bergamotene
6-methyl-4-methylidene-7-(4-methylpent-3-enyl)bicyclo[3.1.1]heptane
Identification
| Name | bergamotene |
| IUPAC | 6-methyl-2-methylidene-6-(4-methylpent-3-enyl)bicyclo[3.1.1]heptane |
| CAS Number | 6895-56-3 |
| FDA UNII | 2H330CKD1Z |
| Molecular Formula | C15 H24 |
| Molecular Weight | 204.35628000 |
| Nikkaji Number | J3.124.840J |
Regulatory
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 |
| Insoluble in | water |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| 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 | 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. |
No supplier data available
Potential Uses
Natural Occurrence
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
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.