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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.)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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

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