MiMeDB: Showing metabocard for 3,4-Dimethylcatechol (MMDBc0015270)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:08:11 UTC

Update Date

2025-10-07 16:06:23 UTC

Metabolite ID

MMDBc0015270

Metabolite Identification

Common Name

3,4-Dimethylcatechol

Description

3,4-Dimethylcatechol is a catechol derivative and a metabolite described in biomedical literature. It plays a significant role in the microbial degradation of aromatic compounds, particularly in the metabolism of o-xylene and toluene. The enzymatic pathway for o-xylene involves the monooxygenation of the benzene nucleus, leading to the formation of dimethylphenol, which is then further metabolized to 3,4-dimethylcatechol. This compound is unique among dimethylcatechol isomers as it can be efficiently cleaved by catechol 2,3-dioxygenase, facilitating its use as a carbon and energy source in microbial metabolism (PMID:16734718 , PMID:16085871 ). In various bacterial strains, such as DK17 and opacus R7, 3,4-dimethylcatechol is produced as an intermediate during the degradation of o-xylene and is subsequently further processed through the meta-cleavage pathway (PMID:15607751 , PMID:11605984 ). Advanced analytical techniques, including gas chromatography-mass spectrometry and nuclear magnetic resonance, have confirmed the accumulation of this metabolite during the degradation processes (PMID:12089003 , PMID:8998974 ). Overall, 3,4-dimethylcatechol serves as a crucial substrate in the microbial catabolism of aromatic hydrocarbons, highlighting its importance in environmental bioremediation.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Dimethylcatechol	MeSH
3,4-Dimethylcatechol, dipotassium salt	MeSH

Molecular Formula

C₈H₁₀O₂

Average Mass

138.166

Monoisotopic Mass

138.068079562

IUPAC Name

3,4-dimethylbenzene-1,2-diol

Traditional Name

3,4-dimethylbenzene-1,2-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H10O2/c1-5-3-4-7(9)8(10)6(5)2/h3-4,9-10H,1-2H3

InChI Key

RYHGQTREHREIBC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

O-xylene
Xylene
P-cresol
O-cresol
M-cresol
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	27.4 g/L	ALOGPS
logP	1.33	ALOGPS
logP	2.39	ChemAxon
logS	-0.7	ALOGPS
pKa (Strongest Acidic)	9.83	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.1 m³·mol⁻¹	ChemAxon
Polarizability	14.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	211.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	33.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	417.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	590.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	579.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	375.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1290.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	123.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	431.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	317.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	208.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	238.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	151.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	150.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	504.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	211.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	379.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1187.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	991.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3,4-Dimethylcatechol_TMS_1	CC1=CC=C(O)C(O[Si](C)(C)C)=C1C	standard non polar	2025-10-23	2212.12
Gas Chromatography	3,4-Dimethylcatechol_TMS_2	CC1=CC=C(O[Si](C)(C)C)C(O)=C1C	standard non polar	2025-10-23	1998.87
Gas Chromatography	3,4-Dimethylcatechol_TMS_3	CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1C	standard non polar	2025-10-23	2207.02
Gas Chromatography	3,4-Dimethylcatechol_TMS_1	CC1=CC=C(O)C(O[Si](C)(C)C)=C1C	standard polar	2025-10-23	2254.66
Gas Chromatography	3,4-Dimethylcatechol_TMS_2	CC1=CC=C(O[Si](C)(C)C)C(O)=C1C	standard polar	2025-10-23	1921.5
Gas Chromatography	3,4-Dimethylcatechol_TMS_3	CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1C	standard polar	2025-10-23	2670.86

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16762

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17738

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 3,4-Dimethylcatechol (MMDBc0015270)

MOL for #<Metabolite:0x00007f9ac44c99b8>

3D MOL for #<Metabolite:0x00007f9ac44c99b8>

3D SDF for #<Metabolite:0x00007f9ac44c99b8>

3D-SDF for #<Metabolite:0x00007f9ac44c99b8>

PDB for #<Metabolite:0x00007f9ac44c99b8>

3D PDB for #<Metabolite:0x00007f9ac44c99b8>

SMILES for #<Metabolite:0x00007f9ac44c99b8>

INCHI for #<Metabolite:0x00007f9ac44c99b8>

Structure for #<Metabolite:0x00007f9ac44c99b8>

3D Structure for #<Metabolite:0x00007f9ac44c99b8>