Caryophyllene oxideCAS# 1139-30-6 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 1139-30-6 | SDF | Download SDF |
PubChem ID | 14350 | Appearance | White powder |
Formula | C15H24O | M.Wt | 220.4 |
Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
Synonyms | β-Caryophyllene epoxide; trans-Caryophyllene oxide; (-)-Epoxydihydrocaryophyllene | ||
Solubility | Soluble in chloroform and ethanol; insoluble in water | ||
SMILES | CC1(CC2C1CCC3(C(O3)CCC2=C)C)C | ||
Standard InChIKey | NVEQFIOZRFFVFW-UHFFFAOYSA-N | ||
Standard InChI | InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | Caryophyllene oxide, an oxygenated terpenoid existed in many plant essential oil, is well known as preservative in food, drugs and cosmetics with antifungal, acaricidal, anti-inflammatory, anti-carcinogenic, significant central as well as peripheral analgesic and skin penetration enhancing properties. Caryophyllene Oxide and lupenone have synergistic effect against Trypanosoma cruzi. It inhibited growth and induces apoptosis through the suppression of PI3K/AKT/mTOR/S6K1 pathways, ROS-mediated MAPKs activation, and via modulation of 15-LOX. |
Targets | PI3K | mTOR | Akt | ROS | p38MAPK | LOX |
In vitro | Beta caryophyllene and caryophyllene oxide, isolated from Aegle marmelos, as the potent anti-inflammatory agents against lymphoma and neuroblastoma cells.[Pubmed: 24484210]Antiinflamm Antiallergy Agents Med Chem. 2014 Mar;13(1):45-55.Aegle marmelos (Indian Bael) is a tree which belongs to the family of Rutaceae. It holds a prominent position in both Indian medicine and Indian culture.
|
In vivo | Analgesic and anti-inflammatory activity of Caryophyllene oxide from Annona squamosa L. bark.[Pubmed: 19576741]Phytomedicine. 2010 Feb;17(2):149-51.Caryophyllene oxide was isolated from an unsaponified petroleum ether extract of the bark of Annona squamosa and studied for its analgesic and anti-inflammatory activity.
β-Caryophyllene oxide inhibits growth and induces apoptosis through the suppression of PI3K/AKT/mTOR/S6K1 pathways and ROS-mediated MAPKs activation.[Pubmed: 21924548]Cancer Lett. 2011 Dec 22;312(2):178-88Both PI3K/AKT/mTOR/S6K1 and mitogen activated protein kinase (MAPK) signaling cascades play an important role in cell proliferation, survival, angiogenesis, and metastasis of tumor cells.
|
Animal Research | Acaricidal activities of β-caryophyllene oxide and structural analogues derived from Psidium cattleianum oil against house dust mites.[Pubmed: 23861316 ]Use of caryophyllene oxide as an antifungal agent in an in vitro experimental model of onychomycosis.[Pubmed: 11189747]Mycopathologia. 1999 Nov;148(2):79-82.Caryophyllene oxide, an oxygenated terpenoid, well known as preservative in food, drugs and cosmetics, has been tested in vitro as an antifungal against dermatophytes. Its antifungal activity has been compared to ciclopiroxolamine and sulconazole, commonly used in onychomycosis treatment and chosen because of their very different chemical structures. Pest Manag Sci. 2014 May;70(5):757-62.BACKGROUND:
This study was to evaluate the acaricidal activities of an active compound isolated from Psidium cattleianum and structural analogues against Dermatophagoides farinae and D. pteronyssinus. β-Caryophyllene oxide was isolated using chromatographic techniques.
|
Caryophyllene oxide Dilution Calculator
Caryophyllene oxide Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 4.5372 mL | 22.686 mL | 45.3721 mL | 90.7441 mL | 113.4301 mL |
5 mM | 0.9074 mL | 4.5372 mL | 9.0744 mL | 18.1488 mL | 22.686 mL |
10 mM | 0.4537 mL | 2.2686 mL | 4.5372 mL | 9.0744 mL | 11.343 mL |
50 mM | 0.0907 mL | 0.4537 mL | 0.9074 mL | 1.8149 mL | 2.2686 mL |
100 mM | 0.0454 mL | 0.2269 mL | 0.4537 mL | 0.9074 mL | 1.1343 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- Cinnamyl 3-aminobut-2-enoate
Catalog No.:BCC8914
CAS No.:113898-97-8
- CX-5461
Catalog No.:BCC3700
CAS No.:1138549-36-6
- Cidofovir
Catalog No.:BCC2546
CAS No.:113852-37-2
- N-p-coumaroyl-N'-caffeoylputrescine
Catalog No.:BCN6018
CAS No.:1138156-77-0
- N1,N12-Diethylspermine tetrahydrochloride
Catalog No.:BCC6669
CAS No.:113812-15-0
- Picrasidine T
Catalog No.:BCN6017
CAS No.:113808-03-0
- Z-Gly-OH
Catalog No.:BCC2770
CAS No.:1138-80-3
- (Z)-FeCP-oxindole
Catalog No.:BCC6079
CAS No.:1137967-28-2
- TAK960
Catalog No.:BCC6411
CAS No.:1137868-52-0
- MDL 72832 hydrochloride
Catalog No.:BCC6637
CAS No.:113777-40-5
- Dexmedetomidine
Catalog No.:BCC4326
CAS No.:113775-47-6
- Eudesm-4(15)-ene-3alpha,11-diol
Catalog No.:BCN4060
CAS No.:113773-90-3
- Koumine N-oxide
Catalog No.:BCN4807
CAS No.:113900-75-7
- PNU 74654
Catalog No.:BCC7704
CAS No.:113906-27-7
- PMPA (NMDA antagonist)
Catalog No.:BCC7308
CAS No.:113919-36-1
- Andrographidine C
Catalog No.:BCN4730
CAS No.:113963-39-6
- Andrographidine E
Catalog No.:BCN4729
CAS No.:113963-41-0
- (Z)-Akuammidine
Catalog No.:BCN6020
CAS No.:113973-31-2
- Cefozopran hydrochloride
Catalog No.:BCC8909
CAS No.:113981-44-5
- 5-Hydroxy-7,8-dimethoxyflavanone
Catalog No.:BCN6021
CAS No.:113981-49-0
- Golgicide A
Catalog No.:BCC4373
CAS No.:1139889-93-2
- Erythromycin
Catalog No.:BCC4778
CAS No.:114-07-8
- Scopolamine hydrobromide
Catalog No.:BCN1199
CAS No.:114-49-8
- Neostigmine Bromide
Catalog No.:BCC4563
CAS No.:114-80-7
Beta caryophyllene and caryophyllene oxide, isolated from Aegle marmelos, as the potent anti-inflammatory agents against lymphoma and neuroblastoma cells.[Pubmed:24484210]
Antiinflamm Antiallergy Agents Med Chem. 2014 Mar;13(1):45-55.
Aegle marmelos (Indian Bael) is a tree which belongs to the family of Rutaceae. It holds a prominent position in both Indian medicine and Indian culture. We have screened various fractions of Aegle marmelos extracts for their anticancer properties using in vitro cell models. Gas chromatography-Mass spectrometry (GC-MS) was employed to analyze the biomolecules present in the Aegle marmelos extract. Jurkat and human neuroblastoma (IMR-32) cells were treated with different concentrations of the fractionated Aegle marmelos extracts. Flow cytometric analysis revealed that optimal concentration (50 microg/ml) of beta caryophyllene and Caryophyllene oxide fractions of Aegle marmelos extract can induce apoptosis in Jurkat cell line. cDNA expression profiling of pro-apoptotic and anti-apoptotic genes was carried out using real time PCR (RT-PCR). Down-regulation of anti-apoptotic genes (bcl-2, mdm2, cox2 and cmyb) and up-regulation of pro-apoptotic genes (bax, bak1, caspase-8, caspase-9 and ATM) in Jurkat and IMR-32 cells treated with the beta caryophyllene and Caryophyllene oxide fractions of Aegle marmelos extract revealed the insights of the downstream apoptotic mechanism. Furthermore, in-silico approach was employed to understand the upstream target involved in the induction of apoptosis by the beta caryophyllene and Caryophyllene oxide fractions of Aegle marmelos extract. Herein, we report that beta caryophyllene and Caryophyllene oxide isolated from Aegle marmelos can act as potent anti-inflammatory agents and modulators of a newly established therapeutic target, 15-lipoxygenase (15-LOX). Beta caryophyllene and Caryophyllene oxide can induce apoptosis in lymphoma and neuroblastoma cells via modulation of 15-LOX (up-stream target) followed by the down-regulation of anti-apoptotic and up-regulation of pro-apoptotic genes.
Biotransformation of alpha-cedrol and caryophyllene oxide by the fungus Neurospora crassa.[Pubmed:20433062]
Nat Prod Commun. 2010 Apr;5(4):515-8.
Incubation of alpha-cedrol and Caryophyllene oxide with Neurospora crassa afforded 12beta-hydroxy cedrol, 10alpha-hydroxy cedrol, and 3beta-hydroxy cedrol, and 12beta-hydroxy Caryophyllene oxide as major metabolites, respectively. The antibacterial and radical scavenging activities of the metabolites were evaluated in vitro using broth microdilution and bioauthographic techniques. However, no significant antibacterial and antioxidant activities were observed when compared with those of standard substances.
Analgesic and anti-inflammatory activity of Caryophyllene oxide from Annona squamosa L. bark.[Pubmed:19576741]
Phytomedicine. 2010 Feb;17(2):149-51.
Caryophyllene oxide was isolated from an unsaponified petroleum ether extract of the bark of Annona squamosa and studied for its analgesic and anti-inflammatory activity. Caryophyllene oxide at the doses of 12.5 and 25mg/kg body wt. and unsaponified petroleum ether extract at a dose of 50mg/kg body wt. showed significant central as well as peripheral analgesic, along with anti-inflammatory, activity. These activities of Caryophyllene oxide were comparable with the standard drug used in the respective experiments.