 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C14H12O3 |
| Molecular Weight | 228.24 |
| Exact Mass | 228.078 |
| Elemental Analysis | C, 73.67; H, 5.30; O, 21.03 |
| CAS # | 61434-67-1 |
| Related CAS # | Resveratrol;501-36-0 |
| PubChem CID | 1548910 |
| Appearance | White to off-white solid powder |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 449.1±14.0 °C at 760 mmHg |
| Melting Point | 167-170ºC (dec) |
| Flash Point | 222.3±14.7 °C |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.763 |
| LogP | 3.14 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 17 |
| Complexity | 246 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1=CC(=CC=C1/C=C\C2=CC(=CC(=C2)O)O)O |
| InChi Key | LUKBXSAWLPMMSZ-UPHRSURJSA-N |
| InChi Code | InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1- |
| Chemical Name | 5[(1Z)-2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol |
| Synonyms | cis-Resveratrol; cis-resveratrol; (Z)-resveratrol; 61434-67-1; Cis resveratrol; Resveratrol, (Z)-; 5-[(Z)-2-(4-hydroxyphenyl)vinyl]benzene-1,3-diol; 5-[(Z)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol; cis-3,4',5-trihydroxystilbene; (Z)-Resveratrol; |
| 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
| Targets | Antiviral; enteroviruse |
| ln Vitro | Three new compounds, (3S)-dihydrobonducellin 8-O-β-D-glucopyranoside (1), 3',5'-dimethoxy-jezonolid (2), and latisilinoid (3), along with 16 known compounds, were isolated from the twigs of Caesalpinia latisiliqua (Leguminosae). The known compounds were identified as flavonoids, stilbenes, and phenolics as determined by extensive spectroscopic methods, including 1D and 2D NMR. All the isolated compounds were evaluated for their antiviral activity in HRV1B-, CVB3-, and EV71-infected cells. Among the tested compounds, three flavonoids (4-6) and two stilbenes (12 and 14) exhibited significant antiviral activity. This is the first phytochemical investigation of C. latisiliqua twigs.[1] |
| Enzyme Assay |
Antiviral assay[1] Antiviral activity was assayed by employing the SRB method using CPE reduction, as recently reported. To evaluate the activity, 3 × 104 cells per well of HeLa or Vero cells were seeded using MEM supplemented with 10% FBS and 0.01% antibiotic–antimycotic solution onto a 96-well culture plate and incubated for 24 h. After the medium was removed and cells were washed with 100 μL of phosphate buffered saline, the diluted virus suspension (0.09 ml), containing a 50% cell culture infective dose (CCID50) of the virus, was added to HeLa or Vero cells to produce the 50% CPE within 48 h after infection. Next, MEM containing 10 μM of the compounds (0.01 ml) was added and the culture plates were incubated at 37 °C in 5% CO2 for 2 days until 50% CPE was achieved. The 96-well plates were washed once with 200 μL of PBS. Ice-cold 70% acetone in water (100 μL) was added to each well and incubated for 30 min at −20 °C. After removing the 70% acetone, plates were dried in a drying oven at 55 °C for 30 min. Next, 0.4% (w/v) SRB in 1% acetic acid solution (100 μL) was added to each well and left for 30 min at room temperature. The SRB solution was then removed and the plates were washed five times with 1% acetic acid in water before oven-drying at 55 °C. Bound SRB was then solubilised with 10 mM unbuffered Tris-base solution (100 μL). After 30 min, the absorbance was read at 540 nm using a VersaMax microplate reader with a reference absorbance at 620 nm. The antiviral activity of each test compounds in HRV1B-, CVB3-, and EV71-infected cells was calculated as a percentage of the corresponding untreated control. |
| Cell Assay |
Cell culture[1] The HRV1B, CVB3, and EV71 were obtained from the Division of Vaccine Research of the Korea Centers for Disease Control and Prevention and were propagated at 37 °C in Vero and 32 °C in HeLa cells. HRV1B was expanded in HeLa cells, while CVB3 and EV71 were expanded in Vero cells. These cells were maintained in minimum essential medium (MEM) supplemented with 10% fetal bovine serum (FBS) and 0.01% antibiotic–antimycotic solution. The cells were incubated in MEM supplemented with 10% FBS and 0.01% antibiotic–antimycotic solution in a humidified atmosphere of 5% CO2 at 37 °C. Cells were detached using trypsin-EDTA. Five subsequent cycles of subculturing were performed before the cells were incubated with isolated compounds. |
| References |
[1]. Chemical components from the twigs of Caesalpinia latisiliqua and their antiviral activity. J Nat Med. 2020 Jan;74(1):26-33. |
| Additional Infomation |
Cis-resveratrol is the cis-stereoisomer of resveratrol. (Z)-resveratrol has been reported in Malus, Botrytis cinerea, and other organisms with data available. A stilbene and non-flavonoid polyphenol produced by various plants including grapes and blueberries. It has anti-oxidant, anti-inflammatory, cardioprotective, anti-mutagenic, and anti-carcinogenic properties. It also inhibits platelet aggregation and the activity of several DNA HELICASES in vitro. |
Solubility Data
| Solubility (In Vitro) | DMSO : 125 mg/mL (547.67 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (9.11 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 20.8 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: ≥ 2.08 mg/mL (9.11 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 20.8 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: ≥ 2.08 mg/mL (9.11 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 20.8 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 | 4.3814 mL | 21.9068 mL | 43.8135 mL | |
| 5 mM | 0.8763 mL | 4.3814 mL | 8.7627 mL | |
| 10 mM | 0.4381 mL | 2.1907 mL | 4.3814 mL |