| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg |
|
||
| 10mg |
|
||
| 100mg |
|
||
| 250mg | |||
| Other Sizes |
| References | |
|---|---|
| Additional Infomation |
It has been reported that Tenuifoliside B is present in Polygala tenuifolia, Polygala japonica, and Polygala sibirica, and relevant data already exist. Tenuifoliside B is a sucrose derivative (a 3',6-mixed diester of sucrose) and was isolated from the traditional Chinese medicine Polygala tenuifolia Willd [1]. This paper reports the first total synthesis of Tenuifoliside B, which uses commercially available raw materials as starting materials [1]. The key to this synthesis lies in two regioselective esterification steps: 1) a metal chelate-directed acylation reaction at the C3'-OH position of sucrose using CoCl₂ and Et₃N to introduce a sinapicoyl group; 2) a Mitsunobu esterification reaction at the C6-OH position of glucose using triphenylphosphine (PPh₃) and diisopropyl azodicarbonate (DIAD) to introduce a p-hydroxybenzoyl group [1]. A phenolic acetate protecting group was used on the acyl donor and removed in a final step using ammonium acetate in an aqueous methanol solution [1]. The synthesized product was characterized by one-dimensional/two-dimensional nuclear magnetic resonance (¹H, ¹³C, HMBC), high-resolution mass spectrometry, and optical rotation, and the data were consistent with reported data for the natural product [1].
The authors pointed out that Tenuifoliside B has shown potential cognitive improvement and neuroprotective effects in previous studies and may be a potential lead compound for anti-Alzheimer's disease. Therefore, this compound was synthesized for further biological evaluation [1]. |
| Molecular Formula |
C30H36O17
|
|---|---|
| Molecular Weight |
668.5967
|
| Exact Mass |
668.195
|
| CAS # |
139726-36-6
|
| PubChem CID |
10055215
|
| Appearance |
White to yellow solid powder
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
926.1±65.0 °C at 760 mmHg
|
| Flash Point |
296.8±27.8 °C
|
| Vapour Pressure |
0.0±0.3 mmHg at 25°C
|
| Index of Refraction |
1.670
|
| LogP |
3.19
|
| Hydrogen Bond Donor Count |
8
|
| Hydrogen Bond Acceptor Count |
17
|
| Rotatable Bond Count |
14
|
| Heavy Atom Count |
47
|
| Complexity |
1040
|
| Defined Atom Stereocenter Count |
9
|
| SMILES |
COC1=CC(=CC(=C1O)OC)/C=C/C(=O)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C4=CC=C(C=C4)O)O)O)O)CO)O
|
| InChi Key |
HBYKIOIUVMDUIK-GUJRDUPISA-N
|
| InChi Code |
InChI=1S/C30H36O17/c1-41-17-9-14(10-18(42-2)22(17)35)3-8-21(34)45-27-24(37)19(11-31)46-30(27,13-32)47-29-26(39)25(38)23(36)20(44-29)12-43-28(40)15-4-6-16(33)7-5-15/h3-10,19-20,23-27,29,31-33,35-39H,11-13H2,1-2H3/b8-3+/t19-,20-,23-,24-,25+,26-,27+,29-,30+/m1/s1
|
| Chemical Name |
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-3-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxyoxan-2-yl]methyl 4-hydroxybenzoate
|
| 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~74.78 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.74 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 (3.74 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4957 mL | 7.4783 mL | 14.9566 mL | |
| 5 mM | 0.2991 mL | 1.4957 mL | 2.9913 mL | |
| 10 mM | 0.1496 mL | 0.7478 mL | 1.4957 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
