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143685

Sigma-Aldrich

3-Hydroxy-4-methoxybenzaldehyde

99%

Synonym(s):

3-Hydroxyanisaldehyde, Isovanillin

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About This Item

Linear Formula:
HOC6H3(OCH3)CHO
CAS Number:
621-59-0
Molecular Weight:
152.15
Beilstein:
1073021
EC Number:
210-694-9
MDL number:
MFCD00003369
UNSPSC Code:
12352100
PubChem Substance ID:
24848602
NACRES:
NA.22

Quality Level

200

Assay

99%

bp

179 °C/15 mmHg (lit.)

mp

113-115 °C (lit.)

functional group

aldehyde

SMILES string

[H]C(=O)c1ccc(OC)c(O)c1

InChI

1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3

InChI key

JVTZFYYHCGSXJV-UHFFFAOYSA-N

Related Categories

General description

3-Hydroxy-4-methoxybenzaldehyde on condensation with furan-2-carboxylic acid hydrazide and thiophene-2-carboxylic acid hydrazide yields Schiff-bases. It undergoes condensation reaction with1-azabicyclo[2.2.2]octan-3-one to give (Z)-2-(3-hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one.

Application

3-Hydroxy-4-methoxybenzaldehyde was used as starting reagent during the two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 and glycitein synthesis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

>212.0 °F

Flash Point(C)

> 100 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

143685-BULK:
143685-100G:
143685-VAR:
143685-25G:
143685-10G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG4158
BCCF4473
BCCC6012
BCBZ9374
BCBV4045

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Caroline Lang'at-Thoruwa et al.
Journal of natural products, 66(1), 149-151 (2003-01-25)
4-Methoxyresorcinol (3) was synthesized as the precursor for glycitein (6) synthesis by the oxidation of 3-hydroxy-4-methoxybenzaldehyde (1) to the aryl formate with H2O2 and a catalytic amount of SeO2. Glycitein (6) was synthesized by cyclization of 2,4,4'-trihydroxy-5-methoxydeoxybenzoin (5) with N,N-dimethylformamide
K Gaukroger et al.
The Journal of organic chemistry, 66(24), 8135-8138 (2001-11-28)
A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline. The iodine-catalyzed
Vijayakumar N Sonar et al.
Acta crystallographica. Section C, Crystal structure communications, 59(Pt 11), o647-o649 (2003-11-08)
Crystals of the title compound, C(15)H(17)NO(3), were obtained from a condensation reaction of 3-hydroxy-4-methoxybenzaldehyde with 1-azabicyclo[2.2.2]octan-3-one and subsequent crystallization of the product from methanol. The title compound, containing a double bond that connects the azabicyclic ring system to the 3-hydroxy-4-methoxybenzylidene
Riyadh M Ahmed et al.
TheScientificWorldJournal, 2013, 754868-754868 (2013-09-13)
New monomeric cobalt and cadmium complexes with Schiff-bases, namely, N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]furan-2-carbohydrazide (L¹) and N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]thiophene-2-carbohydrazide (L²) are reported. Schiff-base ligands L¹ and L² were derived from condensation of 3-hydroxy-4-methoxybenzaldehyde (iso-vanillin) with furan-2-carboxylic acid hydrazide and thiophene-2-carboxylic acid hydrazide, respectively. Complexes of the
Michael D Markey et al.
Organic letters, 9(17), 3255-3257 (2007-07-31)
The first total synthesis of santiagonamine (1) is achieved in 12 steps from isovanillin. A palladium-catalyzed Ullmann cross-coupling reaction and a photocyclization are the key steps in the synthesis.
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Global Trade Item Number

SKUGTIN
143685-25G4061838735003
143685-100G4061838734990

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