GLUCOVANILLIN Chemical Properties

Melting point:

189-190°

alpha 

D20 -89.9° (water)

Boiling point:

574.7±50.0 °C(Predicted)

Density 

1.481±0.06 g/cm3(Predicted)

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)

form 

Solid

color 

White to Off-White

Odor

at 100.00 %. very mild vanilla

Odor Type

vanilla

Stability:

Hygroscopic

LogP

-1.252 (est)

GLUCOVANILLIN Usage And Synthesis

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.

Definition

ChEBI: Glucovanillin is a glycoside.

Synthesis

General procedure for the synthesis of 3-methoxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde from 4-O-(2',3',4',6'-tetraoxo-acetyl-Β-D-glucopyranoside) vanillin: 2,3,4,6-tetra-O- vanillin 2,3,4,6-tetra-O- acetyl-β-D-glucopyranoside (1.36 g, 3.0 mmol) was dissolved in a solvent mixture of THF/CH3OH/H2O (33 mL, 5:5:1, v/v), followed by the addition of K2CO3 (0.83 g, 6.0 mmol). The reaction mixture was stirred at 40 °C for 20 min before the reaction was quenched with 1 M HCl solution and subsequently concentrated. The residue was purified by silica gel column chromatography (eluent CH2Cl2/CH3OH, 15:1, v/v) to afford the target product 4 as a white solid (0.88 g, 94% yield). The specific optical rotation of the product was [a]D20 -11.4 (c 1.0, H2O).1H NMR (DMSO-d6, 400 MHz) δ: 9.86 (s, 1H, CHO), 7.52 (dd, J = 8.3, 1.5 Hz, 1H, Ph-H), 7.43 (d, J = 1.4 Hz, 1H, Ph-H), 7.28 (d, J = 8.4 Hz, 1H, Ph-H), 5.39 (d, J = 4.4 Hz, 1H, -OH), 5.16 (d, J = 3.7 Hz, 1H, -OH), 5.09 (d, J = 5.2 Hz, 2H, -OH, H-1), 4.59 (t, J = 5.6 Hz, 1H, -OH), 3.84 (s, 3H, -OMe). 3.66 (dd, J = 11.2, 4.7 Hz, 1H, H-3), 3.48-3.45 (m, 1H, H-2), 3.40-3.37 (m, 1H, H-4), 3.30-3.25 (m, 2H, H-6), 3.20-3.14 (m, 1H, H-5).13C NMR (DMSO-d6, 150 MHz ) δ: 191.66 (CHO), 151.78, 149.34, 130.56, 125.43, 114.58, 110.52, 99.41 (C-1), 77.17, 76.84, 73.11, 69.58, 60.62, 55.70. ESI-HRMS m/z [M+Na]+ calculated value C14H18NaO8 was 337.0894 and the measured value was 337.0901.

References

[1] Carbohydrate Research, 2018, vol. 460, p. 41 - 46
[2] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 5, p. 2056 - 2064
[3] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588

GLUCOVANILLIN(494-08-6)Related Product Information

• 2-deoxy-2-[(1-oxo-4-pentyn-1-yl)amino]-D-glucose
• Ethyl α-Thioglucopyranoside
• 2-Azido-2-deoxy-D-glucose
• 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-[(2-azidoacetyl)amino]-β-D-glucopyranose
• Glycitin
• BETA-D-GLUCOPYRANOSIDURONIC ACID
• WISTIN
• Tectoridin
• GLUCOVANILLIN
• nepitrin
• HOMOPLANTAGININ
• kakkalide
• androsin
• 6''-O-ACETYLGLYCITIN
• LEIOCARPOSIDE
• centaurein
• 3',4',6-TRIMETHOXYISOFLAVONE-7-O-BETA-D-GLUCOPYRANOSIDE
• NEOLLOYDOSIN