Physicochemical Properties
| Molecular Formula | C30H26O13 |
| Molecular Weight | 594.5196 |
| Exact Mass | 594.137 |
| CAS # | 1229437-75-5 |
| PubChem CID | 102004864 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.7±0.1 g/cm3 |
| Boiling Point | 923.8±65.0 °C at 760 mmHg |
| Flash Point | 305.1±27.8 °C |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.787 |
| LogP | 3.51 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 13 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 43 |
| Complexity | 1050 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | C1=CC(=CC=C1/C=C/C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2C3=C(C=C(C4=C3OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)O)CO)O)O)O |
| InChi Key | XIKYOEXOYRWIOU-HJBGGDBQSA-N |
| InChi Code | InChI=1S/C30H26O13/c31-12-22-26(39)27(40)30(43-23(38)8-3-13-1-5-15(32)6-2-13)29(42-22)25-19(36)10-18(35)24-20(37)11-21(41-28(24)25)14-4-7-16(33)17(34)9-14/h1-11,22,26-27,29-36,39-40H,12H2/b8-3+/t22-,26-,27+,29+,30-/m1/s1 |
| Chemical Name | [(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate |
| 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) |
Biological Activity
| ln Vitro |
Orientin-2''-O-p-trans-coumarate was tested for its ability to promote the proliferation of human embryonic lung diploid fibroblasts (2BS cells) that had been damaged by hydrogen peroxide (H₂O₂). At a concentration of 1.0 µM, it significantly increased the viability rate of H₂O₂-damaged 2BS cells to 29.85%, which was comparable to the effect of the reference substance N-acetyl-L-cysteine (NAC, 28.38%). This indicates a strong antioxidant/pro-proliferative effect under oxidative stress conditions. [1] Structure-activity relationship analysis suggested that the 7-OH and 4'-OH groups on the flavonoid skeleton, as well as the presence of the ortho-diphenolic hydroxyl group in the B ring and the p-coumaroyl substituent, were important for this activity. [1] |
| Cell Assay |
2BS Cell Proliferation Assay: Young 2BS cells were seeded into 96-well plates at a density of 2 × 10³ cells per well. The cells were pre-treated with different concentrations of the test compounds (including Orientin-2''-O-p-trans-coumarate) for 2 hours. After pre-treatment, the cells were exposed to 100 µM H₂O₂ in culture medium and incubated for 20 hours to induce oxidative damage. Subsequently, cell viability was assessed using the MTT assay: 1 mg/ml MTT solution was added to each well and incubated for 2 hours. The medium was then removed, and the formed formazan crystals were dissolved in 100 µl of DMSO. The absorbance (optical density) of each well was measured at 570 nm using a microplate reader. The viability rate was calculated using the formula: [(OD_sample - OD_H₂O₂) / OD_H₂O₂] × 100%. [1] |
| References |
[1]. New flavonoids with 2BS cell proliferation promoting effect from the seeds of Trigonella foenum-graecum L. J Nat Med. 2010 Jul;64(3):358-61. doi: 10.1007/s11418-010-0407-8. |
| Additional Infomation |
Orientin-2''-O-p-trans-coumarate has been reported in Trigonella foenum-graecum with data available. Orientin-2''-O-p-trans-coumarate is a new flavonoid compound isolated from the ethyl acetate-soluble fraction of the ethanolic extract of Trigonella foenum-graecum L. (fenugreek) seeds. [1] Its molecular formula is C₃₀H₂₆O₁₃. Its structure was elucidated using spectroscopic methods (UV, IR, MS, ¹H- and ¹³C-NMR, HMQC, HMBC) and was identified as a flavonoid glycoside where the sugar moiety (glucopyranosyl unit) is linked to C-8 of the aglycone, and a p-trans-coumaroyl group is attached to the C-2'' position of the sugar. [1] It exhibited a strong effect in promoting the proliferation of oxidatively damaged 2BS cells, suggesting potential antioxidant and cell-protective properties. [1] |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~168.20 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (4.21 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. 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 (4.21 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (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 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 | 1.6820 mL | 8.4101 mL | 16.8203 mL | |
| 5 mM | 0.3364 mL | 1.6820 mL | 3.3641 mL | |
| 10 mM | 0.1682 mL | 0.8410 mL | 1.6820 mL |