Citronellol

156.27

156.27

1721507

203-375-0

8779

DTXSID3026726

Colorless oily liquid

29052220

20.2

3.2

Clear almost colorless Liquid

0.867-0.869 g/cm³ @ Temp: 10 °C

<25 °C

224.5 °C

209 °F

n 20/D 1.456(lit.)

H2O: SLIGHTLY soluble ;Miscible in ethanol and ether /(+)-citronellol/; very soluble in ethanol and ether /(-)-citronellol/

2-8°C

~0.02 mm Hg ( 25 °C)

5.4 (vs air)

The acute oral LD 50 value in rats was reported as 3.45 g/kg (3.21-3.69 g/kg) (Moreno, 1973). The acute dermal LE>50 value in rabbits was reported as 2.65 g/kg (1.78-3.52 g/kg) (Moreno, 1973). The im LD 50 value in mice was reported as 4 g/kg (Northover & Verghese, 1962).

Fresh rosy odor

Bitter taste /d-Citronellol/; sweet, peach-like flavor /l-citronellol/

Henry's Law constant = 2.1X10-5 atm-cu m/mole at 25 °C (est)

pKa = 17.11 at 25 °C (est)

Oily liquid; boiling pt: 224.5 °C; specific gravity: 0.8850 20/4 °C; optical rotation: 5.33 deg at 20 °C /(+)-Form/|Optical rotation: -5.3 deg at 18 °C/D /l-Citronellol/|Hydroxyl radical reaction rate constant = 1.70X10-10 cu cm/molec-sec at 24 °C|Atmospheric ozone reaction rate constant = 2.4X10-16 cu cm/molec-sec at 24 °C

9

UN 3082 9 / PGIII

1

36/37/38-51/53-43-36/38

26-36-24/25-61-37-24

RH3400000

Xi,N

Irritant

Stable. Incompatible with oxidizing agents.

P280-P305 + P351 + P338

H315-H317-H319

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. Contaminated packaging Dispose of as unused product.

Strong oxidizing agents

Citronellol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

|Warning|H315 (100%): 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 103 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315 (96.32%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, and P501|Aggregated GHS information provided by 1659 companies from 30 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, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501

Skin protection: Handle with gloves.|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Body Protection: Complete suit protecting against chemicals, 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).

Wear self-contained breathing apparatus for firefighting if necessary.|Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

ACCIDENTAL RELEASE MEASURES Personal precautions, protective equipment and emergency procedures Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. 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.

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.|Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.|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.

...moderate eye irritation...|/Skin/ moderately irritating.

Citronellol is emitted into the ambient air from household products such as pine-oil based cleaners, orange oil-based degreasers and plug-in air fresheners(1). Citronellol was detected in volatile emissions from the leaves of Eucalyptus citriodora(2).

SEDIMENT: Citronellol was detected in sediments collected from Tobin Lake, Saskatchewan(1).

Citronellol (beta-isomer) was chemically detected in household products such as perfume, shampoo, after shave lotion, nail enamel remover, fabric softener(1). Citronellol has been identified as a component of tobacco smoke(2).

IDENTIFICATION AND USE: Citronellol has been found in nature, and it has been reported in about 70 essential oils. It is registered for pesticide use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. It is also used in perfumery. HUMAN EXPOSURE AND TOXICITY: Adult male volunteers with no known allergic reactions were patch-tested on their back for 48 hr with 32% citronellol. After 48 hr, patches were removed and the skin was cleaned of any residual test material. Moderate irritation was observed. A patch test using a 1% concentration of citronellol in acetone gave a positive reaction in subjects allergic to citronella oil. ANIMAL STUDIES: Citronellol applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was moderately irritating. Severe irritation was observed in rabbits and guinea pigs exposed to 100% compound (unoccluded) for 24, 48 or 72 hr. Citronellol was not mutagenic when tested in Salmonella typhimurium strains TA98 and TA100 in the presence and absence of metabolic activation. ECOTOXICITY STUDIES: Golden Orfe (Leuciscus idus) were exposed to this chemical under static conditions for 96 hours. No mortalities were seen in the control and 4.64 mg/L groups. At 10 mg/L, apathy was noted up to 24 hr, but no mortalities were noted at 96 hr. At 21.5, 46.4 and 100 mg/L, 100% mortality was seen 1 hour after exposure.

LD50 Mice im 4 g/kg|LD50 Rabbit dermal 2.65 g/kg|LD50 Rats oral 3.45 g/kg

/AQUATIC SPECIES/ Golden Orfe (Leuciscus idus) were exposed to nominal concentrations of 0, 4.64, 10, 21.5, 46.4 or 100 mg/L of this chemical under static conditions for 96 hours. No mortalities were seen in the control and 4.64 mg/L groups. At 10 mg/L, apathy was noted up to 24 hours, but no mortalities were noted at 96 hours. At 21.5, 46.4 and 100 mg/L, 100% mortality was seen 1 hour after exposure. 96-hr LC50 > 10 mg/L

Citronellol is widespread in nature in both enantiomeric forms, the richest sources being rose and geranium(1). Citronellol is reported to occur in about 70 essential oils(2). Citronellol has been detected and quantified in numerous plant species(3).

Citronellol's production and use as an intermediate in the synthesis of other fragrance chemicals(1) and as a flavoring compound in foods(2) may result in its release to the environment through various waste streams(SRC). Its use as a fragrance ingredient in perfumes, soaps, detergents, and other household products(1) will result in its direct release to the environment(SRC). Citronellol has been identified as a component of tobacco smoke(3).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 94(SRC), determined from a structure estimation method(2), indicates that citronellol is expected to have high mobility in soil(SRC). Volatilization of citronellol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.02 mm Hg(3), and water solubility, 200 mg/L(4). Even though the vapor pressure is low environmentally at standard temperature and pressure, there is a detectable odor; therefore, citronellol may volatilize from dry soil(SRC). An 80-90% of Theoretical BOD using activated sludge in the OECD 301F test(5) suggests that biodegradation is an important environmental fate process in soil(SRC). Citronellol was also classified as readily biodegradable by the results of the OECD 301C test (modified MITI) with 65% degradation in 4 weeks(6) and by a DOC Method F test (100% biodegradation in 15 days)(6). Citronellol absorbs at wavelengths >290 nm(7) and, therefore, may be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 94(SRC), determined from a structure estimation method(2), indicates that citronellol is not 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 2.1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.02 mm Hg(4), and water solubility, 200 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.4 and 21 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 177(SRC), from its log Kow of 3.91(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). An 80-90% of Theoretical BOD using activated sludge in the OECD 301F test(8) suggests that biodegradation is an important environmental fate process in water(SRC). Citronellol was also classified as readily biodegradable by the results of the OECD 301C test (modified MITI) with 65% degradation in 4 weeks(9) and by a DOC Method F test (100% biodegradation in 15 days)(9). Citronellol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Citronellol is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), citronellol, which has a vapor pressure of 0.02 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase citronellol 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 2.3 hours(SRC), calculated from its rate constant of 1.70X10-10 cu cm/molecule-sec at 24 deg(3). Citronellol is also degraded in the atmosphere by reaction with ozone and nitrate radicals. The half-life for the reaction with ozone is estimated to be 1.1 hours(SRC), calculated from its rate constant of 2.4X10-16 cu cm/molecule-sec at 24 °C(3). The half-life for the reaction with nitrate radicals is estimated to be 4 minutes(SRC), calculated from its rate constant of 1.21X10-11 cu cm/molecule-sec at 24 °C(4). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(5), therefore, night-time degradation appears to be a major fate process for citronellol(SRC). Citronellol absorbs at wavelengths >290 nm(6) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of citronellol with photochemically-produced hydroxyl radicals has been measured as 1.70X10-10 cu cm/molecule-sec at 24 °C(1). This corresponds to an atmospheric half-life of about 2.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). The rate constant for the vapor-phase reaction of citronellol with atmospheric ozone has been measured as 2.4X10-16 cu cm/molecule-sec at 24 °C(1); this corresponds to an atmospheric half-life of about 1.1 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Reaction products with hydroxyl radicals and ozone included acetone, ethanedial, and 2-oxopropanal(1). The rate constant for the vapor-phase reaction of citronellol with atmospheric nitrate radicals has been measured as 1.21X10-11 cu cm/molecule-sec at 24 °C(3); this corresponds to an atmospheric half-life of about 4 minutes(SRC) at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(4). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(5), therefore, night-time degradation appears to be a major fate process for citronellol(SRC). Citronellol absorbs at wavelengths >290 nm(6) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Citronellol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). Citronellol is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(8).

An estimated BCF of 177 was calculated in fish for citronellol(SRC), using a log Kow of 3.91(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), provided the compound is not metabolized by the organism(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of citronellol can be estimated to be 94(SRC). According to a classification scheme(2), this estimated Koc value suggests that citronellol is expected to have high mobility in soil.

The Henry's Law constant for citronellol is estimated as 2.1X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 0.02 mm Hg(1), and water solubility, 200 mg/L(2). This Henry's Law constant indicates that citronellol is expected to volatilize from water surfaces(3). 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)(3) is estimated as 2.4 days(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 21 days(SRC). Citronellol's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Even though the vapor pressure is low environmentally at standard temperature and pressure, there is a detectable odor; therefore, citronellol may volatilize from dry soil(SRC). Patch testing to determine the evaporation rate of fragrance chemicals from skin found that citronellol evaporation was not sensitive to pH changes from 4.0 to 7.0 and that 26-27% of applied citronellol was lost within 40 minutes to 24 hours(4).

DRINKING WATER: Citronellol has been qualitatively in drinking water concentrates sampled from 16 US advanced waste treatment facilities(1).|SURFACE WATERS: Citronellol has been detected in waters of the Great Lakes ecosystem(1).

Citronellol is reported to occur in beer, rum, tea, and apple juice(1). Citronellol was detected in the volatile compounds from edible Korean Chamchwi (Aster scaber Thunb)(2).

According to the 2012 TSCA Inventory Update Reporting data, 7 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of citronellol 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 163,706 workers (87,309 of these were female) were potentially exposed to citronellol in the US(1). Occupational exposure to citronellol may occur through inhalation and dermal contact with this compound at workplaces where citronellol is produced or used. Monitoring and use data indicate that the general population may be exposed to citronellol via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this consumer products containing citronellol(SRC).

In rabbits this alcohol metabolizes to 7-carboxy-and 7-hydroxymethyl-3-methylocta-6-enoic acids, and these are excreted in the urine.

We evaluated the effects of rose oil on the peroxisome proliferator-activated receptor (PPAR) and cyclooxygenase-2 (COX-2).Citronellol and geraniol, the major components of rose oil, activated PPAR alpha and gamma, and suppressed LPS-induced COX-2 expression in cell culture assays, although the PPARgamma-dependent suppression of COX-2 promoter activity was evident only with citronellol, indicating that citronellol and geraniol were the active components of rose oil.

/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Higher alcohols (>3 carbons) and related compounds/|/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 necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema 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. Administer activated charcoal ... . /Higher alcohols (>3 carbons) and related compounds/|/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 ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /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. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/

/HUMAN EXPOSURE STUDIES/ The fragrance mix (FM I), established in 1977, detects the majority, but not all cases of contact allergy to fragrances. Based on European research 2002/2003, fragrance mix II (FM II) was developed to supplement FM I. In 2005, the German Contact Dermatitis Research Group (DKG) added FM II to their baseline series. /The objective was/ to evaluate reactions to FM II and its constituents in routine patch testing. Retrospective data analysis of the Information Network of Departments of Dermatology (IVDK), 2005-2008, of patch test results with FM II and its constituents. A total of 35,633 patients were patch tested with FM II as part of the DKG baseline series. Of these, 1742 (4.9%) reacted positively. Concomitant reactions to FM I were observed in 41.9% of the patients reacting to FM II. In 367 FM II-positive patients, a full breakdown test of the mix was performed. Of these, 47.7% reacted to hydroxyisohexyl 3-cyclohexene carboxaldehyde, 16.1% to citral, 11.4% to farnesol, 3.8% to hexyl cinnamal, 2.7% to coumarin, and 2.5% to citronellol. FM II is an important screening and diagnostic tool to detect fragrance allergy. Hydroxyisohexyl 3-cyclohexene carboxaldehyde is the most important fragrance allergen in FM II.|/HUMAN EXPOSURE STUDIES/ Fragrance mix II (FM II) was initiated to detect contact hypersenstitivity (CH) to fragrances that could not have been identified previously. OBJECTIVE: The aim of this multicenter study was to map the frequency of CH to FM II and its components in Hungary. METHODS: Six centers participated in the survey from 2009 to 2010. A total off 565 patients (434 women and 131 men) with former skin symptoms provoked by scented products were patch tested. The tests were performed with Brial GmbH D-Greven allergens. In the environmental patch test series, FM II, FM I, Myroxylon pereirae, colophonium, wood-tar mix, propolis, and sesquiterpene lactone mix were tested as fragrance allergens. The FM II components (citral, farnesol, coumarin, citronellol, alpha-hexyl-cinnamaldehyde, and hydroxy-isohexyl-3-cyclohexene-carboxaldehyde [Lyral]) were also tested. RESULTS: Contact hypersenstitivity to any fragrances was detected in 28.8%, to FM II in 17.2% of the patients. Contact hypersenstitivity to hydroxy-isohexyl-3-cyclohexene-carboxaldehyde was observed in 7.3%, to coumarin in 5.1%, to alpha-hexyl-cinnamaldehyde in 3.5%, to citral in 3.4%, to farnesol in 2.5%, and to citronellol in 1.2%. Of the FM II-positive cases, 48.4% showed isolated CH reaction. CONCLUSIONS: The frequency of CH to FM II is 17.2% in the tested, selected Hungarian population. The CH to FM II and its components could not have been revealed without the present test materials.|/HUMAN EXPOSURE STUDIES/ A 24-hr patch test using full strength citronellol produced no irritation reactions in 20 subjects.|/HUMAN EXPOSURE STUDIES/ A maximization test was carried out on 25 volunteers. The material was tested at a concentration of 6% in petrolatum and produced no sensitization reactions.|For more Human Toxicity Excerpts (Complete) data for Citronellol (6 total), please visit the HSDB record page.

citronellol

Biomite (Natural Plant Protection S.A.): Active ingredient: farnesol 0.1670%; nerolidol 0.4170%; citronellol 0.4170%; and geraniol 0.4170%.

All other basic organic chemical manufacturing|6-Octen-1-ol, 3,7-dimethyl-: ACTIVE

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|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Masking

Flavoring Agents