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  • 苄基-β-D-葡萄糖苷

    Benzyl beta-D-glucopyranoside

    产品编号 CFN95427
    CAS编号 4304-12-5
    分子式 = 分子量 C13H18O6 = 270.3
    产品纯度 >=98%
    物理属性 Powder
    化合物类型 Phenols
    植物来源 The peels of Salix alba L.
    产品名称 产品编号 CAS编号 包装 QQ客服
    苄基-β-D-葡萄糖苷 CFN95427 4304-12-5 1mg QQ客服:2159513211
    苄基-β-D-葡萄糖苷 CFN95427 4304-12-5 5mg QQ客服:2159513211
    苄基-β-D-葡萄糖苷 CFN95427 4304-12-5 10mg QQ客服:2159513211
    苄基-β-D-葡萄糖苷 CFN95427 4304-12-5 20mg QQ客服:2159513211
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    doi: 10.1126/sciadv.aat6994.

    PMID: 30417089
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  • ...
  • 生物活性
    Description: Benzyl β-D-glucopyranoside exhibits strong PTP1B enzyme inhibition (IC50 = 6.97) and antioxidant activity.Benzyl beta-D-glucopyranoside contribute to relieving the tension in M-rats caused by ether stress.
    In vitro:
    Nat Prod Res . 2021 Apr;35(8):1388-1392.
    Phenolic glycosides from Nitraria sibirica leaves and their in vitro biological activities[Pubmed: 31379199]
    Seventeen phenolic glycosides were isolated from the Nitraria sibirica. Their structures were identified by the spectroscopic data and comparison with literatures as isovanillyl alcohol-7-O-β-d-glucopyranoside (1), benzyl β-primeveroside (2), benzyl-O-β-d-glucopyranoside (3), 1-O-β-d-glucopyranosyl-4-(8-hydroxyethyl)-2-methoxyphenyl (4), dehydrosyringin (5), trans-ferulic acid-4-O-β-d-glucoside (6), cis-ferulic acid 4-O-β-d-glucopyranoside (7), glucosyringic acid (8), 1-O-feruloyl-β-d-glucoside (9), sachaloside VII (10), (3S, 5R, 6R, 7E, 9S)-megastigmane-7-ene-3-hydroxy-5,6-epoxy-9-O-β-d-glucopyranoside(11), 3-hydroxy-4,5-dimethoxybenzyl alcohol (12), pinoresinol 4-O-β-d-glucopyranoside (13), eucommin A (14), isoeucommin A (15), acanthoside (16), liriodendrin (17). All these compounds except compound 13 were isolated from the Nitraria genus for the first time. In bioactivity assays for all compounds, the compounds 8 and 15 were exhibited strong antioxidant activity (IC50 = 18.11 and 16.29 μM respectively), while compounds 3 and 11 were exhibited strong PTP1B enzymatic inhibition (IC50 = 6.97 and 11.76 μM, respectively). Furthermore, the compounds 10 and 17 were presented strong inhibitory capacities against Candida albicans (14.5 and 13.5 mm, respectively).
    Carbohydr Res . 2008 Nov 24;343(17):2939-2946.
    Engineering of glucoside acceptors for the regioselective synthesis of beta-(1-->3)-disaccharides with glycosynthases[Pubmed: 18828996]
    Glycosynthase mutants obtained from Thermotogamaritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1-->3)-beta-D-Glcp and aryl beta-D-Glcp-(1-->3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-d-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1-->3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively.
    Carbohydr Res . 1989 Dec 1;194:185-198.
    Selective bromoacetylation of alkyl hexopyranosides: a facile preparation of intermediates for the synthesis of (1----6)-linked oligosaccharides[Pubmed: 2620299]
    Bromoacetylation of methyl beta-D-galacto- (1), alpha-D-galacto- (6), beta-D-gluco- (18), (22), and alpha-D-manno-pyranoside (31), and benzyl beta-D-glucopyranoside (27), gave the corresponding 6-O-bromoacetyl derivatives 2, 7, 19, 23, 32, and 28 in 50-60% yields. Bromoacetylation of methyl 3-O-benzyl-beta-D-galactopyranoside (11) afforded methyl 3-O-benzyl-6-O-bromoacetyl-beta-D-galactopyranoside (12, 60%) as well as methyl 3-O-benzyl-2,6-di-O-bromoacetyl-beta-D-galactopyranoside (13, 14%). Compounds 2, 7, 19, 23, 32, 28, and 12 were benzoylated and the fully protected derivatives obtained were dehaloacetylated with thiourea to afford the methyl 2,3,4-tri-O-benzoyl-D-glycopyranosides of beta-galactose (5), alpha-galactose (9), beta-glucose (21), alpha-glucose (25), and alpha-mannose (34), as well as benzyl 2,3,4-tri-O-benzoyl-beta-D-glucopyranoside (30) and methyl 3-O-benzyl-2,4-di-O-benzoyl-beta-D-galactopyranoside (15). These compounds can be used as nucleophiles for the synthesis of (1----6)-linked oligosaccharides. The conversion 1----5 could be performed without isolation of the intermediates. The treatment of bromoacetyl derivatives with benzoyl chloride in pyridine resulted in the benzoylation of the remaining free hydroxyl groups and the simultaneous substitution of bromine by chlorine, yielding the corresponding mono-O-chloroacetyl derivatives. Benzoylations with benzoyl bromide avoided this secondary event. Glycosyl donors differentially substituted to allow further extension of the oligosaccharide chain at position 6 of D-glucose, D-galactose, and D-mannose, and sequentially at positions 6 and 3 in the case of the D-galactosyl donor derived from 15, were readily obtained by treatment of the appropriate, fully protected methyl glycosides with 1,1-dichloromethyl methyl ether in the presence of a catalytic amount of zinc chloride.
    Bioorg Med Chem Lett . 2014 Sep 1;24(17):4120-4124.
    A new phenylpropanoid and an alkylglycoside from Piper retrofractum leaves with their antioxidant and α-glucosidase inhibitory activity[Pubmed: 25127165]
    Two new compounds, piperoside (1) and isoheptanol 2(S)-O-β-D-xylopyranosyl (1→6)-O-β-D-glucopyranoside (11), along with 10 known compounds 3,4-dihydroxyallylbenzene (2), 1,2-di-O-β-D-glucopyranosyl-4-allylbenzene (3), tachioside (4), benzyl-O-β-D-glucopyranoside (5), icariside F2 (6), dihydrovomifoliol-3'-O-β-D-glucopyranoside (7), isopropyl O-β-D-glucopyranoside (8), isopropyl primeveroside (9), n-butyl O-β-D-glucopyranoside (10), isoheptanol 2(S)-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside (12), were isolated from the leaves of Piper retrofractum. Their structures were determined from 1D-NMR, 2D-NMR, and HR-ESI-MS spectral, a modified Mosher's method, and comparisons with previous reports. All of the isolated compounds showed modest α-glucosidase inhibitory (4.60±1.74% to 11.97±3.30%) and antioxidant activities under the tested conditions.
    In vivo:
    Biol Pharm Bull . 2004 Jan;27(1):136-137.
    Effects of benzyl glucoside and chlorogenic acid from Prunus mume on adrenocorticotropic hormone (ACTH) and catecholamine levels in plasma of experimental menopausal model rats[Pubmed: 14709918]
    To investigate the effectiveness of benzyl beta-D-glucopyranoside (BG) and chlorogenic acid (CA), the constituents of the fruit of Prunus mume, for relieving tension in experimental menopausal model rats (M-rats) caused by ether stress, the effects of BG and CA on adrenocorticotropic hormone (ACTH) and catecholamine (adrenaline, noradrenaline, and dopamine) levels were examined in the plasma of M-rats. Caffeic acid, quinic acid, and rosmarinic acid, which are compounds structurally related to CA, were also examined. BG obviously recovered catecholamine levels decreased by ether stress and increased dopamine to high levels. On the other hand, CA significantly decreased the ACTH level increased by ether stress and showed the greatest effect of all compounds. These results suggest that BG and CA may contribute to relieving the tension in M-rats caused by ether stress.
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.6996 mL 18.498 mL 36.9959 mL 73.9919 mL 92.4898 mL
    5 mM 0.7399 mL 3.6996 mL 7.3992 mL 14.7984 mL 18.498 mL
    10 mM 0.37 mL 1.8498 mL 3.6996 mL 7.3992 mL 9.249 mL
    50 mM 0.074 mL 0.37 mL 0.7399 mL 1.4798 mL 1.8498 mL
    100 mM 0.037 mL 0.185 mL 0.37 mL 0.7399 mL 0.9249 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.
    产品名称 产品编号 CAS编号 分子式 = 分子量 位单 联系QQ
    4-甲氧基苯基β-D-吡喃葡萄糖苷; 4-Methoxyphenyl beta-D-glucopyranoside CFN90721 6032-32-2 C13H18O7 = 286.28 5mg QQ客服:3257982914
    草夹竹桃苷; Androsin CFN93252 531-28-2 C15H20O8 = 328.3 20mg QQ客服:1148253675
    苄基-β-D-葡萄糖苷; Benzyl beta-D-glucopyranoside CFN95427 4304-12-5 C13H18O6 = 270.3 10mg QQ客服:3257982914
    2-Phenylethyl-beta-glucopyranoside; 2-Phenylethyl-beta-glucopyranoside CFN95429 18997-54-1 C14H20O6 = 284.3 10mg QQ客服:1413575084
    D-(-)-水杨苷; D-(-)-水杨甙; D-(-)-Salicin CFN99541 138-52-3 C13H18O7 = 286.27 20mg QQ客服:2932563308
    牡丹酚新甙; Apiopaeonoside CFN90664 100291-86-9 C20H28O12 = 460.43 20mg QQ客服:1413575084
    丹皮酚原苷; Paeonolide CFN90668 72520-92-4 C20H28O12 = 460.43 20mg QQ客服:3257982914
    二酚基水杨苷; 鄂西香茶菜苷; Henryoside CFN97203 72021-23-9 C26H32O15 = 584.5 5mg QQ客服:215959384
    柳匍匐次苷; Salirepin CFN98314 26652-12-0 C13H18O8 = 302.3 5mg QQ客服:215959384
    仙茅苷乙; Curculigoside B CFN92961 143601-09-6 C21H24O11 = 452.41 10mg QQ客服:215959384





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