Milk Composition Database: Showing metabocard for m-Cresol (BMDB0002048)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:50:24 UTC

Update Date

2020-04-22 15:09:32 UTC

MCDB ID

BMDB0002048

Secondary Accession Numbers

BMDB02048

Metabolite Identification

Common Name

m-Cresol

Description

m-Cresol, also known as meta-cresol or 3-hydroxytoluene, belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively. m-Cresol exists as a liquid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. m-Cresol exists in all eukaryotes, ranging from yeast to humans. m-Cresol is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Hydroxy-3-methylbenzene	ChEBI
3-Cresol	ChEBI
3-Hydroxytoluene	ChEBI
3-Methylphenol	ChEBI
m-Kresol	ChEBI
m-Methylphenol	ChEBI
Meta-cresol	ChEBI
Metacresol	ChEBI
3-Cresol, calcium salt(1:2)	MeSH
3-Cresol, sodium salt	MeSH
3-Phenylphenol	ChEBI, HMDB
m-Cresylic acid	HMDB
m-Hydroxytoluene	HMDB
m-Oxytoluene	HMDB
m-Toluol	HMDB
m-Cresol	KEGG

Chemical Formula

C₇H₈O

Average Molecular Weight

108.1378

Monoisotopic Molecular Weight

108.057514878

IUPAC Name

3-methylphenol

Traditional Name

M-cresol

CAS Registry Number

108-39-4

SMILES

CC1=CC=CC(O)=C1

InChI Identifier

InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3

InChI Key

RLSSMJSEOOYNOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cresol (CHEBI:17231 )
a methylphenol (CPD-112 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	11.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	22.7 mg/mL at 25 °C	Not Available
LogP	1.96	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.93	ALOGPS
logP	2.18	ChemAxon
logS	-0.63	ALOGPS
pKa (Strongest Acidic)	10.13	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	33.08 m³·mol⁻¹	ChemAxon
Polarizability	11.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-f2082b2d78602454887c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9700000000-987a7fd82a03c828f2f6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-5900000000-80356192ec6d2f2cce17	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014l-3900000000-5be628cfaed43892ecb6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-f2082b2d78602454887c	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9700000000-987a7fd82a03c828f2f6	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-5900000000-80356192ec6d2f2cce17	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014l-3900000000-5be628cfaed43892ecb6	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-b8ad5789d64b1436f653	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-7900000000-bea1778da40d4c1353e5	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-4900000000-ff165ee98ef540125c4f	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kf-9000000000-606fcb6bc90a29dd8728	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-dcdf60701ebd4f253aff	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a4i-6900000000-8a57217dc9acf65664ce	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0a4i-9700000000-987a7fd82a03c828f2f6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-5900000000-80356192ec6d2f2cce17	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-50eeee8ccda679df8336	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-8d97f02d4ffa2f7ea5d7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-5118914f1ab03a16ca6e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-a61d3231658626b2b393	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-373e69629866322cc176	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9700000000-c3be74dad978cee7d152	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-4900000000-058b7146c5399581303c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-1ab6752f7f0666600263	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3900000000-1564c33b741bc83530e8	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054o-9200000000-627147be2fad4471903e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014u-9000000000-4f6fdf895856dea20b9e	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-f9433af649d30cc0e317	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28306241	details
Detected but not Quantified	Not Applicable		PMID: 29197344	details

External Links

HMDB ID

HMDB0002048

DrugBank ID

DB01776

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

M-cresol

METLIN ID

Not Available

PubChem Compound

342

PDB ID

Not Available

ChEBI ID

17231

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]

Showing metabocard for m-Cresol (BMDB0002048)

Structure for BMDB0002048 (m-Cresol)