4-Allyl-2-methoxyphenol (YMDB01613)

Identification

YMDB ID

YMDB01613

Name

4-Allyl-2-methoxyphenol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Eugenol, also known as 4-allylguaiacol or 1,3,4-eugenol, 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. Eugenol exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Eugenol.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-Hydroxy-2-methoxy-4-allylbenzene
1-Hydroxy-2-methoxy-4-prop-2-enylbenzene
1-Hydroxy-2-methoxy-4-propenylbenzene
1,3,4-Eugenol
1'-Acetoxyeugenol acetate
2-Hydroxy-5-allylanisole
2-Methoxy-1-hydroxy-4-allylbenzene
2-Methoxy-4-(2-propenyl)phenol
2-Methoxy-4-(2-propenyl)phenyl
2-Methoxy-4-(3-propenyl)phenol
2-methoxy-4-(prop-2-en-1-yl)phenol
2-Methoxy-4-allylphenol
2-Methoxy-4-prop-2-enylphenol
2-Metoksy-4-allilofenol
4-(2-Propenyl)-2-methoxyphenol (eugenol)
4-(Acetyloxy)-alpha-ethenyl-3-methoxybenzenemethanol acetate
4-Allyl-1-hydroxy-2-methoxybenzene
4-allyl-2-methoxy-Phenol
4-allyl-2-methoxyphenol
4-allyl-2-methoxyphenol (eugenol)
4-Allyl-2-rnethoxyphenol (eugenol)
4-Allylcatechol 2-methyl ether
4-Allylcatechol-2-methyl ether
4-Allylguaiacol
4-Hydroxy-3-methoxy-1-allylbenzene
4-Hydroxy-3-methoxyallylbenzene
5-Allylguaiacol
Allylguaiacol
Caryophyllic acid
Engenol
Eugenic acid
Eugenol
Eugenol (2-Methoxy-4-(2-propenyl)phenol)
Eugenol (natural)
Eugenol [usan]
P-allylguaiacol
P-eugenol
Phenol, 2-methoxy-4-(2-propenyl)-
Phenol, 4-allyl-2-methoxy-
Synthetic eugenol
1-Allyl-3-methoxy-4-hydroxybenzene
1-Allyl-4-hydroxy-3-methoxybenzene
2-Methoxy-4-(2-propen-1-yl)phenol
2-Methoxy-4-prop-2-enyl-phenol
Caryophyllate
Eugenate
2-Methoxy-4-(2'-propenyl)phenol
2-Methoxy-4-(2’-propenyl)phenol
2-Methoxy-4-[2-allyl]phenol
3-(3-Methoxy-4-hydroxyphenyl)propene
3-(4-Hydroxy-3-methoxyphenyl)-1-propene
4-Allenylguaiacol

CAS number

97-53-0

Weight

Average: 164.2011
Monoisotopic: 164.083729628

InChI Key

RRAFCDWBNXTKKO-UHFFFAOYSA-N

InChI

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3

IUPAC Name

2-methoxy-4-(prop-2-en-1-yl)phenol

Traditional IUPAC Name

eugenol

Chemical Formula

C₁₀H₁₂O₂

SMILES

COC1=CC(CC=C)=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-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:4917 )
phenylpropanoid (CHEBI:4917 )
monomethoxybenzene (CHEBI:4917 )
Monolignols (C10453 )
a monoterpenol (CPD-6481 )
a phenol (CPD-6481 )

Physical Properties

State

Solid

Charge

Melting point

-9.1 °C

Experimental Properties

Property	Value	Reference
Water Solubility	2.46 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	2.27 [SANGSTER (1993)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	1.44 g/L	ALOGPS
logP	2.66	ALOGPS
logP	2.61	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.94	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	3	ChemAxon
Refractivity	48.79 m³·mol⁻¹	ChemAxon
Polarizability	17.9 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

Flavour/Odour	Source
Cinnamon	FDB012171
Clove	FDB012171
Honey	FDB012171
Spicy	FDB012171
Sweet	FDB012171
Woody	FDB012171

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)	splash10-0ik9-5900000000-3d3a9e4f250074741003	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-2900000000-395df8510f0db4933abe	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-6900000000-1afdd3b83f6832b11f70	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-1d96ae8b031e47e13112	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ik9-6900000000-def0c646d72c040b58da	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0900000000-dfa64951eb648f5c9df1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ik9-5900000000-3d3a9e4f250074741003	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-2900000000-395df8510f0db4933abe	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-6900000000-1afdd3b83f6832b11f70	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-1d96ae8b031e47e13112	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ik9-6900000000-def0c646d72c040b58da	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0900000000-dfa64951eb648f5c9df1	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ms-1900000000-da27a86009649c155318	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8790000000-0d0c6f0e58d7dc3e5620	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-4541582e8f6395e2fa87	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-84f950d2fc0742e324d5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ab9-0900000000-4c037643a10913a70f5e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-2900000000-c65a2dab49b8ebb431da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0900000000-65a67ccd1df0d2f1796f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0ab9-0900000000-4c037643a10913a70f5e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-4541582e8f6395e2fa87	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-84f950d2fc0742e324d5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-f5092971e88a27de65e9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-2900000000-c65a2dab49b8ebb431da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-7beab8e102e0252d1a87	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-9d2a857e8a482a061127	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-9c846765367542bf4db1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr6-9500000000-98fcaf3ccca850c34bd3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-835320dc79855273af7f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-3a70eb9601589d9108a1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052e-4900000000-1c4834945c53d64bab3b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-8db47caa9667c101bd0f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ka-0900000000-ab5855c31f23e61c7f54	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03k9-3900000000-868b72d9162a6b307829	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-63a94aabae02f360ee77	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05nr-1900000000-ce4d363c5e701cb34dfd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-8e444a7d43baeb4d68f0	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0il0-6900000000-ff0dc492bab70317bb2a	JSpectraViewer \| MoNA
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

References

References:

Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	4917
HMDB ID	HMDB05809
Pubchem Compound ID	3314
Kegg ID	C10427
ChemSpider ID	13876103
FOODB ID	FDB012171
Wikipedia ID	Eugenol
BioCyc ID	Not Available

Structure for #<Compound:0xab041054>