alpha-bisabolene
4-(1,5-dimethylhexa-1,4-dien-1-yl)-1-methylcyclohexene
 
Notes:
Flavouring ingredient isol. from bisabol myrrh and other natural sources, e.g. lemon, bergamot
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1-methyl-4-(6-methylhepta-2,5-dien-2-yl)cyclohexene (Click)
CAS Number: 17627-44-0Picture of molecule
Other: 57194-38-4
ECHA EINECS - REACH Pre-Reg: 241-610-9
FDA UNII: SUQ209P6FX
XlogP3-AA: 5.20 (est)
Molecular Weight: 204.35628000
Formula: C15 H24
NMR Predictor: Predict (works with chrome or firefox)
Also(can) Contains: alpha-farnesene
EFSA/JECFA Comments: CASrn in Register refers to the racemate, (Z)- or (E)- isomer not specified. Racemate of (R)- and (S)-isomers, mixture of (E)- and (Z)-isomers (EFFA, 2010a). CASrn in Register refers to the racemate. Composition of stereoisomeric mixture to be specified.
Category: flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
Flavis Number: 01.027 (Old)
DG SANTE Food Flavourings: 01.027  bisabola-1,8,12-triene
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Physical Properties:
Appearance: colorless clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.91200 to 0.91800 @  25.00 °C.
Pounds per Gallon - (est).: 7.589 to  7.639
Refractive Index: 1.48300 to 1.48900 @  20.00 °C.
Boiling Point: 276.00 to  277.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.004000 mm/Hg @ 25.00 °C. (est)
Flash Point: 230.00 °F. TCC ( 110.00 °C. )
logP (o/w): 2.696 (est)
Soluble in:
 alcohol
 water, 0.01161 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
Odor Type: balsamic
Odor Strength: medium
 balsamic  spicy  floral  
Odor Description:
at 100.00 %. 
balsamic spicy floral
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: perfuming agents
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Suppliers:
BOC Sciences
For experimental / research use only.
6-methyl-2-(4-methylcyclohex-3-enyl)hept-2,5-diene
Ernesto Ventós
BISABOLENE
Indukern F&F
ALPHA BISABOLENE NATURAL
Odor: CITRUS, BALSAMIC, SPICY, WOODY
CROP CALENDAR
Indukern F&F
BISABOLENE
Odor: SPICY, BALSAMIC, AGRESTIC, TERPENIC
Parchem
alpha-bisabolene
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
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Safety Information:
 
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
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Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for alpha-bisabolene usage levels up to:
  6.0000 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.024 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 3900 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 7.0000035.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 5.0000025.00000
Edible ices, including sherbet and sorbet (03.0): 10.0000050.00000
Processed fruit (04.1): 7.0000035.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 5.0000025.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 20.00000100.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000
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Safety References:
Flavor & Extract Manufacturers Association (FEMA) reference(s):
The FEMA GRAS assessment of aliphatic and aromatic terpene hydrocarbons used as flavour ingredients.View pdf
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
Scientific opinion on Flavouring Group Evaluation 25, Revision 3 (FGE.25Rev3): Aliphatic hydrocarbons from chemical group 31
View page or View pdf
EPI System: View
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 17627-44-0
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 86597
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 1-methyl-4-(6-methylhepta-2,5-dien-2-yl)cyclohexene
Chemidplus: 0017627440
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References:
 1-methyl-4-(6-methylhepta-2,5-dien-2-yl)cyclohexene
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 17627-44-0
Pubchem (cid): 86597
Pubchem (sid): 135042630
Pherobase: View
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
HMDB (The Human Metabolome Database): HMDB35161
FooDB: FDB013799
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Read: Under the conditions of intended use - New developments in the FEMA GRAS program and the safety assessment of flavor ingredients
Read: A GRAS assessment program for flavor ingredients
Read: Sensory testing for flavorings with modifying properties. Food Technology
Read: Criteria for the safety evaluation of flavoring substances
Read: A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils
Read: FEMA Expert Panel: 30 Years of safety evaluation for the flavor industry
Read: Consumption ratio and food predominance of flavoring materials
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Potential Blenders and core components note
 
For Odor
No odor group found for these
 calamenene 
para-menth-1-en-9-alFL/FR
aldehydic
 agrumen nitrileFR
balsamic
 cinnamyl benzoateFL/FR
 copaiba balsam oilFL/FR
 myrrh resinoidFR
 opoponax oil (balsamodendron kafal)FL/FR
 opoponax resinoid (balsamodendron kafal)FR
cheesy
2-heptanoneFL/FR
earthy
3-octen-2-oneFL/FR
floral
 coriander seed oilFL/FR
 perillyl acetateFL/FR
green
sec-butyl-3-methyl but-2-ene thioateFL/FR
 carrot leaf oil (daucus carota ssp.maximus)FR
 privet dioxaneFR
herbal
 carvacryl methyl etherFL/FR
 coriander seed absoluteFL/FR
 coriander seed concreteFR
 herbal acetalFR
1-para-menthen-9-yl acetateFL/FR
T-muurololFL/FR
3-nonanolFL/FR
curled parsley seed oilFL/FR
 saffron indenoneFL/FR
 safranalFL/FR
 thymyl methyl etherFL/FR
spicy
isobutyl (E,E)-2,4-decadienamideFL/FR
 carrot weed oilFL/FR
 carvacryl ethyl etherFL/FR
 cinnamaldehyde dimethyl acetalFL/FR
(-)-cubenolFL/FR
 cuminyl alcoholFL/FR
black currant bud absoluteFL/FR
sweet marjoram oil (origanum majorana var. tenuifolium weston) cyprus 
 origanum majorana oilFL/FR
 origanum majorana oil moroccoFL/FR
woody
 patchouli absoluteFR
 
For Flavor
 
No flavor group found for these
isobutyl (E,E)-2,4-decadienamideFL/FR
sec-butyl-3-methyl but-2-ene thioateFL/FR
 calamenene 
 carvacryl ethyl etherFL/FR
 carvacryl methyl etherFL/FR
 cinnamyl benzoateFL/FR
2,4-dimethyl anisoleFL
sweet marjoram oil (origanum majorana var. tenuifolium weston) cyprus 
para-menth-1-en-9-alFL/FR
T-muurololFL/FR
3-nonanolFL/FR
 saffron indenoneFL/FR
 hexyl 3-mercaptobutanoateFL
balsamic
 copaiba balsam oilFL/FR
 opoponax oil (balsamodendron kafal)FL/FR
berry
 perillyl acetateFL/FR
cheesy
2-heptanoneFL/FR
creamy
3-octen-2-oneFL/FR
fruity
1-para-menthen-9-yl acetateFL/FR
 carrot weed oilFL/FR
herbal
 coriander seed absoluteFL/FR
 coriander seed oilFL/FR
 origanum majorana oilFL/FR
curled parsley seed oilFL/FR
musty
 thymyl methyl etherFL/FR
spicy
 cinnamaldehyde dimethyl acetalFL/FR
(-)-cubenolFL/FR
 cuminyl alcoholFL/FR
black currant bud absoluteFL/FR
 origanum majorana oil moroccoFL/FR
woody
 safranalFL/FR
 
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Potential Uses:
 bergamotFR
 lemonFR
 myrrhFR
 neroliFR
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Occurrence (nature, food, other): note
 basil absolute sweet @ 0.32%
Data  GC  Search Trop  Picture
 basil oil sweet egypt @ 1.29%
Data  GC  Search Trop  Picture
 basil plant
Search Trop  Picture
 basil shoot oil
Search Trop  Picture
 carrot seed oil @ 3.00%
Data  GC  Search Trop  Picture
 celery seed oil egypt @ 0.12%
Data  GC  Search Trop  Picture
 guava fruit oil reunion @ 0.60%
Data  GC  Search Trop  Picture
 laurel leaf oil turkey @ 0.20%
Data  GC  Search Trop  Picture
 lime fruit
Search Trop  Picture
 oregano plant
Search Trop  Picture
 oregano shoot
Search Trop  Picture
 pepper black pepper fruit oil
Search Trop  Picture
 thyme oil red CO2 extract spain @ 0.8%
Data  GC  Search Trop  Picture
 thyme oil wild or creeping france @ 0.05%
Data  GC  Search Trop  Picture
Synonyms   Articles   Notes   Search   Top
Synonyms:
 bisabola-1,8,12-triene
 bisabola-4,7(11),9-triene
1,8,12-bisabolatriene
a-bisabolene
alpha-bisabolene
 cyclohexene, 4-(1,5-dimethyl-1,4-hexadien-1-yl)-1-methyl-
4-(1,5-dimethyl-1,4-hexadienyl)-1-methyl cyclohexene
4-(1,5-dimethylhexa-1,4-dien-1-yl)-1-methylcyclohexene
 methyl methyl cyclohexenyl heptadiene
6-methyl-2-(4-methyl cyclohex-3-enyl) hept-2,5-diene
6-methyl-2-(4-methylcyclohex-3-enyl)hept-2,5-diene
1-methyl-4-(6-methylhepta-2,5-dien-2-yl)cyclohexene
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Articles:
PubMed: Essential oil composition of Ficus benjamina (Moraceae) and Irvingia barteri (Irvingiaceae).
PubMed: A method for fast analysis of volatile components of Citrus aurantium L. leaves.
PubMed: Chemical composition and antibacterial activity of the essential oils of Ferula vesceritensis Coss et Dur. leaves, endemic in Algeria.
PubMed: Structure of a three-domain sesquiterpene synthase: a prospective target for advanced biofuels production.
PubMed: Changes in volatile compound composition of Antrodia camphorata during solid state fermentation.
PubMed: Bioactive compounds and prebiotic activity in Thailand-grown red and white guava fruit (Psidium guajava L.).
PubMed: [Analysis of the chemical constituents of volatile oil from Asarum insigne by GC-MS].
PubMed: Pheromone attraction and cross-attraction of Nezara, Acrosternum, and Euschistus spp. stink bugs (Heteroptera: Pentatomidae) in the field.
PubMed: [Analysis of volatile oil from Ardisia brevicaulis].
PubMed: The influence of different nutrient levels on insect-induced plant volatiles in Bt and conventional oilseed rape plants.
PubMed: Testing of a heterologous, wound- and insect-inducible promoter for functional genomics studies in conifer defense.
PubMed: Antimicrobial activity of some essential oils against microorganisms deteriorating fruit juices.
PubMed: From terpenoids to aliphatic acids: further evidence for late-instar switch in osmeterial defense as a characteristic trait of swallowtail butterflies in the tribe papilionini.
PubMed: Volatile allelochemicals in the Ageratum conyzoides intercropped citrus orchard and their effects on mites Amblyseius newsami and Panonychus citri.
PubMed: Asymmetric alpha-alkylation of N'-tert-butanesulfinyl amidines. Application to the total synthesis of (6R,7S)-7-amino-7,8-dihydro-alpha-bisabolene.
PubMed: Functional characterization of nine Norway Spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily.
PubMed: Genomic organization of plant terpene synthases and molecular evolutionary implications.
PubMed: Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L.
PubMed: Terpenoid-based defenses in conifers: cDNA cloning, characterization, and functional expression of wound-inducible (E)-alpha-bisabolene synthase from grand fir (Abies grandis).
PubMed: Sesquiterpene synthases from grand fir (Abies grandis). Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization, and bacterial expression of delta-selinene synthase and gamma-humulene synthase.
PubMed: Bisabolene epoxides in sex pheromone innezara viridula (L.) (Heteroptera: Pentatomidae): Role ofcis isomer and relation to specificity of pheromone.
PubMed: Identification of the defensive secretion from soldiers of the North American termite,Amitermes wheeleri (Desneux) (Isoptera: Termitidae).
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