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Orientin-2''-O-p-trans-coumarate

Cat No.:V33494 Purity: ≥98%
Orientin-2''-Op-trans-coumarate is a natural flavonoid extracted from fenugreek and has strong antioxidant properties.
Orientin-2''-O-p-trans-coumarate
Orientin-2''-O-p-trans-coumarate Chemical Structure CAS No.: 1229437-75-5
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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5mg
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Product Description
Orientin-2''-Op-trans-coumarate is a natural flavonoid extracted from fenugreek and has strong antioxidant properties.
Biological Activity I Assay Protocols (From Reference)
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''-Op-trans-coumarate has been reported in previous literature. Orientin-2''-Op-trans-coumarate is a new flavonoid compound that was isolated from the ethyl acetate soluble fraction of the ethanol extract of Trigonella foenum-graecum L. seeds. [1] Its molecular formula is C₃₀H₂₆O₁₃. Its structure was determined by spectroscopic methods (UV, IR, MS, ¹H- and ¹³C-NMR, HMQC, HMBC) and identified as a flavonoid glycoside, in which the glycosyl group (pyranose unit) is attached to the C-8 position of the aglycone and the trans-coumaryl group is attached to the C-2'' position of the sugar. [1]
It showed a significant effect on promoting the proliferation of oxidatively damaged 2BS cells, indicating that it has potential antioxidant and cell-protective properties. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
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)
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

*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.

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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.
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