methyl umbelliferyl-beta-D-xyloside

2H-1-benzopyran-2-one, 4-methyl-7-(beta-D-xylopyranosyloxy)-

CAS: 6734-33-4 C15 H16 O7 MW: 308.28692000

Identification

Namemethyl umbelliferyl-beta-D-xyloside
IUPAC4-methyl-7-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-2-one
CAS Number6734-33-4
EINECS229-784-4
FDA UNII766N8850JA
Molecular FormulaC15 H16 O7
Molecular Weight308.28692000
MDL NumberMFCD00037607
Nikkaji NumberJ298.088F
Beilstein0039934
XlogP3-0.70 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 572.10 °C. @ 760.00 mm Hg (est)
Flash Point 423.00 °F. TCC ( 217.30 °C. ) (est)
logP (o/w) 1.020 (est)
Soluble in water, 1.05e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for methyl umbelliferyl-beta-D-xyloside usage levels up tonot for fragrance use.
Recommendation for methyl umbelliferyl-beta-D-xyloside flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

2H-1- benzopyran-2-one, 4-methyl-7-(beta-D-xylopyranosyloxy)- 4- methyl-7-(beta-D-xylopyranosyloxy)-2H-1-benzopyran-2-one 4- methyl-7-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-2-one 4- methylumbelliferyl beta-xyloside methylumbelliferyl-beta-D-xyloside PubMed: Regulation of heparan sulfate and chondroitin sulfate glycosaminoglycan biosynthesis by 4-fluoro-glucosamine in murine airway smooth muscle cells. PubMed: A novel efflux-recapture process underlies the mechanism of high-density lipoprotein cholesteryl ester-selective uptake mediated by the low-density lipoprotein receptor-related protein. PubMed: Effects of [3H]glucosamine concentration on [3H]chondroitin sulphate formation by cultured chondrocytes. PubMed: HNK-1-Reactive oligosaccharide, sulfate-O-3GlcAbeta1-4Xylbeta1-MU, synthesized by cultured human colorectal cancer cells. PubMed: A sulfated proteoglycan is necessary for storage of exocrine secretory proteins in the rat parotid gland. PubMed: Obligatory requirement of sulfation for P-selectin binding to human salivary gland carcinoma Acc-M cells and breast carcinoma ZR-75-30 cells. PubMed: Effects of ATP on regulation of galactosyltransferase-I activity responsible for synthesis of the linkage region between the core protein and glycosaminoglycan chains of proteoglycans. PubMed: Mechanistic studies of active site mutants of Thermomonospora fusca endocellulase E2. PubMed: Enhanced channelling of sulphate through a rapidly exchangeable sulphate pool in response to stimulated glycosaminoglycan synthesis in pancreatic epithelial cells. PubMed: Alterations of matrix- and cell-associated proteoglycans inhibit osteogenesis and growth response to fibroblast growth factor-2 in cultured rat mandibular condyle and calvaria. PubMed: ApoE of the HepG2 cell surface includes a major pool associated with chondroitin sulfate proteoglycans. PubMed: Characterization of beta-D-xyloside-initiated glycosaminoglycan synthesized by human skin fibroblasts in the presence of tunicamycin. PubMed: A novel 4-methylumbelliferyl-beta-D-xyloside derivative, sulfate-O-3-xylosylbeta1-(4-methylumbelliferone), isolated from culture medium of human skin fibroblasts, and its role in methylumbelliferone-initiated glycosaminoglycan biosynthesis. PubMed: Effects of O-glycosylation inhibitors on the differentiation of HL-60 cells. PubMed: Effect of monensin on the synthesis of beta-D-xyloside-initiated glycosaminoglycan and its linkage region oligosaccharides in human skin fibroblasts. PubMed: Uptake of hypertriglyceridemic very low density lipoproteins and their remnants by HepG2 cells: the role of lipoprotein lipase, hepatic triglyceride lipase, and cell surface proteoglycans. PubMed: Lipoprotein lipase reduces secretion of apolipoprotein E from macrophages. PubMed: Secreted glypican binds to the amyloid precursor protein of Alzheimer's disease (APP) and inhibits APP-induced neurite outgrowth. PubMed: Cell surface proteoglycans modulate net synthesis and secretion of macrophage apolipoprotein E. PubMed: Characterization and biological significance of sialyl alpha 2-3galactosyl beta 1-4xylosyl beta 1-(4-methylumbelliferone) synthesized in cultured human skin fibroblasts. PubMed: Inhibitory effect of platelet factor 4 on human erythroleukemic cells is dependent on cell surface heparan sulfate. PubMed: A new approach to mapping co-localization of multiple glycosyl transferases in functional Golgi preparations. PubMed: Reduction of intimal hyperplasia by naroparcil, a 4-methylumbelliferyl beta-D-xyloside analogue, after arterial injury in the hypercholesterolemic rabbit. PubMed: Inhibition of proteoglycan synthesis influences regeneration of goldfish retinal axons on polylysine and laminin. PubMed: HNK-1-reactive novel oligosaccharide, sulfate-O-3GlcA beta 1-4Xyl beta 1-(4-methylumbelliferone), synthesized by cultured human skin fibroblasts. PubMed: Identification of a novel glycosaminoglycan core-like molecule. I. 500 MHz 1H NMR analysis using a nano-NMR probe indicates the presence of a terminal alpha-GalNAc residue capping 4-methylumbelliferyl-beta-D-xylosides. PubMed: A novel oligosaccharide, GlcA beta 1-4Xyl beta 1-(4-methylumbelliferone), synthesized by human cultured skin fibroblasts. PubMed: A novel oligosaccharide, xylosyl beta 1-4xylosyl beta 1-(4-methylumbelliferone), synthesized by cultured human skin fibroblasts in the presence of 4-methylumbelliferyl-beta-D-xyloside. PubMed: A method for determination of galactosyltransferase I activity synthesizing the proteoglycan linkage region. PubMed: Enlarged cell-associated proteoglycans abolish E-cadherin functionality in invasive tumor cells. PubMed: Sulphation of proteochondroitin and 4-methylumbelliferyl beta-D-xyloside-chondroitin formed by mouse mastocytoma cells cultured in sulphate-deficient medium. PubMed: Simple measurement of glycosaminoglycan produced by cultured fibroblasts using 4-methylumbelliferyl beta-D-xyloside. PubMed: Heparin releases newly synthesized cell surface-associated apolipoprotein E from HepG2 cells. PubMed: Alpha- and beta-xylosides alter glycolipid synthesis in human melanoma and Chinese hamster ovary cells. PubMed: The neural cell adhesion molecule (NCAM) heparin binding domain binds to cell surface heparan sulfate proteoglycans. PubMed: Association and release of the amyloid protein precursor of Alzheimer's disease from chick brain extracellular matrix. PubMed: Characterization of beta-D-xyloside-induced glycosaminoglycans and oligosaccharides in cultured human skin fibroblasts. PubMed: Decreased thrombin affinity of cell-surface thrombomodulin following treatment of cultured endothelial cells with beta-D-xyloside. PubMed: Effect of forskolin on synthesis of xyloside-initiated glycosaminoglycans in embryonic chick chondrocytes. PubMed: Preparation and application of a fluorogenic substrate for endo-beta-xylosidase. PubMed: Inhibition of proteoglycan synthesis alters extracellular matrix deposition, proliferation, and cytoskeletal organization of rat aortic smooth muscle cells in culture. PubMed: Cerebellar granule cells contain a membrane mitogen for cultured Schwann cells. PubMed: Inhibition of endothelial cell morphogenetic interactions in vitro by alpha- and beta-xylosides. PubMed: Modulation of glycosaminoglycan production and antithrombin III binding by cultured aortic endothelial cells treated with 4-methylumbelliferyl-beta-D-xyloside. PubMed: Changes in glycosaminoglycan synthesis during the differentiation of HL-60 cells induced by 12-O-tetra-decanoylphorbol-13-acetate. PubMed: Effects of inhibition of proteoglycan synthesis on the differentiation of cultured rat Schwann cells. PubMed: Glycosaminoglycan metabolism of HL-60 cells during differentiation induction by tetradecanoylphorbol-13-acetate. PubMed: Sulfated proteoglycans produced by rat dorsal root ganglion cells. PubMed: Altered glycosaminoglycan production by HL-60 cells treated with 4-methylumbelliferyl-beta-D-xyloside. PubMed: A neuronal cell surface heparan sulfate proteoglycan is required for dorsal root ganglion neuron stimulation of Schwann cell proliferation. PubMed: Increased sulphation level and altered composition of glycosaminoglycans synthesized by cultured smooth muscle cells in the presence of beta-D-xylosides. PubMed: Tissue interactions in the organization and maintenance of the muscle pattern in the chick limb. PubMed: Effect of 4-methylumbelliferyl-beta-d-xyloside on collagen synthesis in chick limb bud mesenchymal cell cultures. PubMed: Fluid and glycosaminoglycan excretion by chick embryos treated with a beta-D-xyloside. PubMed: Development of the biochemical and morphological changes induced by administration of a beta-xyloside to chick embryos. PubMed: Initiation of altered heparan sulphate on beta-D-xyloside in rat hepatocytes. PubMed: The action of somatomedin on glycosaminoglycan synthesis in cultured chick chondrocytes. PubMed: Changes in chemical composition of chick embryos treated with a beta-xyloside and a lathyrogen. PubMed: The effect of beta-xylosides on heparan sulfate synthesis by SV40-transformed Swiss mouse 3T3 cells. PubMed: The mode of action of 4-methylumbelliferyl beta-D-xyloside on the synthesis of chondroitin sulphate in embryonic-chicken sternum. PubMed: Glycosaminoglycan synthesis by cultured human skin fibroblasts after transformation with simian virus 40. PubMed: The effect of beta-D-xylosides on chondroitin sulphate biosynthesis in embryonic chicken cartilage in the absence of protein synthesis inhibitors. PubMed: Collagen synthesis and deposition in cartilage during disrupted proteoglycan production. PubMed: Stimulation of synthesis of free chondroitin sulfate chains by beta-D-xylosides in cultured cells. PubMed: Synthesis of a fluorogenic mucopolysaccharide by chondrocytes in cell culture with 4-methylumbelliferyl beta-D-xyloside.