Cinnamtannin A3CAS# 86631-39-2 |
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| Cas No. | 86631-39-2 | SDF | Download SDF |
| PubChem ID | 16129741 | Appearance | Powder |
| Formula | C75H62O30 | M.Wt | 1443.3 |
| Type of Compound | Procyanidins | Storage | Desiccate at -20°C |
| Synonyms | Procyanidin A3 | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol | ||
| SMILES | C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=C3C(=CC(=C4C5C(C(OC6=C(C(=CC(=C56)O)O)C7C(C(OC8=C(C(=CC(=C78)O)O)C9C(C(OC1=CC(=CC(=C91)O)O)C1=CC(=C(C=C1)O)O)O)C1=CC(=C(C=C1)O)O)O)C1=CC(=C(C=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O)O)O)C1=CC(=C(C=C1)O)O)O | ||
| Standard InChIKey | QRFZGLTZLZZHCM-NWYMYRDLSA-N | ||
| Standard InChI | InChI=1S/C75H62O30/c76-28-16-41(88)51-50(17-28)101-68(24-2-7-31(78)37(84)12-24)63(97)59(51)53-43(90)20-45(92)55-61(65(99)70(103-73(53)55)26-4-9-33(80)39(86)14-26)57-47(94)22-48(95)58-62(66(100)71(105-75(57)58)27-5-10-34(81)40(87)15-27)56-46(93)21-44(91)54-60(64(98)69(104-74(54)56)25-3-8-32(79)38(85)13-25)52-42(89)19-35(82)29-18-49(96)67(102-72(29)52)23-1-6-30(77)36(83)11-23/h1-17,19-22,49,59-71,76-100H,18H2/t49-,59-,60+,61-,62+,63-,64-,65-,66-,67-,68-,69-,70-,71-/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. | ||
Cinnamtannin A3 Dilution Calculator
Cinnamtannin A3 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 0.6929 mL | 3.4643 mL | 6.9286 mL | 13.8571 mL | 17.3214 mL |
| 5 mM | 0.1386 mL | 0.6929 mL | 1.3857 mL | 2.7714 mL | 3.4643 mL |
| 10 mM | 0.0693 mL | 0.3464 mL | 0.6929 mL | 1.3857 mL | 1.7321 mL |
| 50 mM | 0.0139 mL | 0.0693 mL | 0.1386 mL | 0.2771 mL | 0.3464 mL |
| 100 mM | 0.0069 mL | 0.0346 mL | 0.0693 mL | 0.1386 mL | 0.1732 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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Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts.[Pubmed:28798415]
Sci Rep. 2017 Aug 10;7(1):7791.
Since procyanidins (oligomeric catechin or epicatechin) were reported to exhibit health benefits, much attention has been paid to the synthesis of these compounds, especially those that are longer than trimers. In the present study, syntheses of Cinnamtannin A3 (epicatechin pentamer), A4 (epicatechin hexamer), catechin tetramer, pentamer, arecatannin A2 (epicatechin-epicatechin-epicatechin-catechin) and A3 (epicatechin-epicatechin-epicatechin-epicatechin-catechin) were achieved. The key reaction was a Lewis acid mediated equimolar condensation. The antitumor effects of these synthesized compounds against a human prostate cancer cell line (PC-3) were investigated. Among the tested compounds, Cinnamtannin A3, A4 and arecatannin A3, which possess epicatechin oligomers longer than tetramers as the basic scaffold, showed significant activities for suppression of cell growth, invasion and FABP5 (fatty acid-binding protein 5) gene expression. Effects on cell cycle distribution showed that cell cycle arrest in the G2 phase was induced. Furthermore, these epicatechin oligomers suppressed significantly the expression of the cancer-promoting gene, FABP5, which is related to cell proliferation and metastasis in various cancer cells. Interestingly, the suppressive activities were associated with the degree of oligomerization of epicatechin. Thus, synthetic studies clearly demonstrate that epicatechin oligomers longer than trimers have significant anti-tumorigenic activities, but not the catechin counterparts.
Isolation of dimeric, trimeric, tetrameric and pentameric procyanidins from unroasted cocoa beans (Theobroma cacao L.) using countercurrent chromatography.[Pubmed:25722166]
Food Chem. 2015 Jul 15;179:278-89.
The main procyanidins, including dimeric B2 and B5, trimeric C1, tetrameric and pentameric procyanidins, were isolated from unroasted cocoa beans (Theobroma cacao L.) using various techniques of countercurrent chromatography, such as high-speed countercurrent chromatography (HSCCC), low-speed rotary countercurrent chromatography (LSRCCC) and spiral-coil LSRCCC. Furthermore, dimeric procyanidins B1 and B7, which are not present naturally in the analysed cocoa beans, were obtained after semisynthesis of cocoa bean polymers with (+)-catechin as nucleophile and separated by countercurrent chromatography. In this way, the isolation of dimeric procyanidin B1 in considerable amounts (500mg, purity>97%) was possible in a single run. This is the first report concerning the isolation and semisynthesis of dimeric to pentameric procyanidins from T. cacao by countercurrent chromatography. Additionally, the chemical structures of tetrameric (cinnamtannin A2) and pentameric procyanidins (Cinnamtannin A3) were elucidated on the basis of (1)H NMR spectroscopy. Interflavanoid linkage was determined by NOE-correlations, for the first time.
