Showing Compound 4-Methylphenol (FDB008789)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:15 UTC

Update date

2024-11-29 22:27:57 UTC

Primary ID

FDB008789

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Methylphenol

Description

p-Cresol, also known as 4-hydroxytoluene or 4-methylphenol, 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 in all living species, ranging from bacteria to plants to humans. p-Cresol is an animal, medicinal, and mimosa tasting compound. p-Cresol is found, on average, in the highest concentration within a few different foods, such as milk (cow), peppermints (Mentha X piperita), and bilberries (Vaccinium myrtillus). p-Cresol has also been detected, but not quantified in, several different foods, such as almonds (Prunus dulcis), green tea, cherry tomatoes (Solanum lycopersicum var. cerasiforme), green vegetables, and yellow bell peppers (Capsicum annuum). This could make p-cresol a potential biomarker for the consumption of these foods. p-Cresol, with regard to humans, has been found to be associated with several diseases such as autism, nonalcoholic fatty liver disease, diarrhoea predominant irritable bowel syndrome, and enteritis; p-cresol has also been linked to the inborn metabolic disorder celiac disease. Based on a literature review a significant number of articles have been published on p-Cresol.

CAS Number

106-44-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
FEMA 2337	db_source
P-Cresol	ChEBI
p-Cresol, 8CI	db_source
p-Cresylate	biospider
p-Cresylic acid	db_source
p-Hydroxytoluene	db_source
P-Kresol	ChEBI
p-Methyl phenol	biospider
p-Methylhydroxybenzene	biospider
P-Methylphenol	ChEBI
p-Oxytoluene	biospider
p-Toluol	biospider
Para-cresylic acid	biospider
Phenol, 4-methyl-	biospider
Taurylic acid	db_source

Predicted Properties

Property	Value	Source
Water Solubility	23.1 g/L	ALOGPS
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	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

4-methylphenol

InChI Identifier

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

InChI Key

IWDCLRJOBJJRNH-UHFFFAOYSA-N

Isomeric SMILES

CC1=CC=C(O)C=C1

Average Molecular Weight

108.1378

Monoisotopic Molecular Weight

108.057514878

Classification

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 )

Ontology

Ingestion

Source:

Environmental:

Sludge

Biological:

Animal

Microbe:

Clostridium:

Clostridium difficile

Plant:

Biological location:

Tissue and substructures:

Adipose tissue

Cell and elements:

Cell:

Fibroblast

Subcellular:

Biofluid and excreta:

Role

Indirect biological role:

Uremic toxin

Environmental role:

Industrial application:

Food and nutrition

Pharmaceutical industry:

Pharmaceutical

Whole grain cereal products

Nuts and legumes:

Nuts

Legumes:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 77.75%; H 7.46%; O 14.80%	DFC
Melting Point	Mp 36°	DFC
Boiling Point	Bp11 90°	DFC
Experimental Water Solubility	21.5 mg/mL at 25 oC	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	1.94	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 10.27 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 1.03	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-6900000000-729e6f5bdb0da3ed9ded	2014-09-20	View Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-1d2bdfde621a5af9be73	Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-b76093f53701327ab25f	Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-4900000000-7d25deb1e39c6ef4866f	Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-7900000000-15d473146e11e4b049b2	Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-014l-4900000000-14fef90a661a09457976	Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-1d2bdfde621a5af9be73	Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-b76093f53701327ab25f	Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-4900000000-7d25deb1e39c6ef4866f	Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-0a4i-7900000000-15d473146e11e4b049b2	Spectrum
GC-MS	4-Methylphenol, non-derivatized, GC-MS Spectrum	splash10-014l-4900000000-14fef90a661a09457976	Spectrum
Predicted GC-MS	4-Methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-6900000000-27534de20ade11dd5454	Spectrum
Predicted GC-MS	4-Methylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06fr-9700000000-f41dd95ca553de6bafff	Spectrum
Predicted GC-MS	4-Methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-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-ab55ada5cae0538f383e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-385a7a99e0409c7f060d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-02tl-9000000000-205f4e5245868e9debcc	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a4i-5900000000-fd438231ac0ed75fdf09	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-5900000000-b76093f53701327ab25f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0a4i-4900000000-7d25deb1e39c6ef4866f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0a4i-7900000000-0cdab17a1a95f3e65f45	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - NA 35V, negative	splash10-0a6u-9600000000-276b44cbbdb079cac718	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-cf0bed2b3a203309d9aa	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-4f20c8bd2dde845b499c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9100000000-393b5f734646352622f9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-0c45920f40546c2d8944	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-417774c01b748db1609d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9600000000-5583b6dc3ae583b8dab0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-6eb0884733967edc9e6b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3900000000-621936189d60e194cefd	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056u-9100000000-2740c99af64b11309dfb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-1c2034d922354f5d6682	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 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
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

17847

Phenol-Explorer ID

Not Available

DrugBank ID

DB01688

HMDB ID

HMDB01858

CRC / DFC (Dictionary of Food Compounds) ID

DXH45-J:DXH45-J

EAFUS ID

772

Dr. Duke ID

CRESOL|P-CRESOL

BIGG ID

Not Available

KNApSAcK ID

C00002645

HET ID

PCR

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Allelochemic		A chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Name	48318	flavor	DUKE
Hemolytic		An agent that ruptures red blood cells, playing a biological role in breaking down outdated or damaged cells. Therapeutically, it is used to treat conditions like malaria and certain blood disorders. Key medical uses include managing paroxysmal nocturnal hemoglobinuria and other hemolytic diseases, often requiring careful administration to avoid adverse effects.	DUKE
Irritant		An agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.	DUKE
Parasiticide		An agent that kills parasites, used in medicine and veterinary medicine to treat parasitic infections, particularly those caused by protozoa, helminths, and ectoparasites, playing a crucial role in managing diseases such as malaria, worms, and lice infestations.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Rodenticide	33288	An agent that kills rodents, acting as a pesticide to control pest populations. Its biological role is to disrupt normal rodent physiology, often targeting the liver or brain. Therapeutically, rodenticides have limited applications, but are used to manage rodent-borne diseases and protect public health. Key medical uses include preventing the spread of diseases like hantavirus and leptospirosis.	DUKE

Enzymes

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Metabolism and Physiological Effects of Para-cresol	SMP0123214	Not Available
Metabolism and Physiological Effects of Para-cresyl glucuronide	SMP0123299	Not Available
Metabolism and Physiological Effects of p-Cresol sulphate	SMP0126850	Not Available
Metabolism and Physiological Effects of 4-Hydroxyphenylacetic acid	SMP0126879	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
medicine	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
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
smoke	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
medicinal	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
phenolic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
narcissus	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
animal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mimosa	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.