Page last updated: 2024-12-06

1,2,4-trimethoxybenzene

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 1,2,4-Trimethoxybenzene: A Versatile Building Block

1,2,4-trimethoxybenzene is an organic compound with the molecular formula C9H12O3. It is a white crystalline solid with a pleasant odor.

**Structure and Properties:**

* **Structure:** It consists of a benzene ring with three methoxy (CH3O-) groups attached at the 1, 2, and 4 positions.
* **Properties:** It is a highly soluble compound, particularly in organic solvents. It is also relatively stable and easily reacts with various chemical reagents.

**Importance in Research:**

1,2,4-trimethoxybenzene is a valuable building block for the synthesis of various compounds, including:

* **Pharmaceuticals:** It serves as a starting material for synthesizing drugs with diverse biological activities.
* **Natural Products:** It is a key precursor for the synthesis of various naturally occurring compounds, like flavonoids and lignans, with potential medicinal applications.
* **Materials Science:** It has potential applications in the development of new materials, such as polymers and resins, due to its unique reactivity and structural features.
* **Organic Chemistry:** It is a model compound for studying various organic reactions and exploring reaction mechanisms.

**Specific Examples:**

* **Anti-Cancer Agents:** 1,2,4-trimethoxybenzene derivatives have shown promising anti-cancer activity against various tumor cell lines.
* **Anti-Inflammatory Compounds:** Its derivatives exhibit anti-inflammatory properties, suggesting their potential for treating inflammatory diseases.
* **Antimicrobial Agents:** Research indicates the potential of 1,2,4-trimethoxybenzene derivatives for combating bacterial and fungal infections.

**Overall, 1,2,4-trimethoxybenzene plays a crucial role in research due to its versatility as a synthetic precursor, its potential for developing new drugs and materials, and its value as a model compound for studying organic reactions.**

1,2,4-trimethoxybenzene: a volatile organic compound [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID67284
CHEMBL ID1668605
CHEBI ID167092
SCHEMBL ID481491
MeSH IDM0495270

Synonyms (45)

Synonym
CHEBI:167092
bdbm50336489
epa pesticide chemical code 040515
einecs 205-219-7
ai3-20797
1,2,4-trimethoxybenzene
benzene, 1,2,4-trimethoxy-
135-77-3
1,2,4-trimethoxybenzene, 97%
NCGC00164023-01
inchi=1/c9h12o3/c1-10-7-4-5-8(11-2)9(6-7)12-3/h4-6h,1-3h3
agiqioshsmjyjp-uhfffaoysa-
T1130
hydroxyhydroquinone trimethyl ether
A806985
NCGC00164023-02
CHEMBL1668605 ,
unii-3ku3wd07ss
3ku3wd07ss ,
dtxcid3015163
tox21_300993
cas-135-77-3
dtxsid5035163 ,
NCGC00254895-01
FT-0627148
PS-5199
AM20050161
AKOS015851701
1,3,4-trimethoxybenzene
trimethoxybenzene, 1,2,4-
1,2,4-benzenetriol trimethyl ether
1,2,5-trimethoxybenzene
SCHEMBL481491
1,3,4-trimethoxy benzene
2,4,5-trimethoxybenzene
W-108257
STR04198
CS-W017803
AC-23662
mfcd00008360
Z1255382978
SY014691
F11207
Q27257439
EN300-187594

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The essential oil had a significant toxic effect against early fourth-stage larvae of Aedes aegypti L with an LC(50) value of 31."( Immunotoxicity activity of 1,2,4-trimethoxybenzene from the Paulownia coreana Uyeki. against Aedes aegypti L.
Chung, IM; Moon, HI, 2011
)
0.67
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
methoxybenzenesAny aromatic ether that consists of a benzene skeleton substituted with one or more methoxy groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
retinoid X nuclear receptor alphaHomo sapiens (human)Potency24.54120.000817.505159.3239AID1159531
estrogen nuclear receptor alphaHomo sapiens (human)Potency30.63790.000229.305416,493.5996AID743079
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency0.19490.001024.504861.6448AID743215
heat shock protein beta-1Homo sapiens (human)Potency24.54120.042027.378961.6448AID743210
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency48.55770.000627.21521,122.0200AID743202
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 12Homo sapiens (human)Ki7.80000.00021.10439.9000AID568365
Carbonic anhydrase 1Homo sapiens (human)Ki5.96000.00001.372610.0000AID568362
Carbonic anhydrase 2Homo sapiens (human)Ki1.43000.00000.72369.9200AID568363
Carbonic anhydrase 7Homo sapiens (human)Ki3.70000.00021.37379.9000AID729536
Carbonic anhydrase 9Homo sapiens (human)Ki4.06000.00010.78749.9000AID568364
Carbonic anhydrase 14Homo sapiens (human)Ki0.63000.00021.50999.9000AID729533
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
estrous cycleCarbonic anhydrase 12Homo sapiens (human)
chloride ion homeostasisCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 12Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 7Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 7Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 7Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 7Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 7Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 7Homo sapiens (human)
response to hypoxiaCarbonic anhydrase 9Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 9Homo sapiens (human)
response to xenobiotic stimulusCarbonic anhydrase 9Homo sapiens (human)
response to testosteroneCarbonic anhydrase 9Homo sapiens (human)
secretionCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 14Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
zinc ion bindingCarbonic anhydrase 12Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 12Homo sapiens (human)
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 7Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 7Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 9Homo sapiens (human)
molecular function activator activityCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 14Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 14Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
membraneCarbonic anhydrase 12Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 12Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 12Homo sapiens (human)
plasma membraneCarbonic anhydrase 12Homo sapiens (human)
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 7Homo sapiens (human)
cytoplasmCarbonic anhydrase 7Homo sapiens (human)
nucleolusCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
membraneCarbonic anhydrase 9Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 9Homo sapiens (human)
microvillus membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 14Homo sapiens (human)
membraneCarbonic anhydrase 14Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 14Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 14Homo sapiens (human)
plasma membraneCarbonic anhydrase 14Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID1540231Cytotoxicity against human MRC5 cells assessed as cell growth inhibition after 72 hrs by alamar blue assay
AID568362Inhibition of human carbonic anhydrase 1 preincubated for 15 mins by CO2 hydration stopped-flow assay2011Bioorganic & medicinal chemistry, Feb-15, Volume: 19, Issue:4
Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site.
AID1540227Cytotoxicity against human MCF7 cells assessed as cell growth inhibition after 72 hrs by alamar blue assay
AID729533Inhibition of human carbonic anhydrase 14 preincubated for 15 mins by CO2 hydration stopped-flow assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV.
AID1540230Cytotoxicity against human HL60 cells assessed as cell growth inhibition after 72 hrs by alamar blue assay
AID1540229Cytotoxicity against human HepG2 cells assessed as cell growth inhibition after 72 hrs by alamar blue assay
AID568364Inhibition of human carbonic anhydrase 9 preincubated for 15 mins by CO2 hydration stopped-flow assay2011Bioorganic & medicinal chemistry, Feb-15, Volume: 19, Issue:4
Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site.
AID568363Inhibition of human carbonic anhydrase 2 preincubated for 15 mins by CO2 hydration stopped-flow assay2011Bioorganic & medicinal chemistry, Feb-15, Volume: 19, Issue:4
Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site.
AID568365Inhibition of human carbonic anhydrase 12 preincubated for 15 mins by CO2 hydration stopped-flow assay2011Bioorganic & medicinal chemistry, Feb-15, Volume: 19, Issue:4
Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site.
AID729536Inhibition of human carbonic anhydrase 7 preincubated for 15 mins by CO2 hydration stopped-flow assay2013Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6
Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV.
AID1540228Cytotoxicity against human HCT116 cells assessed as cell growth inhibition after 72 hrs by alamar blue assay
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (33.33)29.6817
2010's5 (55.56)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.70

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.70 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.70)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]