AFCDB: 2-Methylphenol (FDB008785)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:15 UTC

Update date

2019-11-26 03:03:12 UTC

Primary ID

FDB008785

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Methylphenol

Description

o-Cresol, also known as ortho-cresol or 2-hydroxytoluene, 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. o-Cresol exists in all living species, ranging from bacteria to plants to humans. o-Cresol is a medicinal, musty, and phenolic tasting compound. o-Cresol is found, on average, in the highest concentration within beer and peppermints (Mentha X piperita). o-Cresol has also been detected, but not quantified in, several different foods, such as herbal tea, garden tomato (var.), green bell peppers (Capsicum annuum), asparagus (Asparagus officinalis), and arabica coffees (Coffea arabica). This could make O-cresol a potential biomarker for the consumption of these foods. o-Cresol, with regard to humans, has been found to be associated with the diseases such as cresol poisoning ibs; O-cresol has also been linked to the inborn metabolic disorder celiac disease. Based on a literature review a small amount of articles have been published on o-Cresol.

CAS Number

95-48-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	27.5 g/L	ALOGPS
logP	1.89	ALOGPS
logP	2.18	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	10.37	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	11.83 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

Chemical Formula

C7H8O

IUPAC name

2-methylphenol

InChI Identifier

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

InChI Key

QWVGKYWNOKOFNN-UHFFFAOYSA-N

Isomeric SMILES

CC1=CC=CC=C1O

Average Molecular Weight

108.1378

Monoisotopic Molecular Weight

108.057514878

Classification

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-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:28054 )
a methylphenol (CPD-109 )

Ontology

Physiological effect

Health effect:

Observation:

Tachycardia

Health condition:

General disorders and administration site conditions:

Pain

Gastrointestinal disorders:

Disposition

Source:

Environmental:

Sludge

Biological:

Microbe:

Pseudomonas:

Pseudomonas sp. CP4

Plant:

Coffea

Route of exposure:

Parenteral:

Enteral:

Ingestion

Biological location:

Subcellular:

Biofluid and excreta:

Role

Environmental role:

Industrial application:

Food and nutrition

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp6 70°	DFC
Charge	Not Available
Density	d204 1.05	DFC
Experimental logP	1.95	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 10.32 (25°)	DFC
Experimental Water Solubility	25.9 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Isoelectric point	Not Available
Mass Composition	C 77.75%; H 7.46%; O 14.80%	DFC
Melting Point	Mp 30°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-c390212681445a7e2727	2014-09-20	View Spectrum
GC-MS	2-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a6r-9600000000-5a01d451557a1b35332a	Spectrum
GC-MS	2-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0pbi-9200000000-be9e6e56af8374e66beb	Spectrum
GC-MS	2-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f	Spectrum
GC-MS	2-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-00ko-5900000000-cef3087dea0c431cce4b	Spectrum
GC-MS	2-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a6r-9600000000-5a01d451557a1b35332a	Spectrum
GC-MS	2-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0pbi-9200000000-be9e6e56af8374e66beb	Spectrum
GC-MS	2-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f	Spectrum
GC-MS	2-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-00ko-5900000000-cef3087dea0c431cce4b	Spectrum
Predicted GC-MS	2-Methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-6900000000-7ba7c816e0edce6b772f	Spectrum
Predicted GC-MS	2-Methylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06di-7900000000-db9d20fae81c588496fe	Spectrum
Predicted GC-MS	2-Methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-5900000000-c7d0037b6de77737b7e4	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-151af99851311002a3fa	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03y3-9000000000-260e2bcf6f7dca1a3c9c	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a6r-9600000000-ac87a40c538d227b6915	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0pbi-9200000000-be9e6e56af8374e66beb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-7900000000-1a7cfac9452c2b14f977	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-5d6424b7db2e7e40d6d7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2900000000-e468ad1b8f28b32d7276	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-9000000000-2629c90f57b18d57c59d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-8feea1e7288d5bc80ea5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-22006f43be347c915292	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-9300000000-d3ec19098100f79d4ebd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0i03-9100000000-267c04454ade05650a34	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-2900000000-c580eec1345db0ab9045	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-9000000000-923877cbbb5c2a1edb9c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016u-9000000000-09eba92f6442b1a88ad5	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28054

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02055

CRC / DFC (Dictionary of Food Compounds) ID

DXH33-E:DXH33-E

EAFUS ID

771

Dr. Duke ID

O-CRESOL

BIGG ID

Not Available

KNApSAcK ID

C00030878

HET ID

JZ0

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Green bell pepper	Expected but not quantified	Not Available	DUKE
Orange bell pepper	Expected but not quantified	Not Available	DUKE
Red bell pepper	Expected but not quantified	Not Available	DUKE
Yellow bell pepper	Expected but not quantified	Not Available	DUKE

Showing 1 to 4 of 4 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
allelochemic			DUKE
anti mutagenic			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
rodenticide	33288	A substance used to destroy rodent pests.	DUKE

Showing 1 to 6 of 6 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
medicinal	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
musty	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
phenol	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
phenolic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Showing 1 to 4 of 4 entries

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

2-Methylphenol (FDB008785)

Structure for FDB008785 (2-Methylphenol)