Cannabis Compound Database: Showing Compound Card for m-Cresol (CDB005791)

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Record Information

Version

1.0

Created at

2020-04-27 16:56:56 UTC

Updated at

2021-01-04 18:49:21 UTC

CannabisDB ID

CDB005791

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

m-Cresol

Description

m-Cresol or 3-Cresol also known as belongs to the class of organic compounds known as meta-Cresols. Meta-Cresols are compounds containing a meta-Cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 3. m-Cresol is one of three known isomers of cresol including o-Cresol, m-Cresol and p-Cresol which differ in the position of the methyl group relative to the hydroxyl groups, on the phenol ring. m-Cresol is also classified as a methylphenol. Methylphenols are a widely occurring natural and manufactured group of aromatic organic compounds which are categorized as phenols (sometimes called phenolics). m-Cresol with a melting point of 11 °C ((52 °F; 284 K) is a colourless, viscous liquid that is water soluble. It has a medicinal, woody or phenolic odor. In the cosmetic industry it is used as an antimicrobial agent and a perfuming agent. It is used as an intermediate in the production of other chemicals. m-Cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from (bituminous) coal. Like other types of phenols, cresols are slowly oxidized by long exposure to air and the impurities often give cresols a yellowish to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell. 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. Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain, and lungs. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. m-Cresol is used as a pesticide, as an antiseptic, and in the synthesis of vitamin E ( Ref:DOI ). m-Cresol is found in wood and tobacco smoke, car exhaust and in wood preservatives such as creosote. m-Cresol is also naturally present in a number of plants and plant foods. Among plants, m-Cresol has been detected in asparagus, coffee, jasmin, tea and myrrh oil. m-Cresol is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).

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

108.14

Monoisotopic Molecular Weight

108.0575

IUPAC Name

3-methylphenol

Traditional Name

M-cresol

CAS Registry Number

108-39-4

SMILES

CC1=CC(O)=CC=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 )

Ontology

Ingestion

Source:

Environmental:

Sludge

Biological:

Microbe:

Lysinibacillus:

Lysinibacillus cresolivorans

Plant:

Coffea

Biological location:

Subcellular:

Biofluid and excreta:

Role

Environmental role:

Industrial application:

Food and nutrition

Pharmaceutical industry:

Pharmaceutical

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	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-f9433af649d30cc0e317	2014-09-20	View Spectrum
GC-MS	m-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a4i-6900000000-f2082b2d78602454887c	Spectrum
GC-MS	m-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a4i-9700000000-987a7fd82a03c828f2f6	Spectrum
GC-MS	m-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-80356192ec6d2f2cce17	Spectrum
GC-MS	m-Cresol, non-derivatized, GC-MS Spectrum	splash10-014l-3900000000-5be628cfaed43892ecb6	Spectrum
GC-MS	m-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a4i-6900000000-f2082b2d78602454887c	Spectrum
GC-MS	m-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a4i-9700000000-987a7fd82a03c828f2f6	Spectrum
GC-MS	m-Cresol, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-80356192ec6d2f2cce17	Spectrum
GC-MS	m-Cresol, non-derivatized, GC-MS Spectrum	splash10-014l-3900000000-5be628cfaed43892ecb6	Spectrum
Predicted GC-MS	m-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-6900000000-b8ad5789d64b1436f653	Spectrum
Predicted GC-MS	m-Cresol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01b9-7900000000-bea1778da40d4c1353e5	Spectrum
Predicted GC-MS	m-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	m-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-4900000000-ff165ee98ef540125c4f	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kf-9000000000-606fcb6bc90a29dd8728	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-dcdf60701ebd4f253aff	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a4i-6900000000-8a57217dc9acf65664ce	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0a4i-9700000000-987a7fd82a03c828f2f6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-5900000000-80356192ec6d2f2cce17	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-50eeee8ccda679df8336	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-8d97f02d4ffa2f7ea5d7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-5118914f1ab03a16ca6e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-a61d3231658626b2b393	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-373e69629866322cc176	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9700000000-c3be74dad978cee7d152	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-4900000000-058b7146c5399581303c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-1ab6752f7f0666600263	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3900000000-1564c33b741bc83530e8	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054o-9200000000-627147be2fad4471903e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014u-9000000000-4f6fdf895856dea20b9e	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
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