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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:31 UTC

Update Date

2023-02-21 17:19:38 UTC

HMDB ID

HMDB0030540

Secondary Accession Numbers

HMDB30540

Metabolite Identification

Common Name

2,5-Dimethylphenol

Description

2,5-Dimethylphenol belongs to the class of organic compounds known as p-xylenols. These are aromatic compounds that contain a p-xylenol moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 4-positions, and at least one hydroxyl group. 2,5-Dimethylphenol is a sweet, bacon, and naphthyl tasting compound. 2,5-Dimethylphenol has been detected, but not quantified in, several different foods, such as alcoholic beverages, arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 2,5-dimethylphenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,5-Dimethylphenol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
25-Dimethylphenol	ChEMBL, HMDB
25-Dimethyl-phenol	ChEMBL, HMDB
1,2,5-Xylenol	HMDB
1,4-Dimethyl-2-hydroxybenzene	HMDB
1-Hydroxy-2,5-dimethylbenzene	HMDB
2,5'-Xylenol	HMDB
2,5-Dimethyl phenol	HMDB
2,5-Dimethyl-phenol	HMDB
2,5-Xylenol	HMDB
2,5-Xylenol, 8ci	HMDB
2-Hydroxy-P-xylene	HMDB
3,6-Dimethylphenol	HMDB
3,6-Xylenol	HMDB
6-Methyl-m-cresol	HMDB
FEMA 3595	HMDB
Hydroxy-P-xylene	HMDB
P-2-Xylenol	HMDB
P-Xylenol	HMDB

Chemical Formula

C₈H₁₀O

Average Molecular Weight

122.1644

Monoisotopic Molecular Weight

122.073164942

IUPAC Name

2,5-dimethylphenol

Traditional Name

2,5-dimethylphenol

CAS Registry Number

95-87-4

SMILES

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

InChI Identifier

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

InChI Key

NKTOLZVEWDHZMU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-xylenols. These are aromatic compounds that contain a p-xylenol moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 4-positions, and at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

p-Xylenols

Alternative Parents

Substituents

P-xylenol
P-xylene
O-cresol
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030540)
Cytoplasm (HMDB: HMDB0030540)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030540)

Source

Endogenous

Endogenous (HMDB: HMDB0030540)

Plant

Coffea (HMDB: HMDB0030540)

Exogenous

Food

Food (HMDB: HMDB0030540)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0030540)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	71 - 73 °C	Not Available
Boiling Point	211.00 to 212.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3.54 mg/mL at 25 °C	Not Available
LogP	2.33	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.13 g/L	ALOGPS
logP	2.35	ALOGPS
logP	2.7	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.47	ChemAxon
pKa (Strongest Basic)	-5.5	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	13.99 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]+	126.304	31661259
DarkChem	[M-H]-	122.794	31661259
DeepCCS	[M+H]+	130.221	30932474
DeepCCS	[M-H]-	126.456	30932474
DeepCCS	[M-2H]-	163.862	30932474
DeepCCS	[M+Na]+	139.401	30932474
AllCCS	[M+H]+	120.9	32859911
AllCCS	[M+H-H2O]+	116.0	32859911
AllCCS	[M+NH4]+	125.5	32859911
AllCCS	[M+Na]+	126.8	32859911
AllCCS	[M-H]-	120.8	32859911
AllCCS	[M+Na-2H]-	122.8	32859911
AllCCS	[M+HCOO]-	125.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dimethylphenol	CC1=CC(O)=C(C)C=C1	2076.7	Standard polar	33892256
2,5-Dimethylphenol	CC1=CC(O)=C(C)C=C1	1087.4	Standard non polar	33892256
2,5-Dimethylphenol	CC1=CC(O)=C(C)C=C1	1146.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dimethylphenol,1TMS,isomer #1	CC1=CC=C(C)C(O[Si](C)(C)C)=C1	1196.6	Semi standard non polar	33892256
2,5-Dimethylphenol,1TBDMS,isomer #1	CC1=CC=C(C)C(O[Si](C)(C)C(C)(C)C)=C1	1459.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-5900000000-0b63ea14970dee15cedb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-00di-8900000000-1425cd74879c3086c0ba	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-00di-8900000000-1425cd74879c3086c0ba	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-05fr-7900000000-836015716b2996224a2b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-00di-3900000000-2d64127f5ece7e1ccc6f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-5900000000-0b63ea14970dee15cedb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-00di-8900000000-1425cd74879c3086c0ba	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-00di-8900000000-1425cd74879c3086c0ba	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-05fr-7900000000-836015716b2996224a2b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylphenol EI-B (Non-derivatized)	splash10-00di-3900000000-2d64127f5ece7e1ccc6f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dimethylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4900000000-14ef861a632bd3f0618e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dimethylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-6900000000-1f78f294a8d53461e019	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dimethylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 10V, Positive-QTOF	splash10-00di-0900000000-b8da4988f6af898d67e1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 20V, Positive-QTOF	splash10-00di-3900000000-af0fc36345f689074982	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 40V, Positive-QTOF	splash10-0kdi-9200000000-4fcd75637b64e3b4da23	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 10V, Negative-QTOF	splash10-00di-0900000000-e85b46bbf9f892bcf76d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 20V, Negative-QTOF	splash10-00di-0900000000-1093825cba6916ba4ec4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 40V, Negative-QTOF	splash10-00di-9500000000-04ac034b2608ef8aad50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 10V, Positive-QTOF	splash10-00di-1900000000-493ff8252c0b6187420a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 20V, Positive-QTOF	splash10-056r-9400000000-b3eaab7808f03a68089d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 40V, Positive-QTOF	splash10-004i-9000000000-8d9e622c62072853b609	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 10V, Negative-QTOF	splash10-00di-0900000000-99acd0a74fdc923b2838	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 20V, Negative-QTOF	splash10-00di-7900000000-5d8b6aeb856295d7d842	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylphenol 40V, Negative-QTOF	splash10-014i-9800000000-010cf97b5ac5d7fb7b80	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002413

KNApSAcK ID

C00052609

Chemspider ID

13839128

KEGG Compound ID

Not Available

BioCyc ID

CPD-16609

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7267

PDB ID

Not Available

ChEBI ID

421375

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1005831

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 2,5-Dimethylphenol (HMDB0030540)

MOL for HMDB0030540 (2,5-Dimethylphenol)

3D MOL for HMDB0030540 (2,5-Dimethylphenol)

3D SDF for HMDB0030540 (2,5-Dimethylphenol)

3D-SDF for HMDB0030540 (2,5-Dimethylphenol)

PDB for HMDB0030540 (2,5-Dimethylphenol)

3D PDB for HMDB0030540 (2,5-Dimethylphenol)

SMILES for HMDB0030540 (2,5-Dimethylphenol)

INCHI for HMDB0030540 (2,5-Dimethylphenol)

Structure for HMDB0030540 (2,5-Dimethylphenol)

3D Structure for HMDB0030540 (2,5-Dimethylphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra