female rats as compared with the controls does not appear to be related to the administration of geranyl acetate but rather the proximity of the rats to fluorescent light. The incidence of retinopathy or cataracts (combined) was: males: control, 0/50, 0%; low dose, 1/50, 2%; high dose, 11/50, 22%; females: control, 1/50, 2%; low dose, 13/50, 26%; high dose, 2/50, 4%. Kidney tubular cell adenomas, an uncommon tumor type, were found in 2/50 (4%) low dose male rats. The historical incidence of male corn oil gavage control F344/N rats with kidney tumors is 1/250 (0.4%) at this laboratory and 4/998 (0.4%) in the program. Squamous cell papillomas in the skin were increased marginally in low dose male rats (control, 0/50; low dose, 4/50, 8%; high dose, 1/50, 2%). In addition, one low dose male rat had a squamous cell carcinoma of the skin. The incidence of low dose male rats with either squamous cell papillomas or carcinomas was greater (P<0.05) in comparison with the controls. The historical incidence of squamous cell papillomas or carcinomas (combined) in gavage control male F344/N rats is 3.6% (9/250) at this laboratory and 2.5% (25/999) throughout the program. The incidence of all epidermal tumors was not significantly elevated in dosed male rats relative to controls (control, 3/50, 6%; low dose, 6/50, 12%; high dose, 1/50, 2%). All high dose (1,000 mg/kg) male and female mice were dead by week 91 as a result of accidentally being administered 2,800 mg/kg for 3 days during week 91; survival of low dose and control male mice was comparable. Survival of high dose male and dosed female mice may have been inadequate for the detection of late-appearing tumors. No evidence of any carcinogenic effect was found in either low or high dose mice of either sex. An infection of the genital tract was probably responsible for the deaths of 14/22 control and 8/32 low dose female mice before the end of the study. Cytoplasmic vacuolization was increased in the liver and in the kidney of male and female mice and was considered to be compound related (liver-- male: control, 1/50, 2%; low dose, 7/50, 14%; high dose, 47/50, 94%; female: 1/50, 2%; 27/50, 54%; 46/50, 92%; kidney or kidney tubule--male: 0/50; 0/50; 41/50, 82%; female: 0/50; 24/49, 49%; 37/50, 74%). Under the conditions of these studies, geranyl acetate was not carcinogenic for F344/N rats or B6C3F1 mice of either sex; however, the reduced survival observed in high dose male rats, high dose male mice, and high and low dose female mice lowered the sensitivity of these studies for detecting neoplastic responses in these groups. In male rats the marginal increases of squamous cell papillomas of the skin and tubular cell adenomas of the kidney may have been related to administration of geranyl acetate. Levels of Evidence of Carcinogenicity: Male Rats: Negative. Female Rats: Negative. Male Mice: Negative. Female Mice: Negative.

Geranyl acetate is a component of essential oils(1) and occurs in varying amounts; up to 60% in oils from Callitris and Eucalyptus species, and up to 14% in palmarosa oil(2). A smaller amount occurs in, for example, geranium, citronella, petitgrain, and lavender oils(2).

Geranyl acetate's production and use as a flavoring and in perfumery(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 3,700(SRC), determined from a log Kow of 4.04(2) and a regression-derived equation(3), indicates that geranyl acetate is expected to have slight mobility in soil(SRC). Volatilization of geranyl acetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Geranyl acetate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.3X10-2 mm Hg(5). Biodegradation data were not available(SRC, 2007).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,700(SRC), determined from a log Kow of 4.04(2) and a regression-derived equation(3), indicates that geranyl 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 2.4X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7.4 hours and 6.5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 30 days if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 260(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Biodegradation data were not available(SRC, 2007).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), geranyl acetate, which has an estimated vapor pressure of 3.3X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase geranyl acetate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hrs(SRC), calculated from its rate constant of 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The rate constant for the vapor-phase reaction of geranyl acetate with ozone has been estimated as 8.60X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 19 minutes(4). Geranyl acetate does contain chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(5).

The rate constant for the vapor-phase reaction of geranyl acetate with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of geranyl acetate with ozone has been estimated as 8.60X10-16 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 19 minutes at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 3.5X10-1 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 231 and 23 days at pH values of 7 and 8, respectively(3). Geranyl acetate does contain chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(4).

An estimated BCF of 260 was calculated in fish for geranyl acetate(SRC), using a log Kow of 4.04(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, provided the compound is not metabolized by the organism(SRC).

The Koc of geranyl acetate is estimated as 3,700(SRC), using a log Kow of 4.04(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that geranyl acetate is expected to have slight mobility in soil.

The Henry's Law constant for geranyl acetate is estimated as 2.4X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that geranyl 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 7.4 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 6.5 days days(SRC). Geranyl acetate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The volatilization half-life from a model pond is about 30 days when adsorption is considered(3). Geranyl acetate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.3X10-2 mm Hg(4).

Geranyl acetate is a component of orange flower (neroli) oil at 2.8%, the citronella oils Cymbopogon nardus, 2%, and C. winterianus, 5%, bay leaf oil Pimenta racemosa (Mill), 1%, Spanish and Italian bitter orange oils, Citrus aurantium L. subsp amara, 0.13 and 0.09%, respectively, Coriander seeds, Coriandrum sativum L. , 2.2 and 15.6% in oil and freshly crushed, respectively(1). It is a component of palmarosa oil at 12.4, 17.3, 9.1, and 8.0% of Brazilian, Guatemalan, Indian, and Madagascan origins, respectively(1). Percentages in sage oils 1.9-3.2, 0.3-0.5, and 0.8-1.2 from the US, France, and Russia, respectively, have been reported(1).|Geranyl acetate was identified, not quantified, as a potent odor compound in extracts of Japanese fresh ginger rhizomes(1). Geranyl acetate was identified as a volatile component in Korean salt-fermented shrimp paste at a mean concentration of 281 ng/g(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 48,026 workers (33,271 of these are female) are potentially exposed to geranyl acetate in the US(1). Occupational exposure to geranyl acetate may occur through inhalation and dermal contact with this compound at workplaces where geranyl acetate is produced or used(SRC). Monitoring data indicate that the general population may be exposed to geranyl acetate via inhalation, ingestion of food, and dermal contact with this compound and other consumer products containing geranyl acetate(SRC).

3(?). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB). /GERANIOL/

ASSUMING THAT THESE TERPENE ESTERS ARE HYDROLYZED TO THE ALCOHOLS, THEY PROBABLY ARE THEN OXIDIZED IN PART TO AN ACID KNOWN AS HILDEBRANDT ACID... IN CASE OF GERANIOL, SOME REDUCED HILDEBRANDT ACID (@ 2-3 DOUBLE BOND) IS ALSO FORMED.

SYMPTOMS: Symptoms of exposure to this compound include skin and eye irritation. It can also cause eye damage and nausea via inhalation. ACUTE/CHRONIC HAZARDS: This compound can cause eye damage and skin irritation. When heated to decomposition this compound emits acrid smoke and fumes of carbon dioxide and carbon monoxide. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/HUMAN EXPOSURE STUDIES/ In human patch test, geraniol at 32% concentration was severely irritating and geranyl acetate mildly irritating.[MOTOYOSKI ET AL; COSMET TOILETRIES 94(8) 41 (1979)]|/OTHER TOXICITY INFORMATION/ NONE OF THESE PERFUME ACETATES SEEMS TO HAVE GIVEN RISE TO ANY HEALTH PROBLEMS IN MANUFACTURING, HANDLING, OR IN THEIR END USES. SKIN SENSITIZATION TO THEM APPEARS TO BE RARE.[Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1864]

geraniol acetate

Consumption (U.S.): Annual: 3933.33 lb. (From the PAFA database, originating from the NAS survey of 1987 and assumes only 60% of poundage was reported.) Individual: 0.003333 mg/kg/day|Use in fragrances in the USA amounts to less than 100,000 lbs/yr|USE IN FRAGRANCES, APPROX 4.54X10+7 GR/YR (1974)|World consumption has been estimated at 650 tpa

Grade: Technical; FCC.

All other chemical product and preparation manufacturing|2,6-Octadien-1-ol, 3,7-dimethyl-, 1-acetate, (2E)-: ACTIVE|1-Octanol, 3,7-dimethyl-, 1-acetate, tetradehydro deriv.: INACTIVE|Reported uses: non-alcoholic beverages 5.68 ppm, frozen dairy 13.60 ppm, hard candy 17.86 ppm, baked goods 29.94 ppm, gelatins & puddings 11.41 ppm, chewing gum 32.75 ppm, syrups 1.0 ppm.|In public use before the 1920s.|Chemical irritants useful as repellents for brown treesnakes (Boiga irregularis) were identified. ... 10 g/L solutions delivered as aerosols of m-anisaldehyde, trans-anethole, cineole, cinnamaldehyde, citral, ethyl phenylacetate, eugenol, geranyl acetate or methyl salicylate all acted as potent irritants for brown treesnakes.

GLC STUDIES OF ESSENTIAL OILS.

Food additives -> Flavoring Agents|Fatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]|Cosmetics -> Tonic

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;