Caryophyllene oxide
Based on 1 Customer Validation
Caryophyllene oxide ((-)-Caryophyllene oxide) is a bicyclic sesquiterpene with anticancer effects. Caryophyllene oxide induces apoptosis of PC-3 cells. Caryophyllene oxide shows analgesic and anti-inflammatory activities. Caryophyllene oxide has insecticidal, antioxidant, antimicrobial, antifungal, and antiparasitic properties.
For research use only. We do not sell to patients.
- Purity : 99.71%
- CAS No.: 1139-30-6
- Formula: C15H24O
- Molecular Weight:220.35
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Storage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Protocols
- Purity & Documentation
- References
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Help & FAQs
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Caryophyllene oxide (Standard)Standard of Caryophyllene oxide
All Parasite Isoforms
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Biological Activity
Description
In Vitro
Caryophyllene oxide shows IC50 values of 22.86 µg/mL and 44.78 µg/mL in PC-3 and MRC5 normal cells, respectively[2].
Caryophyllene oxide (103.7 μM; 24 h) induces early and late apoptosis, and blocks the cell in the G2/M phase[2].
Caryophyllene oxide (103.7 μM; 6-48 h) depolarizes the mitochondrial membrane. Depolarization of the mitochondrial membrane releases the pro-apoptotic protein Bax from Bcl-xL. The apoptosis process is caspase-7 activation-dependent[2].
Caryophyllene oxide inhibits Escherichia coli and Staphylococcus aureus[3].
Caryophyllene oxide shows moderately cytotoxic against A-549, DLD-1, and WS1[3].
Caryophyllene oxide also inhibits NO production induced by Lipopolysaccharides (HY-D1056) (LPS) with an IC50 of 183 µg/mL[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
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Cell Line:PC3 cells
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Concentration:103.7 μM
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Incubation Time:24 h
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Result:Blocked the cell in the G2/M phase. The dense and compact damage around the nuclei, which were undergoing abnormal formations, which were undergoing abnormal formations.
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Cell Line:PC3 cells
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Concentration:103.7 μM
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Incubation Time:24 h
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Result:The early apoptotic population increased from 13.02% (at 8 h) to 15.61% and the late apoptosis population from 6.14% to 28.02%.
Induced cell death through the mitochondrial-dependent apoptotic pathway.
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Cell Line:PC3 cells
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Concentration:103.7 μM
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Incubation Time:6, 16, 24, and 48 h
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Result:The Bax protein expression level increased at 24 h.
Induced a Bcl-2 protein decrease in a time-dependent manner, but Bcl-xL protein remained constant until 48 h.
Increased the cleaved-Caspase-7 in a time-dependent manner.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Male Swiss albino mice (20-25 g) bearing hot plate test or Acetic acid-induced writhing test[1].
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Dosage:12.5 mg/kg and 25 mg/kg
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Administration:i.p.; once
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Result:Did not produce any significant changes of paw licking time in the early phase of pain.
In the late phase, a dose-dependent and significant increase in licking time was observed in mice.
Significantly reduced the number of writhes.
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Animal Model:Albino rats of Wistar strain (150-200 g) by sub plantar injection of 0.1 ml of 1% suspension of carrageenan with 2% gum acacia in normal saline, in the right hind paw of rats[1].
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Dosage:12.5 mg/kg and 25 mg/kg
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Administration:i.p.; once
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Result:Showed significant inhibition of inflammatory edema at the first and second hours after the carrageenan treatment.
Chemical Information
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CAS No. 1139-30-6
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Appearance Solid
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Molecular Weight 220.35
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Formula C15H24O
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Color White to off-white
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SMILES
C=C1CC[C@@]2([H])O[C@]2(C)CC[C@@]3([H])C(C)(C)C[C@]13[H]
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Synonyms
(-)-Caryophyllene oxide
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 2 years -20°C 1 year
Solvent & Solubility
In Vitro:
DMSO : 100 mg/mL (453.82 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
H2O : 1 mg/mL (4.54 mM; ultrasonic and warming and heat to 80°C)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (11.35 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (11.35 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocols
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Research Protocol for Infectious Diseases
Infectious-disease experiments test how pathogens interact with host barriers, innate immune receptors, inflammatory signaling, pathogen replication, and tissue injury; pattern-recognition receptors such as TLRs, RIG-I-like receptors, NOD-like receptors, and inflammasomes detect microbial molecules and activate NF-κB, interferon, and cytokine responses. The central hypothesis is that infection severity reflects the balance between pathogen burden and host response: protective inflammation restricts pathogen growth, whereas excessive or mislocalized inflammation contributes to tissue damage and disease phenotype. Unresolved questions include which host pathways are protective versus pathogenic, why some infection models fail to translate to human disease, and which combined readouts best predict clinically relevant infection outcomes.
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Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
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TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
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Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
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Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
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Research Protocol for Inflammation-related Diseases
The NLRP3 inflammasome is a cytosolic innate immune signaling platform that integrates priming signals and danger-signal activation to promote caspase-1 activation, maturation of IL-1β and IL-18, and gasdermin D-mediated pyroptotic cell death. The core experimental logic is to determine whether inflammatory disease phenotypes are driven by increased NLRP3 expression, ASC-containing inflammasome assembly, caspase-1 cleavage, GSDMD cleavage, and extracellular release of IL-1β/IL-18 rather than by nonspecific cell injury alone. The pathway is strongly linked to inflammation-related disease phenotypes because monosodium urate crystals activate NALP3/NLRP3 inflammasome signaling in gout-like crystal inflammation, cholesterol crystals activate NLRP3 inflammasomes in atherogenesis models, and DSS-induced intestinal inflammation has been reported to involve NLRP3 inflammasome activity. However, experimental colitis studies also show context-dependent protective effects of NLRP3 inflammasome co
Purity & Documentation
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Data Sheet (282 KB)
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SDS (536 KB)
- English - EN (536 KB)
- Français - FR (536 KB)
- Deutsch - DE (536 KB)
- Norwegian - NO (536 KB)
- Español - ES (536 KB)
- Swedish - SV (536 KB)
- Italian - IT (536 KB)
- Korean - KR (536 KB)
- Portuguese - PT (536 KB)
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Handling Instructions (2659 KB)
References
[1]. Chavan MJ, et al. Analgesic and anti-inflammatory activity of Caryophyllene oxide from Annona squamosa L. bark. Phytomedicine. 2010 Feb;17(2):149-51. [Content Brief]
[2]. Delgado C, et al. Caryophyllene Oxide, the Active Compound Isolated from Leaves of Hymenaea courbaril L. (Fabaceae) with Antiproliferative and Apoptotic Effects on PC-3 Androgen-Independent Prostate Cancer Cell Line. Molecules. 2021 Oct 12;26(20):6142. [Content Brief]
[3]. Coté H, et al. Anti-Inflammatory, Antioxidant, Antibiotic, and Cytotoxic Activities of Tanacetum vulgare L. Essential Oil and Its Constituents. Medicines (Basel). 2017 May 25;4(2):34. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| H2O / DMSO | 1 mM | 4.5382 mL | 22.6912 mL | 45.3823 mL | 113.4559 mL |
| DMSO | 5 mM | 0.9076 mL | 4.5382 mL | 9.0765 mL | 22.6912 mL |
| 10 mM | 0.4538 mL | 2.2691 mL | 4.5382 mL | 11.3456 mL | |
| 15 mM | 0.3025 mL | 1.5127 mL | 3.0255 mL | 7.5637 mL | |
| 20 mM | 0.2269 mL | 1.1346 mL | 2.2691 mL | 5.6728 mL | |
| 25 mM | 0.1815 mL | 0.9076 mL | 1.8153 mL | 4.5382 mL | |
| 30 mM | 0.1513 mL | 0.7564 mL | 1.5127 mL | 3.7819 mL | |
| 40 mM | 0.1135 mL | 0.5673 mL | 1.1346 mL | 2.8364 mL | |
| 50 mM | 0.0908 mL | 0.4538 mL | 0.9076 mL | 2.2691 mL | |
| 60 mM | 0.0756 mL | 0.3782 mL | 0.7564 mL | 1.8909 mL | |
| 80 mM | 0.0567 mL | 0.2836 mL | 0.5673 mL | 1.4182 mL | |
| 100 mM | 0.0454 mL | 0.2269 mL | 0.4538 mL | 1.1346 mL |
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
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