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138-52-3 | β-D-Glucopyranoside, 2-(hydroxymethyl)phenyl
CAS No: 138-52-3 Catalog No: AG0017T3 MDL No:MFCD00006590
Product Description
Catalog Number:
AG0017T3
Chemical Name:
β-D-Glucopyranoside, 2-(hydroxymethyl)phenyl
CAS Number:
138-52-3
Molecular Formula:
C13H18O7
Molecular Weight:
286.2778
MDL Number:
MFCD00006590
IUPAC Name:
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
InChI:
InChI=1S/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
InChI Key:
NGFMICBWJRZIBI-UJPOAAIJSA-N
SMILES:
OC[C@H]1O[C@@H](Oc2ccccc2CO)[C@@H]([C@H]([C@@H]1O)O)O
EC Number:
205-331-6
UNII:
4649620TBZ
NSC Number:
758201
Properties
Complexity:
300
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
5
Defined Bond Stereocenter Count:
0
Exact Mass:
286.105g/mol
Formal Charge:
0
Heavy Atom Count:
20
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
5
Isotope Atom Count:
0
Molecular Weight:
286.28g/mol
Monoisotopic Mass:
286.105g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
120A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.2
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| Conflicting demands on detoxification pathways influence how common brushtail possums choose their diets. | Ecology 20060801 |
| Monitoring carbohydrate enzymatic reactions by quantitative in vitro microdialysis. | Journal of chromatography. A 20060616 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Herbal medicine for low back pain. | The Cochrane database of systematic reviews 20060419 |
| The historical analysis of aspirin discovery, its relation to the willow tree and antiproliferative and anticancer potential. | Cell proliferation 20060401 |
| Cloning and comparison of third beta-glucoside utilization (bglEFIA) operon with two operons of Pectobacterium carotovorum subsp. carotovorum LY34. | Bioscience, biotechnology, and biochemistry 20060401 |
| Reclassification of Paenibacillus larvae subsp. pulvifaciens and Paenibacillus larvae subsp. larvae as Paenibacillus larvae without subspecies differentiation. | International journal of systematic and evolutionary microbiology 20060301 |
| Inhibition activities of natural products on serine proteases. | Phytotherapy research : PTR 20060301 |
| The expression of genes encoding lipodepsipeptide phytotoxins by Pseudomonas syringae pv. syringae is coordinated in response to plant signal molecules. | Molecular plant-microbe interactions : MPMI 20060301 |
| Genomic variation in Streptococcus mutans: deletions affecting the multiple pathways of beta-glucoside metabolism. | Oral microbiology and immunology 20060201 |
| Metabolic pathways variability and sequence/networks comparisons. | BMC bioinformatics 20060101 |
| [The Italian contributions to the history of salicylates]. | Reumatismo 20060101 |
| Osteoarthritis and nutrition. From nutraceuticals to functional foods: a systematic review of the scientific evidence. | Arthritis research & therapy 20060101 |
| Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada. | Journal of ethnobiology and ethnomedicine 20060101 |
| Electrophysiological and behavioural characterization of gustatory responses to antennal 'bitter' taste in honeybees. | The European journal of neuroscience 20051201 |
| Purification and characterization of an intracellular beta-glucosidase from the methylotrophic yeast Pichia pastoris. | Biochemistry. Biokhimiia 20051201 |
| Stable isotope characterization of the ortho-oxygenated phenylpropanoids: coumarin and melilotol. | Journal of agricultural and food chemistry 20051130 |
| Purification and characterization of two endo-beta-1,4-glucanases from mollusca, Ampullaria crossean. | Acta biochimica et biophysica Sinica 20051001 |
| Pyrosequencing Bacillus anthracis. | Emerging infectious diseases 20051001 |
| Lactobacillus concavus sp. nov., isolated from the walls of a distilled spirit fermenting cellar in China. | International journal of systematic and evolutionary microbiology 20050901 |
| Analysis of carbohydrates in plants by high-performance anion-exchange chromatography coupled with electrospray mass spectrometry. | Journal of chromatography. A 20050826 |
| A digestive beta-glucosidase from the silkworm, Bombyx mori: cDNA cloning, expression and enzymatic characterization. | Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20050801 |
| Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae). | Journal of agricultural and food chemistry 20050727 |
| Positive selection on a high-sensitivity allele of the human bitter-taste receptor TAS2R16. | Current biology : CB 20050726 |
| Semi-industrial isolation of salicin and amygdalin from plant extracts using slow rotary counter-current chromatography. | Journal of chromatography. A 20050513 |
| Comparison of molecular mobility in the glassy state between amorphous indomethacin and salicin based on spin-lattice relaxation times. | Pharmaceutical research 20050501 |
| Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction. | Journal of biotechnology 20050420 |
| Structural and biochemical analysis of the asc operon encoding 6-phospho-beta-glucosidase in Pectobacterium carotovorum subsp. carotovorum LY34. | Research in microbiology 20050301 |
| [Arbutin, salicin: the possibilities of their biotechnological production]. | Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 20050301 |
| Purification and characterization of recombinant Escherichia coli-expressed Pichia etchellsii beta-glucosidase II with high hydrolytic activity on sophorose. | Applied microbiology and biotechnology 20050201 |
| Emetic toxin formation of Bacillus cereus is restricted to a single evolutionary lineage of closely related strains. | Microbiology (Reading, England) 20050101 |
| Emergence of unusual species of enterococci causing infections, South India. | BMC infectious diseases 20050101 |
| Sample pretreatment and determination of non steroidal anti-inflammatory drugs (NSAIDs) in pharmaceutical formulations and biological samples (blood, plasma, erythrocytes) by HPLC-UV-MS and micro-HPLC. | Current medicinal chemistry 20050101 |
| Aerococcus urinae: polyphasic characterization of the species. | APMIS : acta pathologica, microbiologica, et immunologica Scandinavica 20050101 |
| Genetic variability among Blastoschizomyces capitatus isolates from different clinical sources. | International journal of immunopathology and pharmacology 20050101 |
| HPLC-MS/MS analysis of willow bark extracts contained in pharmaceutical preparations. | Phytochemical analysis : PCA 20050101 |
| Mechanisms involved in the anti-inflammatory effect of a standardized willow bark extract. | Arzneimittel-Forschung 20050101 |
| Differentiation of extractive and synthetic salicin. The 2H aromatic pattern of natural 2-hydroxybenzyl alcohol. | Journal of agricultural and food chemistry 20041229 |
| Purification and characterization of an extracellular b-glucosidase with high transglucosylation activity and stability from Aspergillus niger No. 5.1. | Applied biochemistry and biotechnology 20041201 |
| Bitter taste receptors for saccharin and acesulfame K. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20041110 |
| A randomized double-blind placebo-controlled clinical trial of a product containing ephedrine, caffeine, and other ingredients from herbal sources for treatment of overweight and obesity in the absence of lifestyle treatment. | International journal of obesity and related metabolic disorders : journal of the International Association for the Study of Obesity 20041101 |
| Analysis of bgl operon structure and characterization of beta-glucosidase from Pectobacterium carotovorum subsp. carotovorum LY34. | Bioscience, biotechnology, and biochemistry 20041101 |
| The role of carboxyl, guanidine and imidazole groups in catalysis by a midgut trehalase purified from an insect larvae. | Insect biochemistry and molecular biology 20041001 |
| Isolation and characterization of a cellulolytic Geobacillus thermoleovorans T4 strain from sugar refinery wastewater. | Extremophiles : life under extreme conditions 20041001 |
| [Life threatening intestinal bleeding in a Bearded Collie associated with a food supplement for horses]. | Schweizer Archiv fur Tierheilkunde 20041001 |
| Sympodiomyces attinorum sp. nov., a yeast species associated with nests of the leaf-cutting ant Atta sexdens. | International journal of systematic and evolutionary microbiology 20040901 |
| Catabolite repression and virulence gene expression in Listeria monocytogenes. | Current microbiology 20040801 |
| Enzymatic synthesis of two salicin analogues by reaction of salicyl alcohol with Bacillus macerans cyclomaltodextrin glucanyltransferase and Leuconostoc mesenteroides B-742CB dextransucrase. | Carbohydrate research 20040601 |
| Proposal to accommodate Burkholderia cepacia genomovar VI as Burkholderia dolosa sp. nov. | International journal of systematic and evolutionary microbiology 20040501 |
| Isolation of salicin derivatives from Homalium cochinchinensis and their antiviral activities. | Journal of natural products 20040401 |
| Optimization of carbohydrate silylation for gas chromatography. | Journal of chromatography. A 20040220 |
| Effects of an ethanolic salix extract on the release of selected inflammatory mediators in vitro. | Phytomedicine : international journal of phytotherapy and phytopharmacology 20040201 |
| Identification of aryl-phospho-beta-D-glucosidases in Bacillus subtilis. | Archives of microbiology 20040101 |
| [Purification of lectin from perch (Persa fluviatilis L.) roe specific to cellobiose and study of its characteristics]. | Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20040101 |
| Increased mortality of gypsy moth Lymantria dispar (L.) (Lepidoptera: Lymantriidae) exposed to gypsy moth nuclear polyhedrosis virus in combination with the phenolic gycoside salicin. | Journal of economic entomology 20031201 |
| Substrate specificity of the Arabidopsis thaliana sucrose transporter AtSUC2. | The Journal of biological chemistry 20031107 |
| The effect of willow leaf extracts on human leukemic cells in vitro. | Journal of biochemistry and molecular biology 20030731 |
| Prediction of the relaxation behavior of amorphous pharmaceutical compounds. I. Master curves concept and practice. | Journal of pharmaceutical sciences 20030701 |
| Trade-off between synthesis of salicylates and growth of micropropagated Salix pentandra. | Journal of chemical ecology 20030701 |
| The beta-glucoside genes of Klebsiella aerogenes: conservation and divergence in relation to the cryptic bgl genes of Escherichia coli. | FEMS microbiology letters 20030627 |
| Purification and characterization of two beta-glucosidases from a thermo-tolerant yeast Pichia etchellsii. | Biochimica et biophysica acta 20030626 |
| A single V317A or V317M substitution in Enzyme II of a newly identified beta-glucoside phosphotransferase and utilization system of Corynebacterium glutamicum R extends its specificity towards cellobiose. | Microbiology (Reading, England) 20030601 |
| Purification and characterization of vanilla bean (Vanilla planifolia Andrews) beta-D-glucosidase. | Journal of agricultural and food chemistry 20030507 |
| Salicin and treatment of rheumatic diseases. | The Journal of rheumatology 20030501 |
| Aeromonas hydrophila subsp. ranae subsp. nov., isolated from septicaemic farmed frogs in Thailand. | International journal of systematic and evolutionary microbiology 20030501 |
| In vitro degradation of willow salicylates. | Journal of chemical ecology 20030501 |
| Influence of willow bark extract on cyclooxygenase activity and on tumor necrosis factor alpha or interleukin 1 beta release in vitro and ex vivo. | Clinical pharmacology and therapeutics 20030301 |
| Staphylococcus equorum subsp. linens, subsp. nov., a starter culture component for surface ripened semi-hard cheeses. | Systematic and applied microbiology 20030301 |
| Modification of an approved medium for fecal coliform detection in seawater: A-1 medium minus salicin. | Journal of food protection 20030101 |
| Effects of willow hybridisation and simulated browsing on the development and survival of the leaf beetle Phratora vitellinae. | BMC ecology 20030101 |
| Taste and pheromone perception in mammals and flies. | Genome biology 20030101 |
| Burkholderia cepacia complex genomovars: utilization of carbon sources, susceptibility to antimicrobial agents and growth on selective media. | Journal of applied microbiology 20030101 |
| The human TAS2R16 receptor mediates bitter taste in response to beta-glucopyranosides. | Nature genetics 20021101 |
| Characterization of an extracellular salicyl alcohol oxidase from larval defensive secretions of Chrysomela populi and Phratora vitellinae (Chrysomelina). | Insect biochemistry and molecular biology 20021101 |
| Lactobacillus pantheris sp. nov., isolated from faeces of a jaguar. | International journal of systematic and evolutionary microbiology 20020901 |
| Contribution of different taste cells and signaling pathways to the discrimination of 'bitter' taste stimuli by an insect. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20020815 |
| Evaluation of salicin as an antipyretic prodrug that does not cause gastric injury. | Planta medica 20020801 |
| Phenotypic and genotypic properties of the genus Hafnia. | Journal of medical microbiology 20020701 |
| The treatment of acute rheumatism by salicin, by T.J. Maclagan--The Lancet, 1876. | The Journal of rheumatology 20020601 |
| Laccase down-regulation causes alterations in phenolic metabolism and cell wall structure in poplar. | Plant physiology 20020501 |
| Weissella kimchii sp. nov., a novel lactic acid bacterium from kimchi. | International journal of systematic and evolutionary microbiology 20020301 |
| Phenolic glucosides from Alangium plantanifolium. | Journal of Asian natural products research 20020301 |
| [Pain management with herbal antirheumatic drugs]. | Wiener medizinische Wochenschrift (1946) 20020101 |
| [Willow bark extract--effects and effectiveness. Status of current knowledge regarding pharmacology, toxicology and clinical aspects]. | Wiener medizinische Wochenschrift (1946) 20020101 |
| Treatment of low back pain with a herbal or synthetic anti-rheumatic: a randomized controlled study. Willow bark extract for low back pain. | Rheumatology (Oxford, England) 20011201 |
| Selective adaptation to noxious foods by a herbivorous insect. | The Journal of experimental biology 20011001 |
| Purification and characterization of a beta-glucosidase from Citrus sinensis var. Valencia fruit tissue. | Journal of agricultural and food chemistry 20010901 |
| [Determination of salicin in extract of willow bark by high performance liquid chromatography]. | Se pu = Chinese journal of chromatography 20010901 |
| Differences in host use efficiency of larvae of a generalist moth, Operophtera brumata on three chemically divergent Salix species. | Journal of chemical ecology 20010801 |
| Pharmacokinetics of salicin after oral administration of a standardised willow bark extract. | European journal of clinical pharmacology 20010801 |
| An evolutionary alternative system for aryl beta-glucosides assimilation in bacteria. | Journal of molecular microbiology and biotechnology 20010701 |
| Potential economic impact of using a proprietary willow bark extract in outpatient treatment of low back pain: an open non-randomized study. | Phytomedicine : international journal of phytotherapy and phytopharmacology 20010701 |
| Does excretion of secondary metabolites always involve a measurable metabolic cost? Fate of plant antifeedant salicin in common brushtail possum, Trichosurus vulpecula. | Journal of chemical ecology 20010601 |
| Water-soluble organometallic catalysts from carbohydrates. 2. A strategy for the preparation of catalysts with pendant quaternary ammonium groups using D-salicin. | The Journal of organic chemistry 20010518 |
| Effect of salicis cortex extract on human platelet aggregation. | Planta medica 20010401 |
| [Development of chromogenic agar medium for isolation of enterohaemorrhagic Escherichia coli O26]. | Kansenshogaku zasshi. The Journal of the Japanese Association for Infectious Diseases 20010401 |
| Plants as de-worming agents of livestock in the Nordic countries: historical perspective, popular beliefs and prospects for the future. | Acta veterinaria Scandinavica 20010101 |
| [Effect of human serum albumin on transport of drugs through human erythrocyte membranes]. | Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 19960801 |
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