Roburin A

CAS# 132864-75-6

Roburin A

2D Structure

Catalog No. BCN0805----Order now to get a substantial discount!

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3D structure

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Roburin A

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Chemical Properties of Roburin A

Cas No. 132864-75-6 SDF Download SDF
PubChem ID 101670390 Appearance Powder
Formula C82H50O51 M.Wt 1851.2
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1S,2R,20R,42S,46R)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-15-[(1S,2S,20S,42S,46R)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-4,17,22,40,44-pentaoxo-3,18,21,41,43-pentaoxanonacyclo[27.13.3.138,42.02,20.05,10.011,16.023,28.033,45.034,39]hexatetraconta-5,7,9,11,13,15,23,25,27,29(45),30,32,34(39),35,37-pentadecaen-46-yl]-3,18,21,41,43-pentaoxanonacyclo[27.13.3.138,42.02,20.05,10.011,16.023,28.033,45.034,39]hexatetraconta-5,7,9,11(16),12,14,23,25,27,29(45),30,32,34(39),35,37-pentadecaene-4,17,22,40,44-pentone
SMILES C1C2C(C3C4C(C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)C8=C(C(=C(C9=C8C(=O)OCC2C(C3C4C(C5=C(C(=C(C(=C5C(=O)O4)C4=C(C(=C(C(=C4C(=O)O3)C3=C(C(=C(C=C3C(=O)O2)O)O)O)O)O)O)O)O)O)O)OC(=O)C2=CC(=C(C(=C29)O)O)O)O)O)O)OC(=O)C2=CC(=C(C(=C2C2=C(C(=C(C=C2C(=O)O1)O)O)O)O)O)O
Standard InChIKey QTCMAUFCWPWEDU-DMXGXNKNSA-N
Standard InChI InChI=1S/C82H50O51/c83-13-1-8-20(46(93)41(13)88)21-9(2-14(84)42(89)47(21)94)76(117)128-67-18(6-124-73(8)114)126-74(115)10-3-15(85)43(90)48(95)22(10)26-36-28(54(101)62(109)52(26)99)29-38-33(59(106)65(112)55(29)102)34(69(130-79(38)120)71(67)132-80(36)121)32-35-25(51(98)64(111)58(32)105)24-12(5-17(87)45(92)50(24)97)77(118)129-68-19(7-125-78(35)119)127-75(116)11-4-16(86)44(91)49(96)23(11)27-37-30(56(103)63(110)53(27)100)31-39-40(60(107)66(113)57(31)104)61(108)70(131-82(39)123)72(68)133-81(37)122/h1-5,18-19,34,61,67-72,83-113H,6-7H2/t18-,19+,34+,61+,67-,68+,69-,70-,71+,72+/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.
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.
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.

Source of Roburin A

The heartwood of Quercus robur

Roburin A Dilution Calculator

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Preparing Stock Solutions of Roburin A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.5402 mL 2.701 mL 5.4019 mL 10.8038 mL 13.5048 mL
5 mM 0.108 mL 0.5402 mL 1.0804 mL 2.1608 mL 2.701 mL
10 mM 0.054 mL 0.2701 mL 0.5402 mL 1.0804 mL 1.3505 mL
50 mM 0.0108 mL 0.054 mL 0.108 mL 0.2161 mL 0.2701 mL
100 mM 0.0054 mL 0.027 mL 0.054 mL 0.108 mL 0.135 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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References on Roburin A

Comprehensive analysis of chestnut tannins by reversed phase and hydrophilic interaction chromatography coupled to ion mobility and high resolution mass spectrometry.[Pubmed:31623711]

Anal Chim Acta. 2019 Dec 11;1088:150-167.

In this study, we report a methodology based on reversed phase LC (RP-LC) and hydrophilic interaction chromatography (HILIC) separations coupled to ion mobility (IM) and high resolution mass spectrometry (HR-MS) for the detailed analysis of hydrolysable tannins. The application of this approach to the analysis of an industrial chestnut (Castanea sativa, wood chips) tannin extract is demonstrated. A total of 38 molecular species, including a large number or isomers, were identified in this sample based on HR-MS((E)) and UV absorption spectral information as well as retention behaviour in both separation modes. In total, 128 and 90 isomeric species were resolved by RP- and HILIC-LC-IM-TOF-MS, respectively. The combination of low- and high collision energy mass spectral data with complementary chromatographic separations allowed tentative and putative identification of twenty molecular species, comprising 78 isomers, in chestnut for the first time. Ion mobility resolved six new dimeric and trimeric vescalagin conformers with unique arrival (drift) times, including new conformers of Roburin A-D which were not separated using either RP-LC or HILIC. HILIC was found to be the preferred separation mode for the analysis of vescalagin derivatives, while RP-LC is preferred for the analysis of ellagitannins with a cyclic glucose core. For the complete separation of the galloyl glucose species, comprehensive HILICxRP-LC separation would be required.

Size and molecular flexibility affect the binding of ellagitannins to bovine serum albumin.[Pubmed:25162485]

J Agric Food Chem. 2014 Sep 17;62(37):9186-94.

Binding to bovine serum albumin of monomeric (vescalagin and pedunculagin) and dimeric ellagitannins (Roburin A, oenothein B, and gemin A) was investigated by isothermal titration calorimetry and fluorescence spectroscopy, which indicated two types of binding sites. Stronger and more specific sites exhibited affinity constants, K1, of 10(4)-10(6) M(-1) and stoichiometries, n1, of 2-13 and dominated at low tannin concentrations. Weaker and less-specific binding sites had K2 constants of 10(3)-10(5) M(-1) and stoichiometries, n2, of 16-30 and dominated at higher tannin concentrations. Binding to stronger sites appeared to be dependent on tannin flexibility and the presence of free galloyl groups. Positive entropies for all but gemin A indicated that hydrophobic interactions dominated during complexation. This was supported by an exponential relationship between the affinity, K1, and the modeled hydrophobic accessible surface area and by a linear relationship between K1 and the Stern-Volmer quenching constant, K(SV).

Identification and sensory evaluation of dehydro- and deoxy-ellagitannins formed upon toasting of oak wood (Quercus alba L.).[Pubmed:17444655]

J Agric Food Chem. 2007 May 16;55(10):4109-18.

Traditionally, spirits such as whiskey are matured in toasted wood barrels to improve the sensory quality of the final beverage. In order to gain first insight into the puzzling road map of thermal ellagitannin transformation chemistry and provide evidence for the changes in sensory active nonvolatiles in oak wood during toasting, the purified oak ellagitannins castalagin and vescalagin, their corresponding dimers Roburin A and roburin D, and 33-carboxy-33-deoxyvescalagin were thermally treated in model experiments. Besides mouth-coating and golden-brown colored melanoidin-type polymers, individual major reaction products were produced as transient intermediates which were identified for the first time by means of LC-MS/MS and 1D/2D-NMR spectroscopy. Depending strongly on the stereochemistry, castalagin is oxidized to the previously unreported dehydrocastalagin, whereas its diastereomer vescalagin, differing only in the stereochemistry at carbon C-1, is most surprisingly converted into deoxyvescalagin. Comparative model experiments with 33-carboxy-33-deoxyvescalagin revealed castalagin, vescalagin, dehydrocastalagin, and deoxyvescalagin as typical reaction products, thus indicating decarboxylation as a key step in the thermal degradation of that ellagitannin. Similar to the ellagitannin monomers, LC-MS/MS analyses gave strong evidence that the corresponding dimer Roburin A, containing the vescalagin configuration at C-1, was converted into the deoxyRoburin A, whereas roburin D, exhibiting the castalagin configuration at C-1, was oxidized to give the dehydroroburin D. Human sensory experiments revealed that the ellagitannin derivatives imparted an astringent mouth-coating sensation with threshold concentrations ranging from 1.1 to 126.0 micromol/L, depending strongly on their chemical structure.

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