| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 100mg | |||
| Other Sizes |
| Targets |
- Nuclear factor kappa B (NF-κB) signaling pathway [1]
- Cyclooxygenase-2 (COX-2) [1] |
|---|---|
| ln Vitro |
- Dehydrodiisoeugenol exhibits potent anti-inflammatory activity in LPS-stimulated RAW264.7 macrophages. At concentrations of 10, 20, 40 μM, it dose-dependently inhibited NF-κB activation by 35±3%, 58±4%, and 72±5%, respectively [1]
- It suppressed COX-2 expression: 40 μM reduced COX-2 mRNA levels by 68±4% and protein levels by 63±3% [1] - It inhibited pro-inflammatory cytokine secretion: 40 μM decreased TNF-α and IL-6 production by 59±4% and 55±3%, respectively [1] - It showed no significant cytotoxicity to RAW264.7 cells at concentrations up to 80 μM, with cell viability >90% [1] - In in vitro metabolic studies using liver microsomes, it was metabolized into 8 main metabolites via oxidation (hydroxylation, epoxidation), reduction, and conjugation reactions [2] |
| Enzyme Assay |
- COX-2 activity assay: LPS-stimulated RAW264.7 macrophages were treated with Dehydrodiisoeugenol (10–40 μM) for 24 hours. Cell supernatants were collected to measure PGE2 concentration by enzyme immunoassay, reflecting COX-2 activity [1]
- NF-κB activity assay: RAW264.7 cells were pretreated with the compound (20 μM) for 1 hour, then stimulated with LPS for 30 minutes. Nuclear extracts were prepared, and NF-κB DNA-binding activity was detected by electrophoretic mobility shift assay (EMSA) [1] - Liver microsomal metabolism assay: Dehydrodiisoeugenol (10 μM) was incubated with liver microsomes (from human, rat, mouse) in the presence of cofactors (NADPH, UDP-glucuronic acid). Metabolites were separated by ultra-high performance liquid chromatography (UPLC) and identified by mass spectrometry (MS) [2] |
| Cell Assay |
- Anti-inflammatory cell assay: RAW264.7 macrophages were seeded in 96-well plates (5×10³ cells/well) and 6-well plates (2×10⁵ cells/well). After overnight incubation, cells were pretreated with Dehydrodiisoeugenol (10–40 μM) for 1 hour, then stimulated with LPS (1 μg/mL) for 24 hours. Cytokine (TNF-α, IL-6) levels were measured by ELISA; COX-2 mRNA by RT-PCR; COX-2 and NF-κB pathway proteins by Western blot [1]
- Cytotoxicity assay: RAW264.7 cells were treated with Dehydrodiisoeugenol (20–80 μM) for 48 hours, and cell viability was measured by MTT assay [1] - Metabolite identification assay: Cultured hepatocytes were treated with Dehydrodiisoeugenol (20 μM) for 48 hours. Culture media and cell lysates were collected, extracted, and analyzed by UPLC-MS/MS to identify intracellular and extracellular metabolites [2] |
| ADME/Pharmacokinetics |
Absorption: Oral absorption in rats is moderate, with a bioavailability of approximately 38% [2]
- Distribution: Widely distributed in rat tissues, with the highest concentrations in the liver, kidneys, and lungs [2] - Metabolism: The main metabolic pathways include aromatic ring hydroxylation, olefin chain epoxidation, carbonyl reduction, and glucuronic acid/sulfate binding. Eight metabolites have been identified, with M1 (monohydroxylated derivative) being the most abundant [2] - Excretion: Within 72 hours after oral administration in rats, excretion is mainly via feces (62%) and urine (28%) [2] - Plasma protein binding: The binding rate with rat plasma proteins is 89±2% [2] |
| Toxicity/Toxicokinetics |
In vitro cytotoxicity was not significant: at concentrations up to 80 μM, the cell viability of RAW264.7 macrophages and hepatocytes remained above 90% [1][2]
- Preliminary studies did not observe significant acute toxicity, and no abnormal changes were observed in liver and kidney function indicators in rats after oral administration [2] |
| References |
|
| Additional Infomation |
It has been reported that nutmeg (Myristica fragrans) contains dehydrodiisoeugenol, and there is relevant data.
- Dehydrodiisoeugenol is a natural dimer of isoeugenol, which can be isolated from plants[1] - Its anti-inflammatory mechanism involves inhibiting the NF-κB signaling pathway, thereby inhibiting COX-2 expression and pro-inflammatory cytokine secretion[1] - It is mainly metabolized in the liver through phase I (oxidation, reduction) and phase II (conjugation) reactions, with good tissue distribution and moderate oral bioavailability[2] - It has good metabolism and safety, showing potential as an anti-inflammatory drug[1][2] |
| Molecular Formula |
C20H22O4
|
|---|---|
| Molecular Weight |
326.3863
|
| Exact Mass |
326.151
|
| CAS # |
2680-81-1
|
| PubChem CID |
5379033
|
| Appearance |
White to off-white solid powder
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
452.0±45.0 °C at 760 mmHg
|
| Flash Point |
227.2±28.7 °C
|
| Vapour Pressure |
0.0±1.1 mmHg at 25°C
|
| Index of Refraction |
1.596
|
| LogP |
4.19
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
24
|
| Complexity |
437
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C/C=C/C1=CC2=C(C(=C1)OC)OC(C2C)C3=CC(=C(C=C3)O)OC
|
| InChi Key |
ITDOFWOJEDZPCF-AATRIKPKSA-N
|
| InChi Code |
InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5+
|
| Chemical Name |
2-methoxy-4-[7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
|
| 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 |
| 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 : ~100 mg/mL (~306.38 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.37 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 (6.37 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (6.37 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0638 mL | 15.3191 mL | 30.6382 mL | |
| 5 mM | 0.6128 mL | 3.0638 mL | 6.1276 mL | |
| 10 mM | 0.3064 mL | 1.5319 mL | 3.0638 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
