Page last updated: 2024-11-05

4-methyl anisole

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

4-Methyl anisole, also known as p-methylanisole or 4-methoxytoluene, is a colorless liquid with a sweet, floral odor. It is a common aromatic compound found in various essential oils and fragrances. It is synthesized via methylation of anisole using various methods, including the Friedel-Crafts reaction. 4-Methyl anisole exhibits diverse biological activities, including antimicrobial and anti-inflammatory properties. It is used as a precursor in the production of various pharmaceutical and agrochemical compounds. Its synthesis and properties are actively studied to understand its potential applications in different fields.'

Cross-References

ID SourceID
PubMed CID7731
CHEMBL ID154155
CHEBI ID89728
SCHEMBL ID12464
SCHEMBL ID2489775
SCHEMBL ID12015216
MeSH IDM0052248

Synonyms (91)

Synonym
4-methylanisole
methyl p-tolyl ether
p-methylanisole
104-93-8
4-methyl-1-methoxybenzene
4-methoxytoluene
1-methyl-4-methoxybenzene
anisole, p-methyl-
p-cresyl methyl ether
benzene, 1-methoxy-4-methyl-
p-tolyl methyl ether
1-methoxy-4-methylbenzene
wln: 1or d1
4-methylphenol methyl ether
methyl p-cresyl ether
nsc-6254
nsc6254
methyl 4-methylphenyl ether
p-methoxytoluene
p-cresol methyl ether
para-methoxytoluene
nsc 6254
ai3-07621
methyl p-methylphenyl ether
einecs 203-253-7
4-methyl anisole
para-cresyl methyl ether
fema no. 2681
fema number 2681
methyl-para-cresol
para-methylanisole
methyl p-cresol
hsdb 5363
toluene, 4-methoxy-
inchi=1/c8h10o/c1-7-3-5-8(9-2)6-4-7/h3-6h,1-2h
4-methylanisole, >=99%, fcc, fg
4-methylanisole, 99%
chebi:89728 ,
CHEMBL154155 ,
M0149
bdbm50008555
1-methoxy-4-methyl-benzene
AKOS000121016
NCGC00248917-01
NCGC00258634-01
dtxsid9026710 ,
tox21_201081
dtxcid306710
cas-104-93-8
unii-10fai0or9w
ec 203-253-7
10fai0or9w ,
FT-0618970
STL268886
p- methoxytoluene
1-methoxy-4-methylbenzene [hsdb]
4-cresol methyl ether
p-methyl anisole [fcc]
p-methylanisole [fhfi]
p-methyl anisole
p- methylanisole
SCHEMBL12464
p-methoxy toluene
4-methylanisol
1-methyoxy-4-methylbenzene
SCHEMBL2489775
SCHEMBL12015216
para-methyl anisol
para-methyl anisole
4-methylmethoxybenzene
p-methylanisol
W-108799
F0001-0094
4-methylanizole
mfcd00008413
4-methylanisole, analytical standard
4-methoxy-toluene
fema 2681
p-methyl-anisole
Q15726084
4-methoxy-d3-toluene--d4
CS-W013551
AMY5180
para-cresol deuteromethyl ether
HY-W012835
vanadiumgallide
BS-23266
EN300-16112
4-methoxytoluene-d7
Z53834227
PD164982

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" This information on the dose-proportionality of the internal exposure is crucial for the interpretation of the toxicity data and helps to identify the toxic agent and the appropriate dose metric."( Implementation of toxicokinetics in toxicity studies--Toxicokinetics of 4-methylanisole and its metabolites in juvenile and adult rats.
Bos, PM; Brandon, EF; Piersma, AH; Sanchez, PL; Tienstra, M; Tonk, EC; van Eijkeren, JC; van Kesteren, PC, 2015
)
0.42

Dosage Studied

ExcerptRelevanceReference
"4-Methoxytoluene was given by gavage to 4 groups of 20 rats at dosage levels of 0, 40, 120 or 240 mg kg-1 body weight/day for 4 weeks."( Four-week toxicity study of 4-methoxytoluene in rats.
Brunsborg, B; Meyer, O; Olsen, P; Würtzen, G, 1994
)
0.29
" Large inter-individual variability in adult animals, as observed for 4-methylanisole, may hamper dose-response analyses of the results."( Implementation of toxicokinetics in toxicity studies--Toxicokinetics of 4-methylanisole and its metabolites in juvenile and adult rats.
Bos, PM; Brandon, EF; Piersma, AH; Sanchez, PL; Tienstra, M; Tonk, EC; van Eijkeren, JC; van Kesteren, PC, 2015
)
0.42
[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 (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency68.51990.006038.004119,952.5996AID1159521
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency40.81470.003041.611522,387.1992AID1159555
activating transcription factor 6Homo sapiens (human)Potency1.37950.143427.612159.8106AID1159516
[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)
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)4.26540.00000.933210.0000AID32248; AID32280
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID32248Inhibition of acetylcholinesterase.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
QSAR analyses of the substituted indanone and benzylpiperidine rings of a series of indanone-benzylpiperidine inhibitors of acetylcholinesterase.
AID1555240Octanol/water partition co-efficient, log P of compound by UV-spectrophotometry-based shake-flask method
AID32280IC50 against acetylcholinesterase; value ranges from 1-4900 nM.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
QSAR analyses of the substituted indanone and benzylpiperidine rings of a series of indanone-benzylpiperidine inhibitors of acetylcholinesterase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (10.00)18.7374
1990's2 (20.00)18.2507
2000's3 (30.00)29.6817
2010's4 (40.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.40

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.40 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index57.45 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]