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    2,6,4'-Trihydroxy-4-methoxybenzophenone
    Information
    CAS No. 55051-85-9 Price $318 / 10mg
    Catalog No.CFN89307Purity>=98%
    Molecular Weight260.24Type of CompoundPhenols
    FormulaC14H12O5Physical DescriptionPowder
    Download     COA    MSDSSimilar structuralComparison (Web)  (SDF)
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    2,6,4'-Trihydroxy-4-methoxybenzophenone

    2,6,4'-Trihydroxy-4-methoxybenzophenone
    Product Name 2,6,4'-Trihydroxy-4-methoxybenzophenone
    CAS No.: 55051-85-9
    Catalog No.: CFN89307
    Molecular Formula: C14H12O5
    Molecular Weight: 260.24 g/mol
    Purity: >=98%
    Type of Compound: Phenols
    Physical Desc.: Powder
    Targets: Bcl-2/Bax | NGF
    Source: The rhizomes of Anemarrhena asphodeloides BUNGE.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price: $318 / 10mg
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  • J Ethnopharmacol.2019, 244:112074
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  • Related Screening Libraries
    Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
    10 mM * 1 mL in DMSO / Inquiry / In-stock
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  • Biological Activity
    Description: 2,6,4'-Trihydroxy-4-methoxybenzophenone shows weak inhibitory activity of testosterone 5alpha-reductase, it also shows significant inhibition of pancreatic lipase activity. 2,6,4'-Trihydroxy-4-methoxybenzophenone has neurotrophic activity, it induced neurite outgrowth in PC-12 cells at concentration of 50 microg/ml. 2,6,4′-Trihydroxy-4-methoxybenzophenone exhibits low cytotoxic effect against HeLa and 3T3 cell lines with IC50 values of 132 ug/ml and 158 ug/ml, repectively. It also shows antioxidant activity on DPPH with IC50 of 10.57 ug/mL.
    Targets: Bcl-2/Bax | NGF
    In vitro:
    Biol Pharm Bull. 2005 Sep;28(9):1798-800.
    7-hydroxy-3-(4-hydroxybenzyl)chroman and broussonin b: neurotrophic compounds, isolated from Anemarrhena asphodeloides BUNGE, function as proteasome inhibitors.[Pubmed: 16141565]

    METHODS AND RESULTS:
    The extract of Anemarrhenae Rhizoma (rhizomes of Anemarrhena asphodeloides BUNGE) showed neurotrophic activity toward rat pheochromocytoma (PC-12) cells. Bioassay-guided purification afforded four compounds, 2,6,4'-Trihydroxy-4-methoxybenzophenone (1), 7-hydroxy-3-(4-hydroxybenzyl)chroman (2), broussonin B (3), and cis-hinokiresinol (4).
    CONCLUSIONS:
    Compounds 1-3 induced neurite outgrowth in PC-12 cells at concentration of 50 microg/ml, while 4 was less active. In addition, compounds 2-4 showed moderate inhibitory activities against a chymotrypsin-like activity of the proteasome.
    Biol Pharm Bull. 2001 May;24(5):586-7.
    Testosterone 5alpha-reductase inhibitory active constituents from Anemarrhenae Rhizoma.[Pubmed: 11379787]

    METHODS AND RESULTS:
    The diethyl ether extract of Anemarrhenae Rhizoma (rhizomes of Anemarrhena asphodeloides Bunge) showed testosterone 5alpha-reductase inhibitory activity.
    CONCLUSIONS:
    Two major constituents, cis-hinokiresinol (1) and 2,6,4'-Trihydroxy-4-methoxybenzophenone (2) were identified as the active principles. The inhibitory activity of 1 was superior to that of ethinylestradiol, but that of 2 was weak.
    Jurnal Teknologi, 2013, 64(2).
    Cytotoxic Activity of Major Compounds from Phaleria macrocarpa (Scheff.) Boerl. Fruits.[Reference: WebLink]
    P. macrocarpa is a well known Indonesian medicinal plant which is traditionally claimed to have anticancer properties. To date, there are numerous cytotoxic studies conducted on crude extracts of this plant. However, there are limited informations available regarding cytotoxic activity of the compounds isolated from this plant.
    METHODS AND RESULTS:
    Thus, this study investigated cytotoxic activity of two benzophenones derivatives identified as 2,6,4'-Trihydroxy-4-methoxybenzophenone(1) and 6,4′-dihydroxy-4-methoxybenzophenone-2-O-β-D-glucopyranoside (2) isolated from the ethyl acetate extract. Cytotoxic activities of these compounds were performed against human cervical carcinoma cell line (HeLa) and mouse embryonic fibroblast cell line (3T3) using MTT assay.
    CONCLUSIONS:
    The result showed that benzophenone (1) exhibited low cytotoxic effect against HeLa and 3T3 cell lines with IC50 values of 132 μg/ml and 158 μg/ml, repectively while benzophenone (2) was non toxic against HeLa and 3T3 cell lines are because the IC50 is more than 250 μg/ml. These findings may sheds light on the actual properties of this plant.
    Nat Prod Commun. 2013 Apr;8(4):481-3.
    Inhibitory activity of benzophenones from Anemarrhena asphodeloides on pancreatic lipase.[Pubmed: 23738459]
    Pancreatic lipase is a key enzyme for lipid absorption by hydrolysis of total dietary fats. Therefore, inhibition of pancreatic lipase is suggested to be an effective therapy in the regulation of obesity. The EtOAc-soluble fraction of Anemarrhena asphodeloides rhizomes significantly inhibited pancreatic lipase activity as assessed using porcine pancreatic lipase as an in vitro assay system. Further fractionation of the EtOAc-soluble fraction of A. asphodeloides led to the isolation of a new benzophenone glycoside, zimoside A (1), together with the eleven known compounds iriflophenone (2), 2,4',6-trihydroxy-4-methoxybenzophenone (2,6,4'-Trihydroxy-4-methoxybenzophenone ,3), foliamangiferoside A (4), (2,3-dihydroxy-4-methoxyphenyl)(4-hydroxyphenyl)-methanone (5), 1,4,5,6,-tetrahydroxyxanthone (6), isosakuranetin (7), 4-hydroxybenzoic acid (8), 4-hydroxyacetophenone (9), vanillic acid (10), tyrosol (11) and 5-hydroxymethyl-2-furaldehyde (12). Among the isolated compounds, 3, 5 and 10 showed significant inhibition of pancreatic lipase activity.
    2,6,4'-Trihydroxy-4-methoxybenzophenone Description
    Source: The rhizomes of Anemarrhena asphodeloides BUNGE.
    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 3.8426 mL 19.213 mL 38.4261 mL 76.8521 mL 96.0652 mL
    5 mM 0.7685 mL 3.8426 mL 7.6852 mL 15.3704 mL 19.213 mL
    10 mM 0.3843 mL 1.9213 mL 3.8426 mL 7.6852 mL 9.6065 mL
    50 mM 0.0769 mL 0.3843 mL 0.7685 mL 1.537 mL 1.9213 mL
    100 mM 0.0384 mL 0.1921 mL 0.3843 mL 0.7685 mL 0.9607 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:
    Biomed Res Int. 2014;2014:468157.
    Induction of apoptosis of 2,4',6-trihydroxybenzophenone in HT-29 colon carcinoma cell line.[Pubmed: 24579081]
    2,4',6-Trihydroxy-4-methoxybenzophenone(2,6,4'-Trihydroxy-4-methoxybenzophenone ) was isolated from the ethyl acetate fraction of Phaleria macrocarpa (Scheff.) Boerl. fruits.
    METHODS AND RESULTS:
    It was found to inhibit cell proliferation in HT-29 human colon carcinoma cell line but caused little damage to WRL-68 normal human liver and MRC-5 normal human fibroblast lung cell lines. The compound was found to sharply affect the viability of HT-29 cells in a dose- and time-dependent manner. HT-29 cells treated with the compound showed morphological changes under microscopic examination such as cell shrinkage, membrane blebbing, DNA fragmentation, and the occurrence of apoptotic nuclei. The percentage of early apoptotic, late apoptotic, and dead or necrotic cells was determined by flow cytometry using annexin V-FTIC/PI staining. In addition, flow cytometry showed that, when the HT-29 cells were treated with 115 μM of the compound, it resulted in G0/G1 phase arrest in a time-dependent manner. Western blot revealed an upregulation of PUMA, Bak, Bcl-2, and Mcl-1 proteins suggesting that the compound induced apoptosis in HT-29 cells by regulating these proteins.
    Structure Identification:
    Indonesian Journal of Chemistry, 2011, 11(2):180-185.
    Antioxidant Activity of 2,6,4'-trihydroxy-4-methoxybenzophenone from Ethyl Acetate Extract of Leaves of Mahkota Dewa (Phaleria macrocarpa (Scheff.) Boerl)[Reference: WebLink]
    Mahkota dewa plant (Phaleria macrocarpa (Scheff.) Boerl.) which is included into family of Thymelaeaceae is one of Indonesia's traditional medicines. Chemical constituent has been isolated from ethyl acetate extract of leaves of mahkota dewa.
    METHODS AND RESULTS:
    Sample was extracted with methanol, concentrated then extracted by n-hexane, chloroform and ethyl acetate. The ethyl acetate extract was separated and fractionated by column chromatography. The first fraction was purified by TLC preparative and recrystalization. Compound was isolated as red-brown spherical crystal in 8 mg (m.p. 129-131 °C). Its spot gave dark fluoroscence at TLC plate (UV366) with Rf of 0.3 at TLC chromatogram with eluent of n-hexane : ethyl acetate (7:3); 0.6 with n-hexane : ethyl acetate (1:1); 0.9 with -hexane : ethyl acetate (4:6). This compound was dissolved in methanol. Compound was identified by UV, IR, 1H NMR, 13C NMR and NMR 2 dimension (HMQC, COSY, HMBC and DEPT-135) spectroscopic as 2,6,4'-Trihydroxy-4-methoxybenzophenone.
    CONCLUSIONS:
    This compound as well as the ethyl acetate extract showed antioxidant activity on DPPH with IC50 was 10.57 and 101.06 μg/mL, respectively. This compound showed strong antioxidant activity on DPPH, almost to the standard antioxidant activity of quercetin (IC50 of 2.93 μg/mL)
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