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Also known as 1,2,3,4,6-Pentagalloyl glucose (Penta-O-galloyl-β-D-glucose), DB03208 is a novel and potent inhibitor of receptor tyrosine kinase-like orphan receptor 1 (Ror1), isolated from various plants. Penta-O-galloyl-β-D-glucose inhibited interleukin (IL)-4 induced signal pathway in B cell, and suppressed IgE production partially caused by increasing a population of Treg cells in conjunction with Treg-inducing factors. Pentagalloylglucose has potential anti-rabies virus (RABV) activity.
Physicochemical Properties
| Molecular Formula | C41H32O26 |
| Molecular Weight | 940.68 |
| Exact Mass | 940.118 |
| Elemental Analysis | C, 52.35; H, 3.43; O, 44.22 |
| CAS # | 14937-32-7 |
| PubChem CID | 65238 |
| Appearance | White to light yellow solid powder |
| Density | 2.1±0.1 g/cm3 |
| Boiling Point | 1365.7±65.0 °C at 760 mmHg |
| Melting Point | >250ºC dec. |
| Flash Point | 410.4±27.8 °C |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.870 |
| LogP | 8.51 |
| Hydrogen Bond Donor Count | 15 |
| Hydrogen Bond Acceptor Count | 26 |
| Rotatable Bond Count | 16 |
| Heavy Atom Count | 67 |
| Complexity | 1680 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])OC(C1C([H])=C(C(=C(C=1[H])O[H])O[H])O[H])=O)OC(C1C([H])=C(C(=C(C=1[H])O[H])O[H])O[H])=O)OC(C1C([H])=C(C(=C(C=1[H])O[H])O[H])O[H])=O)OC(C1C([H])=C(C(=C(C=1[H])O[H])O[H])O[H])=O)OC(C1C([H])=C(C(=C(C=1[H])O[H])O[H])O[H])=O |
| InChi Key | QJYNZEYHSMRWBK-NIKIMHBISA-N |
| InChi Code | InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34+,35-,41+/m1/s1 |
| Chemical Name | Beta-1,2,3,4,6-Penta-O-Galloyl-D-Glucopyranose |
| Synonyms | Pentagalloylglucose; DB-03208; DB 03208; DB03208 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References |
[1].The Longevity Properties of 1,2,3,4,6-Penta-O-Galloyl-\u03b2-D-Glucose from Curcuma longa in Caenorhabditis elegans. Biomol Ther (Seoul). 2013 Nov;21(6):442-6 [2].1,2,3,4,6-penta-O-galloyl-\u03b2-D-glucopyranose increases a population of T regulatory cells and inhibits IgE production in ovalbumin-sensitized mice. Int Immunopharmacol. 2015 May;26(1):30-6. [3].Alleviation of transient global ischemia/reperfusion-induced brain injury in rats with 1,2,3,4,6-penta-O-galloyl-\u03b2-d-glucopyranose isolated from Mangifera indica. Eur J Pharmacol. 2013 Nov 15;720(1-3):286-93. |
| Additional Infomation |
1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose is a galloyl-beta-D-glucose compound having five galloyl groups in the 1-, 2-, 3-, 4- and 6-positions. It has a role as a geroprotector, a radiation protective agent, an antineoplastic agent, a radical scavenger, an anti-inflammatory agent, a plant metabolite and a hepatoprotective agent. It is a gallate ester and a galloyl beta-D-glucose. It is a conjugate acid of a 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose(1-). Pentagalloylglucose has been reported in Quercus acutissima, Myrothamnus flabellifolia, and other organisms with data available. See also: Paeonia lactiflora root (part of); Lagerstroemia speciosa leaf (part of). |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~106.31 mM ) H2O : ~6 mg/mL (~6.38 mM ) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.66 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (2.66 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (2.66 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (2.66 mM) Solubility in Formulation 5: 1.43 mg/mL (1.52 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0631 mL | 5.3153 mL | 10.6306 mL | |
| 5 mM | 0.2126 mL | 1.0631 mL | 2.1261 mL | |
| 10 mM | 0.1063 mL | 0.5315 mL | 1.0631 mL |