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    2-Hydroxy-4-methoxybenzaldehyde
    2-Hydroxy-4-methoxybenzaldehyde
    Information
    CAS No. 673-22-3 Price $30 / 20mg
    Catalog No.CFN89524Purity>=98%
    Molecular Weight152.14Type of CompoundPhenols
    FormulaC8H8O3Physical DescriptionPowder
    Download     COA    MSDSSimilar structuralComparison
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    Biological Activity
    Description: 2-Hydroxy-4-methoxybenzaldehyde is an excellent antimicrobial agent with additional antiaflatoxigenic potency. 2-Hydroxy-4-methoxybenzaldehyde has antioxidant and high antimycotic potency, it possesses chemosensitizing capability to magnify the efficacy of monoterpenoid phenols, which improves target-based (viz., cell wall disruption) antifungal intervention.
    Targets: MAPK | Antifection
    In vitro:
    Int J Mol Sci. 2015 Nov 10;16(11):26850-70.
    Augmenting the Activity of Monoterpenoid Phenols against Fungal Pathogens Using 2-Hydroxy-4-methoxybenzaldehyde that Target Cell Wall Integrity.[Pubmed: 26569223]
    Disruption of cell wall integrity system should be an effective strategy for control of fungal pathogens.
    METHODS AND RESULTS:
    To augment the cell wall disruption efficacy of monoterpenoid phenols (carvacrol, thymol), antimycotic potency of benzaldehyde derivatives that can serve as chemosensitizing agents were evaluated against strains of Saccharomyces cerevisiae wild type (WT), slt2Δ and bck1Δ (mutants of the mitogen-activated protein kinase (MAPK) and MAPK kinase kinase, respectively, in the cell wall integrity pathway). Among fourteen compounds investigated, slt2Δ and bck1Δ showed higher susceptibility to nine benzaldehydes, compared to WT. Differential antimycotic activity of screened compounds indicated "structure-activity relationship" for targeting the cell wall integrity, where 2-Hydroxy-4-methoxybenzaldehyde (2H4M) exhibited the highest antimycotic potency. The efficacy of 2H4M as an effective chemosensitizer to monoterpenoid phenols (viz., 2H4M + carvacrol or thymol) was assessed in yeasts or filamentous fungi (Aspergillus, Penicillium) according to European Committee on Antimicrobial Susceptibility Testing or Clinical Laboratory Standards Institute M38-A protocols, respectively. Synergistic chemosensitization greatly lowers minimum inhibitory or fungicidal concentrations of the co-administered compounds. 2H4M also overcame the tolerance of two MAPK mutants (sakAΔ, mpkCΔ) of Aspergillus fumigatus to fludioxonil (phenylpyrrole fungicide).
    CONCLUSIONS:
    Collectively, 2H4M possesses chemosensitizing capability to magnify the efficacy of monoterpenoid phenols, which improves target-based (viz., cell wall disruption) antifungal intervention.
    Indian J Exp Biol. 2006 Oct;44(10):832-7.
    Antioxidant property of Decalepis hamiltonii Wight & Arn.[Pubmed: 17131914]
    Aromatic edible root of D. hamiltonii was subjected to the extraction of the antioxidant rich fraction.
    METHODS AND RESULTS:
    Different parts of root namely whole tuber, peel, tuber without peel and medullary portion were extracted with dichloromethane (European Patent No. W02005063272). The extract was found to contain flavor compound 2-Hydroxy-4-methoxybenzaldehyde (2H4MB), which was identified by TLC and GC. Medullary portion was found to be rich in 2H4MB, (73.73 mg g(-1) dry tissue) followed by peel, containing 68.34 mg g(-1) 2H4MB. Different concentration of dichloromethane extracts were subjected for antioxidant assay by DPPH (1,1 dihydroxy 2-picryl hydrazyl) method, this has shown 44, 46.7% radical scavenging activity in case of medullary, peel extracts and 67.3% in case of pure 2-Hydroxy-4-methoxybenzaldehyde at 100 ppm concentration, whereas ascorbic acid used as standard showed 94.3% activity. In beta-carotene linoleate model system (b-CLAMS) 43.46 and 45.7% antioxidant activity was observed in medullary and peel extracts at 100 ppm concentrations respectively, whereas standard 2-Hydroxy-4-methoxybenzaldehyde exhibited 69.64% at 100 ppm and BHA (butylated hydroxyl anisole) 90.1% activity also at 100-ppm level. Similarly hydroxyl radical scavenging activity was found to be 48.36, 46.86, 48.26 and 73.60% in whole tuber, medullary, peel and standard 2-hydroxy-4-methoxy benzaldehyde respectively at 100 ppm levels. This is the first report on the antioxidant activity of D. hamiltonii. Results have shown that 2H4MB is one of the major constituents responsible for antioxidant activity.
    CONCLUSIONS:
    Hence the extract of D. hamiltonii can be utilized for the production of antioxidant rich fractions required for various health benefits.
    In vivo:
    Eur J Med Chem. 2016 May 23;114:209-19.
    Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.[Pubmed: 26986086 ]
    In our earlier study, we have reported that a phenolic compound 2-Hydroxy-4-methoxybenzaldehyde from Janakia arayalpatra root extract was active against Viper and Cobra envenomations. Based on the structure of this natural product, libraries of synthetic structurally variant phenolic compounds were studied through molecular docking on the venom protein.
    METHODS AND RESULTS:
    To validate the activity of eight selected compounds, we have tested them in in vivo and in vitro models. The compound 21 (2-hydroxy-3-methoxy benzaldehyde), 22 (2-Hydroxy-4-methoxybenzaldehyde) and 35 (2-hydroxy-3-methoxybenzylalcohol) were found to be active against venom-induced pathophysiological changes. The compounds 20, 15 and 35 displayed maximum anti-hemorrhagic, anti-lethal and PLA2 inhibitory activity respectively.
    CONCLUSIONS:
    In terms of SAR, the presence of a formyl group in conjunction with a phenolic group was seen as a significant contributor towards increasing the antivenom activity. The above observations confirmed the anti-venom activity of the phenolic compounds which needs to be further investigated for the development of new anti-snake venom leads.
    2-Hydroxy-4-methoxybenzaldehyde Description
    Source: The roots of Janakia arayalpatra.
    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.

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    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 6.5729 mL 32.8645 mL 65.7289 mL 131.4579 mL 164.3223 mL
    5 mM 1.3146 mL 6.5729 mL 13.1458 mL 26.2916 mL 32.8645 mL
    10 mM 0.6573 mL 3.2864 mL 6.5729 mL 13.1458 mL 16.4322 mL
    50 mM 0.1315 mL 0.6573 mL 1.3146 mL 2.6292 mL 3.2864 mL
    100 mM 0.0657 mL 0.3286 mL 0.6573 mL 1.3146 mL 1.6432 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
    Structure Identification:
    J Agric Food Chem. 2017 Oct 11;65(40):8773-8778.
    Antiaflatoxigenic and Antimicrobial Activities of Schiff Bases of 2-Hydroxy-4-methoxybenzaldehyde, Cinnamaldehyde, and Similar Aldehydes.[Pubmed: 28942637 ]
    2-Hydroxy-4-methoxybenzaldehyde (HMBA) is a nontoxic phenolic flavor from dietary source Decalipus hamiltonii and Hemidesmus indicus. HMBA is an excellent antimicrobial agent with additional antiaflatoxigenic potency. On the other hand, cinnamaldehyde from cinnamon is a widely employed flavor with significant antiaflatoxigenic activity.
    METHODS AND RESULTS:
    We have attempted the enhancement of antiaflatoxigenic and antimicrobial properties of HMBA, cinnamaldehyde, and similar molecules via Schiff base formation accomplished from condensation reaction with amino sugar (d-glucamine). HMBA derived Schiff bases exhibited commendable antiaflatoxigenic activity at the concentration 0.1 mg/mL resulting in 9.6 ± 1.9% growth of Aspergillus flavus and subsequent 91.4 ± 3.9% reduction of aflatoxin B1 with respect to control.