Basic Info

Common Name3,4-Dimethylphenol(F05529)
2D Structure
Description

3,4-Dimethylphenol is found in coffee and coffee products. 3,4-Dimethylphenol is present in coffee. 3,4-Dimethylphenol is a flavouring ingredient. 3,4-Dimethylphenol belongs to the family of Meta Cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and an hydroxyl group at ring positions 1 and 3, respectively.

FRCD IDF05529
CAS Number95-65-8
PubChem CID7249
FormulaC8H10O
IUPAC Name

3,4-dimethylphenol

InChI Key

YCOXTKKNXUZSKD-UHFFFAOYSA-N

InChI

InChI=1S/C8H10O/c1-6-3-4-8(9)5-7(6)2/h3-5,9H,1-2H3

Canonical SMILES

CC1=C(C=C(C=C1)O)C

Isomeric SMILES

CC1=C(C=C(C=C1)O)C

Synonyms
        
            Phenol, 3,4-dimethyl-
        
            3,4-DIMETHYLPHENOL
        
            95-65-8
        
            3,4-Xylenol
        
            4,5-Dimethylphenol
        
            3,4-Dimethyl phenol
        
            1,3,4-Xylenol
        
            4-Hydroxy-1,2-dimethylbenzene
        
            1-Hydroxy-3,4-dimethylbenzene
        
            3,4-dimethyl-phenol
        
Classifies
                

                  
                    Plant Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassPhenols
SubclassCresols
Intermediate Tree NodesNot available
Direct ParentPara cresols
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsO-xylene - Xylene - P-cresol - M-cresol - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as para cresols. These are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.

Properties

Property NameProperty Value
Molecular Weight122.167
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Complexity90.6
Monoisotopic Mass122.073
Exact Mass122.073
XLogP2.2
Formal Charge0
Heavy Atom Count9
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9426
Human Intestinal AbsorptionHIA+0.9944
Caco-2 PermeabilityCaco2+0.9392
P-glycoprotein SubstrateNon-substrate0.7464
P-glycoprotein InhibitorNon-inhibitor0.9608
Non-inhibitor0.9920
Renal Organic Cation TransporterNon-inhibitor0.8893
Distribution
Subcellular localizationMitochondria0.8407
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7499
CYP450 2D6 SubstrateNon-substrate0.5542
CYP450 3A4 SubstrateNon-substrate0.6576
CYP450 1A2 InhibitorInhibitor0.7901
CYP450 2C9 InhibitorNon-inhibitor0.9344
CYP450 2D6 InhibitorNon-inhibitor0.9479
CYP450 2C19 InhibitorNon-inhibitor0.8491
CYP450 3A4 InhibitorNon-inhibitor0.9204
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7701
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8691
Non-inhibitor0.9230
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.7622
Fish ToxicityHigh FHMT0.7423
Tetrahymena Pyriformis ToxicityHigh TPT0.9270
Honey Bee ToxicityHigh HBT0.7995
BiodegradationNot ready biodegradable0.5738
Acute Oral ToxicityIII0.7389
Carcinogenicity (Three-class)Non-required0.6663

Model Value Unit
Absorption
Aqueous solubility-1.3727LogS
Caco-2 Permeability1.7721LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4090LD50, mol/kg
Fish Toxicity1.2092pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1631pIGC50, ug/L

Targets

General Function:
Zinc ion binding
Specific Function:
Transcriptionally controlled transcription factor. Binds to DNA sites required for the transcription of alpha 1-antitrypsin, apolipoprotein CIII, transthyretin genes and HNF1-alpha. May be essential for development of the liver, kidney and intestine.
Gene Name:
HNF4A
Uniprot ID:
P41235
Molecular Weight:
52784.205 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]