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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:09 UTC

Update Date

2023-02-21 17:21:41 UTC

HMDB ID

HMDB0032151

Secondary Accession Numbers

HMDB32151

Metabolite Identification

Common Name

3,4-Dimethylphenol

Description

3,4-Dimethylphenol, also known as 1,3,4-xylenol or 3,4-DMP, belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4. 3,4-Dimethylphenol is a dry and flat tasting compound. 3,4-Dimethylphenol has been detected, but not quantified, in coffee and coffee products and herbs and spices. This could make 3,4-dimethylphenol a potential biomarker for the consumption of these foods. 3,4-Dimethylphenol is a potentially toxic compound.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Dimethyl-4-hydroxybenzene	ChEBI
1,3,4-Xylenol	ChEBI
3,4-DMP	ChEBI
4,5-Dimethylphenol	ChEBI
4-Hydroxy-1,2-dimethylbenzene	ChEBI
1,2,4-Xylenol	HMDB
1-Hydroxy-3, 4-dimethylbenzene	HMDB
1-Hydroxy-3,4-dimethylbenzene	HMDB
3, 4-Xylenol	HMDB
3,4-Dimethyl phenol	HMDB
3,4-Dimethyl-phenol	HMDB
3,4-Xylenol	HMDB
3,4-Xylenol, 8ci	HMDB
4-Hydroxy-O-xylene	HMDB
Asym-O-xylenol	HMDB
FEMA 3596	HMDB
3,4-Dimethylphenol, potassium salt	HMDB
3,4-Dimethylphenol, sodium salt	HMDB
3,4-Dimethylphenol	MeSH

Chemical Formula

C₈H₁₀O

Average Molecular Weight

122.1644

Monoisotopic Molecular Weight

122.073164942

IUPAC Name

3,4-dimethylphenol

Traditional Name

3,4-dimethylphenol

CAS Registry Number

95-65-8

SMILES

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

InChI Identifier

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

InChI Key

YCOXTKKNXUZSKD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

O-xylene
Xylene
P-cresol
M-cresol
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

phenols (CHEBI:39839 )
a phenol (CPD-10888 )

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032151)

Source

Exogenous

Exogenous (HMDB: HMDB0032151)

Food

Food (HMDB: HMDB0032151)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Environmental

Sludge (HMDB: HMDB0032151)

Endogenous

Endogenous (HMDB: HMDB0032151)

Plant

Plant (HMDB: HMDB0032151)
Coffea (HMDB: HMDB0032151)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0032151)

Food and nutrition

Food and nutrition (HMDB: HMDB0032151)

Environmental role

Environmental contaminant (HMDB: HMDB0032151)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	62 - 64 °C	Not Available
Boiling Point	227.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4.76 mg/mL at 25 °C	Not Available
LogP	2.23	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.45 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.47	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	38.12 m³·mol⁻¹	ChemAxon
Polarizability	13.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.654	31661259
DarkChem	[M-H]-	122.159	31661259
DeepCCS	[M+H]+	127.174	30932474
DeepCCS	[M-H]-	124.151	30932474
DeepCCS	[M-2H]-	160.979	30932474
DeepCCS	[M+Na]+	136.069	30932474
AllCCS	[M+H]+	121.8	32859911
AllCCS	[M+H-H2O]+	116.9	32859911
AllCCS	[M+NH4]+	126.3	32859911
AllCCS	[M+Na]+	127.6	32859911
AllCCS	[M-H]-	121.1	32859911
AllCCS	[M+Na-2H]-	123.1	32859911
AllCCS	[M+HCOO]-	125.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.91 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3336 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.42 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dimethylphenol	CC1=CC=C(O)C=C1C	2192.1	Standard polar	33892256
3,4-Dimethylphenol	CC1=CC=C(O)C=C1C	1160.5	Standard non polar	33892256
3,4-Dimethylphenol	CC1=CC=C(O)C=C1C	1181.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dimethylphenol,1TMS,isomer #1	CC1=CC=C(O[Si](C)(C)C)C=C1C	1277.6	Semi standard non polar	33892256
3,4-Dimethylphenol,1TBDMS,isomer #1	CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1C	1519.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethylphenol EI-B (Non-derivatized)	splash10-0ab9-4900000000-fb3dd3acd7e4d6949270	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethylphenol EI-B (Non-derivatized)	splash10-0avi-5900000000-effbac24fad4c27cf9b6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethylphenol EI-B (Non-derivatized)	splash10-05fr-5900000000-208c80e9751e0ba311c2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethylphenol EI-B (Non-derivatized)	splash10-05fr-7900000000-7e46063c7d13680bf6ac	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethylphenol EI-B (Non-derivatized)	splash10-0ab9-4900000000-fb3dd3acd7e4d6949270	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethylphenol EI-B (Non-derivatized)	splash10-0avi-5900000000-effbac24fad4c27cf9b6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethylphenol EI-B (Non-derivatized)	splash10-05fr-5900000000-208c80e9751e0ba311c2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethylphenol EI-B (Non-derivatized)	splash10-05fr-7900000000-7e46063c7d13680bf6ac	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-5900000000-32a69f225ef7c70dfce6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-00fu-8900000000-ed6ce607126822938774	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05fr-4900000000-7a4e8e3b435984a892f6	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 10V, Positive-QTOF	splash10-00di-0900000000-abc71f850acbf3735f8e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 20V, Positive-QTOF	splash10-00di-2900000000-5304f4b7823411c093d9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 40V, Positive-QTOF	splash10-0zi0-9200000000-52e5b599c648a30fd4eb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 10V, Negative-QTOF	splash10-00di-0900000000-699b6f0392371e5d477d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 20V, Negative-QTOF	splash10-00di-0900000000-4fefc20e9390edcf67f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 40V, Negative-QTOF	splash10-00di-9700000000-1865323e874124d48f6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 10V, Positive-QTOF	splash10-00di-1900000000-1768f5d100e7d6ac0dd2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 20V, Positive-QTOF	splash10-0a4i-7900000000-df1c1a05ac515e234f9b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 40V, Positive-QTOF	splash10-0fvi-9000000000-da9f623210616a04673e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 10V, Negative-QTOF	splash10-00di-0900000000-99acd0a74fdc923b2838	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 20V, Negative-QTOF	splash10-00di-4900000000-a8ed7fe514ae00e18111	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethylphenol 40V, Negative-QTOF	splash10-0fdo-9300000000-f2849129145ecb9433bf	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04052

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008879

KNApSAcK ID

Not Available

Chemspider ID

13839105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3,4-Xylenol

METLIN ID

Not Available

PubChem Compound

7249

PDB ID

2MP

ChEBI ID

39839

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036991

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3,4-Dimethylphenol (HMDB0032151)

MOL for HMDB0032151 (3,4-Dimethylphenol)

3D MOL for HMDB0032151 (3,4-Dimethylphenol)

3D SDF for HMDB0032151 (3,4-Dimethylphenol)

3D-SDF for HMDB0032151 (3,4-Dimethylphenol)

PDB for HMDB0032151 (3,4-Dimethylphenol)

3D PDB for HMDB0032151 (3,4-Dimethylphenol)

SMILES for HMDB0032151 (3,4-Dimethylphenol)

INCHI for HMDB0032151 (3,4-Dimethylphenol)

Structure for HMDB0032151 (3,4-Dimethylphenol)

3D Structure for HMDB0032151 (3,4-Dimethylphenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra