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434795

2-Benzyloxy-3-methoxybenzaldehyde

Name: 2-Benzyloxy-3-methoxybenzaldehyde
Brand: ALDRICH

98%

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About This Item

Linear Formula:

C₆H₅CH₂OC₆H₃(OCH₃)CHO

CAS Number:

2011-06-5

Molecular Weight:

242.27

NACRES:

NA.22

PubChem Substance ID:

24867210

UNSPSC Code:

12352100

MDL number:

MFCD00202674

Assay:

98%

Form:

solid

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Properties

assay

98%

form

solid

mp

44-46 °C (lit.)

functional group

aldehyde, phenyl

SMILES string

COc1cccc(C=O)c1OCc2ccccc2

InChI

1S/C15H14O3/c1-17-14-9-5-8-13(10-16)15(14)18-11-12-6-3-2-4-7-12/h2-10H,11H2,1H3

InChI key

KXBGOVZWCRLLOR-UHFFFAOYSA-N

Description

General description

2-Benzyloxy-3-methoxybenzaldehyde (benzyl-o-vanillin) can be prepared from the reaction of o-vanillin with benzyl bromide in acetone (solvent) and K₂CO₃(base) in the presence of tetra-n-butylammonium iodide (catalyst). The dihedral angle between the two benzene rings in 2-benzyloxy-3-methoxybenzaldehyde crystal is 23.33 (6)°. Crystal structure suggests that all O atoms are involved in intra and intermolecular C-HO interactions. It has been reported as key reagent for the synthesis of new anticancer drugs. It is an important pharmacophore in drug discovery. It exhibits anti-proliferative activity in HL60 leukemia cancer cells.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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2-Benzyloxy-3-methoxybenzaldehyde (benzyl-o-vanillin).

Al-Douh MH, et al.

Acta Crystallographica Section E, Structure Reports Online, 62(11), 4768-4770 (2006)

1D and 2D NMR Studies of Benzyl o-Vanillin.

Al-Douh MH, et al.

Indonesian Journal of Chemistry, 8(3), 411-417 (2010)

Conjugation of benzylvanillin and benzimidazole structure improves DNA binding with enhanced antileukemic properties.

Zena A Al-Mudaris et al.

PloS one, 8(11), e80983-e80983 (2013-11-22)

Benzyl-o-vanillin and benzimidazole nucleus serve as important pharmacophore in drug discovery. The benzyl vanillin (2-(benzyloxy)-3-methoxybenzaldehyde) compound shows anti-proliferative activity in HL60 leukemia cancer cells and can effect cell cycle progression at G2/M phase. Its apoptosis activity was due to disruption

Global Trade Item Number

SKU	GTIN
434795-1G	04061825591513