HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Farnesol
trans-Farnesol · (2E,6E)-Farnesol · TRANS,TRANS-FARNESOL · FEMA 2478 · (2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol · (E)-farnesol · 3,7,11-TRIMETHYLDODECA-2,6,10-TRIEN-1-OL · Inhibitor A2
Identifikatoren & physikalische Daten
| CAS No. | 106-28-5 |
|---|---|
| Summenformel | C15H26O |
| Durchschnittliche Molmasse | 222,37 g/mol |
| Monoisotopische Masse | 222,19836545 g/mol |
| SMILES | CC(C)=CCC/C(C)=C/CC/C(C)=C/CO |
| InChIKey | CRDAMVZIKSXKFV-YFVJMOTDSA-N |
| PubChem CID | 445070 |
| ChEMBL | CHEMBL1232800 |
| ChEBI | CHEBI:28600 |
| EC No. | 225-004-1 |
| DTXSID | DTXSID2040789 |
Chemische & physikalische Eigenschaften
| XLogP | 4,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 265 |
| Stoffklassen | Biological Agents -> Plant Oils and Extracts |
| Lipide | Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103] |
| Kosmetika | Cosmetics ingredient -> BaseConditioning/EmollientFlavorFragranceMoisturizing/HumectantOther (Specify)DeodorantSolventSoothing |
| SpringerMaterials Properties | Chemical shift |
| Duftstoffe | Fragrance Ingredient (Farnesol) -> IFRA transparency List |
| Geruch | Delicate flowery odorMild, oilyWEAK CITRUS-LIME ODOR |
| Geschmack | WEAK CITRUS-LIME TASTE |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.8846 at 68 °F (NTP, 1992) - Less dense than waterwill float0.8871 at 20 °C/4 °CSp gr: 0.884-0.8910.884-0.8890.8871 @ 20°C0.886 g/mL at 20 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Colorless liquidSlightly yellow liquid |
| Löslichkeit | Soluble in three volumes of 70% alcoholSOL IN ALCOHOL: 1:3 IN 70% ALCOHOLSolubility in alcohol: 1 mL in 1 mL 95% ethanolInsoluble in watersoluble in oilssoluble (in ethanol)Chloroform (Sparingly), DMSO (Slightly) Ethyl Acetate (Slightly)Miscible with alcohol. Immiscible with water. |
| Schmelzpunkt | 61-63 °C |
| Siedepunkt | 149 °C4 mm Hg(lit.) |
| Brechungsindex | n20/D 1.490(lit.) |
| Flammpunkt | 205 °F |
| Lagerbedingungen | Sealed in dry,2-8°C |
| pKa (Säurekonstante) | 14.42±0.10(Predicted) |
| Aggregatzustand | Liquid |
| Farbe | Colourless |
| Geruch | at 100.00 %. mild muguet floral sweet lily waxy |
| Geruchsart | floral |
| BRN | 1723039 |
| Stabilität | Light Sensitive |
| InChI | 1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+ |
| InChIKey | CRDAMVZIKSXKFV-YFVJMOTDSA-N |
| SMILES | C\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO |
| LogP (Verteilungskoeffizient) | 5.31 |
| CAS Datenbank | 106-28-5(CAS DataBase Reference) |
| NIST chemische Informationen | 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)-(106-28-5) |
| EPA chemische Informationen | (E,E)-Farnesol (106-28-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1980) of reports.WarningH315 (99.3%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1980 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-Hazard Traits - Fragrance AllergenRegulation (EC) No 1831/2003 (amended)PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.Status: Active Update: 24-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23466Farnesol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | A mild irritant on rabbit skin[RTECS] Danger of skin sensitization[MAK] Included in list of established contact allergens in humans[EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] Safe when used as a flavoring agent in food[JECFA] May cause irritation[MSDSonline] |
| FDA-Anforderungen | 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. |
| Reaktive Gruppe | Alcohols and Polyols |
| FIFRA-Anforderungen | New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 128910Type of Pesticide: biological - insecticideUse Site: non-food useYear: 1987. |
| Reactivity Profile | 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. |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| Hazard Classes and Categories | Skin Irrit. 2 (99.3%)Skin Sens. 1 (93.1%)Skin sensitisation - category 1 |
| Brandbekämpfung | To extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguishera water spray may also be used. (NTP, 1992) |
| Erste Hilfe | 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. |
| Freisetung ohne Brand | 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. |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Protective Action Criteria (PAC) | 18 [mg/m3]200 [mg/m3]1200 [mg/m3] |
| Personal Protective Equipment (PPE) | 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. |
| Wechselwirkungen | 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. |
| Ökotoxizitätswerte | LD50 Anas platyrhynchos (Mallard duck, age 21 wk) oral >2150 mg/kg /98% AI formulated product/LD50 Colinus virginianus (Bobwhite quail, age 23 wk) oral >2150 mg/kg /98% AI formulated product/LC50 Anas platyrhynchos (Mallard duck, age 5 days) dietary >5000 ppm/8 days /98% AI formulated product/LC50 Colinus virginianus (Bobwhite quail, age 14 days) dietary >5000 ppm/8 days /98% AI formulated product/For more Ecotoxicity Values (Complete) data for FARNESOL (6 total), please visit the HSDB record page. |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | 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.) volatileit was detected in these plant hybrids at a concentration of 2 ug/kg(1). Farnesol has been identified as a raw beef volatile(2). |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Ökotoxizitätsauszüge | /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. |
| Effluent Concentrations | 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). |
| Soil Adsorption/Mobility | 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. |
| Natural Pollution Sources | 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). |
| Human Toxicity Excerpts | /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 agentLatest evaluation: 2003 ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent. |
| Artificial Pollution Sources | Farnesol's production and use in perfumery and as a flavoring(1) may result in its release to the environment through various waste streamsits use as an insect attractant will result in its direct release to the environment(SRC). |
| Environmental Biodegradation | AEROBIC: Farnesol supported moderate growth of Mycobacterium ratisbonese strain MD4 and good growth of M. fortuitum strain NF4(1). |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29052290 |
| RTECS-Nr. | JR4979000 |
| R-Sätze (R) | 43 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 24/25-36/37 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrenklasse | Skin Sens. 1 |
Anwendungen & Verwendung
Verwenden
Farnesol is a natural organic compound which is present in many essential oils.