2280-44-6

Basic information

• Product Name: D-glucose
• Synonyms: (3R,4S,5S,6R)-6-Hydroxymethyl-tetrahydro-pyran-2,3,4,5-tetraol;Einecs 218-914-5;Glucopyranose, D-;(3R,4S,5S,6R)-6-(hydroxyMethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol
• CAS NO: 2280-44-6
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.1559
• EINECS: 218-914-5
• Product Categories: Carbohydrates & Derivatives
• Mol File: 2280-44-6.mol
• Article Data: 637

Chemical Properties

• Melting Point: 152-155°C
• Boiling Point: 410.8°C at 760 mmHg
• Flash Point: 202.2°C
• Appearance: /
• Density: 1.732g/cm³
• Vapor Pressure: 1.83E-08mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: Refrigerator
• CAS DataBase Reference: D-glucose(CAS DataBase Reference)
• NIST Chemistry Reference: D-glucose(2280-44-6)
• EPA Substance Registry System: D-glucose(2280-44-6)

Safety Data

• Hazardous Substances Data: 2280-44-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 2280-44-6 differently. You can refer to the following data:
1. D-Glucose is a simple sugar that is present in plants. A monosaccharide that may exist in open chain or cyclic conformation if in solution. It plays a vital role in photosynthesis and fuels the energ y required for cellular respiration. D-Glucose is used in various metabolic processes including enzymic synthesis of cyclohexyl-α and β-D-glucosides. Can also be used as a diagnostic tool in detection of type 2 diabetes mellitus and potentially Huntington's disease through analysis of blood-glucose in type 1 diabetes mellitus.
2. Used in enzymic synthesis of cyclohexyl-α and β-D-glucosides

Definition

ChEBI: A glucopyranose having D-configuration.

Brand name

Cartose (Sterling Winthrop) Dextrose.

InChI:InChI=1/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1

Upstream product

• 67-56-1 methanol 
• 10095-76-8 vinyl α-D-glucopyranoside 
• 6743-92-6 isorhamnetin-3-O-glucoside 
• 10236-47-2 naringin 
• 3228-62-4 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-p-tolylamino-tetrahydro-pyran-3,4,5-triol 
• 15132-06-6 6-O-α-D-glucopyranosyl-β-D-fructofuranose 
• 95272-12-1 O-α-D-xylopyranosyl-(1->6)-D-glucopyranose 
• 74213-96-0 glucoside de 4-(-2-nitroethyl) phenol 
• 79154-50-0 3β-hydroxy-5α-cholesta-6,8(14)-dien-23-one-O-β-D-glucopyranosyl-(1-2)-β-D-galactopyranosyl-(1-2)-β-D-glucuronopyranoside 
• 85011-57-0 scopoletin 7-O-(6-O-feruloyl-β-D-glucopyranoside) 
• 75410-53-6 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-(β-D-glucopyranosyl)-(1→4)-(β-D-quinopyranosyl)-(1→2)-4-O-sodium sulfate-β-D-xylopyranosyl}holosta-9(11)-ene-3β,12α,17α-triol 
• 76729-70-9 echinocystic acid-3-O-<β-D-xylopyranosyl(1->2)-α-L-arabinopyranosyl(1->6)-β-D-glucopyranoside>-28-O-<β-D-xylopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)><α-L-rhamnopyranosyl(1->6)>-β-D-glucopyranoside 
• 74774-01-9 3,4,6-tri-O-acetyl-1,2-O-<2-oxa-3-oxocyclopentylidene>-α-D-glucopyranose (endo) 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 17651-11-5 6-O-Dodecanoyl-α-D-glucose 
• 4616-95-9 6-O-(N-Carbobenzoxy-α-L-aspartyl)-D-glucose 
• 906347-92-0 6-O-(N-Benzyloxycarbonyl-glycyl)-D-glucose 
• 91574-77-5 (2R,3R,4R,5S)-6-[(4,5-Diphenyl-oxazol-2-yl)-hydrazono]-hexane-1,2,3,4,5-pentaol 
• 492-62-6 alpha-D-glucopyranose 
• 85249-92-9 N-2-phenylethyl-α-D-glucopyranosylamine 
• 100083-93-0 1,2,3,4,6-Penta-O-(o-toluoyl)-β-D-glucose 
• 100083-77-0 1,2,3,4,6-Penta-O-(o-toluoyl)-α-D-glucose 
• 32739-70-1 N-p-ethoxyphenyl D-glucosylamine 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 1941-52-2 D-glucose diethyl mercaptal 
• 34246-23-6 benzyl D-glucopyranoside 
• 4304-12-5 (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 

Relevant articles and documents

Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium

A methanol extract of everlasting flowers of Helichrysum arenarium L. Moench (Asteraceae) was found to inhibit the increase in blood glucose elevation in sucrose-loaded mice at 500 mg/kg p.o. The methanol extract also inhibited the enzymatic activity against dipeptidyl peptidase-IV (DPP-IV, IC50 = 41.2 μg/ml), but did not show intestinal α-glucosidase inhibitory activities. From the extract, three new dimeric dihydrochalcone glycosides, arenariumosides V-VII (2-4), were isolated, and the stereostructures were elucidated based on their spectroscopic properties and chemical evidence. Of the constituents, several flavonoid constituents, including 2-4, were isolated, and these isolated constituents were investigated for their DPP-IV inhibitory effects. Among them, chalconaringenin 2′-O-β-D-glucopyranoside (16, IC50 = 23.1 μM) and aureusidin 6-O-β-D-glucopyranoside (35, 24.3 μM) showed relatively strong inhibitory activities.

Reductive splitting of cellulose in the ionic liquid 1-butyl-3-methylimidazolium chloride

The depolymerization of cellulose is carried out in the ionic liquid 1-butyl-3-methylimidazolium chloride in the presence of hydrogen gas. First, the ketal 1,1-diethoxycyclohexane and cel-lobiose were used as model substrates. For the depolymerization of cellulose itself, the combination of a heterogeneous metal catalyst and a homogeneous ruthenium catalyst proved effective. One of the possible roles of the ruthenium compound is to enhance the transfer of hydrogen to the metallic surface. The cellulose is fully converted under relatively mild conditions, with sorbitol as the dominant product in 51-74% yield.

New direct production of gluconic acid from polysaccharides using a bifunctional catalyst in hot water

Gluconic acid was produced from polysaccharides, such as starch and cellobiose, in water media at 393 K under air by a one-pot process using a bifunctional sulfonated activated-carbon supported platinum (Pt/AC-SO 3H) catalyst. Pt/AC-SO3H was prepared by the impregnation of platinum on activated-carbon (AC) and the sulfonation of the prepared Pt/AC. It was highly water-tolerant under hot aqueous solutions even including organic acids.

Isatindigodiphindoside, an alkaloid glycoside with a new diphenylpropylindole skeleton from the root of Isatis indigotica

A novel indole alkaloid glycoside with an unprecedented 2-(diphenylpropyl)indole skeleton, isatindigodiphindoside (1), was isolated from an aqueous extract of the roots of Isatis indigotica. The structure was determined by extensive spectroscopic studies, especially by 2D NMR data analysis combined with enzymatic hydrolysis and ECD calculations. Plausible biosynthetic pathways of compound 1 are also discussed.

FLAVONOIDS OF SOME PLANTS OF THE GENUS Haplophyllum

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Indole alkaloids from the leaves of nauclea officinalis

Three new indole alkaloids, named naucleamide G (1), and nauclealomide B and C (5 and 6), were isolated from the n-BuOH-soluble fraction of an EtOH extract of the leaves of Nauclea officinalis, together with three known alkaloids, paratunamide C (2), paratunamide D (3) and paratunamide A (4). The structures with absolute configurations of the new compounds were identified on the basis of 1D and 2D NMR, HRESIMS, acid hydrolysis and quantum chemical circular dichroism (CD) calculation. According to the structures of isolated indole alkaloids, their plausible biosynthetic pathway was deduced.

TWO CHROMONE GLYCOSIDES FROM CASSIA MULTIJUGA

Two new 2-methylchromone glycosides have been identified in the leaves of Cassia multijuga.Key Word Index - Cassia multijuga; Leguminosae; leaves; chromone glycosides.

GENISTEIN 7-(2"-p-COUMAROYLGLUCOSIDE) FROM TRIFOLIUM REPENS

Key Word Index - Trifolium repens; Leguminosae; genistein 7-O-(2"-p-coumaroyl-β-D-glucopyranoside); isoflavone.A new acetylated isoflavone, genistein 7-(2"-p-coumaroylglucoside), has been characterized from Trifolium repens.

RADIOIMMUNOASSAY FOR THE QUANTITATIVE DETERMINATION OF HESPERIDIN AND ANALYSIS OF ITS DISTRIBUTION IN CITRUS SINENSIS

A simple and sensitive radioimmumoassay (RIA) for the citrus flavanone hesperidin and other flavonoid 7-rutinosides is described.The assay utilizes antibodies raised against a hesperidin 4-O-carboxymethyl-oxime hapten and a tritiated radiotracer prepared by direct reduction of hesperidin with NaB4.The detection limit of the assay is 0.2 ng/0.1 ml (0.3 pmol/0.1 ml) and the measuring range extends to 10 ng/0.1 ml (16.4 pmol/0.1 ml).This assay is specific for flavonoid rutinosides, is characterized by a low coefficient of variation, and shows good correlation with HPLC for the quantification of hesperidin in oranges.The application of this method in determining the distribution of hesperidin in leaves, fruit, seeds, and seedlings of Citrus linensis is also reported.Key Word Index - Citrus sinensis; Rutaceae; radioimmunoassay; hesperidin; flavonoidglycosides; rutinosides.

Polygonflavanol A, a novel flavonostilbene glycoside from the roots of Polygonum multiflorum

Polygonflavanol A (1), a novel flavonostilbene glycoside with an unusual coupling pattern, together with five known stilbene glycosides (2-6), was isolated from the roots of Polygonum multiflorum. The structures were elucidated on the basis of extensive spectroscopic analysis and chemical evidence. The absolute configuration of 1 was further determined by CD analysis. Most of the compounds could inhibit nitric oxide (NO) secretion of RAW264.7 cells in respond to lipopolysaccharide (LPS) in a dose dependent manner. Among them, compound 2 displayed the highest inhibitory activity.

Chemical Constituents of Astragalus falcatus

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Two new alkaloids from the roots of Baphicacanthus cusia

Phytochemical investigation of the root of Baphicacanthus cusia (NEES) BREMEK afforded two new alkaloids, baphicacanthin A (1) and baphicacanthin B (2), along with 28 known compounds. The chemical structures of these compounds were elucidated on the basis of one and two dimensional (1D/2D)-NMR and high resolution (HR)-MS spectral evidence.

New cholestane glycosides and sterols from the underground parts of Chamaelirium luteum and their cytotoxic activity

Six new cholestane glycosides (1, 5, 6, 10, 12, and 13) and two new sterols (9 and 11), along with five known compounds (2-4, 7, and 8), were isolated from the underground parts of Chamaelirium luteum (Liliaceae). The structures of these new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds and aglycones were evaluated for their cytotoxic activity against HL-60 human leukemia cells. Compounds 6a, 10a, 12a, 13, and 13a were cytotoxic to HL-60 cells, with IC50 values of 12.8, 9.8, 15.3, 6.2, and 10.2 μM, respectively.

Two antiproliferative triterpene saponins from Nematostylis anthophylla from the highlands of central madagascar

Investigation of the endemic Madagascan plant Nematostylis anthophylla (Rubiaceae) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of the known triterpene saponin randianin (1), and the two new bioactive trit

Two new chlorophenyl glycosides from the bulbs of Lilium brownii var. viridulum

Two rare new chlorophenyl glycosides, 2,4,6-trichlorol-3-methyl-5-methoxy- phenol 1-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside (1) and 4-chlorol-5-hydroxyl-3-methyl-phenol 1-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (2), along with three kno

Six new compounds from Atractylodes lancea and their hepatoprotective activities

Two new phenolic glycosides with a rare β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl moiety (1, 2), one new dihydrobenzofuran derivative (3), one new pyrazine derivative (4), two new furofuran lignan glycosides (5, 6), and six known compounds (7–12) were isolated from the rhizomes of Atractylodes lancea. The structures of these compounds were elucidated by extensive spectroscopic analyses combined with the experimental and calculated electronic circular dichroism and the Rh2(OCOCF3)4-induced circular dichroism for configurational assignments. Notably, compounds 1–3 showed significant hepatoprotective activities against N-acetyl-p-aminophenol-induced HepG2 cell injury. This study is also the first Letter on the isolation of furofuran lignans and pyrazine derivatives (4–7) from the genus Atractylodes.

Hydrolysis of cellulose by amorphous carbon bearing SO3H, COOH, and OH groups

The hydrolysis of cellulose into saccharides using a range of solid catalysts is investigated for potential application in the environmentally benign saccharification of cellulose. Crystalline pure cellulose is not hydrolyzed by conventional strong solid Bronsted acid catalysts such as niobic acid, H-mordenite, Nafion and Amberlyst-15, whereas amorphous carbon bearing SO3H, COOH, and OH function as an efficient catalyst for the reaction. The apparent activation energy for the hydrolysis of cellulose into glucose using the carbon catalyst is estimated to be 110 kJ mol-1, smaller than that for sulfuric acid under optimal conditions (170 kJ mol -1). The carbon catalyst can be readily separated from the saccharide solution after reaction for reuse in the reaction without loss of activity. The catalytic performance of the carbon catalyst is attributed to the ability of the material to adsorb β-1,4 glucan, which does not adsorb to other solid acids.

Flavonoids from Litsea japonica Inhibit AGEs Formation and Rat Lense Aldose Reductase in Vitro and Vessel Dilation in Zebrafish

In our ongoing efforts to identify effective naturally sourced agents for the treating of diabetic complications, two new (1 and 2) and 11 known phenolic compounds (3-13) were isolated from an 80% ethanol extract of Litsea japonica leaves. The structures

New Phenolic Compounds from the Roots of Lentil (Lens?culinaris)

While lentil (Lens?culinaris) seeds are phytochemically well characterized, very little is known about secondary metabolites from lentil roots. Our research on lentil roots led to isolation of five phenolic compounds and five group B soyasaponins. Their structures were established using NMR spectroscopy and mass spectrometry. Four phenolics have not been hitherto described in the literature: 4-O-β-d-glucopyranosyl-2-methoxybenzoic acid, (αS)-4,4′-di-O-β-d-glucopyranosyl-α,2′-dihydroxydihydrochalcone, (αS)-4′-O-β-d-glucopyranosyl-α,2′,4-trihydroxydihydrochalcone, and keto-2-hydroxyglycitein. The DPPH?radical-scavenging activity of the purified phenolic compounds was additionally evaluated.

CHEMICAL STUDY OF PLANTS OF THE MONGOLIAN FLORA COUMARINS OF Salsola laricifolia

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A new triterpene glycoside from the stems of Lagerstroemia indica

A bioassay-guided fractionation and chemical investigation of the stems of Lagerstroemia indica resulted in the isolation and identification of a new triterpene glycoside, lagerindiside (1), along with nine known triterpenes (2–10). The structure of this new compound was elucidated on the basis of 1D and 2D nuclear magnetic resonance spectroscopic data analysis as well as chemical method. The cytotoxic activities of the isolates (1–10) were evaluated by determining their inhibitory effects on four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15) using a sulforhodamine B bioassay. Compounds 3 and 4 showed potent cytotoxicity on the tumor cell lines with IC50values ranging from 3.38 to 6.29?μM.

LILIOSIDE C, A GLYCEROL GLUCOSIDE FROM LILIUM LANCIFOLIUM

A new glycerol glucoside, lilioside C, has been isolated from the leaves and stems of Lilium lancifolium.Its structure including the configuration of the aglycone moiety has been elucidated by chemical and spectroscopic means and by its synthesis.Key Word Index - Lilium lancifolium; Liliaceae; tiger lily; glycerol glucoside; 3-O-β-D-glucopyranosyl-sn-glycerol; lilioside C; stereochemistry; synthesis.

New Diterpenes from arenga pinnata (Wurmb.) merr. Fruits

Three new ent-kauran-type diterpenes (1-3), named arenterpenoids A-C, and five known ones (4-8) were isolated and identified from Arenga pinnata (Wurmb.) Merr. Fruits. The structures of these compounds were established by 1D and 2D NMR spectra and HR-ESI-MS. To the best of our knowledge, this is the first scientific report of diterpenes from Arenga genus.

Lignans from Lepidium meyenii and Their Anti-Inflammatory Activities

Meyeniines A–C (1–3), three new lignans, two known neolignans (4–5), and three known lignans (6–8) were isolated from the rhizomes of Lepidium meyenii. Their structures were identified by comprehensive spectroscopic analyses and computational methods. Compound 1 represents a unique lignan featuring an aromatic ring migration. Compounds 2 and 4–6 were analyzed by chiral HPLC column as enantiomers. Biological evaluation revealed that compound 8 could inhibit IL-6 production in lipopolysaccharide (LPS) induced RAW264.7 cells in a dose-dependent manner.

ISORHAMNETIN 7-GLUCOSIDE FROM CNICUS WALLICHI

Key Word Index - Cnicus wallichi; Compositae; isorhamnetin 7-glucoside; flavonol glycoside.Isorhamnetin 7-glucoside was characterized from Cnicus wallichi.This is the first report of this glycoside in the Compositae and the second in nature.

The phenolic acids from Oplopanax elatus Nakai stems and their potential photo-damage prevention activity

25 phenolic acids, including four new isolates, eurylophenosides A–D (1–4) and 21 known ones (5–25) were isolated and identified from the stems of Oplopanax elatus Nakai. Among the known compounds 5–9, 11–13, 16, 18–25 were isolated from the genus for the first time; 17 was first obtained from the plant; and the NMR data of 22 was reported here first. Meanwhile, the UVB-induced photodamage model of HaCaT cells was used to study the prevent-photodamage abilities of compounds 1–2, 4–8, 11–13 and 15–25 with a nontoxic concentration at 50?μM. Moreover, a dose-dependent experiment was conducted for active compounds at the concentration of 10, 25, and 50?μM, respectively. Consequently, pretreatment with compounds 1, 16, 17, 19, 20, 22, 24 and 25 could suppress the cell viability decreasing induced by UVB irradiation in a concentration-dependent manner. These results indicated that phenolic acids were one kind of material basis with prevent-photodamage activity of O. elatus. Graphic abstract: [Figure not available: see fulltext.].

Ursane-type triterpene oligoglycosides with anti-hepatosteatosis and anti-hyperlipidemic activity from the leaves of Ilex paraguariensis A. St.-Hil.

The methanol extract from the leaves of Ilex paraguariensis A. St.-Hil. (Aquifoliaceae), popularly known as mate, maté, or yerba maté, inhibits the intracellular triglyceride accumulation in HepG2 cells and suppresses the plasma triglyceride elevation in olive oil-treated mice. Three new triterpene saponins, termed mateosides I (1), II (2), and III (3), were isolated from the extract along with 29 known compounds. The structures of 1–3 were elucidated based on chemical and spectroscopic evidence. Among the isolates, principal saponin constituents, 2 and matesaponins 1 (7) and 2 (9), potently inhibited the triglyceride accumulation in HepG2 cells simultaneously treated with oleic acid and high glucose. In vivo assay of the methanol extract of I. paraguariensis revealed that 7 and 9 showed anti-hyperlipidemic activities in olive oil-treated mice. These results suggested that the saponin constituents of I. paraguariensis could be valuable bioactive marker for the anti-obesogenic activity. Graphical abstract: [Figure not available: see fulltext.]

Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides

A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is