ent-16beta,17-Dihydroxy-19-kauranoic acidCAS# 3301-61-9 |
- Ent-16Α,17-Dihydroxy-19-Kauranoic Acid
Catalog No.:BCC9227
CAS No.:74365-74-5
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 3301-61-9 | SDF | Download SDF |
| PubChem ID | 442023 | Appearance | Powder |
| Formula | C20H32O4 | M.Wt | 336.5 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | CC12CCCC(C1CCC34C2CCC(C3)C(C4)(CO)O)(C)C(=O)O | ||
| Standard InChIKey | MRBLTWPEPGRXQN-INIPNLRTSA-N | ||
| Standard InChI | InChI=1S/C20H32O4/c1-17-7-3-8-18(2,16(22)23)14(17)6-9-19-10-13(4-5-15(17)19)20(24,11-19)12-21/h13-15,21,24H,3-12H2,1-2H3,(H,22,23)/t13-,14+,15+,17-,18-,19+,20+/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. | ||
| Structure Identification | Journal of Chinese Pharmaceutical Sciences, 2006, 41(24):1854-1857.Study on chemical constituents of Herba Siegesbeckiae.[Reference: WebLink]To study the chemical constituents in the ethyl acetate fraction of Herba Siegesbeckiae. |
ent-16beta,17-Dihydroxy-19-kauranoic acid Dilution Calculator
ent-16beta,17-Dihydroxy-19-kauranoic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.9718 mL | 14.8588 mL | 29.7177 mL | 59.4354 mL | 74.2942 mL |
| 5 mM | 0.5944 mL | 2.9718 mL | 5.9435 mL | 11.8871 mL | 14.8588 mL |
| 10 mM | 0.2972 mL | 1.4859 mL | 2.9718 mL | 5.9435 mL | 7.4294 mL |
| 50 mM | 0.0594 mL | 0.2972 mL | 0.5944 mL | 1.1887 mL | 1.4859 mL |
| 100 mM | 0.0297 mL | 0.1486 mL | 0.2972 mL | 0.5944 mL | 0.7429 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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Ent-16beta,17-dihydroxy-kauran-19-oic acid, a kaurane diterpene acid from Siegesbeckia pubescens, presents antiplatelet and antithrombotic effects in rats.[Pubmed:21377851]
Phytomedicine. 2011 Jul 15;18(10):873-8.
The antiplatelet and antithrombotic effects of ent-16beta,17-dihydroxy-kauran-19-oic acid (DDKA) isolated from Siegesbeckia pubescens were investigated with different methods both in vitro and in vivo. We tested the antithrombotic activity of DDKA in arterio-venous shunt model. The effects of DDKA on adenosine diphosphate (ADP)-, Thrombin-, Arachidonic acid-induced rat platelets aggregation were tested in vitro. We also assessed its bleeding side effect by measuring coagulation parameters after intravenous administration for 5 days and investigated the potential mechanisms underlying such activities. In vivo, DDKA significantly reduced thrombus weight in the model of arterio-venous shunt. Meanwhile, DDKA increased plasma cAMP level determined by radioimmunoassay in the same model. Notably, DDKA prolonged PT and APTT in rats after intravenous administration DDKA for successive 5 days. In vitro, pretreatment with DDKA on washed rat platelets significantly inhibited various agonists stimulated platelet aggregation and caused an increase in cAMP level in platelets activated by ADP. These findings support our hypothesis that DDKA possesses antiplatelet and antithrombotic activities. The mechanisms underlying such activities may involve the anticoagulatory effect and cAMP induction.
Hydroxylation and glucosidation of ent-16beta-Hydroxybeyeran-19-oic acid by Bacillus megaterium and Aspergillus niger.[Pubmed:15095153]
Planta Med. 2004 Apr;70(4):359-63.
ent-16beta-Hydroxybeyeran-19-oic acid ( 1) has potential antihypertensive activity. To obtain novel and more-effective compounds, 1 was incubated with Bacillus megaterium ATCC 14 581 and Aspergillus niger CCRC 32 720. The structures of the metabolites were determined by HR-FAB-MS, 1D- and 2D-NMR spectral data, and enzymatic hydrolysis. Bacillus megaterium hydroxylated and glucosidated 1 to yield ent-7alpha,16beta-dihydroxybeyeran-19-oic acid ( 2), ent-16beta-hydroxybeyeran-19-oic acid alpha- D-glucopyranosyl ester ( 3), and ent-7alpha,16beta-dihydroxybeyeran-19-oic acid alpha- D-glucopyranosyl ester ( 4). Aspergillus niger hydroxylated 1 to yield ent-1beta,7alpha,16beta-trihydroxybeyeran-19-oic acid ( 5) and ent-1beta,7alpha-dihydroxy-16-oxobeyeran-19-oic acid ( 6). Metabolites 3 - 5 were characterized as new compounds. In addition, 2, 3, 5, and 6 were tested for antihypertensive effects, and we found that 5 and 6 were more potent than the parent compound 1.
Simultaneous quantification of Kirenol and ent-16beta,17-dihydroxy-kauran-19-oic acid from Herba Siegesbeckiae in rat plasma by liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic studies.[Pubmed:24008120]
J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Oct 15;937:18-24.
A rapid and specific liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) method was developed for the simultaneous determination of two active diterpenoids: Kirenol and ent-16beta,17-dihydroxy-kauran-19-oic acid (DHKA) from Herba Siegesbeckiae in rat plasma using osthole as an internal standard (IS). Plasma sample pretreatment involved a one-step liquid-liquid extraction with ethyl acetate. Chromatographic separation was performed on a Waters Symmetry C18 column (2.1mmx100mm, 3.5mum) with isocratic elution using methanol-5mmol/L aqueous ammonium acetate (80:20, v/v) as the mobile phase at a flow rate of 0.2mL/min. The detection was performed on a triple quadrupole tandem mass spectrometer in multiple reaction monitoring (MRM) mode under positive and negative electrospray ionization. The calibration curves were linear over the range of 50.0-25,000ng/mL for Kirenol, and 25.0-12,500ng/mL for DHKA. The extraction recoveries of the two analytes and the IS were all over 85%. The intra- and inter-day precision (relative standard deviation) values were less than 16.8% and the accuracy (relative error) ranged from -10.7 to 10.6% at four quality control levels. The validated method was successfully applied to a comparative pharmacokinetic study of the two diterpenoids in rat plasma after intragastric administration of Kirenol, DHKA and Herba Siegesbeckiae extract. The results showed that there were obvious differences between the pharmacokinetic behaviors after oral administration of Herba Siegesbeckiae extract compared with each of the substances alone.
