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

Description

Glucovanillin, also known as Vanillin 4-O-β-D-Glucoside, is a glucosylated precursor of vanillin found in the seed pods of Vanilla planifolia. It plays a crucial role in the production of the aromatic compound vanillin, which is responsible for the characteristic flavor and scent of vanilla.

Uses

Used in Flavor and Fragrance Industry:
Glucovanillin is used as a precursor for the production of vanillin, which is a key component in the flavor and fragrance industry. The conversion of glucovanillin to vanillin during the curing process of vanilla beans contributes to the unique and desirable aroma of vanilla, making it a valuable ingredient in the creation of various perfumes, cosmetics, and food products.
Used in Pharmaceutical Applications:
Glucovanillin may also have potential applications in the pharmaceutical industry due to its conversion to vanillin. Vanillin has been studied for its various biological activities, including antioxidant, anti-inflammatory, and antimicrobial properties. These properties could potentially be harnessed in the development of new drugs or therapies, with glucovanillin serving as a natural and sustainable source of vanillin for such purposes.
Used in Food Industry:
In the food industry, glucovanillin is used as a natural source of vanillin, which is a widely used flavoring agent. The conversion of glucovanillin to vanillin during the curing process of vanilla beans provides the characteristic taste and aroma associated with vanilla, making it an essential ingredient in the production of various food products such as ice cream, baked goods, and beverages.

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

Downstream Products

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

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.