Macrocarpal CCAS# 142628-53-3 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 142628-53-3 | SDF | Download SDF |
| PubChem ID | 454459 | Appearance | Yellow powder |
| Formula | C28H38O5 | M.Wt | 454.6 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 5-[(1R)-1-[(1aR,4aR,7S,7aR,7bR)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde | ||
| SMILES | CC(C)CC(C1=C(C(=C(C(=C1O)C=O)O)C=O)O)C2(CCC3C2C4C(C4(C)C)CCC3=C)C | ||
| Standard InChIKey | IEWHEHWXBLPFER-HUCVFKCKSA-N | ||
| Standard InChI | InChI=1S/C28H38O5/c1-14(2)11-20(21-25(32)17(12-29)24(31)18(13-30)26(21)33)28(6)10-9-16-15(3)7-8-19-23(22(16)28)27(19,4)5/h12-14,16,19-20,22-23,31-33H,3,7-11H2,1-2,4-6H3/t16-,19+,20-,22+,23+,28+/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. Macrocarpal C, isolated from the fresh leaves of Eucalyptus globulus Labill. (Lan An) and identified as its major antifungal component by bioassay-guided purification, the antifungal action of macrocarpal C was associated with increases of membrane permeability, intracellular ROS and DNA fragmentation. |
| Targets | ROS | Antifection |
Macrocarpal C Dilution Calculator
Macrocarpal C Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1997 mL | 10.9987 mL | 21.9974 mL | 43.9947 mL | 54.9934 mL |
| 5 mM | 0.4399 mL | 2.1997 mL | 4.3995 mL | 8.7989 mL | 10.9987 mL |
| 10 mM | 0.22 mL | 1.0999 mL | 2.1997 mL | 4.3995 mL | 5.4993 mL |
| 50 mM | 0.044 mL | 0.22 mL | 0.4399 mL | 0.8799 mL | 1.0999 mL |
| 100 mM | 0.022 mL | 0.11 mL | 0.22 mL | 0.4399 mL | 0.5499 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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Two antifungal components isolated from Fructus Psoraleae and Folium Eucalypti Globuli by bioassay-guided purification.[Pubmed:20821830]
Am J Chin Med. 2010;38(5):1005-14.
Fructus Psoraleae and Folium Eucalypti Globuli have long been used as Chinese medicines to treat various ailments such as asthma, eczema and dermatomycosis. In previous studies, their antifungal activities were demonstrated. The aim of the present study was to isolate active antidermatophytic compounds from their ethanolic extracts by means of bioassay-guided purification. Guided by the inhibitory activities on Trichophyton mentagrophytes, Trichophyton rubrum and Paecilomyces variotii, bakuchiol was isolated from the n-hexane fraction of Fructus Psoraleae whilst Macrocarpal C was isolated from the n-hexane fraction of Folium Eucalypti Globuli. Both pure compounds could effectively inhibit the growth of dermatophytes in vitro. This is the first paper to report the isolation and identification of active antidermatophytic compounds from Fructus Psoraleae and Folium Eucalypti Globuli by the bioassay-guided purification.
Semisynthesis of macrocarpal C and analogues by selective dehydration of macrocarpal A or B.[Pubmed:24261967]
J Nat Prod. 2013 Dec 27;76(12):2346-9.
Macrocarpals A and C are structurally related compounds that have been extracted from different Eucalyptus species. Although Macrocarpal C is of biological interest, its isolation in pure form is difficult to achieve. We report herein an efficient method for the semisynthesis of Macrocarpal C by selective exo-dehydration of another member of the macrocarpal family, macrocarpal A. We also report the semisynthesis of three new macrocarpal structures derived from either macrocarpal A or B.
Antifungal mode of action of macrocarpal C extracted from Eucalyptus globulus Labill (Lan An) towards the dermatophyte Trichophyton mentagrophytes.[Pubmed:26594235]
Chin Med. 2015 Nov 21;10:34.
BACKGROUND: The fresh leaves of Eucalyptus globulus Labill. (Lan An) have been used in Chinese medicine for many years to treat dermatomycosis. Macrocarpal C was isolated from this herb and identified as its major antifungal component by bioassay-guided purification. This study aims to investigate the antifungal activity of Macrocarpal C against Trichophyton mentagrophytes, which can cause tinea pedis. METHODS: Fresh leaves of E. globulus were extracted with 95 % ethanol, and the resulting ethanolic extracts were dried before being partitioned with n-hexane. The n-hexane layer was then subjected to chromatographic purification to give Macrocarpal C. The antifungal minimum inhibitory concentration (MIC) of Macrocarpal C was determined using the standard M38-A2 method described by the Clinical Laboratory Standards Institute (CLSI). The mode of action of Macrocarpal C was elucidated using three in vitro assays, including (1) a fungal membrane permeability test using SYTOX((R)) Green; (2) a reactive oxygen species (ROS) production test using 5-(and-6)-carboxy-2',7'-dihydrodichlorofluorescein diacetate as a cell-permeable fluorogenic probe; and (3) a DNA fragmentation test based on terminal deoxynucleotidyl transferase dUTP nick-end labeling (TUNEL) detection. Terbinafine hydrochloride and nystatin were used as positive controls. RESULTS: The suppression in the growth of T. mentagrophytes following its treatment with Macrocarpal C was associated with an increase in the permeability of the fungal membrane (P = 0.0043 when compared to control); an increase in the production of intracellular ROS (P = 0.0063); and the induction of apoptosis as a consequence of DNA fragmentation (P = 0.0007). CONCLUSION: This study demonstrated that the antifungal action of Macrocarpal C was associated with increases of membrane permeability, intracellular ROS and DNA fragmentation.
