26184-96-3

Basic information

• Product Name: 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose
• Synonyms: 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose;6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranose
• CAS NO: 26184-96-3
• Molecular Formula: C₁₂H₂₂O₁₀
• Molecular Weight: 326.29708
• EINECS: 247-510-1
• Mol File: 26184-96-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 598°Cat760mmHg
• Flash Point: 315.5°C
• Appearance: /
• Density: 1.66g/cm³
• PKA: 12.10±0.70(Predicted)
• CAS DataBase Reference: 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose(26184-96-3)
• EPA Substance Registry System: 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose(26184-96-3)

Safety Data

• Hazardous Substances Data: 26184-96-3(Hazardous Substances Data)

Usage

Description

6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose is a complex carbohydrate molecule that consists of a beta-D-glucose unit with a 6-deoxy-alpha-L-mannopyranosyl group attached to the 6-O position. This molecule is a type of disaccharide, which is a sugar composed of two monosaccharide units linked together. It plays a crucial role in various biological processes and has potential applications in different industries due to its unique structural and functional properties.

Uses

Used in Pharmaceutical Industry:
6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Nutraceutical Industry:
In the nutraceutical industry, 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose is used as a component in the development of dietary supplements and functional foods. Its presence in these products may contribute to their health-promoting properties, such as antioxidant, antidiabetic, and antihyperlipidemic effects.
Used in Cosmetic Industry:
6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose is used as an ingredient in the cosmetic industry, where it may be incorporated into skincare products for its potential moisturizing and skin-conditioning properties. Its ability to interact with biopolymers and macromolecules could also contribute to the development of novel cosmetic formulations with enhanced efficacy.
Used in Research and Development:
6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose is used as a research tool in the study of carbohydrate chemistry, glycobiology, and related fields. Its unique structure makes it an interesting subject for investigations into the role of carbohydrates in biological processes and the development of new methodologies for carbohydrate synthesis and analysis.
Used in Drug Delivery Systems:
Similar to gallotannin, 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose could potentially be used in the development of novel drug delivery systems. Its ability to interact with various biomolecules may allow for the design of targeted drug delivery platforms, improving the bioavailability and therapeutic outcomes of certain pharmaceutical compounds.

Upstream product

• 123491-26-9 2,3,4-tri-O-acetyl-1-O-geranyloxycarbonyl-6-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranose 
• 153-18-4 rutin 
• 604-80-8 narcissin 
• 1000992-24-4 cyclogalegigenin-3-O-β-D-rutinoside 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 55804-74-5 clitorin 
• 131279-12-4 rhamnosyl-(1<*>2)-O-6)> glucose 
• 74517-04-7 6-O-(4-O-acetyl-2,3-O-carbonyl-β-L-rhamnopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 76951-66-1 1,2:3,4-di-O-isopropylidene-6-O-trityl-α-D-galactopyranose 
• 75512-98-0 Acetic acid (3aR,5S,6S,7R,7aR)-6-acetoxy-2-ethylsulfanyl-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester 
• 62043-20-3 1,2:3,4-di-O-isopropylidene-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-galactopyranose 
• 37074-90-1 1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose 
• 5239-09-8 Neryl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-O-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside 
• 84534-31-6 (E)-3,7-dimethylocta-2,6-dien-1-yl [α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside] 

Downstream Products

• 5239-09-8 Neryl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-O-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside 
• 3615-41-6 L-Rhamnose 
• 50-99-7 D-glucose 

Relevant articles and documents

Unusual carbonate formation in saccharide synthesis

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Synthesis of 6-O-alpha-L-fucopyranosyl-D-galactose.

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Enzymatic deglycosylation of flavonoids in deep eutectic solvents-aqueous mixtures: Paving the way for sustainable flavonoid chemistry

The low solubility of glycosylated flavonoids represents a hurdle to conduct efficient enzymatic deglycosylations in aqueous media. To overcome this drawback, environmentally-unfriendly dimethylsulfoxide (DMSO) is typically used as co-solvent. Using a specific diglycosidase from Acremonium sp. DSM24697 for the deglycosylation of the rutinosylated flavonoid (hesperidin) as model reaction, this communication explores the use of (non-hazardous and biodegradable) deep eutectic solvents (DESs) as co-solvents in flavonoid biocatalysis. The enzymatic deglycosylation was observed when DES composed of choline chloride and glycerol or ethylene-glycol was used at proportions of up to 40% (DES-Buffer, v/v), displaying a promising framework to combine enhanced flavonoid solubilities and high enzymatic activities. The deglycosylation activity significantly increased when the single DES components - glycerol and ethylene-glycol - were added (e.g. 140% of enzyme activity at glycerol at 40% v/v), whereas deleterious effects were observed when choline chloride was solely added, presumably due to its chaotropic effect. Future research opportunities may be envisaged in the genetic design to evolve more robust biocatalysts, and in tailoring DES to deliver more enzyme-compatible solvents.

Access to both anomers of rutinosyl azide using wild-type rutinosidase and its catalytic nucleophile mutant

Rutinosidases hydrolyze β-rutinosylated flavonoids. As retaining glycosidases they also have a transglycosylation activity. Here we show that two newly identified wild-type rutinosidases, which are members of the glycoside hydrolase family 5–23, are capable of glycosylation of an inorganic azide with rutin as a glycosyl donor, yielding rutinosyl β-azide. On the other hand, rutinosyl α-azide was synthesized by the catalytic nucleophile mutant of the rutinosidase from Aspergillus niger, which also belongs to GH5–23. Thus, we were able to synthesize at a preparatory scale both anomers of rutinosyl azide from rutin using either wild-type or mutant rutinosidases of GH5–23.

Dracopalmaside, a New Flavonoid from Dracocephalum palmatum

Phytochemical studies of the aerial part of Dracocephalum palmatum (Lamiaceae) isolated the new flavonoid dracopalmaside that was identified based on UV, MS, and NMR spectral data as luteolin-7,4′-di-O-α -Lrhamnopyranosyl-(1→6)-β-D-glucopyranoside (luteolin-7,4′-di-O-rutinoside) and the two known compounds cynarotriside and luteolin-7,4′-di-O-glucoside.