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

• 24292-52-2 hesperidin methyl chalcone 
• 520-26-3 hesperidin 
• 55804-74-5 clitorin 
• 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 
• 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 
• 153-18-4 rutin 
• 1000992-24-4 cyclogalegigenin-3-O-β-D-rutinoside 
• 84534-31-6 (E)-3,7-dimethylocta-2,6-dien-1-yl [α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside] 
• 84582-21-8 Neryl 6-O-α-L-rhamnopyranosyl-β-D-glucopyranoside 
• 88510-08-1 2-phenylethyl O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside 
• 604-80-8 narcissin 

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.

Transrutinosylation of tyrosol by flower buds of Sophora japonica

Dried flower buds of Japanese sophora (Sophora japonica) comprising rutinosidase activity were tested in rutinosylation of tyrosol via transglycosylation process from rutin. Optimal conditions for transrutinosylation of tyrosol were 49 mM rutin and 290 mM

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.