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138797

Sigma-Aldrich

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:
708-76-9
Molecular Weight:
182.17
Beilstein:
1241679
EC Number:
211-904-1
MDL number:
MFCD00003328
UNSPSC Code:
12352100
PubChem Substance ID:
24848366
NACRES:
NA.22

Assay

98%

mp

68-70 °C (lit.)

functional group

aldehyde

SMILES string

[H]C(=O)c1c(O)cc(OC)cc1OC

InChI

1S/C9H10O4/c1-12-6-3-8(11)7(5-10)9(4-6)13-2/h3-5,11H,1-2H3

InChI key

FQRQWPNYJOFDLO-UHFFFAOYSA-N

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBV5766V
07124MH
20919LG
02207MZ
01818KF

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Ketocoumarins: a new class of triplet sensitizers.
Specht DP, et al.
Tetrahedron, 38(9), 1203-1211 (1982)
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
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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