3-(2H3)methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde; 4-hydroxy-3-methoxybenzaldehyde

• ChemBase ID: 179446
• Molecular Formular: C22H26O11
• Molecular Mass: 466.43524
• Monoisotopic Mass: 466.14751165
• SMILES: c1cc(c(cc1C=O)OC)O.c1cc(c(cc1C=O)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)CO
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2ccc(cc2OC)C=O)[C@H]([C@H]([C@@H]1O)O)O.COc1cc(C=O)ccc1O
• InChI: InChI=1S/C14H18O8.C8H8O3/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14;1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10-14,16-19H,6H2,1H3;2-5,10H,1H3/t10-,11-,12+,13-,14-;/m1./s1
• InChIKey: NQWSTOJMPNBTIR-ABJJILNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(^2H₃)methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde; 4-hydroxy-3-methoxybenzaldehyde
• IUPAC Traditional name: 3-(^2H₃)methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde; vanillin
• Synonyms: 4-(β-D-Glucopyranosyloxy)-3-methoxybenzaldehyde-d3; Avenein-d3; Glucovanillin-d3; Vanillin-d3 Glucoside; Vanillin-d3 β-D-Glucopyranoside; Vanillin-4-O-β-D-Glucopyranoside-d3; Vanillin-O-β-D-glucopyranoside-d3; Vanilloside-d3; Vanillin-d3 4-O-β-D-Glucoside

Database IDs

• PubChem SID: 164235356
• PubChem CID: 71752920

CALCULATED PROPERTIES

• Acid pKa: 12.200015
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.0435566
• LogD (pH = 7.4): -1.0435634
• Log P: -1.0435566
• Molar Refractivity: 73.2305 cm^3
• Polarizability: 29.118189 Å^3
• Polar Surface Area: 125.68 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V097512

Labelled Vanillin 4-O-β-D-Glucoside, 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.

REFERENCES

• Odoux, E. et al.: Fruits, 61, 171 (2006)
• Palama, T.L. et al.: Environ. Exp. Bot., 72, 258 (2006)
• Dunphy, P. et al.: Perf. Flav., 34, 34 (2006)