494-08-6

Basic information

• Product Name: GLUCOVANILLIN
• Synonyms: VANILLIN D-GLUCOSIDE;GLUCOVANILLIN;4-(BETA-D-GLUCOPYRANOSYLOXY)-3-METHOXYBENZALDEHYDE;4-(β-D-Glucopyranosyloxy)-3-Methoxybenzaldehyde;Avenein;Vanillin 4-O-β-D-Glucoside;Vanillin Glucoside;Vanillin β-D-Glucopyranoside
• CAS NO: 494-08-6
• Molecular Formula: C₁₄H₁₈O₈
• Molecular Weight: 314.29
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 494-08-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 189-190°
• Boiling Point: 574.7 °C at 760 mmHg
• Flash Point: 216.6 °C
• Appearance: /
• Density: 1.481g/cm³
• Vapor Pressure: 4.75E-14mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
• PKA: 12.78±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: GLUCOVANILLIN(CAS DataBase Reference)
• NIST Chemistry Reference: GLUCOVANILLIN(494-08-6)
• EPA Substance Registry System: GLUCOVANILLIN(494-08-6)

Safety Data

• Hazardous Substances Data: 494-08-6(Hazardous Substances Data)

Usage

Uses

Vanillin 4-O-β-D-Glucoside is the glucosylated precursor of Vanillin (V097500) found in the seed pods of Vanilla planifola. During the curing process Vanillin 4-O-β-D-Glucoside is transformed into the aromatic vanillin.

InChI:InChI=1/C14H18O8/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14/h2-5,10-14,16-19H,6H2,1H3/t10-,11-,12+,13-,14-/m1/s1

Upstream product

• 121-33-5 vanillin 
• 57-50-1 Sucrose 
• 2280-44-6 D-Glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 18604-50-7 citrusin C 
• 51482-43-0 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin 
• 133-89-1 UDP-glucose 
• 4336-91-8 3-bromo-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 

Downstream Products

• 144677-85-0 4'-formyl-2'-methoxyphenyl 4,6-O-(α-amylcinnamylidene)-β-D-glucopyranoside 
• 23598-08-5 methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate 
• 50-99-7 D-glucose 
• 121-33-5 vanillin 
• 109448-46-6 4-β-D-glucopyranosyloxy-3-methoxy-benzaldehyde thiosemicarbazone 
• 117405-51-3 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside 
• 112572-59-5 1-<4-β-Glucopyranosyl-3-methoxy>-3-<2-hydroxy-4,6-dimethoxy-phenyl>-prop-1-en-3-on 

Relevant articles and documents

Glycosylation of vanillin by amyloglucosidase in organic media

Glycosylation of vanillin using amyloglucosidase from a Rhizopus mold with D-glucose, D-galactose, D-mannose, maltose, sucrose and D-sorbitol in di-isopropyl ether yielded glycosides in the range 13-53%. NMR spectral data confirmed linking between the phenolic OH of vanillin and C1 and/or C6 of the carbohydrate moieties.

Synthesis of eugenol-derived glucosides and evaluation of their ability in inhibiting the angiotensin converting enzyme

We report here a series of glucosides which are active as inhibitors of the angiotensin converting enzyme (ACE). They are structurally related to the natural compound eugenol and exhibited significant inhibition values. Their syntheses were expeditious and we could obtain informative docking plots of them complexed to this enzyme. A glucoside derived from eugenol, carrying a carboxylic group in the aglycone, was the most active of them (with an IC50 of 0.4 mM) and showed good binding energies in docking studies with ACE. Moreover, computational prediction of toxicity risks, physicochemical properties and drug score show that the glucoside derivative of eugenol is a suitable compound for optimisation studies aimed at finding new drug candidates.

Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D

Starting from readily available vanillin and α-D-acetobromo glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O-6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the aldehyde in the aglycon moiety by using Pd(PPh)3-NaBH4 system in one pot.