Cannabis Compound Database: Showing Compound Card for o-Cresol (CDB005787)

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Record Information

Version

1.0

Created at

2020-04-27 16:56:33 UTC

Updated at

2021-01-05 16:40:40 UTC

CannabisDB ID

CDB005787

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

o-Cresol

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. Three isomers of cresol are known, including o-Cresol, m-Cresol and p-Cresol which differ in the position of the methyl relative to the hydroxyl groups, on the phenol ring. o-Cresol exists as a colorless to white crystals. It is moderately soluble in water and has a sweet, phenolic odor. Industrially o-Cresol can be prepared from coal tar (the volatilized materials obtained in the roasting of coal to produce coke) and petroleum residues. It is used a precursor or intermediate in the production of herbicides and drugs. o-Cresol is also employed commercially as a disinfectant. In the cosmetic industry o-Cresol is used as an antimicrobial agent and as a perfuming agent. Cresols, such as o-Cresol are strong germicides, and in low concentrations they are effective disinfectants and antiseptics. Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name Lysol. They are also used in low concentrations in sheep-dips (disinfectants often containing insecticides and pesticides). o-Cresol is an important component of creosote, a wood preservative produced as a by-product of coal tar distillation. Cresols give creosote its antibacterial and insecticidal properties, as well as its toxicity and its ability to irritate bare skin. Most exposures to cresols are at very low levels that are not harmful. When cresols are inhaled, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting; heart damage; anemia; liver and kidney damage; facial paralysis; coma; and death. Breathing high levels of cresols for a short time results in irritation of the nose and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times. Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the blood and nervous system. Ingestion of o-Cresol causes intense burning of the mouth and throat, followed by marked abdominal pain and distress. The minimum lethal dose of cresol by mouth is about 2 g (PMID 15040915 ). Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain, and lungs. o-Cresol is also produced naturally at low levels and is found in a number of plants and animals including the castor sacks of beavers. Among plants, o-Cresol has been detected in peppermints, asparagus, coffee, mustard, garden tomato (var.), tea, pepper (C. annuum), orange bell peppers, and sour cherries. This could make o-Cresol a potential biomarker for the consumption of these foods. o-Cresol can be routinely detected in humans. It is a minor urinary metabolite of toluene, a widely used chemical with known neurotoxicological properties. (PMID: 15687000 ). As a result, o-Cresol is commonly used to assess human inhalation exposures to toluene (PMID: 25601989 ). o-Cresol is also produced from tobacco smoke and auto exhaust and the sulfate derivative of o-Cresol (o-Cresylsulfate) can be detected in blood and urine (PMID: 26721601 ). o-Cresol is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hydroxy-2-methylbenzene	ChEBI
2-Cresol	ChEBI
2-Hydroxy-1-methylbenzene	ChEBI
2-Hydroxytoluene	ChEBI
O-Cresylic acid	ChEBI
O-Kresol	ChEBI
O-Methylphenol	ChEBI
Ortho-cresol	ChEBI
Orthocresol	ChEBI
O-Cresylate	Generator
1-Methyl-2-hydroxybenzene	HMDB
2-Methylphenol	HMDB, MeSH
O-Hydroxytoluene	HMDB
O-Methylphenylol	HMDB
O-Oxytoluene	HMDB
O-Toluol	HMDB
2-Cresol, potassium salt	MeSH, HMDB
2-Cresol, ammonium salt	MeSH, HMDB
2-Cresol, sodium salt	MeSH, HMDB

Chemical Formula

C₇H₈O

Average Molecular Weight

108.14

Monoisotopic Molecular Weight

108.0575

IUPAC Name

2-methylphenol

Traditional Name

o-cresol

CAS Registry Number

95-48-7

SMILES

CC1=CC=CC=C1O

InChI Identifier

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

InChI Key

QWVGKYWNOKOFNN-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-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

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	29.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	25.9 mg/mL at 25 °C	Not Available
logP	1.95	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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

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	o-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a6r-9600000000-5a01d451557a1b35332a	Spectrum
GC-MS	o-Cresol, non-derivatized, GC-MS Spectrum	splash10-0pbi-9200000000-be9e6e56af8374e66beb	Spectrum
GC-MS	o-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f	Spectrum
GC-MS	o-Cresol, non-derivatized, GC-MS Spectrum	splash10-00ko-5900000000-cef3087dea0c431cce4b	Spectrum
GC-MS	o-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a6r-9600000000-5a01d451557a1b35332a	Spectrum
GC-MS	o-Cresol, non-derivatized, GC-MS Spectrum	splash10-0pbi-9200000000-be9e6e56af8374e66beb	Spectrum
GC-MS	o-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f	Spectrum
GC-MS	o-Cresol, non-derivatized, GC-MS Spectrum	splash10-00ko-5900000000-cef3087dea0c431cce4b	Spectrum
Predicted GC-MS	o-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-6900000000-7ba7c816e0edce6b772f	Spectrum
Predicted GC-MS	o-Cresol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06di-7900000000-db9d20fae81c588496fe	Spectrum
Predicted GC-MS	o-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	o-Cresol, 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

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0002055

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

O-Cresol

METLIN ID

Not Available

PubChem Compound

335

PDB ID

Not Available

ChEBI ID

28054

References

General References

Boatto G, Nieddu M, Carta A, Pau A, Lorenzoni S, Manconi P, Serra D: Determination of phenol and o-cresol by GC/MS in a fatal poisoning case. Forensic Sci Int. 2004 Jan 28;139(2-3):191-4. doi: 10.1016/j.forsciint.2003.10.023. [PubMed:15040915 ]
Fustinoni S, Mercadante R, Campo L, Scibetta L, Valla C, Foa V: Determination of urinary ortho- and meta-cresol in humans by headspace SPME gas chromatography/mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Mar 25;817(2):309-17. doi: 10.1016/j.jchromb.2004.12.029. [PubMed:15687000 ]
Marchand A, Aranda-Rodriguez R, Tardif R, Nong A, Haddad S: Human inhalation exposures to toluene, ethylbenzene, and m-xylene and physiologically based pharmacokinetic modeling of exposure biomarkers in exhaled air, blood, and urine. Toxicol Sci. 2015 Apr;144(2):414-24. doi: 10.1093/toxsci/kfv009. Epub 2015 Jan 19. [PubMed:25601989 ]
Gu F, Derkach A, Freedman ND, Landi MT, Albanes D, Weinstein SJ, Mondul AM, Matthews CE, Guertin KA, Xiao Q, Zheng W, Shu XO, Sampson JN, Moore SC, Caporaso NE: Cigarette smoking behaviour and blood metabolomics. Int J Epidemiol. 2016 Oct;45(5):1421-1432. doi: 10.1093/ije/dyv330. Epub 2015 Dec 31. [PubMed:26721601 ]

Showing Compound Card for o-Cresol (CDB005787)

Structure for CDB005787 (o-Cresol)