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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:14:42 UTC

Update Date

2023-02-21 17:28:47 UTC

HMDB ID

HMDB0041553

Secondary Accession Numbers

HMDB41553

Metabolite Identification

Common Name

Methylisoeugenol

Description

Methylisoeugenol belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. Methylisoeugenol is a mild, bitter, and clove tasting compound. Methylisoeugenol is found, on average, in the highest concentration within a few different foods, such as nutmegs (Myristica fragrans), star anises (Illicium verum), and gingers (Zingiber officinale). Methylisoeugenol has also been detected, but not quantified in, several different foods, such as carrots (Daucus carota ssp. sativus), evergreen blackberries (Rubus laciniatus), blackberries (Rubus), tarragons (Artemisia dracunculus), and sweet basils (Ocimum basilicum). This could make methylisoeugenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methylisoeugenol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    1    5                                                       
CONECT    5    4    9                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8    9   11                                                       
CONECT    9    5    6    8                                                  
CONECT   10    7   11   12                                                  
CONECT   11    8   10   13                                                  
CONECT   12    2   10                                                       
CONECT   13    3   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0041553
HETATM    1  C1  UNL     1       3.592  -1.270  -0.262  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.535   0.061   0.354  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.412   0.646   0.639  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.082   0.144   0.430  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.648  -1.089   0.111  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.699  -1.415  -0.136  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.650  -0.426  -0.049  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.986  -0.693  -0.281  1.00  0.00           O  
HETATM    9  C8  UNL     1      -3.494  -1.951  -0.617  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.263   0.857   0.277  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.247   1.855   0.362  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.825   3.166   0.699  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.051   1.119   0.505  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.491  -2.076   0.460  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.665  -1.377  -0.652  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.014  -1.359  -1.209  1.00  0.00           H  
HETATM   17  H4  UNL     1       4.504   0.599   0.593  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.524   1.669   1.119  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.325  -1.914   0.061  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.959  -2.428  -0.387  1.00  0.00           H  
HETATM   21  H8  UNL     1      -3.421  -2.114  -1.712  1.00  0.00           H  
HETATM   22  H9  UNL     1      -2.997  -2.784  -0.092  1.00  0.00           H  
HETATM   23  H10 UNL     1      -4.577  -1.959  -0.306  1.00  0.00           H  
HETATM   24  H11 UNL     1      -2.632   3.894   0.635  1.00  0.00           H  
HETATM   25  H12 UNL     1      -1.020   3.504  -0.018  1.00  0.00           H  
HETATM   26  H13 UNL     1      -1.367   3.188   1.730  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.294   2.150   0.757  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3   17
CONECT    3    4   18
CONECT    4    5    5   13
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8   10
CONECT    8    9
CONECT    9   21   22   23
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   24   25   26
CONECT   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-Methyl isoeugenol	ChEBI
cis-4-Propenyl veratrole	ChEBI
cis-Methyl isoeugenol	ChEBI
(e)-Methyl eugenol	HMDB
(e)-Methyl isoeugenol	HMDB
1,2-Dimethoxy-4-(1-propenyl)benzene, 9ci	HMDB
1,2-Dimethoxy-4-propenyl-(e)-benzene	HMDB
1,2-Dimethoxy-4-propenyl-benzene	HMDB
1,2-Dimethoxy-4-propenylbenzene	HMDB
1,3,4-Isoeugenol methyl ether	HMDB
1-(3,4-Dimethoxyphenyl)-1-propene	HMDB
1-Veratryl-1-propene	HMDB
3,4-Dimethoxypropenylbenzene	HMDB
4-(1-Propenyl)veratrole	HMDB
4-Propenyl-1,2-dimethoxybenzene	HMDB
4-Propenylveratrole	HMDB
4-trans-Propenylveratrole	HMDB
FEMA 2476	HMDB
Isoeugenol methyl ether	HMDB
Isoeugenyl methyl ether	HMDB
Isohomogenol	HMDB
Isomethyleugenol	HMDB, MeSH
Methyl isoeugenol	HMDB, MeSH
O-Methylisoeugenol	HMDB
trans-4-Propenylveratrole	HMDB
trans-Isomethyleugenol	HMDB, MeSH
trans-Methyl isoeugenol	HMDB
1,2-Dimethoxy-4-(1-e-propenyl)benzene	MeSH, HMDB
1,2-Dimethoxy-4-(1-propenyl)benzene	MeSH, HMDB
1,2-Dimethoxy-4-(1-Z-propenyl)benzene	MeSH, HMDB
Isomethyleugenol, (e)-isomer	MeSH, HMDB
Isomethyleugenol, (Z)-isomer	MeSH, HMDB
Methylisoeugenol	MeSH

Chemical Formula

C₁₁H₁₄O₂

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

IUPAC Name

1,2-dimethoxy-4-[(1Z)-prop-1-en-1-yl]benzene

Traditional Name

(Z)-methyl isoeugenol

CAS Registry Number

6379-72-2

SMILES

COC1=C(OC)C=C(\C=C/C)C=C1

InChI Identifier

InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-

InChI Key

NNWHUJCUHAELCL-PLNGDYQASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Styrene
Phenol ether
Anisole
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

isomethyleugenol (CHEBI:50550 )

Ontology

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041553)

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Herb and spice

Spice

Herb

Sweet basil (FooDB: FOOD00119)
Tarragon (FooDB: FOOD00019)

Fruit

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Process

Not Available

Role

Industrial applicationBiological role

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	16 - 17 °C	Not Available
Boiling Point	270.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	144.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.050 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.47	ALOGPS
logP	2.78	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.34 m³·mol⁻¹	ChemAxon
Polarizability	19.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	144.256	31661259
DarkChem	[M-H]-	140.497	31661259
DeepCCS	[M+H]+	144.234	30932474
DeepCCS	[M-H]-	141.474	30932474
DeepCCS	[M-2H]-	177.259	30932474
DeepCCS	[M+Na]+	152.767	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	133.5	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	140.2	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	142.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methylisoeugenol	COC1=C(OC)C=C(\C=C/C)C=C1	2193.0	Standard polar	33892256
Methylisoeugenol	COC1=C(OC)C=C(\C=C/C)C=C1	1433.1	Standard non polar	33892256
Methylisoeugenol	COC1=C(OC)C=C(\C=C/C)C=C1	1489.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methylisoeugenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fs-1900000000-3d41a0d29a7363963fbb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylisoeugenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 10V, Positive-QTOF	splash10-004i-0900000000-1b4a5c893c8cb3d52797	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 20V, Positive-QTOF	splash10-004i-2900000000-dd43f9e1c8e86b7ba6ff	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 40V, Positive-QTOF	splash10-0006-9500000000-20fd1ba2b53cc59be2ea	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 10V, Negative-QTOF	splash10-004i-0900000000-13d0af68ffab1cb5c56d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 20V, Negative-QTOF	splash10-004i-0900000000-02afbb666cbaaa0c075e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 40V, Negative-QTOF	splash10-07cr-4900000000-6a705aba56bdf50c3728	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 10V, Positive-QTOF	splash10-004i-0900000000-cde372377d8e900ad3a3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 20V, Positive-QTOF	splash10-0fb9-0900000000-28cc89aae8d7b76189de	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 40V, Positive-QTOF	splash10-004i-9400000000-219c0ddce8933e6a09c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 10V, Negative-QTOF	splash10-004i-0900000000-583273c8100f9e55b4bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 20V, Negative-QTOF	splash10-004j-0900000000-75e41d1bbbb423dac95f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisoeugenol 40V, Negative-QTOF	splash10-02u9-9800000000-aa3ed6a53e37b0107f0e	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methyl isoeugenol

METLIN ID

Not Available

PubChem Compound

1549045

PDB ID

Not Available

ChEBI ID

50550

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1435081

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Cartus AT, Merz KH, Schrenk D: Metabolism of methylisoeugenol in liver microsomes of human, rat, and bovine origin. Drug Metab Dispos. 2011 Sep;39(9):1727-33. doi: 10.1124/dmd.111.038851. Epub 2011 Jun 1. [PubMed:21632962 ]
Pande C, Tewari G, Singh C, Singh S, Padalia RC: Chemical composition of the essential oil of Feronia elephantum Correa. Nat Prod Res. 2010 Nov;24(19):1807-10. doi: 10.1080/14786411003752078. [PubMed:21104525 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methylisoeugenol (HMDB0041553)

MOL for HMDB0041553 (Methylisoeugenol)

3D MOL for HMDB0041553 (Methylisoeugenol)

3D SDF for HMDB0041553 (Methylisoeugenol)

3D-SDF for HMDB0041553 (Methylisoeugenol)

PDB for HMDB0041553 (Methylisoeugenol)

3D PDB for HMDB0041553 (Methylisoeugenol)

SMILES for HMDB0041553 (Methylisoeugenol)

INCHI for HMDB0041553 (Methylisoeugenol)

Structure for HMDB0041553 (Methylisoeugenol)

3D Structure for HMDB0041553 (Methylisoeugenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra