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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O4
Molecular Weight 196.1999
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3,4,5-TRIMETHOXYBENZALDEHYDE

SMILES

COC1=CC(C=O)=CC(OC)=C1OC

InChI

InChIKey=OPHQOIGEOHXOGX-UHFFFAOYSA-N
InChI=1S/C10H12O4/c1-12-8-4-7(6-11)5-9(13-2)10(8)14-3/h4-6H,1-3H3

HIDE SMILES / InChI
3,4,5-Trimethoxybenzaldehyde is a key intermediate in the synthesis of trimethoprim[2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine], which, in addition to its antibacterial activity, possesses the property of significantly strengthening the bactericidal activity of sulfanilamide preparations. Also, 3,4,5-Trimethoxybenzaldehyde id used for the synthesis of Isoamoenylin, which showed moderate antioxidative and weak antibacterial activities. An A-ring analogue of colchicine, 3,4,5-trimethoxybenzaldehyde, can stop the antimitotic drug IKP104-induced unfolding of tubulin significantly. 3,4,5-trimethoxybenzaldehyde stimulated tubulin-dependent GTP hydrolysis.

Originator

Sources: DOI: 10.15227/orgsyn.051.0008

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2094134
2.5 mM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Concise synthesis and structure-activity relationships of combretastatin A-4 analogues, 1-aroylindoles and 3-aroylindoles, as novel classes of potent antitubulin agents.
2004 Aug 12
Two novel series of allocolchicinoids with modified seven membered B-rings: design, synthesis, inhibition of tubulin assembly and cytotoxicity.
2005 May 16
(E)-1-(4-Bromo-phen-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.
2008 Dec 13
Deprotonative magnesation and cadmation of [1,2,3]triazolo[1,5-a]pyridines.
2009 Jan 2
Investigation of the antioxidant properties of some new 4-hydroxycoumarin derivatives.
2009 Jul
(E)-1-[4-(Prop-2-yn-1-yl-oxy)phen-yl]-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.
2010 Aug 11
Enhanced activity of antifungal drugs using natural phenolics against yeast strains of Candida and Cryptococcus.
2011 May
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
3,4,5-trimethoxybenzaldehyde has a significant stimulation on tubulin dependent GTP hydrolysis reaction at concentration 1 mM. 33.1 nM of GDP were formed at this concentration.
Name Type Language
3,4,5-TRIMETHOXYBENZALDEHYDE
Systematic Name English
BENZALDEHYDE, 3,4,5-TRIMETHOXY-
Systematic Name English
NSC-16692
Code English
Code System Code Type Description
FDA UNII
WL86YD76N6
Created by admin on Sat Dec 16 01:38:28 GMT 2023 , Edited by admin on Sat Dec 16 01:38:28 GMT 2023
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CAS
86-81-7
Created by admin on Sat Dec 16 01:38:28 GMT 2023 , Edited by admin on Sat Dec 16 01:38:28 GMT 2023
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PUBCHEM
6858
Created by admin on Sat Dec 16 01:38:28 GMT 2023 , Edited by admin on Sat Dec 16 01:38:28 GMT 2023
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NSC
16692
Created by admin on Sat Dec 16 01:38:28 GMT 2023 , Edited by admin on Sat Dec 16 01:38:28 GMT 2023
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ECHA (EC/EINECS)
201-701-6
Created by admin on Sat Dec 16 01:38:28 GMT 2023 , Edited by admin on Sat Dec 16 01:38:28 GMT 2023
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EPA CompTox
DTXSID4058948
Created by admin on Sat Dec 16 01:38:28 GMT 2023 , Edited by admin on Sat Dec 16 01:38:28 GMT 2023
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WIKIPEDIA
3,4,5-Trimethoxybenzaldehyde
Created by admin on Sat Dec 16 01:38:28 GMT 2023 , Edited by admin on Sat Dec 16 01:38:28 GMT 2023
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