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beta-caryophyllene

Chemical Structure

General Material Information

Preferred name beta-caryophyllene
Trivial Name (-)-Caryophyllene
Short Description (1R-(1R*,4E,9S))-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene
Formula C15 H24
CAS Number 87-44-5
Deleted CAS Number 1233519-47-5
FEMA Number 2252
Flavis Number 1.007
ECHA Number 201-746-1
FDA UNII BHW853AU9H
Nikkaji Number J3.212C
Beilstein Number 2044564
MDL MFCD00075925
COE Number 2118
xLogP3-AA 4.40 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1324 beta-caryophyllene
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 87-44-5 ; BETA-CARYOPHYLLENE
Synonyms
  • (E)- caryophyllene
  • caryophyllene beta natural
  • caryophyllene beta naturel
  • caryophyllene extra natural
  • beta- caryophyllene FCC (natural)
  • beta- caryophyllene indonesia
  • b- caryophyllene natural
  • beta- caryophyllene natural
  • beta- caryophyllene synthetic
  • (1R-(1R*,4E,9S*))-4,11,11-trimethyl-8-methylene bicyclo(7.2.0)undec-4-ene
  • (1R-(1R*,4E,9S))-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene
  • (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
  • (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
  • Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
  • Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (E)-(1R,9S)-(-)-
  • Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-
  • (1R,4E,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
  • trans-Caryophyllene
  • Caryophyllene
  • l-Caryophyllene
  • β-Caryophyllene
  • β-Caryophyllen
  • (-)-β-Caryophyllene
  • β-Caryophyllene, (-)
  • (-)-Caryophyllene
  • (-)-trans-Caryophyllene
  • (-)-E-Caryophyllene
  • (E)-Caryophyllene
  • (-)-(E)-Caryophyllene
  • NSC 11906
  • Caryophyllene B
  • trans-β-Caryophyllene
  • Caryophylline
  • 9-epi-(E)-Caryophyllene
  • AKY 2348

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Literature & References

(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:87-44-5
Pubchem (cid):5281515
Pubchem (sid):134971569
Flavornet:87-44-5
Pherobase:View
Publications by PubMed
[Study of production of sesquiterpenes of Aquilaria senensis stimulated by Lasiodiplodia theobromae].
Complex refractive indices in the near-ultraviolet spectral region of biogenic secondary organic aerosol aged with ammonia.
Chemical composition of the essential oil of Croton bonplandianus from India.
Diurnal Variation of Essential of the Oil Components of Pycnocycla spinosa Decne. ex Boiss.
Assessment of the antioxidant and antiproliferative effects of sesquiterpenic compounds in in vitro Caco-2 cell models.
The Strained Sesquiterpene β-Caryophyllene as a Probe for the Solvent-Assisted Epoxidation Mechanism.
Chemical composition and major odor-active compounds of essential oil from PINELLIA TUBER (dried rhizome of Pinellia ternata) as crude drug.
Constituents of essential oils from the leaves, stem barks and resins of Canarium parvum Leen., and Canarium tramdenanum Dai et Yakovl. (Burseracea) grown in Vietnam.
Chemotype diversity of indigenous Dalmatian sage (Salvia officinalis L.) populations in Montenegro.
Chemical composition of the essential oil from the leaves of Carapa guianensis collected from Venezuelan Guayana and the antimicrobial activity of the oil and crude extracts.
Ultrasound-assisted extraction and quantitation of oils from Syzygium aromaticum flower bud (clove) with supercritical carbon dioxide.
Identification and characterization of (E)-β-caryophyllene synthase and α/β-pinene synthase potentially involved in constitutive and herbivore-induced terpene formation in cotton.
Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approach.
Development of a high performance liquid chromatography method for quantification of isomers β-caryophyllene and α-humulene in copaiba oleoresin using the Box-Behnken design.
Tomato yellow leaf curl virus alters the host preferences of its vector Bemisia tabaci.
Isolation and characterization of terpene synthases in cotton (Gossypium hirsutum).
Essential oil compositions of Alphonsea philastreana (Pierre) Pierre ex Finet & Gagnep. and Alphonsea gaudichaudiana (Baill.) Finet & Gagnep. from Vietnam.
Chemical composition and antimicrobial activity of the essential oil of Stachys officinalis (L.) Trevis. (Lamiaceae).
Phytochemical analysis, biological evaluation and micromorphological study of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande endemic to central Apennines, Italy.
A comparative analysis of essential oils of Goniothalamus macrocalyx Ban., Goniothalamus albiflorus Ban. and Goniothalamus tamirensis Pierre ex Fin. & Gagnep. from Vietnam.
Essential-oil composition of the Tunisian endemic cypress (Cupressus sempervirens L. var. numidica TRAB.).
Chemical composition and antimicrobial activity of three essential oils from Curcuma wenyujin.
Volatile constituents of Pinus roxburghii from Nepal.
Phytochemical diversity of Murraya koenigii (L.) Spreng. from Western Himalaya.
Chemical composition and biological activity of the essential oil of Amomum biflorum.
Essential oils from the leaves of six medicinal plants of Nigeria.
Composition and in-vitro cytotoxic activities of the leaf essential oil of Beilschmiedia erythrophloia from Taiwan.
Headspace, solid-phase micro-extraction, gas chromatographic-mass spectrometric analysis of terpenoids in the latex of Euphorbia species.
Genetically engineered maize plants reveal distinct costs and benefits of constitutive volatile emissions in the field.
Insecticidal and genotoxic activity of Psoralea corylifolia Linn. (Fabaceae) against Culex quinquefasciatus Say, 1823.
Caryophyllene-rich essential oil of Didymocarpus tomentosa: chemical composition and cytotoxic activity.
Suites of terpene synthases explain differential terpenoid production in ginger and turmeric tissues.
Antibacterial, allelopathic and antioxidant activities of essential oil of Salvia officinalis L. growing wild in the Atlas Mountains of Morocco.
Chemotaxonomical markers in essential oil of Murraya koenigii.
Chemical composition of the essential oil of Zingiber zerumbet var. darcyi.
Mediation of a plant-spider association by specific volatile compounds.
Headspace solid-phase microextraction combined with mass spectrometry as a powerful analytical tool for profiling the terpenoid metabolomic pattern of hop-essential oil derived from Saaz variety.
Differences in the volatile compositions of ginseng species (Panax sp.).
Constituents and antimicrobial activity of the essential oils from flower, leaf and stem of Helichrysum armenium.
The composition and antimicrobial activities of Cyperus conglomeratus, Desmos chinensis var. lawii and Cyathocalyx zeylanicus essential oils.
The antioxidant effect of β-caryophyllene protects rat liver from carbon tetrachloride-induced fibrosis by inhibiting hepatic stellate cell activation.
Natural product studies of U.S. endangered plants: volatile components of Lindera melissifolia (Lauraceae) repel mosquitoes and ticks.
Temporal analysis of sesquiterpene emissions from manuka and phoebe oil lures and efficacy for attraction of Xyleborus glabratus (Coleoptera: Curculionidae: Scolytinae).
Chemical composition of the essential oils of Annona pickelii and Annona salzmannii (Annonaceae), and their antitumour and trypanocidal activities.
The leaf essential oils of five Vietnamese Desmos species (Annonaceae).
Determination of gas-phase ozonolysis rate coefficients of a number of sesquiterpenes at elevated temperatures using the relative rate method.
Acaricidal activity and repellency of essential oil from Piper aduncum and its components against Tetranychus urticae.
Origin of regioselectivity in α-humulene functionalization.
Volatile constituents of two species of Protium from the Atlantic rainforest in the state of Pernambuco, Brazil.
Chemical composition and antimicrobial activity of essential oil of Cupressus atlantica.
Chemical composition, antimicrobial, and cytotoxicity studies on S. erianthum and S. macranthum essential oils.
Chemical composition, antinociceptive and anti-inflammatory effects in rodents of the essential oil of Peperomia serpens (Sw.) Loud.
Chemical diversity in Mentha spicata: antioxidant and potato sprout inhibition activity of its essential oils.
Contact toxicity, feeding reduction, and repellency of essential oils from three plants from the ginger family (Zingiberaceae) and their major components against Sitophilus zeamais and Tribolium castaneum.
Comparative studies of volatile oil composition of Rhododendron anthopogon by hydrodistillation, supercritical carbon dioxide extraction and head space analysis.
RNA-seq discovery, functional characterization, and comparison of sesquiterpene synthases from Solanum lycopersicum and Solanum habrochaites trichomes.
Attraction of the redbay ambrosia beetle, Xyleborus glabratus, to avocado, lychee, and essential oil Lures.
Comparative study of volatile oil compositions of two Plectranthus species from northern India.
A short-chain dehydrogenase involved in terpene metabolism from Zingiber zerumbet.
Attraction and electroantennogram responses of male Mediterranean fruit fly to volatile chemicals from Persea, Litchi and Ficus wood.
Genomic organization of δ-guaiene synthase genes in Aquilaria crassna and its possible use for the identification of Aquilaria species.
The gas-phase ozonolysis of α-humulene.
Analysis of the essential oil of Amsonia illustris.
Chemical composition, antimicrobial and antioxidant activities of essential oil from Gnaphlium affine.
Essential oil composition of aerial parts of Cyclospermum leptophyllum (Pers.) Sprague ex Britton and P. Wilson.
Zerumbone induces heme oxygenase-1 expression in mouse skin and cultured murine epidermal cells through activation of Nrf2.
2-undecanone rich leaf essential oil from Zanthoxylum armatum.
Altered cross-linking of HSP27 by zerumbone as a novel strategy for overcoming HSP27-mediated radioresistance.
Persistency assessment and aerobic biodegradation of selected cyclic sesquiterpenes present in essential oils.
Oil constituents of Artemisia nilagirica var. septentrionalis growing at different altitudes.
Seasonal variation in the chemical composition and antimicrobial activity of volatile oils of three species of Leptospermum (Myrtaceae) grown in Brazil.
Efficient functional analysis system for cyanobacterial or plant cytochromes P450 involved in sesquiterpene biosynthesis.
Composition and antimicrobial activity of the leaf and twig oils of Litsea mushaensis and L. linii from Taiwan.
Chemical investigation of the essential oil from berries and needles of common juniper (Juniperus communis L.) growing wild in Estonia.
Validation of a gas chromatographic method to quantify sesquiterpenes in copaiba oils.
GC-MS analysis of headspace and liquid extracts for metabolomic differentiation of citrus Huanglongbing and zinc deficiency in leaves of 'Valencia' sweet orange from commercial groves.
Accumulation of phenylpropanoid and sesquiterpenoid volatiles in male rectal pheromonal glands of the guava fruit fly, Bactrocera correcta.
Characterization of delta-guaiene synthases from cultured cells of Aquilaria, responsible for the formation of the sesquiterpenes in agarwood.
Inhibitor and substrate activities of sesquiterpene olefins toward +-δ-cadinene-8-hydroxylase, a cytochrome P450 monooxygenase (CYP706B1).
Chemical composition of the essential oil and hexane extract of Salvia chionantha and their antioxidant and anticholinesterase activities.
Zingiber zerumbet CYP71BA1 catalyzes the conversion of α-humulene to 8-hydroxy-α-humulene in zerumbone biosynthesis.
Chemical composition and larvicidal activity of the essential oil of Plectranthus amboinicus (Lour.) Spreng against Anopheles stephensi: a malarial vector mosquito.
Chemical composition and antibacterial activity of essential oils of Lantana camara, Ageratum houstonianum and Eupatorium adenophorum.
Chemical composition and larvicidal activity of edible plant-derived essential oils against the pyrethroid-susceptible and -resistant strains of Aedes aegypti (Diptera: Culicidae).
Chemical composition and biological activities of Santiria trimera (Burseraceae) essential oils from Gabon.
Terpenoid composition of the essential oils of Teucrium royleanum and T. quadrifarium.
Psychoactive plants described in a Brazilian literary work and their chemical compounds.
Composition and immunotoxicity activity of essential oils from Lindera obtusiloba Blume against Aedes aegypti L.
Chemical composition and antibacterial, antifungal and antioxidant activities of the flower oil of Retama raetam (Forssk.) Webb from Tunisia.
Studies of a biochemical factory: tomato trichome deep expressed sequence tag sequencing and proteomics.
Species-specific responses of pine sesquiterpene synthases to sawfly oviposition.
Birch (Betula spp.) leaves adsorb and re-release volatiles specific to neighbouring plants--a mechanism for associational herbivore resistance?
Chemical composition and evaluation of the anti-hypernociceptive effect of the essential oil extracted from the leaves of Ugni myricoides on inflammatory and neuropathic models of pain in mice.
Essential oils from two Lantana species with antimycobacterial activity.
In vitro cytotoxic effects of Senecio stabianus Lacaita (Asteraceae) on human cancer cell lines.
Variations in essential oil, phenolic compounds, and antioxidant activity of tunisian cultivated Salvia officinalis L.
Solid-phase micro-extraction (SPME) in the early detection of potentially active volatile compounds from organic wastes used for the management of soil-borne pathogens.
Protective Effects of the Essential Oil of Salvia fruticosa and Its Constituents on Astrocytic Susceptibility to Hydrogen Peroxide-Induced Cell Death.
Chemical composition and antibacterial activity of Cordia verbenacea extracts obtained by different methods.
Composition and antimicrobial activity of the leaf essential oil of Litsea nakaii from Taiwan.
Identification, functional characterization and developmental regulation of sesquiterpene synthases from sunflower capitate glandular trichomes.
Chemical composition and cytotoxic, mutagenic and genotoxic activities of the essential oil from Pipergaudichaudianum Kunth leaves.
Constituents of Cajanus cajan (L.) Millsp., Moringa oleifera Lam., Heliotropium indicum L. and Bidens pilosa L. from Nigeria.
The chemical composition of the essential oils of Euphorbia caracasana and E. cotinifolia (Euphorbiaceae) from Venezuela.
Antimicrobial activity of the essential oil obtained from roots and chemical composition of the volatile constituents from the roots, stems, and leaves of Ballota nigra from Serbia.
Chemical and genetic relationships among sage ( Salvia officinalis L.) cultivars and Judean sage ( Salvia judaica Boiss.).
Preventive and therapeutic anti-inflammatory properties of the sesquiterpene alpha-humulene in experimental airways allergic inflammation.
Essential oil constituents of Eclipta prostrata (L.) L. and Vernonia amygdalina Delile.
GC-MS analysis and antimicrobial activity of essential oil of Stachys cretica subsp. smyrnaea.
Floral and insect-induced volatile formation in Arabidopsis lyrata ssp. petraea, a perennial, outcrossing relative of A. thaliana.
Evolution of volatile compounds during the development of cabernet sauvignon grapes (Vitis vinifera L.).
Chemical composition and mechanisms underlying the spasmolytic and bronchodilatory properties of the essential oil of Nepeta cataria L.
Zerumbone down-regulates chemokine receptor CXCR4 expression leading to inhibition of CXCL12-induced invasion of breast and pancreatic tumor cells.
Pharmacokinetics and tissue distribution of the sesquiterpene alpha-humulene in mice.
Efficient synthesis of functional isoprenoids from acetoacetate through metabolic pathway-engineered Escherichia coli.
Variability of the needle essential oils of Pinus peuce from different populations in Montenegro and Serbia.
Chemical composition and fungitoxic activity of essential oil of Thuja orientalis L. grown in the north-western Himalaya.
Does egg deposition by herbivorous pine sawflies affect transcription of sesquiterpene synthases in pine?
Development of a host-based semiochemical lure for trapping emerald ash borer Agrilus planipennis (Coleoptera: Buprestidae).
Molecular cloning and functional characterization of alpha-humulene synthase, a possible key enzyme of zerumbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith).
Effects of cis-beta-ocimene, cis-sabinene hydrate, and monoterpene and sesquiterpene mixtures on alfalfa pellet intake by lambs.
Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting.
GC/MS of terpenes in walnut-tree leaves after accelerated solvent extraction.
Potentiating effect of beta-caryophyllene on anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel.
Cytotoxic activity of essential oils from labiatae and lauraceae families against in vitro human tumor models.
Volatile chemical constituents of Piper aduncum L and Piper gibbilimbum C. DC (Piperaceae) from Papua New Guinea.
Bioactive constituents of the roots of Polyalthia cerasoides.
Chemotherapeutic potential of the volatile oils from Zanthoxylum rhoifolium Lam leaves.
Jacaranone: a cytotoxic constituent from Senecio ambiguus subsp. ambiguus (biv.) DC. against renal adenocarcinoma ACHN and prostate carcinoma LNCaP cells.
[Extraction and identification of volatile constituents in the flowers of Aglaia odorata Lour].
[Roles of infochemicals in host-selection process of Anastatus japonicus].
Anti-inflammatory effects of compounds alpha-humulene and (-)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea.
The rice (E)-beta-caryophyllene synthase (OsTPS3) accounts for the major inducible volatile sesquiterpenes.
Essential oil composition of Hypericum triquetrifolium Turra. aerial parts.
Variability of the needle essential oils of Pinus heldreichii from different populations in Montenegro and Serbia.
Effect of two active compounds obtained from the essential oil of Cordia verbenacea on the acute inflammatory responses elicited by LPS in the rat paw.
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.
Analysis of aromatic and terpenic constituents of pepper extracts by capillary electrochromatography.
Zerumbone suppresses phorbol ester-induced expression of multiple scavenger receptor genes in THP-1 human monocytic cells.
Induction of plant volatiles by herbivores with different feeding habits and the effects of induced defenses on host-plant selection by thrips.
Composition and cytotoxic activity of the leaf essential oil of Comptonia peregrina (L.) Coulter.
Essential oil from two populations of Echinodorus grandiflorus Micheli.
Anti-inflammatory and anti-allergic properties of the essential oil and active compounds from Cordia verbenacea.
Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: Chemical characterization and antimicrobial activity.
Chemical composition and antioxidant properties of clove leaf essential oil.
Simultaneous determination of aromatic and terpenic constituents of cloves by means of HPLC with diode array detection.
Isolation of Seseli bocconi Guss., subsp. praecox Gamisans (Apiaceae) volatile oil by supercritical carbon dioxide extraction.
Composition and antibacterial activity of Abies balsamea essential oil.
Analysis of atmospheric sesquiterpenes: sampling losses and mitigation of ozone interferences.
Chemical composition and biological activities of essential oil from the leaves of Sesuvium portulacastrum.
Essential oil analysis and anticancer activity of leaf essential oil of Croton flavens L. from Guadeloupe.
Traceability of Asiago mountain cheese: a rapid, low-cost analytical procedure for its identification based on solid-phase microextraction.
Isolation and identification of mosquito bite deterrent terpenoids from leaves of American (Callicarpa americana) and Japanese (Callicarpa japonica) beautyberry.
Zerumbone abolishes NF-kappaB and IkappaBalpha kinase activation leading to suppression of antiapoptotic and metastatic gene expression, upregulation of apoptosis, and downregulation of invasion.
Chemical composition and antimicrobial activity of the essential oil of Artemisia lavandulaefolia.
Changes in anatomy and terpene chemistry in roots of Douglas-fir seedlings following treatment with methyl jasmonate.
Analysis of leaf surface sesquiterpenes in potato varieties.
Regulation of interleukin-8 secretion in human intestinal epithelial Caco-2 cells by alpha-humulene.
Isogermacrene A, a proposed intermediate in sesquiterpene biosynthesis.
Chemical composition and larvicidal activity of the essential oils from Eupatorium betonicaeforme (D.C.) Baker (Asteraceae).
Zerumbone, a tropical ginger sesquiterpene, activates phase II drug metabolizing enzymes.
[The crop-producing power and chemical composition of the essential oil of the cones of hop cultivars].
Characterization of carrot root oil arising from supercritical fluid carbon dioxide extraction.
Essential oil of Valeriana officinalis L. cultivars and their antimicrobial activity as influenced by harvesting time under commercial organic cultivation.
Evaluation of toxic/protective effects of the essential oil of Salvia officinalis on freshly isolated rat hepatocytes.
Antennal responses to floral scents in the butterfly Heliconius melpomene.
Supercritical carbon dioxide extraction of essential oils from Perovskia atriplicifolia Benth.
Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage.
Ovicidal and adulticidal effects of Eugenia caryophyllata bud and leaf oil compounds on Pediculus capitis.
Antitumor activity of balsam fir oil: production of reactive oxygen species induced by alpha-humulene as possible mechanism of action.
Solid-phase microextraction of volatile compounds from the chopped leaves of three species of Eucalyptus.
Essential oils produced by in vitro shoots of sage (Salvia officinalis L.).
Essential oil from fruit of Peucedanum tauricum Bieb.
Induction of volatile emissions in maize by different larval instars of Spodoptera littoralis.
Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry.
Antibacterial activity of the essential oil from Aristolochia indica.
(+)-(10R)-Germacrene A synthase from goldenrod, Solidago canadensis; cDNA isolation, bacterial expression and functional analysis.
Zerumbone, a Southeast Asian ginger sesquiterpene, markedly suppresses free radical generation, proinflammatory protein production, and cancer cell proliferation accompanied by apoptosis: the alpha,beta-unsaturated carbonyl group is a prerequisite.
[New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)].
Essential oil from herb and rhizome of Peucedanum ostruthium (L. Koch.) ex DC.
Quantitative analysis of aroma compounds in carrot (Daucus carota L.) cultivars by capillary gas chromatography using large-volume injection technique.
Exogenous methyl jasmonate induces volatile emissions in cotton plants.
Attraction of a leaf beetle (Oreina cacaliae) to damaged host plants.
Organ- and season-dependent variation in the essential oil composition of Salvia officinalis L. cultivated at two different sites.
Genetic control and evolution of sesquiterpene biosynthesis in Lycopersicon esculentum and L. hirsutum.
Inter-population differences in the essential oils of Pinus caribaea needles.
Antifungal activity of volatile constituents of Eugenia dysenterica leaf oil.
A biomimetic synthesis of lucidene.
Composition and some biological activities of the essential oil of Callicarpa americana (L.).
Aroma-active compounds of miniature beefsteakplant (Mosla dianthera Maxim).
Effect of individual terpenes on consumption of alfalfa pellets by sheep.
Grapefruit gland oil composition is affected by wax application, storage temperature, and storage time.
Dynamics of yield components and essential oil production in a commercial hybrid sage (Salvia officinalis x Salvia fruticosa cv. Newe Ya'ar no. 4).
Identification of zerumbone in Zingiber zerumbet Smith as a potent inhibitor of 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus activation.
Germacrene C synthase from Lycopersicon esculentum cv. VFNT cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase.
Behavioral response of femaleHelicoverpa (Heliothis)armigera HB. (Lepidoptera: Noctuidae) moths to synthetic pigeonpea (Cajanus cajan L.) kairomone.
Sesquiterpenes in the frontal gland secretions of nasute soldier termites from New Guinea.
Sesquiterpenes from clove (Eugenia caryophyllata) as potential anticarcinogenic agents.
[Miscellaneous contributions to the essential oils of plants from various territories. LI. On the components of essential oils of Torilis japonica (Houtt.) DC].
Chemical constituents and inhibitory activities of essential oils fromCyperus brevifolius andC. kyllingia.
Toxicity studies on clove cigarette smoke and constituents of clove: determination of the LD50 of eugenol by intratracheal instillation in rats and hamsters.
Multichemical defense of plant bugHotea gambiae (westwood) (Heteroptera: Scutelleridae) : Sesquiterpenoids from abdominal gland in larvae.
Isolation and identification of cotton synomones mediating searching behavior by parasitoidCampoletis sonorensis.
[Sesquiterpene hydrocarbons from grapes (author's transl)].

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
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09629
HMDB (The Human Metabolome Database):HMDB36792
FooDB:FDB015736
Export Tariff Code:2902.19.0050
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 204.35627746582
Specific gravity @ 25 °C
Pounds per Gallon 7.481 to 7.555
Refractive Index 1.498 to 1.504 @ 20 °C
Optical Rotation -5 to -10
Boiling Point 256 to 259°C @ 760 mm Hg
Boiling Point 160 to 161°C @ 50 mm Hg
Vapor Pressure 0.013 mmHg @ 25 °C
Flash Point TCC Value 93.33 °C TCC
logP (o/w) 6.3
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
propylene glycol Yes
water, 0.05011 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Spicy
sweet, woody, spicy, clove, dry
Odor strength medium
Substantivity 44 hour(s) at 100.00 %
Luebke, William tgsc, (1999) At 100.00 %. sweet woody spice clove dry
Flavor Type: Spicy
spicy, clove, woody, nut skin, powdery, peppery
Luebke, William tgsc, (1999) Spicy clove woody nut skin powdery peppery
General comment Spicy, oily, citrus

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 38 - Irritating to skin.
R 65 - Harmful: may cause lung damage if swallowed.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
S 62 - If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P330 - Rinse mouth.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Oral/Parenteral Toxicity:
oral-rat LD50 [sex: M,F] > 5000 mg/kg
One dose tested
(Hart & Wong, 1971)

intratracheal-rat LD > 48 mg/kg
LUNGS, THORAX, OR RESPIRATION: PULMONARY EMBOLI
Archives of Toxicology. Vol. 59, Pg. 78, 1986.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for beta-caryophyllene usage levels up to:
12.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 330.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 508.00 (μg/capita/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -27.00000
beverages(nonalcoholic): -14.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -200.00000
condiments / relishes: -50.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -2.00000
fruit ices: -2.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -34.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

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
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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)
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Scientific Opinion on Flavouring Group Evaluation 25Rev1: Aliphatic and aromatic hydrocarbons from chemical group 31
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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
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Scientific Opinion on Flavouring Group Evaluation 25, Revision 2 (FGE.25Rev2): Aliphatic and aromatic hydrocarbons from chemical group 31
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Statement on List of Representative Substances for Testing. The current Statement lays down a list of substances in sub-groups with representative substances for which additional data are required prior to their evaluation through the Procedure (Regulation (EC) No 1565/2000).
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Scientific Opinion on the safety and efficacy of aliphatic and aromatic hydrocarbons (chemical group 31) when used as flavourings for all animal species
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Scientific Opinion on Flavouring Group Evaluation 78, Revision 2 (FGE.78Rev2): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic hydrocarbons evaluated by EFSA in FGE.25Rev3
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Safety and efficacy of eight compounds belonging to chemical group 31 (aliphatic and aromatic hydrocarbons) when used as flavourings for all animal species and categories
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EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):87-44-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281515
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Chemidplus:0000087445
EPA/NOAA CAMEO:hazardous materials
RTECS:DT8400000 for cas# 87-44-5