138797
4,6-Dimethoxysalicylaldehyde
98%
Synonym(s):
2,4-Dimethoxy-6-hydroxybenzaldehyde, 4,6-Dimethoxy-2-hydroxybenzaldehyde
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About This Item
Linear Formula:
HOC6H2(OCH3)2CHO
CAS Number:
Molecular Weight:
182.17
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
211-904-1
Beilstein/REAXYS Number:
1241679
MDL number:
Assay:
98%
InChI key
FQRQWPNYJOFDLO-UHFFFAOYSA-N
InChI
1S/C9H10O4/c1-12-6-3-8(11)7(5-10)9(4-6)13-2/h3-5,11H,1-2H3
SMILES string
[H]C(=O)c1c(O)cc(OC)cc1OC
assay
98%
mp
68-70 °C (lit.)
functional group
aldehyde
General description
4,6-Dimethoxysalicylaldehyde on condensation with methylamine yields Schiff bases.
Application
4,6-Dimethoxysalicylaldehyde was used in the preparation of a new class of efficient ketocoumarin triplet sensitizers. It was used as staring reagent in the total synthesis of (+/-)-linderol A, a hexahydrodibenzofuran.
Biochem/physiol Actions
4,6-Dimethoxysalicylaldehyde has antimicrobial activity against Candida albicans.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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M Yamashita et al.
Organic letters, 3(9), 1359-1362 (2001-05-12)
[reaction in text] The first total synthesis of (+/-)-linderol A, a hexahydrodibenzofuran isolated from Lindera umbellata bark, with potent inhibitory activity on melanin biosynthesis of cultured B-16 melanoma cells was achieved via a 20-step of reaction in 7.64% overall yield
Ketocoumarins: a new class of triplet sensitizers.
Specht DP, et al.
Tetrahedron, 38(9), 1203-1211 (1982)
Wojciech Schilf et al.
Magnetic resonance in chemistry : MRC, 42(6), 556-560 (2004-05-12)
Hydrogen bonding within the structures of three Schiff bases (1-3), obtained by condensation of 4-methoxy-, 5-methoxy- and 4,6-dimethoxysalicylaldehyde with methylamine, was investigated by measuring deuterium and tritium NMR isotope effects. The primary deuterium and tritium isotope effects (delta(XH)-delta(XD/T)) and secondary
Eila Pelttari et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 62(7-8), 487-497 (2007-10-05)
A systematic survey of the antimicrobial properties of substituted salicylaldehydes and some related aromatic aldehydes is reported. A total of 23 different compounds, each at four different concentrations, were studied using a panel of seven microbes (Aspergillus niger, Bacillus cereus
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