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143685

Sigma-Aldrich

3-Hydroxy-4-methoxybenzaldehyde

99%

Synonym(s):

3-Hydroxyanisaldehyde, Isovanillin

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25 G
$70.40
100 G
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About This Item

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

$70.40

Available to ship onApril 22, 2025Details

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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[1]. 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[2].

application

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

>212.0 °F

flash_point_c

> 100 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8869
BCCG4158
BCCF4473
BCCC6012
BCBZ9374

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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
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
Georgios I Panoutsopoulos et al.
European journal of drug metabolism and pharmacokinetics, 29(2), 111-118 (2004-07-03)
2-Phenylethylamine is an endogenous constituent of human brain and is implicated in cerebral transmission. It is also found in certain foodstuffs and may cause toxic side-effects in susceptible individuals. Metabolism of 2-phenylethylamine to phenylacetaldehyde is catalyzed by monoamine oxidase and
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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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