Milk Composition Database: Showing metabocard for p-Cresol (BMDB0001858)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:48:14 UTC

Update Date

2020-06-04 19:54:49 UTC

MCDB ID

BMDB0001858

Secondary Accession Numbers

BMDB01858

Metabolite Identification

Common Name

p-Cresol

Description

p-Cresol, also known as 4-methylphenol or paracresol, 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. p-Cresol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. p-Cresol exists in all living species, ranging from bacteria to humans. p-Cresol is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hydroxy-4-methylbenzene	ChEBI
4-Cresol	ChEBI
4-Hydroxytoluene	ChEBI
4-Methylphenol	ChEBI
p-Kresol	ChEBI
p-Methylphenol	ChEBI
p-Tolyl alcohol	ChEBI
Paracresol	ChEBI
1-Methyl-4-hydroxybenzene	HMDB
4-(Pentafluorosulfanyl)phenol	HMDB
4-Methyl phenol	HMDB
4-Methyl-phenol	HMDB
P-Cresylate	HMDB
P-Cresylic acid	HMDB
P-Hydroxytoluene	HMDB
P-Methyl phenol	HMDB
P-Methylhydroxybenzene	HMDB
P-Oxytoluene	HMDB
P-Toluol	HMDB
Paramethyl phenol	HMDB
4-Cresol, potassium salt	MeSH, HMDB
m-Cresol	MeSH, HMDB
4-Cresol, aluminum salt	MeSH, HMDB
4-Cresol, sodium salt	MeSH, HMDB
Para-cresol	MeSH, HMDB

Chemical Formula

C₇H₈O

Average Molecular Weight

108.1378

Monoisotopic Molecular Weight

108.057514878

IUPAC Name

4-methylphenol

Traditional Name

P-cresol

CAS Registry Number

106-44-5

SMILES

CC1=CC=C(O)C=C1

InChI Identifier

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

InChI Key

IWDCLRJOBJJRNH-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

P-cresol
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:17847 )
a methylphenol (CPD-108 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	35.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	21.5 mg/mL at 25 °C	Not Available
LogP	1.94	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.95	ALOGPS
logP	2.18	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	10.36	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	33.08 m³·mol⁻¹	ChemAxon
Polarizability	11.93 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-5900000000-1d2bdfde621a5af9be73	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-5900000000-b76093f53701327ab25f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-4900000000-7d25deb1e39c6ef4866f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-7900000000-15d473146e11e4b049b2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014l-4900000000-14fef90a661a09457976	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-5900000000-1d2bdfde621a5af9be73	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-5900000000-b76093f53701327ab25f	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-4900000000-7d25deb1e39c6ef4866f	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-7900000000-15d473146e11e4b049b2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014l-4900000000-14fef90a661a09457976	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-27534de20ade11dd5454	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-06fr-9700000000-f41dd95ca553de6bafff	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-5900000000-ab55ada5cae0538f383e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-385a7a99e0409c7f060d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-02tl-9000000000-205f4e5245868e9debcc	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a4i-5900000000-fd438231ac0ed75fdf09	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-5900000000-b76093f53701327ab25f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0a4i-4900000000-7d25deb1e39c6ef4866f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0a4i-7900000000-0cdab17a1a95f3e65f45	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA 35V, negative	splash10-0a6u-9600000000-276b44cbbdb079cac718	2020-07-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-cf0bed2b3a203309d9aa	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-4f20c8bd2dde845b499c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9100000000-393b5f734646352622f9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-0c45920f40546c2d8944	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-417774c01b748db1609d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9600000000-5583b6dc3ae583b8dab0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-6eb0884733967edc9e6b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3900000000-621936189d60e194cefd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056u-9100000000-2740c99af64b11309dfb	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-1c2034d922354f5d6682	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-6900000000-729e6f5bdb0da3ed9ded	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	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
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 and Quantified	13 +/- 10 uM	PMID: 29642378	details
Detected and Quantified	9.4 +/- 2.04 uM	PMID: 29642378	details
Detected and Quantified	14 +/- 12 uM	PMID: 29642378	details

External Links

HMDB ID

HMDB0001858

DrugBank ID

DB01688

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

P-cresol

METLIN ID

4236

PubChem Compound

2879

PDB ID

Not Available

ChEBI ID

17847

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 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]

Showing metabocard for p-Cresol (BMDB0001858)

Structure for BMDB0001858 (p-Cresol)