| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| Other Sizes |
| Targets |
Human Endogenous Metabolite
Damascenone targets the NF-κB signaling pathway, a master regulator of inflammation and immune responses. By inhibiting NF-κB-dependent transcription, the compound suppresses the expression of pro-inflammatory cytokines such as TNF-α and leukocyte adhesion molecules including E-selectin. Damascenone also targets human endogenous metabolite pathways. The compound's mechanism involves inhibition of inflammatory protein upregulation, which may contribute to its anti-inflammatory effects in various cellular systems. |
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| ln Vitro |
Immune assays for cell surface E-selectin and secreted TNF-α showed that β-Damascenone also inhibits the upregulation of inflammatory proteins[1].
In vitro, when human cellular systems are activated by various inflammatory stimuli, β-Damascenone inhibits the NF-κB signaling pathway[1]. In vitro studies demonstrate that β-Damascenone inhibits the upregulation of inflammatory proteins, as shown by immune assays for cell surface E-selectin and secreted TNF-α. In human cellular systems activated with various inflammatory stimuli, β-Damascenone inhibits the NF-κB signaling pathway. Using a luciferase reporter construct, it has been shown that the compound inhibits NF-κB-dependent transcription. These findings confirm that inhibition of NF-κB represents one of the mechanisms underlying the in vitro anti-inflammatory activity of Damascenone. |
| ln Vivo |
Specific in vivo data for Damascenone as an anti-inflammatory agent are limited. Most research has focused on in vitro characterization of its anti-inflammatory mechanisms. However, given its ability to inhibit NF-κB signaling and reduce pro-inflammatory cytokine expression, the compound has potential for in vivo studies in animal models of inflammation, such as carrageenan-induced paw edema, DSS-induced colitis, or LPS-induced systemic inflammation. Such studies would evaluate the compound's efficacy in reducing inflammation, tissue damage, and inflammatory cytokine levels in vivo.
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| Enzyme Assay |
The in vitro anti-inflammatory activity is assessed using immune assays in human cellular systems. Cells (e.g., endothelial cells, monocytes, or macrophages) are activated with inflammatory stimuli such as TNF-α, LPS, or IL-1β. Cells are treated with β-Damascenone, and the expression of cell surface adhesion molecules (e.g., E-selectin) is measured by flow cytometry or ELISA. Secreted TNF-α levels are quantified by ELISA. NF-κB activity is assessed using a luciferase reporter construct, where cells are transfected with an NF-κB-responsive luciferase plasmid and treated with the compound, with luciferase activity measured as a readout of NF-κB-dependent transcription.
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| Cell Assay |
For cellular studies, human cell lines such as endothelial cells (e.g., HUVEC), monocytes (e.g., THP-1), or macrophages are cultured in appropriate media. Cells are pre-treated with β-Damascenone at various concentrations for 1-2 hours, then stimulated with inflammatory activators such as TNF-α (10 ng/mL) or LPS (1 μg/mL) for 4-24 hours. Cell surface E-selectin expression is measured by flow cytometry using fluorescently labeled antibodies. Cytokine levels in culture supernatants are quantified by ELISA. NF-κB luciferase reporter assays are performed in transfected cells, with luciferase activity normalized to cell viability or a control reporter.
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| Animal Protocol |
In vivo anti-inflammatory studies for Damascenone would be conducted in standard rodent models. For acute inflammation, the carrageenan-induced paw edema model in rats would involve subplantar injection of carrageenan followed by oral or intraperitoneal administration of Damascenone, with paw volume measured plethysmographically. For chronic inflammation, DSS-induced colitis or LPS-induced systemic inflammation models in mice would be used. Endpoints would include inflammatory cytokine levels, histopathology, and clinical scores. However, specific published protocols for Damascenone are not available.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic data for Damascenone are not extensively reported in the pharmacological literature. The compound has a molecular weight of 190.28 g/mol and is a volatile terpene ketone. In the fragrance industry, it is known to have suitable volatility for olfactory applications. For pharmacological research, formal PK studies would be required to determine absorption, distribution, metabolism, and excretion profiles. The compound's lipophilicity suggests potential for tissue distribution and possible blood-brain barrier penetration.
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| Toxicity/Toxicokinetics |
Toxicological data for Damascenone in pharmacological contexts are limited. As a fragrance compound, it has been evaluated for safety in cosmetic and flavor applications, but comprehensive toxicology data for systemic administration are not available. The compound is generally recognized as safe for use in fragrances at low concentrations. However, for research purposes, appropriate safety precautions should be taken, and the compound should be handled in accordance with standard laboratory safety practices.
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| References | |
| Additional Infomation |
β-Damamilone is a cyclic monoterpene ketone formed by the substitution of 2,6,6-trimethylcyclohexane-1,3-diene at the 1-position with a crotonyl group. It is a fragrance, volatile oil component, and plant metabolite. It is an enone, apocologne-carotenoid monoterpene, and a cyclic monoterpene ketone. Damasmilone has been reported in tea (Camellia sinensis), apple (Malus), and other organisms with relevant data. 1-[2,6,6-trimethyl-1,3-cyclohexadien-1-yl]-2-buten-1-one is a metabolite found or produced in Saccharomyces cerevisiae. trans-β-Damamilone is a metabolite found or produced in Saccharomyces cerevisiae.
Damascenone (β-Damascenone) is a C13 megastigmane from Epipremnum pinnatum with anti-inflammatory activity mediated through NF-κB inhibition. It inhibits the upregulation of inflammatory proteins including E-selectin and TNF-α in vitro. Widely used in the fragrance industry, it also serves as a research tool for studying inflammatory pathways. No clinical trials or regulatory approvals exist for therapeutic use. For research use only. |
| Molecular Formula |
C13H18O
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|---|---|
| Molecular Weight |
190.28142
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| Exact Mass |
190.135
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| CAS # |
23696-85-7
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| Related CAS # |
23696-85-7
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| PubChem CID |
5366074
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
275.6±10.0 °C at 760 mmHg
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| Flash Point |
111.0±14.0 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.491
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| LogP |
4.04
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
14
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| Complexity |
327
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C/C=C/C(C1=C(C)C=CCC1(C)C)=O
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| InChi Key |
POIARNZEYGURDG-FNORWQNLSA-N
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| InChi Code |
InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
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| Chemical Name |
(E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
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| Synonyms |
Damascenone; (E/Z)-Damascenone
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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: 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)
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| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~525.5 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.14 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 (13.14 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 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 (13.14 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 | 5.2554 mL | 26.2771 mL | 52.5541 mL | |
| 5 mM | 1.0511 mL | 5.2554 mL | 10.5108 mL | |
| 10 mM | 0.5255 mL | 2.6277 mL | 5.2554 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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