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(E,E)-farnesol

Chemical Structure

General Material Information

Preferred name (E,E)-farnesol
Trivial Name trans-Farnesol
Short Description all-(E)-farnesol
Formula C15 H26 O
CAS Number 106-28-5
FDA UNII X23PI60R17
Nikkaji Number J5.049K
Beilstein Number 1763926
MDL MFCD00002918
xLogP3-AA 4.80 (est)
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • 2,6-di-trans-farnesol
  • 2,6,10-dodecatrien-1-ol, 3,7,11-trimethyl-, (2E,6E)-
  • 2,6,10-dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)-
  • (2-trans,6-trans)- farnesol
  • (2E,6E)- farnesol
  • (E,E)-2,6-farnesol
  • (E)- farnesol
  • 2-trans,6-trans- farnesol
  • all-(E)- farnesol
  • all-trans- farnesol
  • trans, trans- farnesol
  • trans,trans- farnesol
  • (2E,6E)-3,7,11-trimethyl-1-dodeca-2,6,10-trienol
  • (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol
  • (E,E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol
  • trans,trans-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol
  • (2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trien-1-ol
  • 3,7,11-trimethyldodeca-2-trans,6-trans,10-trien-1-ol
  • (2-trans,6-trans)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
  • (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
  • (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
  • 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (2E,6E)-
  • 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)-
  • 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-(farnesol)
  • (2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
  • trans-2,trans-6-Farnesol
  • trans,trans-Farnesol
  • 2,6-Di-trans-farnesol
  • 2,6-trans,trans-Farnesol
  • trans-Farnesol
  • Inhibitor A2
  • 2-trans,6-trans-Farnesol
  • 3,7,11-Trimethyldodeca-2-trans,6-trans,10-trien-1-ol
  • (2E,6E)-Farnesol
  • all-trans-Farnesol
  • (t,t)-Farnesol
  • all-E-Farnesol
  • (E)-β-Farnesol
  • (E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
  • (E,E)-Farnesyl alcohol
  • trans-1-Hydroxy-3,7,11-trimethyl-2,6,10-dodecatriene

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Literature & References

(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):445070
Pubchem (sid):135024870
Flavornet:106-28-5
Pherobase:View
Publications by Info
Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.)
Publications by PubMed
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
Essential oil composition and antimicrobial activities of two closely related species, Alpinia mutica Roxb. and Alpinia latilabris Ridl., from Peninsular Malaysia.
Gold(I) as an artificial cyclase: short stereodivergent syntheses of (-)-epiglobulol and (-)-4β,7α- and (-)-4α,7α-aromadendranediols.
Assessment of the antioxidant and antiproliferative effects of sesquiterpenic compounds in in vitro Caco-2 cell models.
[Tobacco--once a medicinal plant. Does it contain substances with medicinal properties?].
Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach.
Chemical composition and in vitro antimicrobial and antioxidant activities of Citrus aurantium l. flowers essential oil (Neroli oil).
Characterization of essential oil from Citrus aurantium L. flowers: antimicrobial and antioxidant activities.
Determination of E,E-farnesol in Makgeolli (rice wine) using dynamic headspace sampling and stir bar sorptive extraction coupled with gas chromatography-mass spectrometry.
Study of trans-trans farnesol effect on hyphae formation by Yarrowia lipolytica.
β-ionone induces cell cycle arrest and apoptosis in human prostate tumor cells.
Engineered heterologous FPP synthases-mediated Z,E-FPP synthesis in E. coli.
Chemical composition and antifungal activity of Matricaria recutita flower essential oil against medically important dermatophytes and soil-borne pathogens.
Specific involvement of two amino acid residues in cis-nerolidol binding to odorant-binding protein 5 AlinOBP5 in the alfalfa plant bug, Adelphocoris lineolatus (Goeze).
A convergent stereocontrolled total synthesis of (-)-terpestacin.
Comparative study of the chemical composition and biological activities of Magnolia grandiflora and Magnolia virginiana flower essential oils.
Quorum sensing activity in Ophiostoma ulmi: effects of fusel oils and branched chain amino acids on yeast-mycelial dimorphism.
Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis).
Effect of exogenous administration of Candida albicans autoregulatory alcohols in a murine model of hematogenously disseminated candidiasis.
Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
Drimenol: A versatile synthon for compounds with trans-drimane skeleton.
Influences of trans-trans farnesol, a membrane-targeting sesquiterpenoid, on Streptococcus mutans physiology and survival within mixed-species oral biofilms.
Evaluation of the mutagenicity of sesquiterpenic compounds and their influence on the susceptibility towards antibiotics of two clinically relevant bacterial strains.
Application of a multidimensional gas chromatography system with simultaneous mass spectrometric and flame ionization detection to the analysis of sandalwood oil.
Variation in volatile leaf oils of eleven eucalyptus species harvested from korbous arboreta (Tunisia).
The quorum-sensing molecule E,E-farnesol--its variable secretion and its impact on the growth and metabolism of Candida species.
Candida species extracellular alcohols: production and effect in sessile cells.
Production of geranylgeraniol on overexpression of a prenyl diphosphate synthase fusion gene in Saccharomyces cerevisiae.
Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.
Determination of the volatile composition in essential oil of Descurainia sophia (L.) Webb ex Prantl (Flixweed) by gas chromatography/mass spectrometry (GC/MS).
Recovery of E,E-farnesol from cultures of yeast erg9 mutants: extraction with polymeric beads and purification by normal-phase chromatography.
Flowerhead volatile oil composition of soilless culture-grown Chrysanthemum balsamita L.
Quantification approach for assessment of sparkling wine volatiles from different soils, ripening stages, and varieties by stir bar sorptive extraction with liquid desorption.
Overexpression of the gene encoding HMG-CoA reductase in Saccharomyces cerevisiae for production of prenyl alcohols.
Optimisation of stir bar sorptive extraction and liquid desorption combined with large volume injection-gas chromatography-quadrupole mass spectrometry for the determination of volatile compounds in wines.
Synthesis of cordiaquinones B, C, J, and K on the basis of a bioinspired approach and the revision of the relative stereochemistry of cordiaquinone C.
Secretion of E,E-farnesol and biofilm formation in eight different Candida species.
Morphogenesis control in Candida albicans and Candida dubliniensis through signaling molecules produced by planktonic and biofilm cells.
Characterization of (E,E)-farnesol and its fatty acid esters from anal scent glands of nutria (Myocastor coypus) by gas chromatography-mass spectrometry and gas chromatography-infrared spectrometry.
The rice (E)-beta-caryophyllene synthase (OsTPS3) accounts for the major inducible volatile sesquiterpenes.
Analysis of the essential oil of Grindelia discoidea.
Zoledronate inhibits endothelial cell adhesion, migration and survival through the suppression of multiple, prenylation-dependent signaling pathways.
Structure of the human mitochondrial monoamine oxidase B: new chemical implications for neuroprotectant drug design.
Determination of terpenes in tequila by solid phase microextraction-gas chromatography-mass spectrometry.
A soluble form of phosphatase in Saccharomyces cerevisiae capable of converting farnesyl diphosphate into E,E-farnesol.
Isolation and characterization of a monoamine oxidase B selective inhibitor from tobacco smoke.
Volatile constituents of redblush grapefruit (Citrus paradisi) and pummelo (Citrus grandis) peel essential oils from Kenya.
Monitoring farnesol-induced toxicity in tobacco BY-2 cells with a fluorescent analog.
Farnesol concentrations required to block germ tube formation in Candida albicans in the presence and absence of serum.
Responses to sex pheromone and plant odours by olfactory receptor neurons housed in sensilla auricillica of the codling moth, Cydia pomonella (Lepidoptera: Tortricidae).
Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors.
Comprehensive two-dimensional gas chromatography with flame ionization and time-of-flight mass spectrometry detection: qualitative and quantitative analysis of West Australian sandalwood oil.
Farnesol-DMPC phase behaviour: a (2)H-NMR study.
Quorum sensing in Candida albicans: probing farnesol's mode of action with 40 natural and synthetic farnesol analogs.
Detection of farnesyl diphosphate accumulation in yeast ERG9 mutants.
The maize gene terpene synthase 1 encodes a sesquiterpene synthase catalyzing the formation of (E)-beta-farnesene, (E)-nerolidol, and (E,E)-farnesol after herbivore damage.
Squalestatin 1-inducible expression of rat CYP2B: evidence that an endogenous isoprenoid is an activator of the constitutive androstane receptor.
African elephant sesquiterpenes. II. Identification and synthesis of new derivatives of 2,3-dihydrofarnesol.
Alendronate inhibits invasion of PC-3 prostate cancer cells by affecting the mevalonate pathway.
Quorum sensing in the dimorphic fungus Candida albicans is mediated by farnesol.
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
Metabolism of farnesyl diphosphate in tobacco BY-2 cells treated with squalestatin.
Synthesis and biological evaluation of the geometric farnesylated analogues of the a-factor mating peptide of Saccharomyces cerevisiae.
Effects of statins on vascular wall: vasomotor function, inflammation, and plaque stability.
Sex pheromone mimicry in the early spider orchid (ophrys sphegodes): patterns of hydrocarbons as the key mechanism for pollination by sexual deception.
Farnesyl anthranilate suppresses the growth, in vitro and in vivo, of murine B16 melanomas.
Pleiotropic effects of statins in atherosclerosis and diabetes.
Comparison of headspace techniques for sampling volatile natural products in a dynamic system.
Direct vascular effects of HMG-CoA reductase inhibitors.
Studies on the Synthesis of Elegan-Type Linear Diterpenes: The Efficient Total Syntheses of Eleganolone, Eleganolone Acetate, Elegandiol, Eleganonal, and Epoxyeleganolone
Lovastatin induces apoptosis by inhibiting mitotic and post-mitotic events in cultured mesangial cells.
Activators of the nuclear hormone receptors PPARalpha and FXR accelerate the development of the fetal epidermal permeability barrier.
Pharmacological control of the mevalonate pathway: effect on arterial smooth muscle cell proliferation.
Male sex pheromone of a giant danaine butterfly,Idea leuconoe.
Identification and characterization of geranylgeraniol kinase and geranylgeranyl phosphate kinase from the Archaebacterium Sulfolobus acidocaldarius.
Effects of farnesol on the thermotropic behavior of dimyristoylphosphatidylcholine.
Directed cell killing (apoptosis) in human lymphoblastoid cells incubated in the presence of farnesol: effect of phosphatidylcholine.
Differences in sensitivity to farnesol toxicity between neoplastically- and non-neoplastically-derived cells in culture.
Requirement for isoprenoid-dependent posttranslational modifications in the cell-cycle progression of human breast-cancer cells.
Growth inhibition of leukemia cell line CEM-C1 by farnesol: effects of phosphatidylcholine and diacylglycerol.
Chemical analysis of temporal gland secretions collected from an Asian bull elephant during a four-month musth episode.
The conformation of dolichol.
Chemosensory responses in two species of elephants to constituents of temporal gland secretion and musth urine.
Odor mimetism? : Key substances inOphrys lutea-Andrena pollination relationship (Orchidaceae: Andrenidae).
Total synthesis of chain-length-uniform dolichyl phosphates and their fitness to accept hexoses in the enzymatic formation of lipoglycans.
Constituents of temporal gland secretion of the African elephant,Loxodonta africana.
The Nasonov pheromone of the honeybeeApis mellifera L. (Hymenoptera, Apidae). Part II. Bioassay of the components using foragers.
Photosynthetic pigments of green sulfur bacteria. The esterifying alcohols of bacteriochlorophylls c from Chlorobium limicola.
Levels of short-chain fatty acids and of abscisic acid in water-stressed and non-stressed leaves and their effects on stomata in epidermal strips and excised leaves.
Hydrolysis and isomerization of trans,trans-farnesyl diphosphate by Andrographis tissue-culture enzymes.
Comparison between Biosynthesis of ent-Kaurene in Germinating Tomato Seeds and Cell Suspension Cultures of Tomato and Tobacco.
Detection and preliminary identification of endogenous antitranspirants in water-stressed Sorghum plants.
Biosynthesis of trans, trans- and cis, trans-farnesols by soluble enzymes from tissue cultures of Andrographis paniculata.
All-trans-farnesol: a naturally occurring antitranspirant?
Synthesis of cecropia juvenile hormone from trans,trans-farnesol.
Lipid metabolism in helminth parasites--VI. Synthesis of 2-cis,6-trans farnesol by Hymenolepis diminuta (Cestoda).

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C01126
HMDB (The Human Metabolome Database):Search
FooDB:FDB014516
YMDB (Yeast Metabolome Database):YMDB00404
Export Tariff Code:2905.22.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•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

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 222.37141418457
Specific gravity @ 25 °C
Pounds per Gallon 7.356 to 7.397
Refractive Index 1.487 to 1.494 @ 20 °C
Boiling Point 283 to 284°C @ 760 mm Hg
Vapor Pressure 0.00037 mmHg @ 25 °C
Vapor Density 1
Flash Point TCC Value 110 °C TCC
logP (o/w) 5.314 est
Solubility
alcohol Yes
water, 1.287 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Floral
muguet, floral, sweet, lily, waxy
Odor strength low
General comment At 100.00 %. mild muguet floral sweet lily waxy
Used in rose and other floral compositions. Subtle, green, floral

Occurrences

Potential Uses

Applications
Odor purposes Aldehydic, Floral, Lily, Lily of the valley
Other purposes Waxy

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 6000 mg/kg
THERAP
27,893,1972

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
27,893,1972

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
IFRA Critical Effect:
Sensitization
View IFRA Standards Library for complete information.
Please review Amendment 49 IFRA documentation for complete information.
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%):
Category 1: Products applied to the lips
0.08 %
Category 2: Products applied to the axillae
0.11 %
Category 3: Products applied to the face/body using fingertips
0.40 %
Category 4: Products related to fine fragrance
1.20 %
Category 5: Products applied to the face and body using the hands (palms), primarily leave-on
Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on
0.60 %
Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on
Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on
Category 5D: Baby Creams, baby Oils and baby talc
Category 6: Products with oral and lip exposure
2.00 %
Category 7: Products applied to the hair with some hand contact
Category 7A: Rinse-off products applied to the hair with some hand contact
0.20 %
Category 7B: Leave-on products applied to the hair with some hand contact
Category 8: Products with significant anogenital exposure
2.00 %
Category 9: Products with body and hand exposure, primarily rinse off
5.00 %
Category 10: Household care products with mostly hand contact
Category 10A: Household care excluding aerosol products (excluding aerosol/spray products)
2.50 %
Category 10B: Household aerosol/spray products
Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate
Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
See Note %
Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin
Notes:
IFRA FLAVOR REQUIREMENTS:

Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.

(1) IFRA would recommend that any material used to impart perfume or flavour in products intended for human ingestion should consist of ingredients that are in compliance with appropriate regulations for foods and food flavourings in the countries of planned distribution and, where these are lacking, with the recommendations laid down in the Code of Practice of IOFI (International Organisation of the Flavor Industry). Further information about IOFI can be found on its website (www.iofi.org).

(2) Category 11 includes all non-skin contact or incidental skin contact products. Due to the negligible skin contact from these types of products there is no justification for a restriction of the concentration of this fragrance ingredient in the finished product.

Recommendation for (E,E)-farnesol flavor usage levels up to:
2.0000 ppm in the finished product.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):106-28-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :445070
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Chemidplus:0000106285
RTECS:JR4979000 for cas# 106-28-5