E-4-Propenyl-2-methoxyphenol (YMDB01677)

Identification

YMDB ID

YMDB01677

Name

E-4-Propenyl-2-methoxyphenol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Isoeugenol, also known as propenylgualacol, 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. Based on a literature review a significant number of articles have been published on Isoeugenol.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(E)-2-methoxy-4-(prop-1-enyl)phenol
(E)-Isoeugenol
2-methoxy-4-(1-propenyl)phenol
2-Methoxy-4-[(1E)-1-propenyl]phenol
4-(1-Propenyl)-2-methoxyphenol (trans-isoeugenol)
4-Vinylguaiacol
iso-Eugenol 2
Isoeugenol (E)
Isoeugenol (I)
Isoeugenol (II)
Isoeugenol E
Isoeugenol trans-form
Isoeugenol Z
Phenol, 2-methoxy-4-(1-propenyl)-, (E)-
Phenol, 2-methoxy-4-propenyl-, (E)-
trans-2-methoxy-4-(1-propenyl)phenol
trans-2-Methoxy-4-propenylphenol
trans-Isoeugenol
trans-p-Propenylquaiacol
2-Methoxy-4-propenylphenol
3-Methoxy-4-hydroxy-1-propen-1-ylbenzene
3-Methoxy-4-hydroxypropenylbenzene
4-Hydroxy-3-methoxy-1-propenylbenzene
Propenylgualacol
trans-4-Propenylgualacol
2-Methoxy-4-(prop-1-en-1-yl)phenol
(e)-2-Methoxy-4- (1-propenyl)-phenol
(e)-2-Methoxy-4-(1-propenyl)-phenol
(e)-2-Methoxy-4-propenyl-phenol
1-(3-Methoxy-4-hydroxyphenyl)-1-propane
1-Hydroxy-2-methoxy-4-propen-1-ylbenzene
2-Methoxy-4-(1-propenyl)-phenol
2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0)
2-Methoxy-4-propenyl-phenol
2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol
4-Hydroxy-3-methoxy-1-propen-1-ylbenzene
4-Hydroxy-3-methoxypropenylbenzene
Isoeugenol, (e)-isomer
Isoeugenol
(E)-2-Methoxy-4-(1-propenyl)phenol
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenol
1-(3-Methoxy-4-hydroxyphenyl)-1-propene
2-Methoxy-4(E)-1-propenylphenol
2-Methoxy-4-(1-propen-1-yl)phenol
2-Methoxy-4-(1E)-1-propen-1-ylphenol
2-Methoxy-4-[(E)-1-propenyl]phenol
3-Methoxy-4-hydroxy-1-propenylbenzene
4-(1-Propenyl) Guaiacol
4-Hydroxy-3-methoxy-beta-methylstyrene
4-Hydroxy-3-methoxy-β-methylstyrene
4-Propenylguaiacol
iso-Eugenol
trans-4-Propenylguaiacol
trans-p-Propenylguaiacol

CAS number

5932-68-3

Weight

Average: 164.2011
Monoisotopic: 164.083729628

InChI Key

BJIOGJUNALELMI-ONEGZZNKSA-N

InChI

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+

IUPAC Name

2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol

Traditional IUPAC Name

isoeugenol

Chemical Formula

C₁₀H₁₂O₂

SMILES

COC1=CC(\C=C\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
Styrene
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

isoeugenol (CHEBI:50545 )

Physical Properties

State

Solid

Charge

Melting point

33.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.64	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	10.01	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	2	ChemAxon
Refractivity	49.86 m³·mol⁻¹	ChemAxon
Polarizability	18.3 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
Carnation	FDB012403
Clove	FDB012403
Floral	FDB012403
Flower	FDB012403
Phenolic	FDB012403
Spicy	FDB012403
Sweet	FDB012403

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)	splash10-03di-5900000000-d5e9036e83fd9c1033b0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-f0dd30e91dc041336262	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-1900000000-1530d67ee6f2740c4978	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-5900000000-d5e9036e83fd9c1033b0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-4900000000-f0dd30e91dc041336262	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-1900000000-1530d67ee6f2740c4978	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ds-1900000000-54cb7bf6efac012f1f93	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7790000000-39afffdef59235ab22a4	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0019-0900000000-95d2bb40c1282fcc841b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0a4i-0900000000-66bdcdfc1f3c9d7059ef	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0a4i-2900000000-1eef4e3fa8cc372a7bd0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-000i-0900000000-568dabede3d6d65eef27	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000i-0900000000-704d8c207b799f62a165	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0079-1900000000-dc5eb5b27b41f37fff51	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-00du-6900000000-724fc19b181ae95ed7f0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0006-9400000000-e33fcab9c4877cbfaaa8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-00kf-9100000000-7581434dd013744b10fe	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-014l-9000000000-a332174b204c08062e14	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-014i-9000000000-eca4e980b9dcfbfa0d88	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-51b1ddd89b75760804fb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-59e54fb66a534d3ff6dc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-92bea35f22ee86583e9f	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-976746f8642ed9cede8f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-aeeef853384070786115	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9400000000-28c3454817ba3f918700	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ba4c51d900ead0baa741	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-b71be30e0aefb9374dd3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0535-4900000000-dc2d63615991af22ecd9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-6f75a3780b4d03c3f78f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00m3-2900000000-f418214add56c19743ea	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-9000000000-95268ee51bd407edd9b8	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	splash10-03ds-0900000000-c240e3167c4ef90295d0	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0ik9-7900000000-d378eaa3d6e1b33ea92e	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	50545
HMDB ID	HMDB0005802
Pubchem Compound ID	332
Kegg ID	C10469
ChemSpider ID	21106129
FOODB ID	FDB012403
Wikipedia	Isoeugenol
BioCyc ID	Not Available

Structure for #<Compound:0xaaf4e91c>