Physicochemical Properties
| Molecular Formula | C30H26O12 |
| Molecular Weight | 578.5202 |
| Exact Mass | 578.142 |
| CAS # | 29106-51-2 |
| PubChem CID | 147299 |
| Appearance | White to off-white solid powder |
| Density | 1.705g/cm3 |
| Boiling Point | 955.3ºC at 760 mmHg |
| Flash Point | 531.6ºC |
| Vapour Pressure | 0mmHg at 25°C |
| Index of Refraction | 1.803 |
| LogP | 2.995 |
| Hydrogen Bond Donor Count | 10 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 42 |
| Complexity | 925 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | C1[C@H]([C@H](OC2=C1C(=CC(=C2[C@H]3[C@@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O |
| InChi Key | XFZJEEAOWLFHDH-VUGKQVTMSA-N |
| InChi Code | InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28-,29-/m1/s1 |
| Chemical Name | (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol |
| 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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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
| ln Vitro |
- Procyanidol B4 exhibited significant anti-inflammatory activity by inhibiting the production of nitric oxide (NO) in LPS-stimulated macrophages. It showed a dose-dependent inhibitory effect with an IC50 value of 32.6 ± 2.8 μM [1] - The compound suppressed the secretion of pro-inflammatory cytokines, including tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6), in LPS-induced macrophages. At 50 μM, TNF-α and IL-6 levels were reduced by 48.3% and 52.7%, respectively, compared to the model group [1] - It inhibited the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein level in inflamed macrophages, as detected by western blot analysis [1] |
| Cell Assay |
- Anti-inflammatory cell assay: Murine macrophage cells were seeded in 96-well plates at a density of 1×10⁴ cells/well and incubated overnight. Cells were pretreated with Procyanidol B4 at concentrations of 10, 20, 30, 40, and 50 μM for 2 hours, then stimulated with LPS for 24 hours. The supernatant was collected to measure NO concentration using a Griess reagent assay, and TNF-α/IL-6 levels were quantified by enzyme-linked immunosorbent assay (ELISA) [1] - Western blot assay for iNOS/COX-2: Macrophage cells were seeded in 6-well plates, pretreated with Procyanidol B4 (20, 40 μM) for 2 hours, and stimulated with LPS for 24 hours. Cells were lysed, and proteins were separated by SDS-PAGE, transferred to membranes, and incubated with primary antibodies against iNOS, COX-2, and β-actin. Band intensities were quantified by densitometry [1] |
| References |
[1]. Synthesis of Procyanidin B1, B2, and B4 and Their Anti-Inflammatory Activity: The Effect of 4-Alkoxy Group of Catechin and/or Epicatechin Electrophiles for Condensation. |
| Additional Infomation |
Procyanidin B4 is a proanthocyanidin obtained by the condensation of (-)-epicatechin and (+)-catechin units. It has a role as an antioxidant, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor and an antineoplastic agent. It is a proanthocyanidin and a hydroxyflavan. It is functionally related to a (-)-epicatechin and a (+)-catechin. Procyanidin B4 has been reported in Camellia sinensis, Cinnamomum iners, and other organisms with data available. - Procyanidol B4 is a dimeric procyanidin composed of two catechin/epicatechin units linked by a C4→C8 bond [1] - It was synthesized via condensation of catechin and/or epicatechin electrophiles, with the 4-alkoxy group of the electrophiles playing a key role in the formation of the dimeric structure [1] - The anti-inflammatory mechanism of Procyanidol B4 is associated with the inhibition of the NF-κB signaling pathway, which regulates the expression of iNOS, COX-2, TNF-α, and IL-6 [1] - Among the tested procyanidins (B1, B2, B4), Procyanidol B4 showed moderate anti-inflammatory activity compared to B2 but stronger activity than B1 [1] |
Solubility Data
| Solubility (In Vitro) | DMSO : ~50 mg/mL (~86.43 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (2.16 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 12.5 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: ≥ 1.25 mg/mL (2.16 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 12.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 3: 1.25 mg/mL (2.16 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7285 mL | 8.6427 mL | 17.2855 mL | |
| 5 mM | 0.3457 mL | 1.7285 mL | 3.4571 mL | |
| 10 mM | 0.1729 mL | 0.8643 mL | 1.7285 mL |