beta-bisabolene
(1R)-bisabola-4,7(11),10(15)-triene
Identification
| Name | beta-bisabolene |
| IUPAC | (4R)-1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohexene |
| CAS Number | 495-61-4 |
| FDA UNII | S19BRC22QA |
| Molecular Formula | C15 H24 |
| Molecular Weight | 204.35628000 |
| Nikkaji Number | J677.682E |
Regulatory
| DG SANTE Food Flavourings | 01.028 beta-bisabolene |
| FEMA Number | 4940 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.87900 to 0.88500 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.314 to 7.364 |
| Refractive Index | 1.48900 to 1.49500 @ 20.00 °C. |
| Boiling Point | 129.00 to 130.00 °C. @ 10.50 mm Hg, 274.00 to 275.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.009000 mmHg @ 25.00 °C. (est) |
| Flash Point | 229.00 °F. TCC ( 109.44 °C. ) |
| logP (o/w) | 6.439 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Description | at 100.00 %. |
Safety Information
| Oral/Parenteral Toxicity | oral-rat LD50 > 5000 mg/kg |
| Dermal Toxicity | Not determined |
| 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 | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for beta-bisabolene usage levels up to | 6.0000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 2.70 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 3900 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| baked goods | 10.00000 |
| beverages(nonalcoholic) | 5.00000 |
| beverages(alcoholic) | 10.00000 |
| breakfast cereal | 5.00000 |
| cheese | - |
| chewing gum | 10.00000 |
| condiments / relishes | - |
| confectionery froastings | 10.00000 |
| egg products | - |
| fats / oils | 5.00000 |
| fish products | - |
| frozen dairy | 7.00000 |
| fruit ices | 10.00000 |
| gelatins / puddings | 5.00000 |
| granulated sugar | - |
| gravies | - |
| hard candy | 10.00000 |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | 5.00000 |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | 7.00000 |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | 10.00000 |
| soups | - |
| sugar substitutes | - |
| sweet sauces | 5.00000 |
| Dairy products, excluding products of category 02.0 (01.0) | 7.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 5.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 10.00000 |
| Processed fruit (04.1) | 7.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 10.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 5.00000 |
| Bakery wares (07.0) | 10.00000 |
| Meat and meat products, including poultry and game (08.0) | 2.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 2.00000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 5.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 10.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 5.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 10.00000 |
| Ready-to-eat savouries (15.0) | 20.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 5.00000 |
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Potential Uses
Natural Occurrence
Synonyms
(1R)-
bisabola-4,7(11),10(15)-triene
(-)-beta-
bisabolene
b-
bisabolene
6-
methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene
(S)-1-
methyl-4-(5-methyl-1-methylene-4-hexenyl) cyclohexene
(4R)-1-
methyl-4-(5-methyl-1-methylenehex-4-en-1-yl)cyclohexene
(4R)-1-
methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohexene
PubMed:
Infection of Corn Ears by Fusarium spp. Induces the Emission of Volatile Sesquiterpenes.
PubMed:
A seco-laurane sesquiterpene and related laurane derivatives from the red alga Laurencia okamurai Yamada.
PubMed:
Isolation of jasmonate-induced sesquiterpene synthase of rice: product of which has an antifungal activity against Magnaporthe oryzae.
PubMed:
Chemical composition, antioxidant, anti-inflammatory and anti-proliferative activities of essential oils of plants from burkina faso.
PubMed:
Chemical composition of the tuber essential oil from Helianthus tuberosus L. (Asteraceae).
PubMed:
Variation of the chemical composition and antimicrobial activity of the essential oils of natural populations of Tunisian Daucus carota L. (Apiaceae).
PubMed:
Chemical composition, larvicidal action, and adult repellency of Thymus magnus against Aedes albopictus.
PubMed:
Variability in the essential-oil composition of Sideritis scardica GRISEB. from native Bulgarian populations.
PubMed:
Suites of terpene synthases explain differential terpenoid production in ginger and turmeric tissues.
PubMed:
Study on the volatile oil contents of Annona glabra L., Annona squamosa L., Annona muricata L. and Annona reticulata L., from Vietnam.
PubMed:
Differences in the volatile compositions of ginseng species (Panax sp.).
PubMed:
Chemotypification of Astrantia major L. (Apiaceae): essential-oil and lignan profiles of fruits.
PubMed:
Comparative study of the chemical composition and biological activities of Magnolia grandiflora and Magnolia virginiana flower essential oils.
PubMed:
A single amino acid determines the site of deprotonation in the active center of sesquiterpene synthases SbTPS1 and SbTPS2 from Sorghum bicolor.
PubMed:
Composition and antioxidant activities of leaf and root volatile oils of Morinda lucida.
PubMed:
Chemical composition and biological activity of the volatile extracts of Achillea millefolium.
PubMed:
Chemical composition and antioxidant activities of essential oils and methanol extracts of three wild Lavandula L. species.
PubMed:
Comparison of headspace solid-phase microextraction with conventional extraction for the analysis of the volatile components in Melia azedarach.
PubMed:
Chemical composition of the essential oil of aerial parts of Haussknechtia elymaitica Boiss. from Iran: a good natural source for trans-asaron.
PubMed:
Dynamic evolution of herbivore-induced sesquiterpene biosynthesis in sorghum and related grass crops.
PubMed:
Identification of essential oil components of Marrubium thessalum Boiss. & Heldr., growing wild in Greece.
PubMed:
Biosynthesis of sesquiterpenes by the fungus Fusarium verticillioides.
PubMed:
Chemical composition and larvicidal activity of Blumea densiflora essential oils against Anopheles anthropophagus: a malarial vector mosquito.
PubMed:
Chemical variability of Copaifera reticulata Ducke oleoresin.
PubMed:
Inter-population variability of terpenoid composition in leaves of Pistacia lentiscus L. from Algeria: a chemoecological approach.
PubMed:
Composition of the essential oil of Bidens tripartita L. roots and its antibacterial and antifungal activities.
PubMed:
Pharmacological evaluation of Copaifera multijuga oil in rats.
PubMed:
Free Radical Scavenging Potential and Essential Oil Composition of the Dorema glabrum Fisch. C.A. Mey Roots from Iran.
PubMed:
Essential oil polymorphism of wild growing Hungarian thyme (Thymus pannonicus) populations in the Carpathian Basin.
PubMed:
Antiplasmodial volatile extracts from Cleistopholis patens Engler & Diels and Uvariastrum pierreanum Engl. (Engl. & Diels) (Annonaceae) growing in Cameroon.
PubMed:
Chemical composition and antibacterial activity of essential oils of Lantana camara, Ageratum houstonianum and Eupatorium adenophorum.
PubMed:
Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers.
PubMed:
Essential oil variation among natural populations of Lavandula multifida L. (Lamiaceae).
PubMed:
Cloning and characterization of a novel gene that encodes (S)-beta-bisabolene synthase from ginger, Zingiber officinale.
PubMed:
[Study on the volatile oil of Murraya exotica].
PubMed:
Chemical composition and antioxidant activities of the essential oil and methanol extracts of Psammogeton canescens.
PubMed:
Chemical composition of the essential oils from the roots of Erigeron acris L. and Erigeron annuus (L.) Pers.
PubMed:
[Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry].
PubMed:
Enrichment of the thymoquinone content in volatile oil from Satureja montana using supercritical fluid extraction.
PubMed:
Antioxidant, alpha-amylase inhibitory and brine-shrimp toxicity studies on Centaurea centaurium L. methanolic root extract.
PubMed:
Chemical characterization and biological activity of essential oils from Daucus carota L. subsp. carota growing wild on the Mediterranean coast and on the Atlantic coast.
PubMed:
Analysis of volatiles in dehydrated carrot samples by solid-phase microextraction followed by GC-MS.
PubMed:
Overexpression of the lemon basil alpha-zingiberene synthase gene increases both mono- and sesquiterpene contents in tomato fruit.
PubMed:
Protonation of a neutral (S)-beta-bisabolene intermediate is involved in (S)-beta-macrocarpene formation by the maize sesquiterpene synthases TPS6 and TPS11.
PubMed:
Antimicrobial activity of essential oils of Ocimum gratissimum L. From different populations of Kenya.
PubMed:
[Analysis of volatile oil in herb of pimpinella candolleana by SPME-GC-MS].
PubMed:
Variability of the needle essential oils of Pinus heldreichii from different populations in Montenegro and Serbia.
PubMed:
Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus.
PubMed:
Quantitative co-occurrence of sesquiterpenes; a tool for elucidating their biosynthesis in Indian sandalwood, Santalum album.
PubMed:
Quantitative determination of eight components in rhizome (Jianghuang) and tuberous root (Yujin) of Curcuma longa using pressurized liquid extraction and gas chromatography-mass spectrometry.
PubMed:
Bisabolanes from the red alga Laurencia scoparia.
PubMed:
Changes in terpene content in milk from pasture-fed cows.
PubMed:
Essential oil composition of diploid and tetraploid clones of ginger (Zingiber officinale Roscoe) grown in Australia.
PubMed:
Analysis by gas chromatography-mass spectrometry of the essential oils from the aerial parts of Pimpinella anagodendron Bolle and Pimpinella rupicola Svent., two endemic species to the Canary Islands, Spain.
PubMed:
Chemical composition, antimicrobial and antioxidant activity of the essential oil of Teucrium marum (Lamiaceae).
PubMed:
Composition and antibacterial activity of essential oil of Lantana achyranthifolia Desf. (Verbenaceae).
PubMed:
Chemical composition and in vitro antimicrobial activities of the essential oils from endemic Psiadia species growing in mauritius.
PubMed:
Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India).
PubMed:
The sesquiterpene hydrocarbons of maize (Zea mays) form five groups with distinct developmental and organ-specific distributions.
PubMed:
Analysis by gas chromatography-mass spectrometry of the essential oil from the aerial parts of Pimpinella junoniae Ceb. & Ort., gathered in La Gomera, Canary Islands, Spain.
PubMed:
Essential oils from two endemic species of Apiaceae from Iran.
PubMed:
Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage.
PubMed:
Analysis of some Italian lemon liquors (limoncello).
PubMed:
Evidence for differential folding of farnesyl pyrophosphate in the active site of aristolochene synthase: a single-point mutation converts aristolochene synthase into an (E)-beta-farnesene synthase.
PubMed:
Volatile sesquiterpene hydrocarbons characteristic for Penicillium roqueforti strains producing PR toxin.
PubMed:
Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew).
PubMed:
[Chemical constituents of essential oil from roots and rhizomes of Valeriana alernifolia Bunge].
PubMed:
Correspondence of soldier defense secretion mixtures with cuticular hydrocarbon phenotypes for chemotaxonomy of the termite genus Reticulitermes in North America.
PubMed:
Production of yarrow (Achillea millefolium L.) in Norway: essential oil content and quality.
PubMed:
The cyclization of farnesyl diphosphate and nerolidyl diphosphate by a purified recombinant delta-cadinene synthase.
PubMed:
The main citral-geraniol and carvacrol chemotypes of the essential oil of thymus pulegioides L. growing wild in vilnius district (Lithuania).
PubMed:
Production of volatile sesquiterpenes by Fusarium sambucinum strains with different abilities to synthesize trichothecenes.
PubMed:
Quantitative analysis of pheromone production in irradiated Caribbean fruit fly males,Anastrepha suspensa (Loew).
PubMed:
[Stomachic principles in ginger. II. Pungent and anti-ulcer effects of low polar constituents isolated from ginger, the dried rhizoma of Zingiber officinale Roscoe cultivated in Taiwan. The absolute stereostructure of a new diarylheptanoid].
PubMed:
Comparison of volatiles emitted by male caribbean and mexican fruit flies.
PubMed:
The essential oil from Thymus praecox ssp. arcticus growing in Iceland.
PubMed:
Identification of the defensive secretion from soldiers of the North American termite,Amitermes wheeleri (Desneux) (Isoptera: Termitidae).