GaultherinCAS# 490-67-5 |
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| Cas No. | 490-67-5 | SDF | Download SDF |
| PubChem ID | 71307455 | Appearance | Powder |
| Formula | C19H26O12 | M.Wt | 446.40 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Synonyms | Monotropitoside; Monotropitin | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | methyl 2-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxybenzoate | ||
| SMILES | COC(=O)C1=CC=CC=C1OC2C(C(C(C(O2)COC3C(C(C(O3)CO)O)O)O)O)O | ||
| Standard InChIKey | XJOQBSUAJMEVGS-KFRLPSNLSA-N | ||
| Standard InChI | InChI=1S/C19H26O12/c1-27-17(26)8-4-2-3-5-9(8)29-19-16(25)14(23)13(22)11(31-19)7-28-18-15(24)12(21)10(6-20)30-18/h2-5,10-16,18-25H,6-7H2,1H3/t10-,11-,12+,13-,14+,15-,16-,18-,19-/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 | 1. Gaultherin has analgesic activity. 2. Gaultherin has anti-inflammatory activity. 3. Gaultherin lacks gastric ulcerogenic effect, because of it released salicylate in intestine slowly, not in stomach and it left the cyclooxygenase-1 unaffected, which was the source of cytoprotective prostaglandins in gastric epithelium. |
| Targets | COX |
Gaultherin Dilution Calculator
Gaultherin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2401 mL | 11.2007 mL | 22.4014 mL | 44.8029 mL | 56.0036 mL |
| 5 mM | 0.448 mL | 2.2401 mL | 4.4803 mL | 8.9606 mL | 11.2007 mL |
| 10 mM | 0.224 mL | 1.1201 mL | 2.2401 mL | 4.4803 mL | 5.6004 mL |
| 50 mM | 0.0448 mL | 0.224 mL | 0.448 mL | 0.8961 mL | 1.1201 mL |
| 100 mM | 0.0224 mL | 0.112 mL | 0.224 mL | 0.448 mL | 0.56 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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Analgesic and anti-inflammatory activities of a fraction rich in gaultherin isolated from Gaultheria yunnanensis (FRANCH.) REHDER.[Pubmed:17329839]
Biol Pharm Bull. 2007 Mar;30(3):465-9.
The analgesic and anti-inflammatory activities of a salicylate derivatives fraction (SDF) isolated from Gaultheria yunnanensis (FRANCH.) REHDER and the mechanisms of actions were investigated in the present study. The major constituent of SDF, which represented around 50% of this fraction, was a methyl salicylate diglycoside named Gaultherin. SDF showed a significant inhibition on the hind paw edema in rats (200, 400 mg/kg body wt., p.o.) and ear swelling in mice (200, 400, 800 mg/kg body wt., p.o.) caused by carrageenin and croton oil, respectively. In addition, SDF (400, 800 mg/kg body wt., p.o.) inhibited only the second phase (inflammatory) in the formalin test, and showed no effect in the hot-plate test in mice. The antinociceptive activity of SDF was predominantly peripheral and independent of the opioid system. These findings demonstrate that SDF from Gaultheria yunnanensis (FRANCH.) REHDER possesses analgesic and anti-inflammatory activities, which may be mediated, at least partly, through the suppression of inflammatory mediators or their release suggested by the animal experiment. The observed effects of SDF are probably due to the presence of high content of salicylate derivatives (80%), including Gaultherin, MSTG-A and MSTG-B.
Synthesis and anti-nociceptive and anti-inflammatory effects of gaultherin and its analogs.[Pubmed:21830886]
J Asian Nat Prod Res. 2011 Sep;13(9):817-25.
The synthesis of Gaultherin (1) and its analogs was carried out to provide 11 glycosides under phase-transfer catalytic conditions. The activities of all synthesized compounds were evaluated by nitric oxide production inhibitory assay in vitro. Methyl 2-O-(4-O-beta-d-galactopyranosyl)-beta-d-glucopyranosylbenzoate (5f) showed significantly anti-nociceptive and anti-inflammatory effects by the evaluation in vivo. Structure-activity relationships within these compounds were discussed.
Gaultherin, a natural salicylate derivative from Gaultheria yunnanensis: towards a better non-steroidal anti-inflammatory drug.[Pubmed:16375889]
Eur J Pharmacol. 2006 Jan 13;530(1-2):166-71.
One of the major factors limiting the use of non-steroidal anti-inflammatory drugs is gastrointestinal toxicity. Gaultherin, 2-[(6-O-beta-D-Xylopyranosyl-beta-D-glucopyranosyl)oxy] benzoic acid methyl ester, a natural salicylate derivative extracted from Gaultheria yunnanensis, has been shown to have analgesic and anti-inflammatory effects and lack gastric ulcerogenic effect compared to aspirin in our primary study. The aim of this study was to investigate the mechanism of action of Gaultherin, which may rely on its active metabolite, and the mechanism responsible for the non-ulcerogenic property. The results showed that Gaultherin (200 mg/kg) significantly inhibited the abdominal contractions in the acetic acid-induced writhing test in mice. The anti-inflammatory effect of Gaultherin was demonstrated in the croton oil-induced ear edema model in mice. The results showed that Gaultherin and equimolar dose of aspirin produced comparable inhibitory effects. The study of the metabolism characters of Gaultherin in mice and rats indicated that Gaultherin could be metabolically converted to salicylate, which produced the pharmacological effects, and provided effective concentrations for an extended period. In vitro metabolism experiment showed that Gaultherin was metabolized by beta-glycosidase produced by human intestinal bacteria and esterases in intestine, blood and liver successively to release salicylate finally. The study suggested Gaultherin did not cause gastric ulcer for the reason that it released salicylate in intestine slowly, not in stomach and it left the cyclooxygenase-1 unaffected, which was the source of cytoprotective prostaglandins in gastric epithelium.
