434795
2-Benzyloxy-3-methoxybenzaldehyde
98%
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About This Item
Linear Formula:
C6H5CH2OC6H3(OCH3)CHO
CAS Number:
Molecular Weight:
242.27
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
98%
Form:
solid
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
SMILES string
COc1cccc(C=O)c1OCc2ccccc2
InChI key
KXBGOVZWCRLLOR-UHFFFAOYSA-N
assay
98%
form
solid
mp
44-46 °C (lit.)
functional group
aldehyde, phenyl
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)
Regulatory Information
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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)
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
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