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METHYL-BETA-D-GALACTOPYRANOSIDE is a beta-D-galactopyranoside with a methyl substituent at the anomeric position. It is a white crystalline solid that serves as a weak substrate and an effective inducer of beta-D-galactosidase.

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  • 1824-94-8 Structure
  • Basic information

    1. Product Name: METHYL-BETA-D-GALACTOPYRANOSIDE
    2. Synonyms: METHYL-BETA-D-GALACTOPYRANOSIDE;METHYL BETA-D-GALACTOSIDE;METHYL BETA-D-GALACTOSIDE(1,5);METHYL B-D-GALACTOPYRANOSIDE;BETA-METHYL-D-GALACTOSIDE;1-O-METHYL-GALACTOSIDE;1-O-METHYL-BETA-D-GALACTOPYRANOSIDE;1-OME-BETA-D-GAL
    3. CAS NO:1824-94-8
    4. Molecular Formula: C7H14O6
    5. Molecular Weight: 194.18
    6. EINECS: 217-361-7
    7. Product Categories: Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Biochemistry;Galactose;Glycosides;Sugars;Carbohydrates & Derivatives
    8. Mol File: 1824-94-8.mol
  • Chemical Properties

    1. Melting Point: 172-180 °C
    2. Boiling Point: 250.62°C (rough estimate)
    3. Flash Point: 189.1 °C
    4. Appearance: White/Crystalline Powder
    5. Density: 1.47
    6. Vapor Pressure: 1.15E-07mmHg at 25°C
    7. Refractive Index: -16.5 ° (C=1.5, MeOH)
    8. Storage Temp.: 2-8°C
    9. Solubility: Methanol (Slightly), Water (Slightly)
    10. PKA: 12.92±0.70(Predicted)
    11. Water Solubility: Soluble in water and methanol.
    12. Stability: Stable. Incompatible with strong oxidizing agents.
    13. BRN: 81569
    14. CAS DataBase Reference: METHYL-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
    15. NIST Chemistry Reference: METHYL-BETA-D-GALACTOPYRANOSIDE(1824-94-8)
    16. EPA Substance Registry System: METHYL-BETA-D-GALACTOPYRANOSIDE(1824-94-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. F: 3-10
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1824-94-8(Hazardous Substances Data)

1824-94-8 Usage

Uses

Used in Enzyme Induction:
METHYL-BETA-D-GALACTOPYRANOSIDE is used as an inducer for beta-D-galactosidase, an enzyme that plays a crucial role in the metabolism of lactose and other galactosides. Its ability to induce the enzyme makes it valuable in research and applications related to enzyme activity and regulation.
Used in Biochemical Research:
In the field of biochemical research, METHYL-BETA-D-GALACTOPYRANOSIDE is used as a weak substrate to study the activity and specificity of beta-D-galactosidase and related enzymes. This allows researchers to gain insights into enzyme mechanisms and develop potential therapeutic agents targeting these enzymes.
Used in Pharmaceutical Development:
METHYL-BETA-D-GALACTOPYRANOSIDE may also be utilized in the development of pharmaceuticals targeting beta-D-galactosidase or related enzymes. Its properties as a weak substrate and effective inducer can aid in the design and optimization of drugs for various therapeutic applications.
Used in Food Industry:
In the food industry, METHYL-BETA-D-GALACTOPYRANOSIDE can be used as a component in the development of lactose-free or reduced-lactose products. Its ability to induce beta-D-galactosidase activity can help in the breakdown of lactose, making it a valuable ingredient for individuals with lactose intolerance or those seeking lactose-reduced options.

Check Digit Verification of cas no

The CAS Registry Mumber 1824-94-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,2 and 4 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1824-94:
(6*1)+(5*8)+(4*2)+(3*4)+(2*9)+(1*4)=88
88 % 10 = 8
So 1824-94-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3?,4-,5+,6?,7+/m0/s1

1824-94-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl β-D-galactoside

1.2 Other means of identification

Product number -
Other names methyl beta-D-galactoside

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1824-94-8 SDS

1824-94-8Relevant articles and documents

Temporary Protection and Activation in the Regioselective Synthesis of Saccharide Sulfates

Langston, Steven,Bernet, Bruno,Vasella, Andrea

, p. 2341 - 2353 (1994)

Regioselective sulfation with Et3N*SO3 of partially protected or unprotected glycosides via stannanediyl acetals or stannyl ethers, combined with persistent or temporary protecting groups is described.Stannylation of phenylboronates, followed by sulfation and aqueous workup, is an efficient way for the synthesis of monosulfated monosaccharides.The stannanediyl acetal 2 led in high yields to 3a, while sulfation of the diol 1 proceeded more slowly and led in lower yield to a mixture 1/3a/4a/5a (Scheme 1).The trehalose disulfate 8a was obtained in high yields from 7; reducing the amount of sulfating agent led to a mixture 6/8a/9a.Stannylation and sulfation of the galactoside 11 afforded 13a, while direct sulfation of 11 gave a mixture of the 2- and 3-sulfates 13a/14a besides some disulfate 15a.Sulfation of the lactose derivative 16 and the stannanediyl acetal 17 gave the 3-sulfate 18a, with some disulfate 19a being formed from 16.The mannopyranoside 21 was selectively sulfated at OH-C(2), leading to 22a, while the corresponding diol 20 yielded mostly the isomer 23a and some disulfate 24a.Sulfation of the stannyl ethers derived from the gluco- and galactopyranosides 25 and 28 and (Bu3Sn)2O afforded high yields of the 2,6-disulfate 26a and the 3,6-disulfate 29a, respectively.Stannylation of 25 and 28 with Bu2SnO and sulfation proceeded less satisfactorily.Stannylation of the phenylboronate 32 (Bu2SnO) and sulfation gave good yields of the 2-sulfate 27a; stannylation and benzoylation yielded the 2-benzoate 34 (Scheme 2).Similarly, the galactose-derived 37 provided high yields of the 3-sulfate 30a and of the 3-benzoate 39.Direct sulfation of the phenylboronates 32 and 37 proceeded in lower yields and gave mixtures.

Operationally simple and efficient workup procedure for TBAF-mediated desilylation: Application to halichondrin synthesis

Kaburagi, Yosuke,Kishi, Yoshito

, p. 723 - 726 (2007)

An operationally simple and efficient workup method for tetrabutylammonium fluoride (TBAF)-mediated t-butyldimethylsilyl (TBS) deprotection has been developed. The procedure includes addition of a sulfonic acid resin and calcium carbonate, followed by filtration and evaporation. This method eliminates the tedious aqueous-phase extraction process to remove excess TBAF and materials derived from TBAF, thereby making the protocol highly amenable to multiple TBS deprotections. Its efficiency and usefulness were demonstrated by using the transformation of 1 a to 3a in the halichondrin synthesis.

Preliminary 1H NMR investigation of sialic acid transfer by the trans-sialidase from Trypanosoma cruzi

Wilson, Jennifer C,Kiefel, Milton J,Albouz-Abo, Samia,Von Itzstein, Mark

, p. 2791 - 2794 (2000)

1H NMR spectroscopy has been used to investigate the transfer of sialic acid from sialic acid donor molecules to acceptor molecules using the trans-sialidase from Typanosoma cruzi. It is clearly demonstrated that NMR spectroscopy is an efficien

STEROIDAL ALKALOIDS FROM SOLANUM CAPSICASTRUM

Lin, Chun-Nan,Chung, Mei-Ing,Lin, Son-Yuan

, p. 305 - 308 (1987)

From the rootbark of Solanum capsicastrum, in addition to etioline and isoteinemine, a new 22,26-epiminocholestene glycoside named capsicastrine was isolated and its structure elucidated as isoteinemine O(3)-β-D-galactopyranoside by physical and chemical

Catalytic Consequences of Experimantal Evolution. Part 1. Catalysis by the Wild-type Second β-Galactosidase (ebg0) of Escherichia coli: a Comparison with the lacZ Enzyme

Burton, John,Sinnott, Michael L.

, p. 359 - 364 (1983)

β-D-Galactopyranose is the initial product of the hydrolysis of β-D-galactopyranosyl fluoride by ebg0 enzyme.Transfer to methanol of a β-D-galactopyranosyl residue from either m-nitrophenol or 3-bromopyridine is seven times more favourable than

Three new glycosides from the whole plant of Clematis lasiandra Maxim and their cytotoxicity

Tian, Xiang-Rong,Feng, Jun-Tao,Ma, Zhi-Qing,Xie, Na,Zhang, Jing,Zhang, Xing,Tang, Hai-Feng

, p. 168 - 172 (2014)

Phytochemical investigation on the whole plant of Clematis lasiandra Maxim led to the isolation of two new phenolic glycosides (1 and 2), one new lignanoid glycoside (3), together with three known lignanoid glycosides (4-6). The structures of the new comp

Carbon glycoside glycosylated tetravalent platinum compound as well as synthesis method and application thereof

-

Paragraph 0064-0067, (2021/07/08)

The invention provides a carbon glycoside glycosylated tetravalent platinum compound, a synthesis method and application thereof. R1 and R2 are independently C1-C4 lower alkanes, R3 is glucose, galactose, mannose and ribose, different sugars are used as raw materials, and a series of carbon glycoside glycosylated tetravalent platinum compounds are synthesized through protection and deprotection reaction and metallization reaction of the sugars. The synthesis method is simple, the used raw materials are cheap and easy to obtain, the glycosylated tetravalent platinum compound has the capacity of targeting glucose transporter protein and has potential application value in the field of cancer treatment, introduction of a C-glucosidic bond enables the series of compounds to have the capacity of resisting hydrolysis of beta-glucosidase, and the compound is expected to be applied to the field of oral antitumor drugs.

Calixanthomycin A: Asymmetric Total Synthesis and Structural Determination

Chen, Kuanwei,Xie, Tao,Shen, Yanfang,He, Haibing,Zhao, Xiaoli,Gao, Shuanhu

supporting information, p. 1769 - 1774 (2021/03/08)

We report the first asymmetric total synthesis and structural determination of calixanthomycin A. Taking advantage of a modular strategy, a concise approach was developed to assemble the hexacyclic skeleton with both enantiomers of the lactone A ring. Stereoselective glycosylation coupled the angular hexacyclic framework with a monosaccharide fragment to produce calixanthomycin A and its stereoisomers. This enable us to determine and assign the absolute configuration of C-25 (25S) and monosaccharide (derivative of l-glucose).

Structure of the unusual Sinorhizobium fredii HH103 lipopolysaccharide and its role in symbiosis

Di Lorenzo, Flaviana,Speciale, Immacolata,Silipo, Alba,Alías-Villegas, Cynthia,Acosta-Jurado, Sebastián,Rodríguez-Carvajal, Miguel-ángel,Dardanelli, Marta S.,Palmigiano, Angelo,Garozzo, Domenico,Ruiz-Sainz, José-Enrique,Molinaro, Antonio,Vinardell, José-María

, p. 10969 - 10987 (2021/01/07)

Rhizobia are soil bacteria that form important symbiotic associations with legumes, and rhizobial surface polysaccharides, such as K-antigen polysaccharide (KPS) and lipopolysaccharide (LPS), might be important for symbiosis. Previously, we obtained a mutant of Sinorhizobium fredii HH103, rkpA, that does not produce KPS, a homopolysaccharide of a pseudaminic acid derivative, but whose LPS electrophoretic profile was indistinguishable from that of the WT strain. We also previously demonstrated that the HH103 rkpLMNOPQ operon is responsible for 5-acetamido-3,5,7,9-tetradeoxy-7-(3-hydroxybutyramido)-L-glyc-ero-L-manno-nonulosonic acid [Pse5NAc7(3OHBu)] production and is involved in HH103 KPS and LPS biosynthesis and that an HH103 rkpM mutant cannot produce KPS and displays an altered LPS structure. Here, we analyzed the LPS structure of HH103 rkpA, focusing on the carbohydrate portion, and found that it contains a highly heterogeneous lipid A and a peculiar core oligosaccharide composed of an unusually high number of hexuronic acids containing b-configured Pse5NAc7(3OHBu). This pseudaminic acid derivative, in its a-configuration, was the only structural component of the S. fredii HH103 KPS and, to the best of our knowledge, has never been reported from any other rhizobial LPS. We also show that Pse5NAc7(3OHBu) is the complete or partial epitope for a mAb, NB6-228.22, that can recognize the HH103 LPS, but not those of most of the S. fredii strains tested here. We also show that the LPS from HH103 rkpM is identical to that of HH103 rkpA but devoid of any Pse5NAc7(3OHBu) residues. Notably, this rkpM mutant was severely impaired in symbiosis with its host, Macroptilium atropurpureum.

Chemical constituents of the aerial parts of Algerian Galium brunneum: Isolation of new hydroperoxy sterol glucosyl derivatives

Bertella, Anis,Bitam, Fatma,Carbone, Marianna,Ciavatta, Maria Letizia,Gavagnin, Margherita,Smadi, Abla

, p. 39 - 45 (2020/05/25)

The liposoluble extract of Galium brunneum aerial parts from North-eastern Algeria was chemically investigated. The EtOAc soluble portion contained a series of glycosyl cucurbitacins and sterols including three new glucosyl hydroperoxy sterols 1–3 among other phenolic components whereas the BuOH soluble fraction was dominated by glycosyl derivatives of flavonoids, iridoids and lignans, according to the chemistry reported in the literature for the genus Galium. The structure of new oxidized sterols 1–3 was determined by spectroscopic methods as well as by comparison with related known metabolites. Selected main compounds from both extracts, which revealed moderate antibacterial activities, were tested for their growth inhibitory properties against Gram-positive and Gram-negative bacteria. This is the first report of cucurbitacins in plants of genus Galium.

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