2-methoxyphenol (YMDB01430)

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Identification

YMDB ID

YMDB01430

Name

2-methoxyphenol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Guaiacol (2-methoxyphenol) is a naturally occurring organic compound with the formula C6H4(OH)(OCH3). Although it is biosynthesized by a variety of organisms, this colorless aromatic oil is usually derived from guaiacum or wood creosote. Samples darken upon exposure to air and light. Guaiacol is present in wood smoke, resulting from the pyrolysis of lignin. The compound contributes to the flavor of many compounds, e.g. roasted coffee. [Wikipedia]

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-Hydroxy-2-methoxybenzene
2-Hydroxyanisole
2-Methoxy phenol (guiacol)
2-methoxy-Phenol
2-methoxyphenol (guaiacol)
4-(3-Hydroxy-1-propenyl)-2-methoxyphenol
Anastil
Catechol monomethyl ether
Coniferol
Coniferyl alcohol
Creodon
Guaiacol
Guaiastil
Guaicol
Guaicolina
Guajakol
Guajol
Guasol
guiacol
Methoxyphenol
Methylcatachol
Methylcatechol
o-Guaiacol
o-Guiacol
o-Hydroxyanisole
o-methoxy-Phenol
o-Methoxyphenol
O-Methyl catechol
ortho-Guaiacol
Phenol, 2-methoxy-
Phenol, o-methoxy-
Pyrocatechol monomethyl ether
Pyroguaiac acid
2-Methoxyphenol
Guaiacol (liquid) extra pure
2-Hydroxy-anisole
Catechol, methyl
Methyl catechol
2-Methoxyl-4-vinylphenol

CAS number

90-05-1

Weight

Average: 124.1372
Monoisotopic: 124.0524295

InChI Key

LHGVFZTZFXWLCP-UHFFFAOYSA-N

InChI

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

IUPAC Name

2-methoxyphenol

Traditional IUPAC Name

guaiacol

Chemical Formula

C₇H₈O₂

SMILES

COC1=CC=CC=C1O

Chemical Taxonomy

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 )

Physical Properties

State

Liquid

Charge

Melting point

28 °C

Experimental Properties

Property	Value	Reference
Water Solubility	18.7 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	1.32 [HANSCH,C ET AL. (1995)]	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-49cb804087a42b1d1a22	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-5900000000-b580cbc25d4176ce3894	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pir-9700000000-f1436b3de82cff342b65	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05fr-4900000000-c09a31d9523d2eab5598	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-283fdedfda9e853e0cac	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-49cb804087a42b1d1a22	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-5900000000-b580cbc25d4176ce3894	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pir-9700000000-f1436b3de82cff342b65	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05fr-4900000000-c09a31d9523d2eab5598	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-283fdedfda9e853e0cac	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-8900000000-562c1e6a4f3289578f75	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fl0-7900000000-93aa107b2b3f584b3e44	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-0a4i-6900000000-49cb804087a42b1d1a22	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0ab9-5900000000-b580cbc25d4176ce3894	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0pir-9700000000-12606badb77d4257635d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 8V, negative	splash10-0a4i-0900000000-053a1c4e865e710614d5	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-6b7a2fdf4e9a28ec6045	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-ff014b7b55a5237cf91e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9100000000-8785b2e2d86c6294a754	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-8856c60866e810389af7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-8db14d5e5710471f76a7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9400000000-bc0d3592d62ec26dad6f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-7b4303f129d3e70a570e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9100000000-3ec9cfe154e8a98b3596	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w29-9000000000-ba9e4cd4adef59feb26e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-ee9e9b8403f62cfc7fdf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-4900000000-d36c74cf39c4ddda0024	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbc-9000000000-1b43386dae7e3252cd81	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0ac0-9800000000-5e89a9881e848e1b6c90	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Mahadevan, K., Farmer, L. (2006). "Key odor impact compounds in three yeast extract pastes." J Agric Food Chem 54:7242-7250.16968089

Synthesis Reference:

Chen, Jiehua; Xu, Baocai; Zhang, Hong; Ye, Jianfeng. Method for preparing guaiacol from catechol and dimethyl carbonate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 6pp.

External Links:

Resource	Link
CHEBI ID	28591
HMDB ID	HMDB01398
Pubchem Compound ID	460
Kegg ID	C00590
ChemSpider ID	447
FOODB ID	FDB011885
Wikipedia	Guaiacol
BioCyc ID	CPD-400

Structure for #<Compound:0xb04364fc>