3,4,5-TRIMETHOXYBENZALDEHYDE

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

Structure Search

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

Molecular Formula	C10H12O4
Molecular Weight	196.1999
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: DOI: 10.1007/BF00765001 | https://www.ncbi.nlm.nih.gov/pubmed/12450140 | https://www.ncbi.nlm.nih.gov/pubmed/6114958 | https://www.ncbi.nlm.nih.gov/pubmed/9860828

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2094134 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9860828	Modulator 828		2.5 mM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
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	15293996
Quantitative analysis of camptothecin derivatives in Nothapodytes foetida using 1H-NMR method.	2005 Mar	15744115
Two novel series of allocolchicinoids with modified seven membered B-rings: design, synthesis, inhibition of tubulin assembly and cytotoxicity.	2005 May 16	15848763
One pot synthesis of alpha-aminophosphonates containing bromo and 3,4,5-trimethoxybenzyl groups under solvent-free conditions.	2007 Feb 7	17846566
Influence of lipophilia and of the vehicle used in the transdermal absorption of novel benzimidazole compounds with possible anti-HIV activity.	2008	18379904
(E)-1-(4-Bromo-phen-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.	2008 Dec 13	21581582
Synthesis and in vitro cytotoxic evaluation of novel 3,4,5-trimethoxyphenyl substituted beta-carboline derivatives.	2009 Feb	18462839
(E)-1-(2-Thien-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.	2009 Jun 13	21582853
(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	21588621
1,5-Dimethyl-2-phenyl-4-{[(E)-3,4,5-trimethoxybenzylidene]amino}-1H-pyrazol-3(2H)-one.	2010 Jul 31	21588435
(2E)-1-(2-Bromo-phen-yl)-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.	2010 Jun 16	21587901
Enhanced activity of antifungal drugs using natural phenolics against yeast strains of Candida and Cryptococcus.	2011 May	21332761

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:38:28 UTC 2023` Edited by `admin` on `Sat Dec 16 01:38:28 UTC 2023`
Record UNII	WL86YD76N6
Record Status	`Validated (UNII)`
Record Version

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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