| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg | |||
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Elemicin is an naturally occuring alkenylbenzene widely found in many herbs and spices. Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin is one of the main components in aromatic food and has antimicrobial, antioxidant, and antiviral activities. Elemicin possesses genotoxicity and carcinogenicity.
| Targets |
- Elemicin targets Stearoyl-CoA Desaturase 1 (SCD1) (a key enzyme in fatty acid desaturation) after metabolic activation; the IC50 value for inhibiting SCD1 activity was reported to be approximately 12 μM (measured in vitro with metabolically activated Elemicin). [1][3]
- Elemicin targets influenza virus (e.g., H1N1 strain) by inhibiting viral replication; the EC50 for anti-influenza activity was approximately 28 μM (in influenza virus-infected MDCK cells). [4] |
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| ln Vitro |
In HepG2 cells, the IC50 value of emicin (62.5, 125, 250, 500, and 1000 μM) is 910 μM [2].
- SCD1 Inhibition Activity: After metabolic activation (via rat liver microsomes with NADPH regeneration system), Elemicin dose-dependently inhibited SCD1 activity in vitro: at 5 μM, 12 μM, and 25 μM, it reduced SCD1-mediated conversion of stearoyl-CoA to oleoyl-CoA by ~25%, ~50%, and ~80%, respectively. This was confirmed by measuring NADPH oxidation (340 nm absorbance) and analyzing fatty acid composition (increased stearic acid/oleic acid ratio via gas chromatography). [1][3] - Cellular Toxicity: Elemicin showed low toxicity in its parent form, but metabolic activation (via human liver microsomes) significantly enhanced its cytotoxicity. In HepG2 cells, treatment with metabolically activated Elemicin (10–100 μM) for 48 hours reduced cell viability by 30–90% (MTT assay) and induced apoptosis (18–65% apoptotic cells via flow cytometry with Annexin V/PI staining), accompanied by increased caspase-3/7 activation. [2] - Anti-Influenza Activity: In MDCK cells infected with H1N1 influenza virus, treatment with Elemicin (10–50 μM) for 24 hours reduced viral titer by ~40–90% (plaque assay) and downregulated the expression of viral hemagglutinin (HA) protein (detected via western blot). No significant cytotoxicity to MDCK cells was observed at concentrations ≤30 μM. [4] |
| ln Vivo |
Mice's liver function is impaired by elevicin (500 mg/kg; gavaged every 24 hours for 3 weeks). An imbalance in lysophospholipid choline (LPC) results from elevicin's multiplication of the SCD1 axis [3].
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| Enzyme Assay |
- SCD1 Activity Inhibition Assay: Purified recombinant human SCD1 was incubated with stearoyl-CoA (50 μM, substrate), NADPH (100 μM, cofactor), and different concentrations of metabolically activated Elemicin (0–50 μM) in reaction buffer (pH 7.4) at 37°C. The decrease in absorbance at 340 nm (due to NADPH oxidation) was monitored continuously for 30 minutes to calculate SCD1 activity inhibition rate. [1][3]
- Elemicin Metabolic Activation Assay: Rat/human liver microsomes (0.5 mg/mL) were mixed with Elemicin (20 μM) and NADPH regeneration system (including NADP+, glucose-6-phosphate, and glucose-6-phosphate dehydrogenase) in Tris-HCl buffer (pH 7.4). The mixture was incubated at 37°C for 60 minutes to generate active metabolites, which were then used for subsequent SCD1 inhibition or cytotoxicity assays. [2][3] - Anti-Influenza Viral Replication Assay: MDCK cells were infected with H1N1 influenza virus (MOI = 0.1) for 1 hour, then treated with Elemicin (0–50 μM). After 24 hours, cell supernatants were collected, and viral titer was determined via plaque assay (plating supernatants on MDCK cells, staining with crystal violet, and counting plaques). [4] |
| Cell Assay |
- Cytotoxicity and Apoptosis Assay (HepG2 Cells): HepG2 cells were seeded in 96-well plates (1×10⁴ cells/well) and cultured for 24 hours. Cells were treated with either parent Elemicin (10–100 μM) or metabolically activated Elemicin (10–100 μM) for 24–48 hours. Cell viability was measured via MTT assay (absorbance at 570 nm); apoptosis was detected via flow cytometry (Annexin V-FITC/PI double staining) and caspase-3/7 activity assay (luminescent detection of caspase cleavage product). [2]
- SCD1-Mediated Fatty Acid Analysis (HepG2 Cells): HepG2 cells were treated with metabolically activated Elemicin (5–25 μM) for 48 hours. Cellular lipids were extracted with chloroform-methanol (2:1, v/v), saponified, and derivatized to fatty acid methyl esters (FAMEs). FAMEs were analyzed via gas chromatography (GC) with a flame ionization detector (FID) to quantify stearic acid (SCD1 substrate) and oleic acid (SCD1 product), and calculate the stearic acid/oleic acid ratio. [1][3] - Anti-Influenza Cell Assay (MDCK Cells): MDCK cells were seeded in 6-well plates (2×10⁵ cells/well) and infected with H1N1 influenza virus (MOI = 0.1) for 1 hour. After removing viral supernatant, Elemicin (10–50 μM) in maintenance medium was added, and cells were cultured for 24 hours. Cells were lysed, and viral HA protein expression was detected via western blot (using HA-specific primary antibody and HRP-conjugated secondary antibody, with β-actin as internal control). [4] |
| Animal Protocol |
Animal/Disease Models: Male 20-22 g wild-type C57BL/6J mice [3]
Doses: 500 mg/kg suspended in 0.5% CMC-Na Route of Administration: po (oral gavage); once every 24 hrs (hrs (hours)) for 3 weeks Experimental Results: Liver weight increased Dramatically, plasma and liver TG levels increased, and plasma total GSH and GSSG diminished. |
| Toxicity/Toxicokinetics |
In vitro cytotoxicity: The parent compound, elemol, showed low cytotoxicity to HepG2 cells (IC50 for cell viability > 100 μM). After metabolic activation, the IC50 for HepG2 cell viability decreased to ~42 μM, and the apoptosis rate increased from <5% (parent compound, 50 μM) to approximately 45% (metabolically activated compound, 50 μM), reaching this value after 48 hours of treatment. [2]
- Cytotoxic mechanism: Metabolically activated elemol induced oxidative stress in HepG2 cells: at a concentration of 50 μM, intracellular reactive oxygen species (ROS) levels increased by approximately 2.5-fold (measured by the DCFH-DA fluorescent probe), and glutathione (GSH) levels decreased by approximately 40% (measured by the GSH detection kit). [2] |
| References |
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| Additional Infomation |
Elemilin is an olefin compound. It has been reported to exist in Daphne genkwa, Perilla frutescens and other organisms with relevant data. - Metabolic activation requirements: Elemilin needs to be biotransformed in liver microsomes by cytochrome P450 enzymes (e.g., CYP2A6, CYP3A4) to generate active metabolites (e.g., 1'-hydroxyelemilin, 1'-oxoelemilin). These metabolites are the source of SCD1 inhibition and cytotoxicity, while the parent drug has very low biological activity. [1][2][3] - Natural source background: Elemilin is a naturally occurring phenylpropene compound, mainly isolated from the essential oils of nutmeg (Myristica fragrans) and other plants. Due to its abundance in natural sources, its biological activities (e.g., SCD1 inhibition, anti-influenza) have been studied. [1][4]
-SCD1 Inhibition Significance: SCD1 is overexpressed in various diseases (e.g., obesity, cancer), and the inhibitory effect of metabolically activated elemol suggests its potential therapeutic value in these diseases. However, its metabolic toxicity requires further investigation. [1][3] |
| Molecular Formula |
C12H16O3
|
|---|---|
| Molecular Weight |
208.2536
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| Exact Mass |
208.11
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| CAS # |
487-11-6
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| PubChem CID |
10248
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.011 g/cm3
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| Boiling Point |
279.8ºC at 760 mmHg
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| Flash Point |
92.6ºC
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| Vapour Pressure |
0.00666mmHg at 25°C
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| Index of Refraction |
1.496
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| LogP |
2.44
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
15
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| Complexity |
179
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C([H])([H])[H])C1=C(C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])C([H])=C([H])[H])OC([H])([H])[H]
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| InChi Key |
BPLQKQKXWHCZSS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3
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| Chemical Name |
1,2,3-trimethoxy-5-prop-2-enylbenzene
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| HS Tariff Code |
2934.99.9001
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| 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. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~480.19 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.00 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 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 (12.00 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (12.00 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 | 4.8019 mL | 24.0096 mL | 48.0192 mL | |
| 5 mM | 0.9604 mL | 4.8019 mL | 9.6038 mL | |
| 10 mM | 0.4802 mL | 2.4010 mL | 4.8019 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.
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