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General Material Information

Preferred name alpha-farnesene
Trivial Name Farnesene
Short Description (3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene
Formula C15 H24
CAS Number 502-61-4
Deleted CAS Number 21499-64-9
FEMA Number 3839
Flavis Number 1.04
ECHA Number 207-948-6
FDA UNII 7E1785CZ0H
Nikkaji Number J47.112G
MDL MFCD00036650
COE Number 10998
xLogP3-AA 6.10 (est)
NMR Predictor External link
JECFA Food Flavoring 1343 alpha-farnesene
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 502-61-4 ; FARNESENE
Synonyms
  • (E)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene
  • 7,11-dimethyl-3-methylene-1,6,10-dodecatriene
  • (E)-7,11-dimethyl-3-methylenedodeca-1,6,10-triene
  • 1,3,6,10-dodecatetraene, 3,7,11-trimethyl-, (3E,6E)-
  • (3E,6E)-3,7,11-trimethyl-1,3,6,10-dodecatetraene
  • (E,E)-3,7,11-trimethyl-1,3,6,10-dodecatetraene; 2,6,10-trimethyl-2,6,9,10-dodecatetrene
  • (3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene
  • (E,E)-alpha- farnesene
  • (3E,6E)-alpha- farnesene
  • (3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene
  • 1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-, (3E,6E)-
  • Farnesene
  • 1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-, (E,E)-
  • (3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene
  • α-Farnesene
  • trans-2,6,10-Trimethyl-2,6,9,11-dodecatetraene
  • trans-3,7,11-Trimethyl-1,3,6,10-dodecatetraene
  • trans,trans-α-Farnesene
  • trans-α-Farnesene
  • (E,E)-α-Farnesene
  • (3E,6E)-α-Farnesene

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:502-61-4
Pubchem (cid):5281516
Pubchem (sid):134978777
Flavornet:502-61-4
Pherobase:View
Publications by US Patents
Use of isomeric farnesene product-by-process for augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles
Use of isomeric mixtures of farnesene for augmenting or enhancing the aroma of detergent compositions
Use of isomeric farnesene product-by-process for augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles
Publications by PubMed
Use of hydrodistillation and headspace solid-phase microextraction to characterize the volatile composition of different hop cultivars.
Cell wall, cell membrane, and volatile metabolism are altered by antioxidant treatment, temperature shifts, and peel necrosis during apple fruit storage.
Isolation and characterization of terpene synthases potentially involved in flavor development of ripening olive (Olea europaea) fruits.
The compositions of volatiles and aroma-active compounds in dried omija fruits (Schisandra chinensis Baillon) according to the cultivation areas.
Heritability and genetic and phenotypic correlations of apple (Malus x domestica) fruit volatiles in a genetically diverse breeding population.
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
Changes in the volatile compounds and chemical and physical properties of Kuerle fragrant pear (Pyrus serotina Reld) during storage.
Screening for key odorants in Moroccan green olives by gas chromatography-olfactometry/aroma extract dilution analysis.
Aroma evaluation of an aquatic herb, Changpo (Acorus calamus Var. angustatus Bess), by AEDA and SPME.
Changes of the volatile profile and artifact formation in Daidai (Citrus aurantium) cold-pressed peel oil on storage.
Character impact odorants of Citrus Hallabong [(C. unshiu Marcov x C. sinensis Osbeck) x C. reticulata Blanco] cold-pressed peel oil.
Volatile flavor components of ripe and overripe ki-mikans (Citrus flaviculpus Hort. ex Tanaka) in comparison with Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
Characterization of the key aroma compounds in dried fruits of the West African peppertree Xylopia aethiopica (Dunal) A. Rich (Annonaceae) using aroma extract dilution analysis.
Relationship between ethylene response manipulation and volatile production in Jonagold variety apples.
Expression of terpene synthase genes associated with the formation of volatiles in different organs of Vitis vinifera.
Narrow tuning of an odorant receptor to plant volatiles in Spodoptera exigua (Hübner).
'Scarlett Spur Red Delicious' apple volatile production accompanying physiological disorder development during low pO2 controlled atmosphere storage.
A new source of elemol rich essential oil and existence of multicellular oil glands in leaves of the Dioscorea species.
Combined effect of temperature and controlled atmosphere on storage and shelf-life of 'Rocha' pear treated with 1-methylcyclopropene.
Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach.
Modulation of aphid alarm pheromone emission of pea aphid prey by predators.
Apple volatiles synergize the response of codling moth to pear ester.
Use of hydrodistillation and headspace solid-phase microextraction to characterize the volatile composition of different hop cultivars.
Cell wall, cell membrane, and volatile metabolism are altered by antioxidant treatment, temperature shifts, and peel necrosis during apple fruit storage.
Functional genomics reveals that a compact terpene synthase gene family can account for terpene volatile production in apple.
Volatiles from apple trees infested with light brown apple moth larvae attract the parasitoid Dolichogenidia tasmanica.
Aphid alarm pheromone as a cue for ants to locate aphid partners.
Aerosol delivery of trail pheromone disrupts the foraging of the red imported fire ant, Solenopsis invicta.
Differences in the volatile compositions of ginseng species (Panax sp.).
Aphid alarm pheromone: an overview of current knowledge on biosynthesis and functions.
Essential oil from Ocimum basilicum (Omani Basil): a desert crop.
The compositions of volatiles and aroma-active compounds in dried omija fruits (Schisandra chinensis Baillon) according to the cultivation areas.
A non-synonymous nucleotide substitution can account for one evolutionary route to sesquiterpene synthase activity in the TPS-b subgroup.
New analogues of (E)-β-farnesene with insecticidal activity and binding affinity to aphid odorant-binding proteins.
Constitutive emission of the aphid alarm pheromone, (E)-β-farnesene, from plants does not serve as a direct defense against aphids.
Floral sesquiterpenes and their synthesis in dioecious kiwifruit.
Trail pheromone disruption of red imported fire ant.
Evolution of sesquiterpene hydrocarbons in virgin olive oil during fruit ripening.
Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.
Biotic and abiotic factors affect green ash volatile production and emerald ash borer adult feeding preference.
Heritability and genetic and phenotypic correlations of apple (Malus x domestica) fruit volatiles in a genetically diverse breeding population.
Studies on the antioxidant activity of essential oil and different solvent extracts of Vitexagnuscastus L. fruits from Turkey.
Two terpene synthases are responsible for the major sesquiterpenes emitted from the flowers of kiwifruit (Actinidia deliciosa).
Plant odor analysis of potato: response of guatemalan moth to above- and belowground potato volatiles.
Attraction of New Zealand flower thrips, Thrips obscuratus, to cis-jasmone, a volatile identified from Japanese honeysuckle flowers.
Chemical composition, antibacterial and antioxidant activities of leaf essential oil and extracts of Metasequioa glyptostroboides Miki ex Hu.
Superficial scald and bitter pit development in cold-stored transgenic apples suppressed for ethylene biosynthesis.
Defining the potassium binding region in an apple terpene synthase.
In vivo ESR spin trapping detection of carbon-centered alpha-Farnesene radicals.
In situ volatile collection, analysis, and comparison of three Centaurea species and their relationship to biocontrol with herbivorous insects.
Ethylene and alpha-farnesene metabolism in green and red skin of three apple cultivars in response to 1-methylcyclopropene (1-MCP) treatment.
Oxidation products of alpha-farnesene associated with superficial scald development in d'Anjou pear fruits are conjugated trienols.
Unusual features of a recombinant apple alpha-farnesene synthase.
Changes in the volatile compounds and chemical and physical properties of Kuerle fragrant pear (Pyrus serotina Reld) during storage.
Volatile constituents of redblush grapefruit (Citrus paradisi) and pummelo (Citrus grandis) peel essential oils from Kenya.
Effects of cyclamen mite (Phytonemus pallidus) and leaf beetle (Galerucella tenella) damage on volatile emission from strawberry (Fragaria x ananassa Duch.) plants and orientation of predatory mites (Neoseiulus cucumeris, N. californicus, and Euseius finlandicus).
Relationship of superficial scald development and alpha-farnesene oxidation to reactions of diphenylamine and diphenylamine derivatives in Cv. Granny Smith apple peel.
1-Methylcyclopropene interactions with diphenylamine on diphenylamine degradation, alpha-farnesene and conjugated trienol concentrations, and polyphenol oxidase and peroxidase activities in apple fruit.
Identification of characteristic aroma-active compounds from water dropwort (Oenanthe javanica DC.).
Analysis of hop-derived terpenoids in beer and evaluation of their behavior using the stir bar-sorptive extraction method with GC-MS.
Screening for key odorants in Moroccan green olives by gas chromatography-olfactometry/aroma extract dilution analysis.
Aroma evaluation of an aquatic herb, Changpo (Acorus calamus Var. angustatus Bess), by AEDA and SPME.
Ester variability in apple varieties as determined by solid-phase microextraction and gas chromatography-mass spectrometry.
Chemical composition and in vitro antimicrobial activities of the essential oils from endemic Psiadia species growing in mauritius.
Character impact odorants of Citrus Hallabong [(C. unshiu Marcov x C. sinensis Osbeck) x C. reticulata Blanco] cold-pressed peel oil.
Solid-phase microextraction of volatile compounds from the chopped leaves of three species of Eucalyptus.
Differences in the fragrances of pollen, leaves, and floral parts of garland (Chrysanthemum coronarium) and composition of the essential oils from flowerheads and leaves.
Volatiles from leaves, fruits, and virgin oil from Olea europaea Cv. Olivastra Seggianese from Italy.
Effects of storage conditions on the composition of Citrus tamurana Hort. ex Tanaka (hyuganatsu) essential oil.
Plant odor analysis of apple: antennal response of codling moth females to apple volatiles during phenological development.
Sesquiterpene, alkene, and alkane hydrocarbons in virgin olive oils of different varieties and geographical origins.
Volatile flavor components of ripe and overripe ki-mikans (Citrus flaviculpus Hort. ex Tanaka) in comparison with Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
Composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu).
Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps pamp.).
Volatile components of green walnut husks.
Stripped corn oil controls scald and maintains volatile production potential in golden supreme and delicious apples.
Characterization of the key aroma compounds in dried fruits of the West African peppertree Xylopia aethiopica (Dunal) A. Rich (Annonaceae) using aroma extract dilution analysis.
Relationship between ethylene response manipulation and volatile production in Jonagold variety apples.
Effect of superficial scald suppression by diphenylamine application on volatile evolution by stored Cortland apple fruit.
Aphids, predators and parasitoids.
Chemical, physical and antimicrobial properties of essential oils of Leptospermum scoparium and Kunzea ericoides.
Solid phase microextraction for quantitative headspace sampling of apple volatiles.
(Z,E)-alpha-farnesene--an electroantennogram-active component of Maladera matrida volatiles.
[The effect of a controlled gas atmosphere on farnesene dynamics and the development of sunburn in apples].
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.

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
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09665
HMDB (The Human Metabolome Database):HMDB36066
FooDB:FDB014895
Export Tariff Code:2901.29.6000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 204.35627746582
Specific gravity @ 25 °C
Pounds per Gallon 7.023 to 7.314
Refractive Index 1.49 to 1.505 @ 20 °C
Boiling Point 260 to 262°C @ 760 mm Hg
Vapor Pressure 0.01 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 6.139 est
Solubility
alcohol Yes
water, 0.01053 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Woody
citrus, herbal, lavender, bergamot, myrrh, neroli, green, woody, vegetable, floral
Luebke, William tgsc, (1996) At 100.00 %. citrus herbal lavender bergamot myrrh neroli green
Mosciano, Gerard P&F 25, No. 1, 49, (2000) At 1.00 % in ethyl alcohol. Woody, green vegetative with a hint of a floral nuance. It has a slight gin herbal and citrus dry out
Flavor Type: Green
fresh, green, vegetable, celery, hay, fatty, tropical, fruity
Mosciano, Gerard P&F 25, No. 1, 49, (2000) At 10.00 - 20.00 ppm. Fresh green vegetative, with celery and hay nuances and somewhat fatty and tropical fruity afternotes
Excellent for terpene notes of gin, carrot, mango, lime, herbal notes of celery, parsley. Terpeny, herbal, slight celery notes

Occurrences

Potential Uses

Applications
Odor purposes Bergamot, Berry, Citrus, Gardenia, Green, Herbal, Juniper berry, Lavender, Melon, Myrrh, Neroli, Raspberry, Woody
Flavoring purposes Gin, Tea, Tropical
Cosmetic purposes Fragrance, Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 36 - Wear suitable protective clothing.
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:
Not determined
Dermal Toxicity:
Not determined
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
Recommendation for alpha-farnesene usage levels up to:
8.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.61 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 40.00 (μg/capita/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 18
Click here to view publication 18
average usual ppmaverage maximum ppm
baked goods: 10.0000050.00000
beverages(nonalcoholic): 5.0000020.00000
beverages(alcoholic): 5.0000020.00000
breakfast cereal: 10.0000050.00000
cheese: 2.0000010.00000
chewing gum: 30.0000090.00000
condiments / relishes: 5.0000015.00000
confectionery froastings: 20.0000060.00000
egg products: --
fats / oils: 5.0000030.00000
fish products: 1.000005.00000
frozen dairy: 5.0000040.00000
fruit ices: 5.0000020.00000
gelatins / puddings: 2.0000010.00000
granulated sugar: --
gravies: 5.0000020.00000
hard candy: 10.0000050.00000
imitation dairy: 1.000005.00000
instant coffee / tea: 5.0000020.00000
jams / jellies: 2.0000010.00000
meat products: 1.000005.00000
milk products: 10.0000030.00000
nut products: 5.0000020.00000
other grains: 10.0000050.00000
poultry: 1.000005.00000
processed fruits: 5.0000030.00000
processed vegetables: 2.0000010.00000
reconstituted vegetables: 5.0000020.00000
seasonings / flavors: 10.0000050.00000
snack foods: 5.0000020.00000
soft candy: 10.0000030.00000
soups: 5.0000020.00000
sugar substitutes: 1.0000010.00000
sweet sauces: 2.0000010.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 25, (FGE.25)[1] - Aliphatic and aromatic hydrocarbons from chemical group 31 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 78 (FGE.78)[1] - Consideration of Aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25 - Scientific Opinion of the Panel on Food Additives,Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 25Rev1: Aliphatic and aromatic hydrocarbons from chemical group 31
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 78, Revision 1 (FGE.78Rev1): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25Rev2
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 25, Revision 2 (FGE.25Rev2): Aliphatic and aromatic hydrocarbons from chemical group 31
View page or View pdf

Statement on List of Representative Substances for Testing. The current Statement lays down a list of substances in sub-groups with representative substances for which additional data are required prior to their evaluation through the Procedure (Regulation (EC) No 1565/2000).
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 78, Revision 2 (FGE.78Rev2): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic hydrocarbons evaluated by EFSA in FGE.25Rev3
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):502-61-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281516
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene
Chemidplus:0000502614