alpha-bergamotene

(1R*,5R*,6R*)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

CAS: 17699-05-7 C15 H24 MW: 204.35628000

Identification

Namealpha-bergamotene
CAS Number17699-05-7
EINECS241-702-9
FDA UNIISearch
Molecular FormulaC15 H24
Molecular Weight204.35628000
Nikkaji NumberJ38.585I

Regulatory

Physical Properties

Appearance pale green clear liquid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 259.00 to 260.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.021000 mmHg @ 25.00 °C. (est)
Flash Point 213.00 °F. TCC ( 100.56 °C. )
logP (o/w) 7.302 (est)
Soluble in alcohol

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for alpha-bergamotene usage levels up tonot for fragrance use.
Recommendation for alpha-bergamotene flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

alpinia galanga oil @ 10.70% Data basil oil basil plant bergamot oil turkey @ 0.28% Data calamus root oil mongolia @ 1.00% Data carrot root carrot seed carrot seed oil @ 0.28% Data curcuma amada roxb. rhizome oil india @ 0.20% Data daucus carota ssp. maximus leaf oil @ 0.51% Data grapefruit oil c.p. @ 0.01% Data grapefruit oil CO2 extract @ 0.07% Data guaiacwood oil @ 0.07% Data lemon oil lemon petiole lemongrass oil yunnan @ 0.21% Data lime fruit lime oil expressed florida @ 0.8% Data mace oil CO2 extract @ 0.10% Data nutmeg extract CO2 west indian @ trace% Data nutmeg oil ocimum basilicum herb oil poland @ 2.18% Data orange fruit parsley leaf oil @ 0.02% Data sugandha kokila berry oil @ 0.70% Data turmeric root oil CO2 extract @ 1.40% Data zingiber officinale oil CO2 extract australia @ 10.83% Data

Synonyms

a- bergamotene bicyclo(3.1.1)hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- bicyclo[3.1.1]hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-penten-1-yl)- bicyclo[3.1.1]hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- (1R*,5R*,6R*)-2,6- dimethyl-6-(4-methyl pent-3-en-1-yl) bicyclo(3.1.1)hept-2-ene 2,6- dimethyl-6-(4-methyl-3-pentenyl) bicyclo(3.1.1)hept-2-ene 2,6- dimethyl-6-(4-methyl-3-pentenyl)-2-norpinene 2,6- dimethyl-6-(4-methyl-3-pentenyl)bicyclo(3.1.1)hept-2-ene 2,6- dimethyl-6-(4-methyl-3-pentenyl)bicyclo[3.1.1]hept-2-ene (1R*,5R*,6R*)-2,6- dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene 2,6- dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene 4,7- dimethyl-7-(4-methylpent-3-enyl)bicyclo[3.1.1]hept-3-ene 2- norpinene, 2,6-dimethyl-6-(4-methyl-3-pentenyl) 2- norpinene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- PubMed: Ectopic Terpene Synthase Expression Enhances Sesquiterpene Emission in Nicotiana attenuata without Altering Defense or Development of Transgenic Plants or Neighbors. PubMed: Characterization of two monoterpene synthases involved in floral scent formation in Hedychium coronarium. PubMed: The volatome of Aspergillus fumigatus. PubMed: Chemical composition, antioxidant, anti-inflammatory and anti-proliferative activities of essential oils of plants from burkina faso. PubMed: Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway. PubMed: Biosynthesis of Sandalwood Oil: Santalum album CYP76F cytochromes P450 produce santalols and bergamotol. 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: Molecular regulation of santalol biosynthesis in Santalum album L. 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: 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: 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: Characterization of two genes for the biosynthesis of the labdane diterpene Z-abienol in tobacco (Nicotiana tabacum) glandular trichomes. PubMed: Sesquiterpenes from the inner bark of the silver birch and the paper birch. PubMed: Less is more: treatment with BTH and laminarin reduces herbivore-induced volatile emissions in maize but increases parasitoid attraction. PubMed: Volatile constituents of two species of Protium from the Atlantic rainforest in the state of Pernambuco, Brazil. PubMed: Chemical composition and antioxidant activity of essential oil from berries of Schisandra chinensis (Turcz.) Baill. 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: Dynamic evolution of herbivore-induced sesquiterpene biosynthesis in sorghum and related grass crops. PubMed: Comparison of the essential oils of leaves and stem bark from two different populations of Drimys winteri a Chilean herbal medicine. PubMed: Topical anti-inflammatory constituents of lipophilic leaf fractions of Alchornea floribunda and Alchornea cordifolia. PubMed: [Microscopic anatomy and volatile secondary metabolites at three stages of development of the inflorescences of Lantana camara (Verbenaceae)]. PubMed: Chemical variability of Copaifera reticulata Ducke oleoresin. PubMed: Sandalwood fragrance biosynthesis involves sesquiterpene synthases of both the terpene synthase (TPS)-a and TPS-b subfamilies, including santalene synthases. 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: Chemical composition of essential oils from leaves, stems, flower heads and roots of Conyza bonariensis L. from Tunisia. 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: Chemical composition and larvicidal activity against Aedes aegypti larvae of essential oils from four Guarea species. PubMed: [Study on the volatile oil of Murraya exotica]. PubMed: Analysis of sesquiterpene emissions by plants using solid phase microextraction. PubMed: Molecular and biochemical evolution of maize terpene synthase 10, an enzyme of indirect defense. PubMed: Polymorphism in jasmonate signaling partially accounts for the variety of volatiles produced by Nicotiana attenuata plants in a native population. PubMed: A novel pathway for sesquiterpene biosynthesis from Z,Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites. 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: 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: Yield and oil composition of 38 basil (Ocimum basilicum L.) accessions grown in Mississippi. 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: Evaluation of extracts and oils of mosquito (Diptera: Culicidae) repellent plants from Sweden and Guinea-Bissau. PubMed: Silencing of a germin-like gene in Nicotiana attenuata improves performance of native herbivores. PubMed: The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores. PubMed: Using 'mute' plants to translate volatile signals. PubMed: Analysis of leaf surface sesquiterpenes in potato varieties. PubMed: The piercing-sucking herbivores Lygus hesperus and Nezara viridula induce volatile emissions in plants. PubMed: The sesquiterpene hydrocarbons of maize (Zea mays) form five groups with distinct developmental and organ-specific distributions. PubMed: Individual variability in herbivore-specific elicitors from the plant's perspective. PubMed: Silencing the jasmonate cascade: induced plant defenses and insect populations. PubMed: Nitrogen supply influences herbivore-induced direct and indirect defenses and transcriptional responses in Nicotiana attenuata. PubMed: [Study of chemical constituents of essential oil from flowers of Mikania micrantha H.B.K]. PubMed: Chemical composition of volatile oil from Cinnamomum zeylanicum buds. PubMed: Trans-bergamotenes-male pheromone of the ectoparasitoid Melittobia digitata. PubMed: Synthesis of the racemate of (Z)-exo-alpha-bergamotenal, a pheromone component of the white-spotted spined bug, Eysarcoris parvus Uhler. PubMed: The influence of intact-plant and excised-leaf bioassay designs on volicitin- and jasmonic acid-induced sesquiterpene volatile release in Zea mays. 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: Identification of volatile constituents of Tambourissa leptophylla. PubMed: Defensive function of herbivore-induced plant volatile emissions in nature. 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. PubMed: Genetic control and evolution of sesquiterpene biosynthesis in Lycopersicon esculentum and L. hirsutum. PubMed: Chemical composition of the flower oil of Cinnamomum zeylanicum blume. 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.