146-72-5

Basic information

• Product Name: 3-O-(3H-METHYL)-D-GLUCOSE
• Synonyms: methylglucose;3-OMG
• CAS NO: 146-72-5
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18246
• EINECS: 205-677-8
• Mol File: 146-72-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 474.2 °C at 760 mmHg
• Flash Point: 196.1 °C
• Appearance: /aqueous ethanol solution
• Density: 1.394 g/cm³
• Vapor Pressure: 5.53E-11mmHg at 25°C
• Refractive Index: 1.52
• Storage Temp.: 2-8°C
• PKA: 12.33±0.20(Predicted)
• CAS DataBase Reference: 3-O-(3H-METHYL)-D-GLUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-(3H-METHYL)-D-GLUCOSE(146-72-5)
• EPA Substance Registry System: 3-O-(3H-METHYL)-D-GLUCOSE(146-72-5)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16
• RIDADR: UN 2910 7
• WGK Germany: 1
• Hazardous Substances Data: 146-72-5(Hazardous Substances Data)

Usage

Description

3-O-(3H-METHYL)-D-GLUCOSE, also known as a D-aldohexose, is a non-metabolizable glucose analogue derived from D-glucose. In this compound, the hydrogen of the hydroxy group at position 3 is substituted by a methyl group. It is not phosphorylated by hexokinase and is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems.

Uses

Used in Pharmaceutical Research:
3-O-(3H-METHYL)-D-GLUCOSE is used as a research tool for studying glucose transport mechanisms in cells and organ systems. Its non-metabolizable nature allows scientists to investigate the uptake and transport of glucose without the complications of cellular metabolism.
Used in Diagnostic Applications:
In the medical field, 3-O-(3H-METHYL)-D-GLUCOSE is used as a diagnostic agent to assess the functionality of glucose transport systems in patients with diabetes or other metabolic disorders. By measuring the uptake of this compound, healthcare professionals can gain insights into the efficiency of glucose transport and identify potential issues in glucose metabolism.
Used in Cell Biology Research:
3-O-(3H-METHYL)-D-GLUCOSE serves as a valuable tool in cell biology research, particularly in the study of cellular glucose uptake and transport. Researchers can use this compound to investigate the role of glucose transporters and their regulation in various cell types, contributing to a better understanding of cellular metabolism and its regulation.
Used in Drug Development:
In the pharmaceutical industry, 3-O-(3H-METHYL)-D-GLUCOSE can be employed in the development of new drugs targeting glucose metabolism and transport. By studying the interactions of this compound with cellular transport systems, researchers can identify potential drug targets and develop novel therapeutics for conditions related to glucose metabolism, such as diabetes and obesity.
Used in Nutritional Studies:
3-O-(3H-METHYL)-D-GLUCOSE can also be utilized in nutritional studies to investigate the effects of dietary components on glucose transport and metabolism. This can help researchers understand how different nutrients and dietary patterns influence glucose uptake and utilization in the body, leading to the development of more effective dietary recommendations and interventions for managing glucose metabolism.

InChI:InChI=1/C7H14O6/c1-13-7(5(11)3-9)6(12)4(10)2-8/h3-8,10-12H,2H2,1H3

Upstream product

• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 71072-42-9 3-O-Methyl-D-glucal 
• 1220913-36-9 3β-O-{2-O-[3-O-methyl-β-D-glucopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-β-D-quinovopyranosyl]-4-O-[β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl]-β-D-xylopranosyl}holosta-7(8),25(26)-dien-16-one 
• 1220913-35-8 3β-O-{2-O-[3-O-methyl-β-D-glucopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-β-Dglucopyranosyl]-4-O-[3-O-β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl]-β-D-xylopranosyl}holosta-9(11),25(26)-dien-16-one 
• 43138-64-3 1,2-:5,6-di-O-isopropylidene-3-O-methyl-α-D-glucofuranose 

Downstream Products

• 111210-92-5 p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside 
• 43138-64-3 1,2-:5,6-di-O-isopropylidene-3-O-methyl-α-D-glucofuranose 
• 50-00-0 formaldehyd 
• 1518-59-8 D-arabino-3-deoxy-hexonic acid 
• 498-43-1 3-deoxy-D-ribo-hexonic acid 
• 36256-85-6 3-O-methyl-Δ-fructose 
• 1333966-00-9 C₁₃H₁₇BO₆ 
• 1333965-99-3 C₁₃H₁₇BO₆ 
• 1333966-01-0 C₁₃H₁₇BO₆ 
• 1333966-04-3 C₁₉H₂₀B₂O₆ 
• 499-87-6 3-deoxy-D-ribo-hexono-1,4-lactone 
• 3254-27-1 O²,O⁴;O⁵,O⁶-((S,S)-dibenzylidene)-O³-methyl-D-glucitol 
• 3254-27-1 O²,O⁴;O⁵,O⁶-((S,R)-dibenzylidene)-O³-methyl-D-glucitol 
• 2887-05-0 O¹,O²,O⁴,O⁶-Tetrabenzoyl-O³-methyl-β-D-glucopyranose 

Relevant articles and documents

A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities

Our continuing search for marine bioactive secondary metabolites led to the screening of crude extracts of sea cucumbers by the model of Pyricularia oryzae. A new sulfated triterpene glycoside, coloquadranoside A (1), together with four known triterpene glycosides, philinopside A, B, E and pentactaside B (2–5) were isolated from the sea cucumber Colochirus quadrangularis, and their structures were elucidated using extensive spectroscope analysis (ESI-MS, 1D and 2D NMR) and chemical methods. Coloquadranoside A possesses a 16-acetyloxy group in the holostane-type triterpene aglycone with a 7(8)–double bond, a double bond (25,26) at its side chain, and two β-D-xylose in the carbohydrate chain. Coloquadranoside A exhibits in vitro some antifungus, considerable cytotoxicity (IC50 of 0.46–2.03 μM) against eight human tumor cell lines, in vivo antitumor, and immunomodulatory activity.

Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka

A nortriterpene glycoside, 26-nor-25-oxo-holotoxin A1 (1), four triterpene glycosides, including both holostane and non-holostane types analogues, holotoxins D-G (2-5), together with three known triterpene glycosides, holotoxins A1 and B (6, 7), and cladoloside B (8), were isolated from the warty sea cucumber Apostichopus japonicus Selenka, a traditional tonic with high economic value in China. The structures of the new compounds were elucidated by a combination of detailed spectroscopic analysis and chemical methods. This is the first report of a nortriterpene glycoside isolated from sea cucumbers. These compounds showed potent antifungal activities in the in vitro biotest. A preliminary structure-activity analysis suggests that the 18(20) lactone group and the Δ25 terminal double bond may increase the activity. The component of the carbohydrate chain seems play an important role whereas the double bond transformation from Δ 9(11) to Δ7 in the aglycone moiety contributes little to the bioactivity.

Triterpene glycosides from Antarctic sea cucumbers. 1. Structure of liouvillosides A1, A2, A3, B1, and B2 from the sea cucumber Staurocucumis liouvillei: New procedure for separation of highly polar glycoside fractions and taxonomic revision

Five new triterpene glycosides, liouvillosides A1 (1), A 2 (2), A3 (3), B1 (4), and B2 (5), have been isolated from the Antarctic sea cucumber Staurocucumis liouviellei along with the known liouvilloside A (6), isolated earlier from the same species, and hemoiedemosides A (7) and B (8), isolated earlier from the Patagonian sea cucumber Hemioedema spectabilis. The isolation was carried out using a new chromatographic procedure including application of ion-pair reversed-phase chromatography followed by chiral chromatography on a cyclodextrin ChiraDex column. The structures of the new glycosides were elucidated using extensive NMR spectroscopy (1H and 13C NMR spectrometry, DEPT, 1H-1H COSY, HMBC, HMQC, and NOESY), ESI-FTMS, and CID MS/MS, and chemical transformations. Glycosides 1-3 are disulfated tetraosides and glycosides 4 and 5 are trisulfated tetraosides. Glycosides 2 and 3 contain 3-O-methylquinovose, found for the first time as a natural monosaccharide in sea cucumber glycosides. On the basis of analyses of glycoside structures a taxonomic revision is proposed.