bergamotene
6-methyl-4-methylidene-7-(4-methylpent-3-enyl)bicyclo[3.1.1]heptane
 
Notes:
None found
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CAS Number: 6895-56-3Picture of molecule3D/inchi
FDA UNII: 2H330CKD1Z
Nikkaji Web: J3.124.840J
XlogP3-AA: 5.10 (est)
Molecular Weight: 204.35628000
Formula: C15 H24
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Appearance: pale green clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 260.00 to  261.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.020000 mmHg @ 25.00 °C. (est)
Flash Point: 213.00 °F. TCC ( 100.56 °C. )
logP (o/w): 6.535 (est)
Soluble in:
 alcohol
 water, 0.02557 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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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: natural substances and extractives
Recommendation for bergamotene usage levels up to:
 not for fragrance use.
 
Recommendation for bergamotene flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 521569
National Institute of Allergy and Infectious Diseases: Data
 6-methyl-2-methylidene-6-(4-methylpent-3-enyl)bicyclo[3.1.1]heptane
Chemidplus: 0006895563
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References:
 6-methyl-2-methylidene-6-(4-methylpent-3-enyl)bicyclo[3.1.1]heptane
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 521569
Pubchem (sid): 135199796
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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
HMDB (The Human Metabolome Database): Search
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 lavender oil CO2 extract france @ 0.19%
Data  GC  Search Trop  Picture
 lavender oil spike spain @ 0.11%
Data  GC  Search Trop  Picture
 lavender oil spike spain @ 0.13%
Data  GC  Search Trop  Picture
 lavender oil spike spain @ 0.22%
Data  GC  Search Trop  Picture
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Synonyms:
beta-bergamotene
 bicyclo(3.1.1)heptane, 6-methyl-2-methylene-6-(4-methyl-3-pentenyl)-
6-methyl-2-methylene-6-(4-methyl-3-pentenyl) bicyclo(3.1.1)heptane
6-methyl-2-methylidene-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]heptane
6-methyl-4-methylidene-7-(4-methylpent-3-enyl)bicyclo[3.1.1]heptane
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Articles:
PubMed: The fumagillin biosynthetic gene cluster in Aspergillus fumigatus encodes a cryptic terpene cyclase involved in the formation of β-trans-bergamotene.
PubMed: Revisiting sesquiterpene biosynthetic pathways leading to santalene and its analogues: a comprehensive mechanistic study.
PubMed: Biosynthesis of Sandalwood Oil: Santalum album CYP76F cytochromes P450 produce santalols and bergamotol.
PubMed: Sesquiterpenes from the inner bark of the silver birch and the paper birch.
PubMed: Dynamic evolution of herbivore-induced sesquiterpene biosynthesis in sorghum and related grass crops.
PubMed: Molecular and biochemical evolution of maize terpene synthase 10, an enzyme of indirect defense.
PubMed: Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway.
PubMed: Chemical composition, antioxidant, anti-inflammatory and anti-proliferative activities of essential oils of plants from burkina faso.
PubMed: Chemical composition and antioxidant activity of essential oil from berries of Schisandra chinensis (Turcz.) Baill.
PubMed: Molecular regulation of santalol biosynthesis in Santalum album L.
PubMed: Topical anti-inflammatory constituents of lipophilic leaf fractions of Alchornea floribunda and Alchornea cordifolia.
PubMed: Bacteria isolated from roots and rhizosphere of Vitis vinifera retard water losses, induce abscisic acid accumulation and synthesis of defense-related terpenes in in vitro cultured grapevine.
PubMed: Priming of Production in Maize of Volatile Organic Defence Compounds by the Natural Plant Activator cis-Jasmone.
PubMed: Analyzing blends of herbivore-induced volatile organic compounds with factor analysis: revisiting "cotton plant, Gossypium hirsutum L., defense in response to nitrogen fertilization".
PubMed: Essential oils from five species of Annonaceae from Vietnam.
PubMed: Sandalwood fragrance biosynthesis involves sesquiterpene synthases of both the terpene synthase (TPS)-a and TPS-b subfamilies, including santalene synthases.
PubMed: GC-MS profiling of the phytochemical constituents of the oleoresin from Copaifera langsdorffii Desf. and a preliminary in vivo evaluation of its antipsoriatic effect.
PubMed: Molecular cloning and characterization of (+)-epi-α-bisabolol synthase, catalyzing the first step in the biosynthesis of the natural sweetener, hernandulcin, in Lippia dulcis.
PubMed: Chemical variability of Copaifera reticulata Ducke oleoresin.
PubMed: Characterization of two genes for the biosynthesis of the labdane diterpene Z-abienol in tobacco (Nicotiana tabacum) glandular trichomes.
PubMed: Chemical composition of essential oils from leaves, stems, flower heads and roots of Conyza bonariensis L. from Tunisia.
PubMed: Less is more: treatment with BTH and laminarin reduces herbivore-induced volatile emissions in maize but increases parasitoid attraction.
PubMed: Multidimensional enantio gas chromtography/mass spectrometry and gas chromatography-combustion-isotopic ratio mass spectrometry for the authenticity assessment of lime essential oils (C. aurantifolia Swingle and C. latifolia Tanaka).
PubMed: Theoretical calculations on carbocations involved in the biosynthesis of bergamotenes and related terpenes--the same and not the same.
PubMed: Chemical composition and antioxidant activity of the essential oil of Schisandra chinensis fruits.
PubMed: Volatile constituents of two species of Protium from the Atlantic rainforest in the state of Pernambuco, Brazil.
PubMed: Comparison of the essential oils of leaves and stem bark from two different populations of Drimys winteri a Chilean herbal medicine.
PubMed: A novel pathway for sesquiterpene biosynthesis from Z,Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites.
PubMed: [Microscopic anatomy and volatile secondary metabolites at three stages of development of the inflorescences of Lantana camara (Verbenaceae)].
PubMed: Pharmacological evaluation of Copaifera multijuga oil in rats.
PubMed: Solid-phase microextraction (SPME) analysis of six Italian populations of Ephedra nebrodensis Tineo ex Guss. subsp. nebrodensis.
PubMed: Behavioral responses of the leafhopper, Cicadulina storeyi China, a major vector of maize streak virus, to volatile cues from intact and leafhopper-damaged maize.
PubMed: [Study on the volatile oil of Murraya exotica].
PubMed: Chemical composition and larvicidal activity against Aedes aegypti larvae of essential oils from four Guarea species.
PubMed: Analysis of sesquiterpene emissions by plants using solid phase microextraction.
PubMed: Molecular interactions between the specialist herbivore Manduca sexta (Lepidoptera, Sphigidae) and its natural host Nicotiana attenuata. VIII. An unbiased GCxGC-ToFMS analysis of the plant's elicited volatile emissions.
PubMed: Polymorphism in jasmonate signaling partially accounts for the variety of volatiles produced by Nicotiana attenuata plants in a native population.
PubMed: Comparison of cultivars of ornamental crop Gerbera jamesonii on production of spider mite-induced volatiles, and their attractiveness to the predator Phytoseiulus persimilis.
PubMed: Yield and oil composition of 38 basil (Ocimum basilicum L.) accessions grown in Mississippi.
PubMed: Overexpression of the lemon basil alpha-zingiberene synthase gene increases both mono- and sesquiterpene contents in tomato fruit.
PubMed: In situ volatile collection, analysis, and comparison of three Centaurea species and their relationship to biocontrol with herbivorous insects.
PubMed: Individual variability in herbivore-specific elicitors from the plant's perspective.
PubMed: Nitrogen supply influences herbivore-induced direct and indirect defenses and transcriptional responses in Nicotiana attenuata.
PubMed: The influence of intact-plant and excised-leaf bioassay designs on volicitin- and jasmonic acid-induced sesquiterpene volatile release in Zea mays.
PubMed: Evaluation of extracts and oils of mosquito (Diptera: Culicidae) repellent plants from Sweden and Guinea-Bissau.
PubMed: The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores.
PubMed: Analysis of leaf surface sesquiterpenes in potato varieties.
PubMed: Identification of volatile constituents of Tambourissa leptophylla.
PubMed: Defensive function of herbivore-induced plant volatile emissions in nature.
PubMed: Genetic control and evolution of sesquiterpene biosynthesis in Lycopersicon esculentum and L. hirsutum.
PubMed: Increased SA in NPR1-silenced plants antagonizes JA and JA-dependent direct and indirect defenses in herbivore-attacked Nicotiana attenuata in nature.
PubMed: Nitroalkenes and sesquiterpene hydrocarbons from the frontal gland of three prorhinotermes termite species.
PubMed: Cloning and functional characterization of three terpene synthases from lavender (Lavandula angustifolia).
PubMed: Co(i)-ordinating defenses: NaCOI1 mediates herbivore- induced resistance in Nicotiana attenuata and reveals the role of herbivore movement in avoiding defenses.
PubMed: Chemical composition and anti-inflammatory activity of copaiba oils from Copaifera cearensis Huber ex Ducke, Copaifera reticulata Ducke and Copaifera multijuga Hayne--a comparative study.
PubMed: Sesquiterpene emissions from pine trees--identifications, emission rates and flux estimates for the contiguous United States.
PubMed: Quantitative co-occurrence of sesquiterpenes; a tool for elucidating their biosynthesis in Indian sandalwood, Santalum album.
PubMed: Silencing of a germin-like gene in Nicotiana attenuata improves performance of native herbivores.
PubMed: The piercing-sucking herbivores Lygus hesperus and Nezara viridula induce volatile emissions in plants.
PubMed: [Study of chemical constituents of essential oil from flowers of Mikania micrantha H.B.K].
PubMed: Trans-bergamotenes-male pheromone of the ectoparasitoid Melittobia digitata.
PubMed: Male lures for mediterranean fruitfly (Ceratitis capitata wied.): Structural analogs of α-copaene.
PubMed: Additional male mediterranean fruitfly (Ceratitis capitata wied.) Attractants from Angelica seed oil (Angelica archangelica L.).
PubMed: Comparison of volatiles emitted by male caribbean and mexican fruit flies.
PubMed: Isolation and identification of allelochemicals that attract the larval parasitoid,Cotesia marginiventris (Cresson), to the microhabitat of one of its hosts.
PubMed: Composition of the essential oil of Ocimum canum grown in Rwanda.
PubMed: Using 'mute' plants to translate volatile signals.
PubMed: The sesquiterpene hydrocarbons of maize (Zea mays) form five groups with distinct developmental and organ-specific distributions.
PubMed: Chemical composition of volatile oil from Cinnamomum zeylanicum buds.
PubMed: Synthesis of the racemate of (Z)-exo-alpha-bergamotenal, a pheromone component of the white-spotted spined bug, Eysarcoris parvus Uhler.
PubMed: Chemical composition of the flower oil of Cinnamomum zeylanicum blume.
PubMed: Silencing the jasmonate cascade: induced plant defenses and insect populations.
PubMed: Molecular interactions between the specialist herbivore Manduca sexta (Lepidoptera, Sphingidae) and its natural host Nicotiana attenuata. III. Fatty acid-amino acid conjugates in herbivore oral secretions are necessary and sufficient for herbivore-specific plant responses.
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