α-Pinene, α-fellandrene, α-terpinene, linalyl acetate, neral, geranial were purchased from Sigma-Aldrich Co. (Italy). β-Pinene, p-cimene, γ-terpinene, terpinolene, linalool, α-terpineol were purchased from Fluka. Mircene, ocimene, neryl acetate, octyl acetate, β-caryophyllene and limonene were purchased from Merck KGaA. Anisole was purchased from Sigma-Aldrich Co (Italy) and used as internal standard.
β caryophyllene
Manufactured by Merck Group
Sourced in United States, Germany, Italy, Brazil, France, United Kingdom, Spain, Mexico
β-caryophyllene is a naturally occurring bicyclic sesquiterpene hydrocarbon. It is a core chemical compound found in the essential oils of many plants, including cloves, black pepper, and various herbs and spices. β-caryophyllene serves as a major constituent in these plant-derived oils and extracts.
Automatically generated - may contain errors
Lab products found in correlation
α pinene, by Merck Group (29 mentions)
β pinene, by Merck Group (26 mentions)
Linalool, by Merck Group (20 mentions)
Limonene, by Merck Group (18 mentions)
α humulene, by Merck Group (15 mentions)
Caryophyllene oxide, by Merck Group (15 mentions)
1 8 cineole, by Merck Group (12 mentions)
Camphene, by Merck Group (11 mentions)
γ terpinene, by Merck Group (10 mentions)
Eugenol, by Merck Group (9 mentions)
α terpineol, by Merck Group (8 mentions)
P cymene, by Merck Group (8 mentions)
Myrcene, by Merck Group (7 mentions)
β myrcene, by Merck Group (7 mentions)
Aromadendrene, by Merck Group (6 mentions)
Camphor, by Merck Group (6 mentions)
Terpinen 4 ol, by Merck Group (6 mentions)
β caryophyllene oxide, by Merck Group (5 mentions)
α terpinene, by Merck Group (5 mentions)
Thymol, by Merck Group (5 mentions)
94 protocols using β caryophyllene
1
Comprehensive Analysis of Terpenic Compounds
2
Compound Isolation and Solubilization
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The chemicals β-caryophyllene (≥98.5% purity), β-caryophyllene oxide (95% purity), and verapamil hydrochloride (≥98.0% purity) were purchased from Merck Life Science S.r.l. (Milan, Italy), while sorafenib tosylate (≥99.0% purity) and MK571 (≥96.0% purity) were purchased from Santa Cruz Biotechnology, Inc. (Santa Cruz, CA, USA). Dulbecco’s Modified Eagle’s medium (DMEM), Roswell Park Memorial Institute (RPMI) 1640 culture medium, fetal bovine serum, buffer, and cofactors were from Aurogene S.r.l. (Rome, Italy). EtOH (100% v/v) was used to dissolve β-caryophyllene and β-caryophyllene oxide, while DMSO (100% v/v) was used for sorafenib tosylate, verapamil hydrochloride, and MK571. Solvents were used up to 1% v/v nontoxic concentration.
3
Volatile Organic Compound Analysis
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α-pinene, camphene, β-pinene, D-limonene, cis-β-ocimene, trans-β-ocimene, γ-terpinene, α-terpinolene, (Z)-3-hexenylacetate, (E)-3-hexenylacetate, linalool, methyl salicylate, longicyclene, β-caryophyllene, α-humulene, valencene, (E-E)-α-farnesene, and α-sabinene were purchased from Merck (Isle d’Abeau Chesnes, Saint Quentin Fallavier, France). Stock solutions of each standard were prepared at 10 g/L in ethanol (ethanol absolute, VWR, Fontenay sous Bois, France) and kept at 4 °C. A stock solution of a mixture of all standards was prepared at 100 mg/L in ethanol and stored at 4 °C up to 6 months. For analysis, the stock solution was diluted successively to 1 mg/L in water (LC-MS grade water, Fisher Scientific, Illkirch, France) and then to 50 µg/L. An external calibration was performed with monoterpenes, sesquiterpenes, and green leaf volatile standards prepared in water in the 12.5 μg/L to 1000 μg/L concentration range. The final standard mixture solution was placed into a 20-mL headspace vial, and a stir bar was exposed in the headspace of the vial for 1 h at 50 °C. The VOCs collected on the stir bar were desorbed and analysed according to the method described below. Standards and parameters are listed in Supplemental Table S2 .
4
Enzymatic Synthesis of Terpene Derivatives
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Catechol, L-DOPA, trisodium citrate, HP-β-CD, and GlcDH from Bacillus sp. were purchased from FUJIFILM Wako Pure Chemical (Osaka, Japan). NTA•3Na•H 2 O, EDTA•2Na•2H 2 O, DTPA, phen, cyclam, and TPA were purchased from Tokyo Chemical Industry (Tokyo, Japan). (+)-Valencene, (+)-nootkatone, (-)isolongifolene, (-)-β-caryophyllene, and (-)-βcaryophyllene oxide were purchased from Merck (Darmstadt, Germany). (+)-Valencene oxide, (-)isolongifolene oxide, and (-)-isolongifolenone were synthesized and provided by T. Hasegawa (Kanagawa, Japan). (+)-Valencene oxide and (-)-isolongifolene oxide were synthesized using mCPBA from (+)-Valencene and (-)-isolongifolene by reference to previous studies [21, 22] . (+)-Valencene oxide was obtained as a mixture of diastereomers (α:β = 1:2) and used as the mixed authentic sample. (-)-Isolongifolenone was synthesized using chromium hexacarbonyl and tert-butyl hydroperoxide from (-)-isolongifolene, as previously reported [6] . All other chemicals were of analytical grade.
5
Quantification of Volatile Compounds in Essential Oils
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[Std][i.s.] Area std : Area i.s. where RF, response factor; [Std], concentration (g/100 g) of the standard to be calibrated; [i.s.], concentration of the internal standard (g/100 g); Area std, FID peak area of the standard; Area i.s., FID peak area of the internal standard (n-nonane). The concentration of each volatile component in essential oils real samples was then calculated:
[VOC] = (Area VOC : Area i.s.)•RF•[i.s.]•100 W oil
where Area VOC , FID peak area of each volatile constituent; W oil , weight (g) of the oil. The reference standards β-caryophyllene, caryophyllene oxide, farnesol, and citronellal, all supplied by Merck, were chosen as representative compounds of the different chemical groups.
[VOC] = (Area VOC : Area i.s.)•RF•[i.s.]•100 W oil
where Area VOC , FID peak area of each volatile constituent; W oil , weight (g) of the oil. The reference standards β-caryophyllene, caryophyllene oxide, farnesol, and citronellal, all supplied by Merck, were chosen as representative compounds of the different chemical groups.
6
Chemical Compound Characterization for Research
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Caryophyllene oxide (95%), β-caryophyllene (98.5%), geranyl acetate (97%), 6-methyl-5-hepten-2-one (98%), octanal (99%), 2-octenal (95%), 2,4-octadienal (95%), 3,7-dimethyl-6-octenal (95%), 3,7-dimethyl-2,6-octadienal (96%), 3,7-dimethyl-1-octene (97%), and 3,7-dimethyl-1,3,6-octatrien (90%) were purchased from Aldrich (Missouri, USA). 3,7-Dimethyl-1,6-octadiene (98%) was provided by Sigma-Aldrich (Dorset, UK), and DEET (95%) was supplied by Fluka (Buchs, Switzerland). Permethrin (cis:trans, 25:75) 2.5 g/L was purchased from Avention Co. Ltd (Incheon, South Korea). Ethoxylated castor oil (emulsifier), was a gift from the Special Fine Chemical (SFC) Co. Ltd. (Yeosu, South Korea).
7
Characterization of Volatile Compounds
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The necessary chemical standards were obtained from the suppliers shown in parenthesis. Acetic acid, 99% (Merck, Darmstadt, Germany); 3-methyl butanal, 98%; butanoic acid, 97%; pentan-2-one, 98%; dihydro-2-methyl-3(2H) furan, 97%; 2-methylpyrazine, 98%; 3-furaldehyde, 99%; 2-furamethanol, 97%; 2-acetyl furan, 99%; 2-ethylpyrazine, 98%; benzaldehyde, 98%; 5-methyl-2-furfural, 99%; 2-pentyl furan, 98%; ethyl furfural, 98%; limonene, 99%; phenyl acetaldehyde, 99%; 2-acetylpyrrole, 98%; 2-pyrrole carboxaldehyde, 97%; 3-methyl phenol, 99%; 2-ethyl-3,5-dimethylpyrazine, 98%; linalool, 98%; 5-hydroxy methyl furfural, 99%; β-cyclocitral, 97%; 2,6-dimethoxyphenol, 98%; β-caryophyllene, 98%; α-ionone, 98%; α-copaene, 99%; β-ionone, 98% (Aldrich, Steinheim, Germany).
8
Characterization of Essential Oil Compounds
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The following compounds were purchased from commercial sources (Sigma-Aldrich, St. Louis, Missouri, USA): β-pinene, α-terpinene, γ-terpinene, p-cymen, α-terpinolene, acetic acid, bornyl acetate, β-caryophyllene, carvone, thymoquinone, cuminaldehyde, 2-tridecanone, anethole, 2-pentadecanone, nonanoic acid, decanoic acid, methyl hexadecanoate, methyl linoleate, vanillin, ethyl lactate, d-Limonene, linalool, 4-Terpineol, α-terpineol, p-cymen-8-ol, thymol and piperitenone. Longifolene was a gift (Takasago Co. Ltd., Tokyo, Japan). They were of the highest purity available. All reagents and solvents were of analytical grade and were purchased from Wako Pure Chemical Industries, Osaka, Japan.
9
GC-MS Analysis of Headspace Extract
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The pooled MR3 headspace extract was analysed on a combined gas chromatograph and mass spectrometer (GC-MS; 6890 GC and 5975 MS; Agilent Technologies), operated in the electron impact ionization mode at 70 eV. The GC was equipped with fused silica capillary columns (60 m × 0.25 mm, 0.25 μm film thickness), coated with DB-wax (J&W Scientific, Folsom, CA, USA) or HP-5MS (Agilent Technologies). Helium was used as the mobile phase at an average linear flow rate of 35 cm s−1. Two micro-litres of the sample were injected. The temperature programmes were the same as for the GC-EAD analysis. Compounds were identified according to retention times (Kovat’s indices) and mass spectra, in comparison with custom made and NIST05 libraries (Agilent), and confirmed by co-injection of authentic standards: (±)-α-pinene (CAS no. 7785-70-8; Aldrich, 98%), (−)-β-pinene (CAS no. 18172-67-3; Sigma, 99%), 3-carene (CAS no. 13466-78-9; Aldrich, 90%), (±)-limonene (CAS no. 5989-27-5; Sigma, 97%), nonanal (CAS no. 124-19-6; Aldrich, 95%), decanal (CAS no. 112-31-2; Aldrich, 92%), β-caryophyllene (CAS no. 87-44-5; Sigma, 98.5%) and sulcatone (6-methyl-5-hepten-2-one; CAS no. 110-93-0; Fluka, 96%). For quantification, 100 ng of heptyl acetate (99.8% chemical purity; Aldrich) was added as an internal standard to a 20 μl aliquot out of the total 400 μl headspace extract.
10
Leaf Essential Oil Extraction and Analysis
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Leaf essential oils were obtained by hydrodistillation (100 g leaves) using a Clevenger type apparatus for 3 h. The essential oils were collected in dichloromethane, dried over silica gel, and stored at 4 °C in amber glass vials until analysis. Essential oil yield was calculated on a moisture-free basis as 0.08–0.19% (w/w). GC-MS used an Agilent technologies 7820A instrument with a HP-5 capillary columns (30 m × 0.32 mm I.D. covered with a 0.25 µm of 5:95 phenyl-dimethylpolysiloxane plate). The mobile phase was helium at 1 mL min−1 flow rate and 180 °C injector temperature; the oven program was from 60 °C for 3 min, 75 °C for 5 min, 150 °C for 10 min, and up to 250 °C for 20 min. Software was set for 30–600 m/z range, and the mass spectra was recorded at 70 eV. The relative retention index (RRI) was calculated with a standard mix of C8–C20n-alkanes (Sigma-Aldrich Co., St Louis, MO, USA) under identical conditions [74 (link)]. Data were compared with the NIST 2.0 database, with authentic d-limonene, β-linalool, β-caryophyllene, caryophyllene oxide, and (+) aromadendrene standards (Sigma-Aldrich Co., St Louis, MO, USA) and related literature [75 ,76 ]. The percentage of abundance was calculated from GC chromatograms.
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