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    Dehydrodiisoeugenol
    Information
    CAS No. 2680-81-1 Price $128 / 20mg
    Catalog No.CFN99750Purity>=98%
    Molecular Weight326.39Type of CompoundLignans
    FormulaC20H22O4Physical DescriptionWhite powder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: Dehydrodiisoeugenol has anti-inflammatory activity, it inhibited the expression of the COX-2, proteolysis of inhibitor κB-α and transcriptional activity of NF-κB. Dehydrodiisoeugenol can cross the blood-brain barrier rapidly, it may be developed into an effective anxiogenic agent.
    Targets: NF-kB | COX | IκB/IKK
    In vitro:
    Planta Med. 2011 Oct;77(15):1712-7.
    Metabolism of the lignan dehydrodiisoeugenol in rats.[Pubmed: 21544774]
    Dehydrodiisoeugenol (DDIE), a major active lignan from the seed and aril of the fruit of Myristica fragrans Houtt., functions as a potential anti-inflammatory agent by inhibiting lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages. However, the metabolism of DDIE remains unknown.
    METHODS AND RESULTS:
    This report describes the metabolic fate of DDIE in liver microsomes, urine, and feces of rats treated with DDIE. DDIE metabolites were isolated by sequential column chromatography and high-performance liquid chromatography from liver microsomes incubations, urine, and feces. Nine metabolites ( M-1 to M-9), including 5 new metabolites, were determined spectroscopically using ultra-violet (UV), mass spectrometry (MS), nuclear magnetic resonance (NMR), and circular dichroism (CD). Analysis of the isolated metabolites showed that DDIE undergoes four major pathways of metabolism in the rat: oxidation (including hydroxylation, hydroformylation, and acetylation), demethylation, ring-opening, and dehydrogenation. In contrast to the metabolites from liver microsomes, the major metabolites In vivo were generated from DDIE by multiple metabolic reactions.
    CONCLUSIONS:
    Given these results, we describe a metabolic pathway for DDIE in the rat that gives insight into the metabolism of DDIE and the mechanism of DDIE bioactivity in humans.
    Dehydrodiisoeugenol Description
    Source: The seeds of Myristica fragrans Houtt.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.0638 mL 15.3191 mL 30.6382 mL 61.2764 mL 76.5955 mL
    5 mM 0.6128 mL 3.0638 mL 6.1276 mL 12.2553 mL 15.3191 mL
    10 mM 0.3064 mL 1.5319 mL 3.0638 mL 6.1276 mL 7.6595 mL
    50 mM 0.0613 mL 0.3064 mL 0.6128 mL 1.2255 mL 1.5319 mL
    100 mM 0.0306 mL 0.1532 mL 0.3064 mL 0.6128 mL 0.766 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Cell Research:
    Arch Biochem Biophys. 2005 Feb 15;434(2):326-32.
    Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages.[Pubmed: 15639233]
    o-Methoxyphenols such as eugenol and isoeugenol exhibit anti-oxidant and anti-inflammatory activities, but at higher concentrations act as oxidants and potent allergens.
    METHODS AND RESULTS:
    We recently demonstrated the eugenol dimer bis-eugenol to be an efficient inhibitor of lipopolysaccharide (LPS)-induced inflammatory cytokine expression in macrophages without cytotoxicity. This result suggested that dimer compound of o-methoxyphenols may possess anti-inflammatory activity. Thus, we further synthesized Dehydrodiisoeugenol and alpha-diisoeugenol from isoeugenols, and investigated whether these dimers could inhibit LPS-stimulated nuclear factor kappa B (NF-kappaB) activation and cyclooxygenase (COX)-2 gene expression, both of which are closely involved in inflammation and mutagenesis. The expression of the COX-2 gene was strongly inhibited by Dehydrodiisoeugenol in RAW264.7 murine macrophages stimulated with LPS. In contrast, isoeugenol and alpha-diisoeugenol did not inhibit it. Dehydrodiisoeugenol also significantly inhibited LPS-stimulated phosphorylation-dependent proteolysis of inhibitor kappaB-alpha and transcriptional activity of NF-kappaB in the cells.
    CONCLUSIONS:
    These findings suggest that Dehydrodiisoeugenol acts as a potent anti-inflammatory agent.
    Structure Identification:
    Fitoterapia. 2013 Jan;84:47-53.
    Cerebral nuclei distribution study of dehydrodiisoeugenol as an anxiogenic agent determined by RP-HPLC.[Pubmed: 23059843]

    METHODS AND RESULTS:
    A sensitive RP-HPLC-DAD method was established to quantify Dehydrodiisoeugenol (DDIE) in rat cerebral nuclei. The assay procedure involved one-step extraction of Dehydrodiisoeugenol and daidzein, as an internal standard, from rat plasma and various cerebral nuclei with ethyl acetate. Chromatographic separation was performed on a Diamonsil™ ODS C(18) column with methanol-water (81:19, v/v) as a mobile phase. The UV absorbance of the samples was measured at the wavelength of 270nm. The analysis method was proved to be precise and accurate at linearity ranges in plasma and each cerebral nucleus with correlation coefficients of ≥0.9971. The results indicated that the method established was successfully applied to cerebral nuclei distribution study of Dehydrodiisoeugenol after intravenous administration at a single dose of 40mg/kg to rat. Dehydrodiisoeugenol showed high concentration in all of cerebral nuclei at 8min, which indicated that Dehydrodiisoeugenol could cross the blood-brain barrier rapidly and might be one of the main bioactive substances of nutmeg.
    CONCLUSIONS:
    The results provide fundamental data for evaluating the effects of Dehydrodiisoeugenol on the central nervous system and to be developed into an effective anxiogenic agent.