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

Uses

β-Rutinose is an intermediate used in the synthesis of Isorhoifolin (Diosmin EP Impurity C) (I819700), which is a naturally occurring flavonoid that was shown to exhibit potential antidiabetic, antihyperlipidemic and antioxidant effects. Also, it is an extract from the medicinal plant, Viola tricolor, for the potential treatment of acne.

Upstream product

• 6130-58-1 kaempferol-3-rutinoside 
• 153-18-4 rutin 
• 24292-52-2 hesperidin methyl chalcone 
• 520-26-3 hesperidin 
• 604-80-8 narcissin 
• 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 
• 501-94-0 p-hydroxyphenethyl alcohol 

Downstream Products

• 3615-41-6 L-Rhamnose 
• 50-99-7 D-glucose 
• 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 

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.

α-L-Rhamnosyl-β-D-glucosidase (rutinosidase) from Aspergillus niger: Characterization and synthetic potential of a novel diglycosidase

We report the first heterologous production of a fungal rutinosidase (6-O-α-L-rhamnopyranosyl-β-D-glucopyranosidase) in Pichia pastoris. The recombinant rutinosidase was purified from the culture medium to apparent homogeneity and biochemically characterized. The enzyme reacts with rutin and cleaves the glycosidic linkage between the disaccharide rutinose and the aglycone. Furthermore, it exhibits high transglycosylation activity, transferring rutinose from rutin as a glycosyl donor onto various alcohols and phenols. The utility of the recombinant rutinosidase was demonstrated by its use for the synthesis of a broad spectrum of rutinosides of primary (saturated and unsaturated), secondary, acyclic and phenolic alcohols as well as for the preparation of free rutinose. Moreover, the α-L-rhamnosidase-catalyzed synthesis of a chromogenic substrate for a rutinosidase assay - para-nitrophenyl β-rutinoside - is described.