DipterocarpolCAS# 471-69-2 |
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| Cas No. | 471-69-2 | SDF | Download SDF |
| PubChem ID | 466377 | Appearance | Powder |
| Formula | C30H50O2 | M.Wt | 442.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (5R,8R,9R,10R,14R)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one | ||
| SMILES | CC(=CCCC(C)(C1CCC2(C1CCC3C2(CCC4C3(CCC(=O)C4(C)C)C)C)C)O)C | ||
| Standard InChIKey | NJICGAVMYWKCMW-AUROBHDASA-N | ||
| Standard InChI | InChI=1S/C30H50O2/c1-20(2)10-9-16-30(8,32)22-13-18-28(6)21(22)11-12-24-27(5)17-15-25(31)26(3,4)23(27)14-19-29(24,28)7/h10,21-24,32H,9,11-19H2,1-8H3/t21?,22?,23-,24+,27-,28+,29+,30-/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. Dipterocarpol is a dammarane-type triterpenoid, as are the major bioactive compounds of ginseng. 2. Dipterocarpol A and hopeahainol A show moderate acetylcholinesterase inhibitory activity with IC50 values of 8.28 uM and 11.28 uM, respectively. |
| Targets | P450 (e.g. CYP17) | AChR |
Dipterocarpol Dilution Calculator
Dipterocarpol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2589 mL | 11.2943 mL | 22.5887 mL | 45.1773 mL | 56.4717 mL |
| 5 mM | 0.4518 mL | 2.2589 mL | 4.5177 mL | 9.0355 mL | 11.2943 mL |
| 10 mM | 0.2259 mL | 1.1294 mL | 2.2589 mL | 4.5177 mL | 5.6472 mL |
| 50 mM | 0.0452 mL | 0.2259 mL | 0.4518 mL | 0.9035 mL | 1.1294 mL |
| 100 mM | 0.0226 mL | 0.1129 mL | 0.2259 mL | 0.4518 mL | 0.5647 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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Hydroxylation of the triterpenoid dipterocarpol with CYP106A2 from Bacillus megaterium.[Pubmed:22269065]
FEBS J. 2012 May;279(9):1663-74.
The bacterial steroid-hydroxylase CYP106A2 from Bacillus megaterium ATCC 13368 hydroxylates a variety of 3-oxo-Delta-4-steroids and has recently been shown to catalyse regioselective hydroxylation of the diterpene abietic acid, as well as the pentacyclic triterpene 11-keto-beta-boswellic acid. The broad substrate spectrum of this enzyme makes it an excellent candidate for biotechnological application. Because the natural substrate of this enzyme is not known, we assumed that the whole substrate spectrum might not yet be fully discovered. The difference spectroscopy method was used to screen a natural product library of 502 compounds. Screening of the library resulted in the identification of twelve hits, among them eight potential and four known substrates for CYP106A2. Interestingly, when testing the potential substrates, product formation was obtained only with triterpenes, namely Dipterocarpol and betulin. Dipterocarpol is the most promising compound for biotechnological application because it is a dammarane-type triterpenoid, as are the major bioactive compounds of ginseng. The Dipterocarpol hydroxylation products were analysed by NMR and identified as 7beta-hydroxyDipterocarpol and 7beta,11alpha-dihydroxyDipterocarpol. To investigate the putative bioactive properties of these novel compounds, in vitro cytotoxicity assays with HeLa and COS-1 cells were performed. The substrate Dipterocarpol and the dihydroxylated product did not show cytotoxic activity in our study. By contrast, the 7beta-hydroxylated product was found to be cytotoxic to both tested cell lines. This study highlights the potency of CYP106A2 as a versatile biocatalyst for the bioconversion of natural products into pharmaceutically relevant bioactive products.
