Farnesol

222.37

222.37

1763926

225-004-1

J03523NK03

DTXSID3032389

Colorless liquid|Slightly yellow liquid

2905290000

20.2

log Kow = 5.77 (est)

Clear colorless to faint yellow Liquid

0.8871 g/cm³ @ Temp: 20 °C

<25 °C

110-113 °C

205 °F

1.485

Not miscible or difficult to mix in water.

−20°C

3.94X10-5 mm Hg at 25 °C (est)

Delicate flowery odor

WEAK CITRUS-LIME TASTE

Henry's Law constant = 2.52X10-4 atm-cu m/mol at 25 °C (est)

FROM PETITGRAIN: BP: 131-132 °C @ 3 MM HG; SPECIFIC GRAVITY: 0.8880; INDEX OF REFRACTION: 1.4891|FROM TOLU BALSAM: BP: 124-125 °C @ 2.2 MM HG; SPCIFIC GRAVITY: 0.8883 @ 20 °C; INDEX OF REFRACTION: 1.4892 @ 20 °C/D|FROM CABREUVA: BP: 118-120 °C @ 2 MM HG; SPECIFIC GRAVITY: 0.8886; INDEX OF REFRACTION: 1.4894|FROM GERANYL ACETONE: BP: 118-120 °C @ 2 MM HG; SPECIFIC GRAVITY: 0.8886; INDEX OF REFRACTION: 1.48906|INDEX OF REFRACTION: 1.4877 @ 20 °C/D; INSOL IN WATER; SOL IN ETHER, ACETONE; SOL IN ORGANIC SOLVENTS /TRANS,TRANS-FARNESOL/|Hydroxyl radical reaction rate constant = 2.69X10-10 cu cm/molec-sec at 25 °C (est)|Oil; BP: 156 °C at 12 mm Hg, 120 °C at 0.3 mm Hg; density: 0.8908 g/cu cm at 20 °C; index of refraction: 1.4877 at 20 °C/D. Very soluble in acetone, ether, ethanol /2-cis, 6-trans-Farnesol/|Oil; BP: 160 °C at 10 mm Hg, 137 °C at 3 mm Hg; density: 0.888 g/cu cm at 20 °C; index of refraction: 1.4877 at 20 °C/D. Insoluble in water. Very soluble in ethanol; soluble in acetone, ether /2-trans, 6-trans-Farnesol/

No rapid reaction with air. No rapid reaction with water.

Alcohols and Polyols

Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Ⅲ

UN 3082 9 / PGIII

3

9

24/25-22

JR4979000

Xi

Irritant

Stable. Combustible. Incompatible with strong oxidizing agents.

P273-P280-P333 + P313-P337 + P313-P391-P501

H315-H317-H319-H411

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.

Farnesol 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 2) 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 (99.38%): 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 1951 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501

To extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguisher; a water spray may also be used. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, 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 alcohol followed by washing with a strong 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 store this material in a refrigerator. (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. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that butyl rubber gloves may provide protection to contact with this compound. Butyl rubber over latex gloves is recommended. However, if this chemical makes direct contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992)

Farnesol was tentatively identified in the effluent from shoe-sole and tire manufacturing plants in Italy at a concentration range of not detected (detection limit not specified) to 25 ug/cu m(1).

Hamster pancreatic cancer was initiated at time 0 with N-nitrosobis(2-oxopropyl)amine. Animals were fed control, 2% (w/w) perillyl alcohol, or 1% (w/w) farnesol diets from weeks 5-42. Pancreatic carcinoma incidence was decreased by perillyl alcohol and farnesol. Hyperplastic pancreatic ductal neoplasms from perillyl alcohol and farnesol-treated animals had higher Bak protein expression (p < 0.05), and somewhat higher apoptotic rates, diminished expression of the antiapoptotic protein BCL-xL, and lower rates of DNA synthesis than the controls.|... the antigenotoxic and antioxidant efficacy of farnesol against cadmium chloride (CdCl2)-induced renal oxidative stress and genotoxicity in Swiss albino mice /was assessed/. Single, intraperitoneal doses of CdCl2(5 mg/kg body weight) for 24 hr resulted in a significant (p < 0.001) increase in chromosomal aberration and micronuclei formation. The oral administration of farnesol at two doses (1% and 2%/kg bw) for seven consecutive days showed significant (p < 0.05) suppression of the genotoxic effects of CdCl2 in the modulator groups. ...|... In this study, the protective effects of farnesol (FL), against Fe-NTA (9 mg iron/kg body weight ip)-induced oxidative damage and early tumor promotion markers are evaluated. The pretreatment of iron-intoxicated rats with 1% and 2%/kg body weight oral dose of FL for 7 consecutive days significantly reversed the iron-induced increase in H2O2 content (p < 0.001), malondialdehyde formation, xanthine oxidase activity (p < 0.001), ornithine decarboxylase activity (p < 0.001) and 3(H)thymidine incorporation in renal DNA (p < 0.005) with simultaneous significant depletion in serum toxicity markers blood urea nitrogen (BUN) and creatinine (p < 0.001). Significant dose-dependent restoration was recorded in renal glutathione content, its dependent enzymes and other phase II metabolizing enzymes viz., catalase, glutathione-S-transferase and quinone reductase (p < 0.001) with prophylactic treatment of FL. Present results support that FL markedly lowers the oxidative damage and appearance of tumor markers ...|FARNESOL PROLONGED BARBITURATE SLEEPING TIME WITHOUT ITSELF BEING HYPNOTIC.

LD50 Rat oral > 20 mL/kg (17742 mg/kg bw)|LD50 Rat oral >5000 mg/kg bw|LD50 Mouse oral 8764 mg/kg bw

/AQUATIC SPECIES/ Farnesol is toxic to the larvae at concn above 1 times 10-5 (vol/vol). The number of cyprids /barnacles/ and adults produced and the rate of metamorphosis are affected by the concn of farnesol in seawater, within the range 5X10-7 to 1X10-6 (vol/vol). Abnormal cyprids result from exposure to farnesol. They do not metamorphose into attached adults. The degree of abnormality is related to the strength of farnesol and length of exposure. The effect of farnesol is related to the physiological age of the larvae.|/OTHER TERRESTRIAL SPECIES/ Two-spotted spider mite females treated topically with 200 ppm farnesol in 40% ethanol laid more eggs than females treated with ethanol only, suggesting possibility of farnesol having gonadotropic effects on two-spotted spider mite.

PRESENCE OF THIS TERPENE ALCOHOL IN NATURE HAS BEEN REPORTED IN MORE THAN 30 ESSENTIAL OILS. LEVELS ARE GENERALLY LOW (0.5-1.0%) WITH EXCEPTION OF CABREUVA, WHICH CONTAINS UP TO 2.5% FARNESOL, & DISTILLATE FROM FLOWERS OF OXYSTIGMA BUCCHOLTZII HARMS...UP TO 18%... AMONG ESSENTIAL OILS CONTAINING FARNESOL ARE...CEYLON CITRONELLA, CANANGA, AMBRETTE SEEDS, YLANG-YLANG, ACACIA FARNESIANA...PALMAROSA...|Farnesol is found in oils of citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam peru, and tolu(1). It is found in many flowers and other essential oils such as cassia and cananga(2).

Farnesol's production and use in perfumery and as a flavoring(1) may result in its release to the environment through various waste streams; its use as an insect attractant will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,300(SRC), determined from a structure estimation method(2), indicates that farnesol is expected to have low mobility in soil(SRC). Volatilization of farnesol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.5X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Farnesol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.9X10-5 mm Hg(SRC), determined from a fragment constant method(4). Data regarding biodegradation using mixed cultures were not available(SRC, 2007).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,300(SRC), determined from a structure estimation method(2), indicates that farnesol 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 2.5X10-4 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 9.5 hrs and 7.4 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 5,500(SRC), from an estimated log Kow of 5.8(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Data regarding biodegradation using mixed cultures were not available(SRC, 2007).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), farnesol, which has an estimated vapor pressure of 3.9X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase farnesol 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 1.4 hrs(SRC), calculated from its rate constant of 2.7X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase farnesol may be removed from the air by wet or dry deposition(SRC). Farnesol does not absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of farnesol with photochemically-produced hydroxyl radicals has been estimated as 2.7X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of farnesol with ozone has been estimated as 1.3X10-15 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 13 minutes at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Reaction with nitrate radicals may also be important(SRC). Farnesol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Farnesol does not absorb light at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 5,500 was calculated in fish for farnesol(SRC), using an estimated log Kow of 5.7(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very 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 farnesol can be estimated to be 1,300(SRC). According to a classification scheme(2), this estimated Koc value suggests that farnesol is expected to have low mobility in soil.

The Henry's Law constant for farnesol is estimated as 2.5X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that farnesol 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 9 hrs(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 7 days(SRC). Farnesol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.9X10-5 mm Hg(SRC), determined from a fragment constant method(3).

Farnesol is a volatile from apricot (Prunus armeniaca L.) at concentrations of 15 and 3 ug/kg fresh fruit tissue but was not identified as a plum (Prunus salisina Lindl.) volatile; it was detected in these plant hybrids at a concentration of 2 ug/kg(1). Farnesol has been identified as a raw beef volatile(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,557 workers (276 of these are female) are potentially exposed to farnesol in the US(1). Occupational exposure to farnesol may occur through inhalation and dermal contact with this compound at workplaces where farnesol is produced or used(SRC). Monitoring and use data indicate that the general population may be exposed to farnesol via inhalation, ingestion of food, and dermal contact with this compound and other consumer products containing farnesol(SRC).

/Exptl Ther/ .../This study/ investigated whether farnesol induces apoptosis of blasts from patients with acute myeloid leukemia (AML) and leukemic cell lines, as compared with normal, human primary hemopoietic cells. ... apoptosis of leukemic cell lines of T- and B-lymphocyte, myeloid or erythroid lineages and primary blasts obtained from patients with AML /was caused by 30 uM farnesol/. However, the same concentration did not kill primary monocytes, or quiescent or proliferating T-lymphocytes. /The authors/ conclude that farnesol selectively kills AML blasts and leukemic cell lines in preference to primary hemopoietic cells.

Farnesol is metabolized to farnesyl glucuronide, hydroxyfarnesol and hydroxyfarnesyl glucuronide by human tissue microsomes. ... Farnesol metabolism was examined by a sensitive LC (liquid chromatography)-MS/MS method. Results indicate that farnesol is a good substrate for glucuronidation in human liver, kidney and intestine microsomes (values in nmol/min per mg). Initial analysis using expressed human UGTs indicated that UGTs 1A1 and 2B7 were primarily responsible for glucuronidation in vitro, with significantly lower activity for all the other UGTs tested (UGTs 1A3, 1A4, 1A6, 1A9 and 2B4). Kinetic analysis and inhibition experiments indicate that, in liver microsomes, UGT1A1 is primarily responsible for farnesol glucuronidation; however, in intestine microsomes, UGT2B7 is probably the major isoform involved, with a very-low-micromolar K(m). ...

... the effect of 20 uM farnesol on the distribution of protein kinase C (PKC) between cytosolic and membrane fractions of HeLa S3K cells and fibroblasts line CF-3 was examined. In HeLa cells farnesol caused translocation of PKC from membrane fraction to cytosol after 1h of incubation and also prevented PMA-stimulated induction of PKC translocation from cytosol to membranes. Up to 6 h of incubation, there was no effect of farnesol on PKC localization in CF-3 fibroblasts. The results point to possible involvement of PKC in the toxic effect of farnesol ...|... in MCF-7 human breast cancer cells, farnesol induced the expression of thyroid hormone receptor (THR) beta1 mRNA and protein at concentrations that inhibited cell growth. Changes in the expression of THR responsive genes, however, suggested that farnesol inhibits THR-mediated signaling. Protein extracts from cells treated with farnesol displayed decreased binding to oligodeoxynucleotides containing a consensus sequence for the THR response element, despite the higher THRbeta1 content, providing a mechanism to explain the decreased transcriptional activity of cellular THRs.|Farnesol-mediated apoptosis was prevented by transformation with a plasmid coding for the phosphatidic acid (PA) phosphatase LPP3, but not by an inactive LPP3 point mutant. Farnesol did not directly inhibit LPP3 PA phosphatase enzyme activity in an in vitro mixed micelle assay. ...

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)

/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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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/

/ALTERNATIVE and IN VITRO TESTS/ Perillyl alcohol, farnesol and geraniol have chemotherapeutic activity toward pancreatic and other cancers...After 48 hrs of treatment with farnesol geraniol or perillyl alcohol, human BxPC3 pancreatic cancer cells exhibited a 3 to 10-fold increase in apoptosis and higher Bak expression than the controls...|/OTHER TOXICITY INFORMATION/ Farnesol: Flavoring agent; Latest evaluation: 2003 ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent.

Farnesol

BIOMITE Active Ingredient 0.1670% Farnesol, 0.4170% Nerolidol, 0.4170% 3,7-Dimethyl-6-octen-1-ol, 0.4170% Geraniol|STIRRUP - M Active Ingredient 0.9720% Farnesol, 0.7880% Nerolidol

2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-: ACTIVE|REPORTED USES: Non-alcoholic beverages 0.76 ppm; ice cream, ices, etc 0.40 ppm; candy 1.4 ppm; baked goods 1.7 ppm; gelatins & puddings 0.10 ppm.|TRANS-TRANS-FARNESOL IS ONLY STEREOISOMER PRESENT IN MANY ESSENTIAL OILS BUT OCCURS MIXED WITH CIS-TRANS FARNESOL IN PETITGRAIN OIL & SEVERAL OTHER OILS /TRANS-TRANS-FARNESOL/|/It is/ found in oils of citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam peru, & tolu.|PRESENCE OF THIS TERPENE ALCOHOL IN NATURE HAS BEEN REPORTED IN MORE THAN 30 ESSENTIAL OILS. LEVELS ARE GENERALLY LOW (0.5-1.0%) WITH EXCEPTION OF CABREUVA, WHICH CONTAINS UP TO 2.5% FARNESOL, & DISTILLATE FROM FLOWERS OF OXYSTIGMA BUCCHOLTZII HARMS...UP TO 18%... AMONG ESSENTIAL OILS CONTAINING FARNESOL ARE...CEYLON CITRONELLA, CANANGA, AMBRETTE SEEDS, YLANG-YLANG, ACACIA FARNESIANA...PALMAROSA...|For more General Manufacturing Information (Complete) data for FARNESOL (7 total), please visit the HSDB record page.

FARNESOL WAS IDENTIFIED BY GAS CHROMATOGRAPHY IN ESSENTIAL OIL FRACTION FROM FRUITS OF PTERODON PUBESCENS.|FARNESOL WAS SEPARATED FROM A MIXTURE BY LOW-PRESSURE CHROMATOGRAPHY ON PHASE BONDED SILICA IN GLASS COLUMN.

Food additives -> Flavoring Agents|Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]|Cosmetics -> Deodorant; Solvent; Soothing

Flavoring Agents