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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:08 UTC

Update Date

2023-02-21 17:21:40 UTC

HMDB ID

HMDB0032148

Secondary Accession Numbers

HMDB32148

Metabolite Identification

Common Name

2,3-Dimethylphenol

Description

2,3-Dimethylphenol, also known as 1,2,3-xylenol or 3-hydroxy-O-xylene, belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively. 2,3-Dimethylphenol has been detected, but not quantified in, several different foods, such as black tea, arabica coffees (Coffea arabica), green tea, herbal tea, and red tea. This could make 2,3-dimethylphenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,3-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
1,2,3-Xylenol	HMDB
2,3-Xylenol	HMDB
3-Hydroxy-O-xylene	HMDB
O-3-Xylenol	HMDB
Vic-O-xylenol	HMDB

Chemical Formula

C₈H₁₀O

Average Molecular Weight

122.1644

Monoisotopic Molecular Weight

122.073164942

IUPAC Name

2,3-dimethylphenol

Traditional Name

2,3-dimethylphenol

CAS Registry Number

526-75-0

SMILES

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

InChI Identifier

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

InChI Key

QWBBPBRQALCEIZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

O-xylene
Xylene
O-cresol
M-cresol
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

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0032148)
Cytoplasm (HMDB: HMDB0032148)

Source

Exogenous

Exogenous (HMDB: HMDB0032148)

Endogenous

Endogenous (HMDB: HMDB0032148)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	75 °C	Not Available
Boiling Point	216.00 to 218.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4.57 mg/mL at 25 °C	Not Available
LogP	2.48	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.01 g/L	ALOGPS
logP	2.34	ALOGPS
logP	2.7	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.48	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	13.84 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]+	125.311	31661259
DarkChem	[M-H]-	121.07	31661259
DeepCCS	[M+H]+	127.533	30932474
DeepCCS	[M-H]-	124.195	30932474
DeepCCS	[M-2H]-	161.381	30932474
DeepCCS	[M+Na]+	136.613	30932474
AllCCS	[M+H]+	121.6	32859911
AllCCS	[M+H-H2O]+	116.7	32859911
AllCCS	[M+NH4]+	126.2	32859911
AllCCS	[M+Na]+	127.5	32859911
AllCCS	[M-H]-	119.8	32859911
AllCCS	[M+Na-2H]-	121.8	32859911
AllCCS	[M+HCOO]-	124.1	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.	3.43 minutes	32390414
Predicted by Siyang on May 30, 2022	13.5697 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.74 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1545.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	471.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	193.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	318.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	305.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	608.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	612.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	140.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1158.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	452.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1245.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	396.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	495.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	270.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	77.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dimethylphenol	CC1=C(C)C(O)=CC=C1	2079.8	Standard polar	33892256
2,3-Dimethylphenol	CC1=C(C)C(O)=CC=C1	1112.9	Standard non polar	33892256
2,3-Dimethylphenol	CC1=C(C)C(O)=CC=C1	1166.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dimethylphenol,1TMS,isomer #1	CC1=CC=CC(O[Si](C)(C)C)=C1C	1247.3	Semi standard non polar	33892256
2,3-Dimethylphenol,1TBDMS,isomer #1	CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1C	1500.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,3-Dimethylphenol EI-B (Non-derivatized)	splash10-0adi-6900000000-3ac5300f3e71fb52e12d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,3-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-8900000000-3b3350d848cc8afdd0e2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,3-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-8900000000-51d723e665d09753d245	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,3-Dimethylphenol EI-B (Non-derivatized)	splash10-0adi-6900000000-3ac5300f3e71fb52e12d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,3-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-8900000000-3b3350d848cc8afdd0e2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,3-Dimethylphenol EI-B (Non-derivatized)	splash10-05i0-8900000000-51d723e665d09753d245	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dimethylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-5900000000-6d3a2b764669c2b9ae97	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dimethylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-00fu-7900000000-8b03283ba96f632c8fc8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-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 - 2,3-Dimethylphenol 10V, Positive-QTOF	splash10-00di-0900000000-9d491d780c6f5e5be58f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 20V, Positive-QTOF	splash10-00di-3900000000-4c98bbbf34096c768b62	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 40V, Positive-QTOF	splash10-1029-9100000000-c64141bf91bceb259557	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 10V, Negative-QTOF	splash10-00di-0900000000-d65dd8473638a08aac10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 20V, Negative-QTOF	splash10-00di-0900000000-7479370ac382e82a9903	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 40V, Negative-QTOF	splash10-05fr-9500000000-04a0e609dc88df5f860f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 10V, Positive-QTOF	splash10-00di-3900000000-5b62385bf049d5cf284e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 20V, Positive-QTOF	splash10-0ab9-4900000000-493f64849c4cc668c07f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 40V, Positive-QTOF	splash10-0fvi-9000000000-e3a105276033c65a223d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 10V, Negative-QTOF	splash10-00di-0900000000-99acd0a74fdc923b2838	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 20V, Negative-QTOF	splash10-00di-2900000000-0ab9a2e2d25c035e378e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethylphenol 40V, Negative-QTOF	splash10-0g4i-9700000000-4dece85c9f1422dcf0f2	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004551

KNApSAcK ID

C00052590

Chemspider ID

13839151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10687

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1162081

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 2,3-Dimethylphenol (HMDB0032148)

MOL for HMDB0032148 (2,3-Dimethylphenol)

3D MOL for HMDB0032148 (2,3-Dimethylphenol)

3D SDF for HMDB0032148 (2,3-Dimethylphenol)

3D-SDF for HMDB0032148 (2,3-Dimethylphenol)

PDB for HMDB0032148 (2,3-Dimethylphenol)

3D PDB for HMDB0032148 (2,3-Dimethylphenol)

SMILES for HMDB0032148 (2,3-Dimethylphenol)

INCHI for HMDB0032148 (2,3-Dimethylphenol)

Structure for HMDB0032148 (2,3-Dimethylphenol)

3D Structure for HMDB0032148 (2,3-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