Germacrone 4,5-epoxideCAS# 92691-35-5 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 92691-35-5 | SDF | Download SDF |
| PubChem ID | 11637239 | Appearance | Cryst. |
| Formula | C15H22O2 | M.Wt | 234.33 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (1S,6E,10S)-6,10-dimethyl-3-propan-2-ylidene-11-oxabicyclo[8.1.0]undec-6-en-4-one | ||
| SMILES | CC1=CCCC2(C(O2)CC(=C(C)C)C(=O)C1)C | ||
| Standard InChIKey | DWGVRYKQVZGSIB-NCKTXVJMSA-N | ||
| Standard InChI | InChI=1S/C15H22O2/c1-10(2)12-9-14-15(4,17-14)7-5-6-11(3)8-13(12)16/h6,14H,5,7-9H2,1-4H3/b11-6+/t14-,15-/m0/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 | 1. (4S,5S)-(+)-Germacrone-4,5-epoxide inhibits certain subtypes of cytochrome P450 (CYP). |
| Targets | P450 (e.g. CYP17) | IL Receptor | gp120/CD4 | IFN-γ |
Germacrone 4,5-epoxide Dilution Calculator
Germacrone 4,5-epoxide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.2675 mL | 21.3374 mL | 42.6749 mL | 85.3497 mL | 106.6872 mL |
| 5 mM | 0.8535 mL | 4.2675 mL | 8.535 mL | 17.0699 mL | 21.3374 mL |
| 10 mM | 0.4267 mL | 2.1337 mL | 4.2675 mL | 8.535 mL | 10.6687 mL |
| 50 mM | 0.0853 mL | 0.4267 mL | 0.8535 mL | 1.707 mL | 2.1337 mL |
| 100 mM | 0.0427 mL | 0.2134 mL | 0.4267 mL | 0.8535 mL | 1.0669 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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Compounds isolated from Curcuma aromatica Salisb. inhibit human P450 enzymes.[Pubmed:21287405]
J Nat Med. 2011 Jul;65(3-4):583-7.
Curcuma species (Zingiberaceae) are used as both food and medicine in Asia. Ten sesquiterpenes (1-10) and two curcuminoids (11 and 12) were isolated from the rhizomes of Curcuma aromatica Salisb. and identified. The compounds were evaluated for their ability to inhibit cytochrome P450 (CYP). Among them, the sesquiterpene (4S,5S)-(+)-germacrone-4,5-epoxide (7) inhibited certain subtypes of CYP more potently than or at levels comparable to the curcuminoids curcumin (11) and demethoxycurcumin (12); 7 (IC(50) = 1.0 +/- 0.2 muM) > 12 (IC(50) = 7.0 +/- 1.7 muM) > 11 (IC(50) = 14.9 +/- 1.4 muM) for CYP3A4 inhibition; 12 (IC(50) = 1.4 +/- 0.2 muM) > 11 (IC(50) = 6.0 +/- 1.4 muM) > 7 (IC(50) = 7.6 +/- 2.5 muM) for CYP2C9 inhibition; and 7 (IC(50) = 33.2 +/- 3.6 muM) = 12 (IC(50) = 34.0 +/- 14.2 muM) > 11 (IC(50) > 100 muM) for CYP1A2 inhibition. These results suggest the possibility that Curcuma aromatica Salisb. may cause food-drug interactions via cytochrome P450 inhibition by sesquiterpene 7 and curcuminoids 11 and 12.
Suppression of Inflammatory cytokine production by ar-Turmerone isolated from Curcuma phaeocaulis.[Pubmed:25044589]
Chem Biodivers. 2014 Jul;11(7):1034-41.
Rhizomes of Curcuma phaeocaulis Valeton (Zingiberaceae) have traditionally been used for controlling inflammatory conditions. Numerous studies have aimed to isolate and characterize the bioactive constituents of C. phaeocaulis. It has been reported that its anti-inflammatory properties are a result of cyclooxygenase-2 inhibition; however, its effect on the T-cell function remains to be elucidated. In this study, four known sesquiterpenoids, viz., ar-turmerone (TM), germacrone (GM), (+)-(4S,5S)-germacrone-4,5-epoxide (GE), and curzerenone (CZ), were isolated from C. phaeocaulis rhizomes and evaluated for their effects on the CD4(+) T-cell function. While GM, GE, and CZ had no effect on the activation of splenic T cells or CD4(+) T cells, TM suppressed the interferon (IFN)-gamma production, without affecting the interleukin (IL)-4 expression. TM also decreased the expression of IL-2 in CD4(+) T cells, but did not change their cell-division rates upon stimulation. These results suggest that TM, a major constituent of C. phaeocaulis rhizomes selectively exerts potent anti-inflammatory effects via suppression of the inflammatory cytokines IFN-gamma and IL-2.
