trans-CaryophylleneCAS# 87-44-5 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 87-44-5 | SDF | Download SDF |
| PubChem ID | 5281515 | Appearance | Colorless liquid |
| Formula | C15H24 | M.Wt | 204.36 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Synonyms | trans-Caryophyllene | ||
| Solubility | Ethanol : ≥ 176.67 mg/mL (864.55 mM) DMSO : < 1 mg/mL (insoluble or slightly soluble) H2O : < 0.1 mg/mL (insoluble) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene | ||
| SMILES | CC1=CCCC(=C)C2CC(C2CC1)(C)C | ||
| Standard InChIKey | NPNUFJAVOOONJE-GFUGXAQUSA-N | ||
| Standard InChI | InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1 | ||
| 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. |
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| 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. |
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| 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 | trans-Caryophyllene, a PPAR-α agonist, which has neuroprotective effects in various neurological disorders, such as chemical induced seizure and brain damage. trans-Caryophyllene suppresses the hypoxia-induced neuroinflammatory response through inhibition of NF-κB activation in microglia.trans-Caryophyllene also reduces both acute and chronic pain in mice, which may be mediated through the opioid and endocannabinoid systems. |
| Targets | PPAR | IL Receptor | TNF-α | SOD | ROS | NF-kB |
| In vitro | A role for trans-caryophyllene in the moderation of insulin secretion.[Pubmed: 24486541]Biochem Biophys Res Commun. 2014 Feb 21;444(4):451-4.Glucose-stimulated insulin secretion (GSIS) is essential for the control of metabolic fuel homeostasis and its impairment is a key element in the failure of β-cells in type 2 diabetes. Trans-caryophyllene suppresses hypoxia-induced neuroinflammatory responses by inhibiting NF-κB activation in microglia.[Pubmed: 24488604]J Mol Neurosci. 2014 Sep;54(1):41-8.trans-Caryophyllene (TC), may have protective effects against hypoxia-induced neuroinflammatory responses. |
| In vivo | Neuroprotective effects of trans-caryophyllene against kainic acid induced seizure activity and oxidative stress in mice.[Pubmed: 25417010]Neurochem Res. 2015 Jan;40(1):118-23.trans-Caryophyllene (TC), a component of essential oil found in many flowering plants, has shown its neuroprotective effects in various neurological disorders. However, the effects of TC on epilepsy haven't been reported before. |
| Kinase Assay | trans-Caryophyllene is a natural agonistic ligand for peroxisome proliferator-activated receptor-α.[Pubmed: 24856059]Bioorg Med Chem Lett. 2014 Jul 15;24(14):3168-74.Intake of dietary aroma compounds may regulate cellular lipid metabolism. We demonstrated that trans-Caryophyllene, a flavor compound in plant foods and teas, activates peroxisome proliferator-activated receptor (PPAR)-α through direct interaction with the ligand-binding domain of PPAR-α.
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| Animal Research | The oral administration of trans-caryophyllene attenuates acute and chronic pain in mice.[Pubmed: 24055516]Phytomedicine. 2014 Feb 15;21(3):356-62.trans-Caryophyllene is a sesquiterpene present in many medicinal plants' essential oils, such as Ocimum gratissimum and Cannabis sativa. |
trans-Caryophyllene Dilution Calculator
trans-Caryophyllene Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.8933 mL | 24.4666 mL | 48.9333 mL | 97.8665 mL | 122.3331 mL |
| 5 mM | 0.9787 mL | 4.8933 mL | 9.7867 mL | 19.5733 mL | 24.4666 mL |
| 10 mM | 0.4893 mL | 2.4467 mL | 4.8933 mL | 9.7867 mL | 12.2333 mL |
| 50 mM | 0.0979 mL | 0.4893 mL | 0.9787 mL | 1.9573 mL | 2.4467 mL |
| 100 mM | 0.0489 mL | 0.2447 mL | 0.4893 mL | 0.9787 mL | 1.2233 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. | |||||
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The oral administration of trans-caryophyllene attenuates acute and chronic pain in mice.[Pubmed:24055516]
Phytomedicine. 2014 Feb 15;21(3):356-62.
trans-Caryophyllene is a sesquiterpene present in many medicinal plants' essential oils, such as Ocimum gratissimum and Cannabis sativa. In this study, we evaluated the antinociceptive activity of trans-Caryophyllene in murine models of acute and chronic pain and the involvement of trans-Caryophyllene in the opioid and endocannabinoid systems. Acute pain was determined using the hot plate test (thermal nociception) and the formalin test (inflammatory pain). The chronic constriction injury (CCI) of the sciatic nerve induced hypernociception was measured by the hot plate and von Frey tests. To elucidate the mechanism of action, mice were pre-treated with naloxone or AM630 30 min before the trans-Caryophyllene treatment. Afterwards, thermal nociception was evaluated. The levels of IL-1beta were measured in CCI-mice by ELISA. trans-Caryophyllene administration significantly minimized the pain in both the acute and chronic pain models. The antinociceptive effect observed during the hot plate test was reversed by naloxone and AM630, indicating the participation of both the opioid and endocannabinoid system. trans-Caryophyllene treatment also decreased the IL-1beta levels. These results demonstrate that trans-Caryophyllene reduced both acute and chronic pain in mice, which may be mediated through the opioid and endocannabinoid systems.
A role for trans-caryophyllene in the moderation of insulin secretion.[Pubmed:24486541]
Biochem Biophys Res Commun. 2014 Feb 21;444(4):451-4.
Glucose-stimulated insulin secretion (GSIS) is essential for the control of metabolic fuel homeostasis and its impairment is a key element in the failure of beta-cells in type 2 diabetes. trans-Caryophyllene (TC), an important constituent of the essential oil of several species of plants, has been reported to activate the type 2 cannabinoid receptor (CB2R). The effects of TC on GSIS are still unknown. Our results demonstrate that administration of TC in MIN6 cells promotes GSIS in a dose dependent manner. However, inhibition of CB2R by a specific inhibitor or specific RNA interference abolished the effects of TC on GSIS, which suggests that the effects of TC on GSIS are dependent on activation of CB2R. Further study demonstrated that treatment with TC leads to the activation of small G protein Arf6 as well as Rac1 and Cdc42. Importantly, Arf6 silencing abolished the effects of TC on GSIS, which suggests that Arf6 participates in mediating the effects of TC on GSIS. We conclude from these data that TC has a novel role in regulating GSIS in pancreatic beta-cells.
Trans-caryophyllene suppresses hypoxia-induced neuroinflammatory responses by inhibiting NF-kappaB activation in microglia.[Pubmed:24488604]
J Mol Neurosci. 2014 Sep;54(1):41-8.
Microglia cells have been reported to mediate hypoxia-induced inflammation through the production of proinflammatory cytokines, including interleukin-1 beta (IL-1beta), tumor necrosis factor alpha (TNF-alpha), and IL-6. Given the fact that the activation of the type 2 cannabinoid receptor (CB2R) provides antioxidative and anti-inflammatory results, it is suspected that its selective agonist, trans-Caryophyllene (TC), may have protective effects against hypoxia-induced neuroinflammatory responses. In this study, TC was found to significantly inhibit hypoxia-induced cytotoxicity as well as the release of proinflammatory cytokines, including IL-1beta, TNF-alpha, and IL-6, through activation of BV2 microglia following hypoxic exposure (1 % O2, 24 h). Furthermore, TC significantly inhibited hypoxia-induced generation of reactive oxygen species (ROS) in mitochondria as well as the activation of nuclear factor kappa B (NF-kappaB) in microglia. Importantly, TC's effects on inhibiting the activation of NF-kappaB and the secretion of inflammatory cytokines can be abolished by muting the CB2R using small RNA interference. These observations indicate that TC suppresses the hypoxia-induced neuroinflammatory response through inhibition of NF-kappaB activation in microglia. Therefore, TC may be beneficial in preventing hypoxia-induced neuroinflammation.
Neuroprotective effects of trans-caryophyllene against kainic acid induced seizure activity and oxidative stress in mice.[Pubmed:25417010]
Neurochem Res. 2015 Jan;40(1):118-23.
trans-Caryophyllene (TC), a component of essential oil found in many flowering plants, has shown its neuroprotective effects in various neurological disorders. However, the effects of TC on epilepsy haven't been reported before. In this study, we investigated the effect of TC on kainic acid-induced seizure activity caused by oxidative stress and pro-inflammation. We found that TC pretreatment significantly decreased seizure activity score compared to kainic acid treated group. Importantly, TC pretreatment leads to lowering the mortality in kainic acid treated mice. In addition, TC was found to significantly inhibit KA-induced generation of malondialdehyde. TC pretreatment also preserved the activity of GPx, SOD, and CAT. Notably, our data shows that an important property of TC is its capacity to exert cerebral anti-inflammatory effects by mitigating the expression of proinflammatory cytokines, such as TNF-alpha and IL-1beta. These data suggest that TC has a potential protective effect on chemical induced seizure and brain damage.
trans-Caryophyllene is a natural agonistic ligand for peroxisome proliferator-activated receptor-alpha.[Pubmed:24856059]
Bioorg Med Chem Lett. 2014 Jul 15;24(14):3168-74.
Intake of dietary aroma compounds may regulate cellular lipid metabolism. We demonstrated that trans-Caryophyllene, a flavor compound in plant foods and teas, activates peroxisome proliferator-activated receptor (PPAR)-alpha through direct interaction with the ligand-binding domain of PPAR-alpha. The agonistic activity of trans-Caryophyllene was investigated by the luciferase reporter assay, surface plasmon resonance, and time-resolved fluorescence resonance energy transfer assay. Following the stimulation of cells with trans-Caryophyllene, intracellular triglyceride concentrations were significantly reduced by 17%, and hepatic fatty acid uptake was significantly increased by 31%. The rate of fatty acid oxidation was also significantly increased. The expressions of PPAR-alpha and its target genes and proteins in fatty acid uptake and oxidation were significantly up-regulated as well. In HepG2 cells transfected with small interfering RNA of PPAR-alpha, the effects of trans-Caryophyllene on PPAR-alpha responsive gene expressions, intracellular triglyceride, fatty acid uptake and oxidation were disappeared. These results indicate that the aroma compound, trans-Caryophyllene, is PPAR-alpha agonist thus regulates cellular lipid metabolism in PPAR-alpha dependent manners.
