AFCDB: 2-Methoxyphenol (FDB011885)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:53 UTC

Update date

2019-11-26 03:05:40 UTC

Primary ID

FDB011885

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Methoxyphenol

Description

Guaiacol, also known as O-methoxyphenol or 2-hydroxyanisole, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Guaiacol is an extremely weak basic (essentially neutral) compound (based on its pKa). Guaiacol exists in all living species, ranging from bacteria to humans. Guaiacol is a sweet, medicinal, and phenolic tasting compound. Guaiacol is found, on average, in the highest concentration within a few different foods, such as sesames, coffee, and white wines and in a lower concentration in peppermints. Guaiacol has also been detected, but not quantified in, several different foods, such as white mustards, peppers, red bell peppers, cherry tomato, and turmerics. This could make guaiacol a potential biomarker for the consumption of these foods. Guaiacol is a potentially toxic compound.

CAS Number

90-05-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	67.4 g/L	ALOGPS
logP	1.32	ALOGPS
logP	1.51	ChemAxon
logS	-0.27	ALOGPS
pKa (Strongest Acidic)	9.98	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.5 m³·mol⁻¹	ChemAxon
Polarizability	12.69 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

C7H8O2

IUPAC name

2-methoxyphenol

InChI Identifier

InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3

InChI Key

LHGVFZTZFXWLCP-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(O)C=CC=C1

Average Molecular Weight

124.139

Monoisotopic Molecular Weight

124.052429498

Classification

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:28591 )
monomethoxybenzene (CHEBI:28591 )
a guaiacol (CPD-400 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 67.73%; H 6.50%; O 25.78%	DFC
Melting Point	Mp 32° (prisms)	DFC
Boiling Point	Bp 205°	DFC
Experimental Water Solubility	18.7 mg/mL at 15 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	1.32	HANSCH,C ET AL. (1995)
Experimental pKa	9.98
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d21.44 1.13	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0ac0-9800000000-5e89a9881e848e1b6c90	2015-03-01	View Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-0a4i-6900000000-49cb804087a42b1d1a22	Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-0ab9-5900000000-b580cbc25d4176ce3894	Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-0pir-9700000000-f1436b3de82cff342b65	Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-05fr-4900000000-c09a31d9523d2eab5598	Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-283fdedfda9e853e0cac	Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-0a4i-6900000000-49cb804087a42b1d1a22	Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-0ab9-5900000000-b580cbc25d4176ce3894	Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-0pir-9700000000-f1436b3de82cff342b65	Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-05fr-4900000000-c09a31d9523d2eab5598	Spectrum
GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-283fdedfda9e853e0cac	Spectrum
Predicted GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-8900000000-562c1e6a4f3289578f75	Spectrum
Predicted GC-MS	Beechwood, creosote (fagus spp.), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fl0-7900000000-93aa107b2b3f584b3e44	Spectrum
Predicted GC-MS	Beechwood, creosote (fagus spp.), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-0a4i-6900000000-49cb804087a42b1d1a22	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0ab9-5900000000-b580cbc25d4176ce3894	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0pir-9700000000-12606badb77d4257635d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 8V, negative	splash10-0a4i-0900000000-053a1c4e865e710614d5	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-6b7a2fdf4e9a28ec6045	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-ff014b7b55a5237cf91e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9100000000-8785b2e2d86c6294a754	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-8856c60866e810389af7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-8db14d5e5710471f76a7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9400000000-bc0d3592d62ec26dad6f	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-7b4303f129d3e70a570e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9100000000-3ec9cfe154e8a98b3596	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w29-9000000000-ba9e4cd4adef59feb26e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-ee9e9b8403f62cfc7fdf	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-4900000000-d36c74cf39c4ddda0024	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbc-9000000000-1b43386dae7e3252cd81	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 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	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 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

28591

Phenol-Explorer ID

650

DrugBank ID

Not Available

HMDB ID

HMDB01398

CRC / DFC (Dictionary of Food Compounds) ID

HBN48-K:HBN48-K

EAFUS ID

1544

Dr. Duke ID

GUAIACOL

BIGG ID

Not Available

KNApSAcK ID

C00002654

HET ID

JZ3

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

Knapsack: C00029459

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
anesthetic			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti dermatitic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti eczemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti esophagitic			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti tuberculic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cardiodepressant	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
cardiotonic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
dermal	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
emetic			DUKE
expectorant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
irritant			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
prostaglandin synthesis inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
transdermal			DUKE

Enzymes

Name	Gene Name	UniProt ID
Transmembrane O-methyltransferase	LRTOMT	Q8WZ04

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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

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.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

2-Methoxyphenol (FDB011885)

Structure for FDB011885 (2-Methoxyphenol)