farnesol
3,7,11-trimethyl-2,6,10-dodecatrien-1-ol
Identification
| Name | farnesol |
| IUPAC | 3,7,11-trimethyldodeca-2,6,10-trien-1-ol |
| CAS Number | 4602-84-0 |
| EINECS | 225-004-1 |
| FDA UNII | EB41QIU6JL |
| Molecular Formula | C15 H26 O |
| Molecular Weight | 222.37142000 |
| MDL Number | MFCD00002918 |
| Beilstein | 1763926 |
| CoE Number | 78 |
Regulatory
| JECFA Food Flavoring | 1230 farnesol |
| DG SANTE Food Flavourings | 02.029 3,7,11-trimethyl-2,6,10-dodecatrien-1-ol |
| FEMA Number | 2478 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 4602-84-0 ; FARNESOL |
| FDA Regulation | FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION |
Physical Properties
| Appearance | colorless to pale yellow clear oily liquid (est) |
| Assay | 96.00 to 100.00 sum of isomers |
| Food Chemicals Codex Listed | Yes |
| Specific Gravity | 0.88400 to 0.88900 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.356 to 7.397 |
| Refractive Index | 1.48700 to 1.49200 @ 20.00 °C. |
| Boiling Point | 149.00 °C. @ 4.00 mm Hg, 263.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.000370 mmHg @ 25.00 °C. (est) |
| Vapor Density | >1 ( Air = 1 ) |
| Flash Point | 205.00 °F. TCC ( 96.11 °C. ) |
| logP (o/w) | 4.828 (est) |
| Shelf Life | 12.00 month(s) or longer if stored properly. |
| Storage | store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Soluble in | alcohol |
| Insoluble in | water |
| Stability | cream |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | deodorants |
Organoleptic Properties
| Odor Strength | low |
| Substantivity | 400 hour(s) at 100.00 % |
| Odor Description |
at 100.00 %. A delicate, fresh, green muguet note anise; apricot; balsam; clove; grapefruit; oily; orange; floral; peach; pear very mild and delicate green floral odor with typical lily of the valley character characteristic
|
| Odor sample from | Berje Inc. |
| Taste Description |
floral juicy green tropical plum pear peach cilantro metallic Floral, woody, dry sweet, flowery, juicy
|
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 6000 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 > 5000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic, flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| IFRA Critical Effect | Dermal sensitization |
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%) | Category 1: Products applied to the lips |
| Notes | IFRA FLAVOR REQUIREMENTS: |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 7.70 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 2.60 (μg/capita/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| baked goods | - |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Indukern, S.A. F&F Ingredients Division
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Potential Uses
Natural Occurrence
Synonyms
2,6,10-
dodecatrien-1-ol, 3,7,11-trimethyl-
dragosantol (Symrise)
farnesol FCC
farnesol special
farnesol synthetic
farnesyl alcohol
3,7,11-
trimethyl dodeca-2,6,10-trienol
3,7,11-
trimethyl-2,6,10-dodecatrien-1-ol
2,6,10-
trimethyl-2,6,10-dodecatrien-12-ol
3,7,11-
trimethyl-2,6,10-dodecatrienol
3,7,11-
trimethyldodeca-2,6,10-trien-1-ol
PubMed:
Effects of farnesol and the off-flavor derivative geosmin on Streptomyces tendae.
PubMed:
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
PubMed:
Improved production of isoamyl acetate by a sake yeast mutant resistant to an isoprenoid analog and its dependence on alcohol acetyltransferase activity, but not on isoamyl alcohol production.
PubMed:
Differential neural responses evoked by orthonasal versus retronasal odorant perception in humans.
PubMed:
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
PubMed:
Development of a multianalyte method based on micro-matrix-solid-phase dispersion for the analysis of fragrance allergens and preservatives in personal care products.
PubMed:
Assessment of the antioxidant and antiproliferative effects of sesquiterpenic compounds in in vitro Caco-2 cell models.
PubMed:
A new source of elemol rich essential oil and existence of multicellular oil glands in leaves of the Dioscorea species.
PubMed:
Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach.
PubMed:
Characterization of essential oil from Citrus aurantium L. flowers: antimicrobial and antioxidant activities.
PubMed:
Determination of E,E-farnesol in Makgeolli (rice wine) using dynamic headspace sampling and stir bar sorptive extraction coupled with gas chromatography-mass spectrometry.
PubMed:
Anti-inflammatory effects of 27 selected terpenoid compounds tested through modulating Th1/Th2 cytokine secretion profiles using murine primary splenocytes.
PubMed:
β-ionone induces cell cycle arrest and apoptosis in human prostate tumor cells.
PubMed:
Novel antibiofilm chemotherapy targets exopolysaccharide synthesis and stress tolerance in Streptococcus mutans to modulate virulence expression in vivo.
PubMed:
Chemoprevention of hepatocarcinogenesis with dietary isoprenic derivatives: cellular and molecular aspects.
PubMed:
Analgesic potential of intrathecal farnesyl thiosalicylic acid and GW 5074 in vincristine-induced neuropathic pain in rats.
PubMed:
Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis).
PubMed:
Alcohol-based quorum sensing plays a role in adhesion and sliding motility of the yeast Debaryomyces hansenii.
PubMed:
Food components with anticaries activity.
PubMed:
Increasing intake of long-chain n-3 PUFA enhances lipoperoxidation and modulates hepatic gene expression in a dose-dependent manner.
PubMed:
Farnesol, an isoprenoid, improves metabolic abnormalities in mice via both PPARα-dependent and -independent pathways.
PubMed:
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
PubMed:
Chemical composition, cytotoxicity effect and antimicrobial activity of Ceratonia siliqua essential oil with preservative effects against Listeria inoculated in minced beef meat.
PubMed:
Development of a novel PPARγ ligand screening system using pinpoint fluorescence-probed protein.
PubMed:
Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.
PubMed:
In vivo and in vitro skin absorption of lipophilic compounds, dibutyl phthalate, farnesol and geraniol in the hairless guinea pig.
PubMed:
d-δ-Tocotrienol-mediated suppression of the proliferation of human PANC-1, MIA PaCa-2, and BxPC-3 pancreatic carcinoma cells.
PubMed:
Fragrance material review on farnesol.
PubMed:
Biphenylalkylacetylhydroquinone ethers suppress the proliferation of murine B16 melanoma cells.
PubMed:
Electrochemical impedance spectroscopy for the study of juvenile hormones-recombinant protein interactions.
PubMed:
Evaluation of an alcohol-based surgical hand disinfectant containing a synergistic combination of farnesol and benzethonium chloride for immediate and persistent activity against resident hand flora of volunteers and with a novel in vitro pig skin model.
PubMed:
Effect of a short contact time with lees on volatile composition of Airen and Macabeo wines.
PubMed:
Farnesol and geraniol chemopreventive activities during the initial phases of hepatocarcinogenesis involve similar actions on cell proliferation and DNA damage, but distinct actions on apoptosis, plasma cholesterol and HMGCoA reductase.
PubMed:
Differential neural responses evoked by orthonasal versus retronasal odorant perception in humans.
PubMed:
Chemical compounds of the foraging recruitment pheromone in bumblebees.
PubMed:
Some advances in the knowledge of grape, wine and distillates chemistry as achieved by mass spectrometry.
PubMed:
Modulation of hepatic and renal drug metabolizing enzyme activities in rats by subchronic administration of farnesol.
PubMed:
Stir bar sorptive extraction applied to volatile constituents evolution during Vitis vinifera ripening.
PubMed:
Studies of the isoprenoid-mediated inhibition of mevalonate synthesis applied to cancer chemotherapy and chemoprevention.
PubMed:
Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone.
PubMed:
Juvenile hormone biosynthesis in larval and adult stick insects, Carausius morosus.
PubMed:
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
PubMed:
Influence of plant growth stage on the essential oil content and composition in Davana (Artemisia pallens wall.).
PubMed:
[Reproductive and developmental toxicity study of prednisolone farnesylate (PNF)--study of subcutaneous administration of PNF during the perinatal and lactation periods in rats].
PubMed:
[Reproductive and developmental toxicity study of prednisolone farnesylate (PNF)--teratogenicity study in rabbits by subcutaneous administration].
PubMed:
[Reproductive and developmental toxicity study of prednisolone farnesylate (PNF)--study by subcutaneous administration of PNF during the period of fetal organogenesis in rats].
PubMed:
[Reproductive and developmental toxicity study of prednisolone farnesylate (PNF)--study by subcutaneous administration of PNF prior to and in the early stages of pregnancy in rats].
PubMed:
Activity of the corpora allata of adult female Leucophaea maderae: effects of mating and feeding.
PubMed:
[The effect of a controlled gas atmosphere on farnesene dynamics and the development of sunburn in apples].
PubMed:
Model studies in terpene biosynthesis.
PubMed:
Superficial scald, a functional disorder of stored apples. IV. Effect of variety, maturity, oiled wraps and diphenylamine on the concentration of alpha-farnesene in the fruit.