MiMeDB: Showing metabocard for E-4-Propenyl-2-methoxyphenol (MMDBc0033627)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:56:30 UTC

Update Date

2022-08-31 22:37:11 UTC

Metabolite ID

MMDBc0033627

Metabolite Identification

Common Name

E-4-Propenyl-2-methoxyphenol

Description

Isoeugenol, also known as E-4-propenyl-2-methoxyphenol, is an isomer of eugenol, wherein the double bond on the alkyl chain is shifted by one carbon. It 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. Isoeugenol is also classified as a phenylpropene, a propenyl-substituted guaiacol. Isoeugenol may occur as either the cis (Z) or trans (E) isomer. Trans (E) isoeugenol is crystalline while cis (Z) isoeugenol is a pale, yellow liquid. Isoeugenol is very slightly soluble in water and soluble in organic solvents. It has a spicy, sweet, carnation-like odour and tastes of sweet spice and clove. Isoeugenol is a widely used food flavoring agent and a perfuming agent. As a food flavoring agent, it is responsible for the flavor of nutmeg (in pumpkin pies), As a fragrance, it is extensively used as a scent agent in consumer products such as soaps, shampoos, perfumes, detergents and bath tissues (often labeled as ‚ÄúFragrance‚Äù rather than isoeugenol). However, some individuals can develop allergies to isoeugenol as it appears to be a strong contact allergen (PMID:10554062 ). Isoeugenol can be prepared from eugenol by heating. In addition to its industrial production via eugenol, isoeugenol can also be extracted from certain essential oils especially from clove oil and cinnamon. It is found naturally in a wide number of foods, spices and plants including allspice, basil, blueberries, cinnamon, cloves, coffee, dill, ginber, nutmeg, thyme and turmeric. Isoeugenol is also a component of wood smoke and liquid smoke. It is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses. Isoeugenol (specifically the acetate ester) has also been used in the production of vanillin. Isoeugenol is one of several non-cannabinoid phenols found in cannabis plants (PMID:6991645 ).

Structure

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

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.0188667.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.3518667.070   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8660.6818667.840   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8663.3488667.840   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.0148667.070   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.0148665.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.3488664.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.6828665.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.6828667.070   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.6858667.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8659.3478667.071   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8660.6818664.759   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   10                                                       
CONECT    3    5   11                                                       
CONECT    4    5    9                                                       
CONECT    5    4    6    3                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4    1                                                  
CONECT   10    2                                                            
CONECT   11    3                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
(e)-2-Methoxy-4-(prop-1-enyl)phenol	ChEBI
2-Methoxy-4-[(1E)-1-propenyl]phenol	ChEBI
2-Methoxy-4-propenylphenol	ChEBI
3-Methoxy-4-hydroxy-1-propen-1-ylbenzene	ChEBI
3-Methoxy-4-hydroxypropenylbenzene	ChEBI
4-Hydroxy-3-methoxy-1-propenylbenzene	ChEBI
Iso-eugenol 2	ChEBI
Isoeugenol (I)	ChEBI
Isoeugenol e	ChEBI
Isoeugenol trans-form	ChEBI
Propenylgualacol	ChEBI
trans-2-Methoxy-4-(1-propenyl)phenol	ChEBI
trans-2-Methoxy-4-propenylphenol	ChEBI
trans-4-Propenylgualacol	ChEBI
trans-p-Propenylquaiacol	ChEBI
2-Methoxy-4-(prop-1-en-1-yl)phenol	Kegg
(e)-2-Methoxy-4- (1-propenyl)-phenol	HMDB
(e)-2-Methoxy-4-(1-propenyl)-phenol	HMDB
(e)-2-Methoxy-4-propenyl-phenol	HMDB
(E)-Isoeugenol	HMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propane	HMDB
1-Hydroxy-2-methoxy-4-propen-1-ylbenzene	HMDB
2-Methoxy-4-(1-propenyl)-phenol	HMDB
2-Methoxy-4-(1-propenyl)phenol	HMDB
2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0)	HMDB
2-Methoxy-4-propenyl-phenol	HMDB
2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol	HMDB
4-Hydroxy-3-methoxy-1-propen-1-ylbenzene	HMDB
4-Hydroxy-3-methoxypropenylbenzene	HMDB
trans-Isoeugenol	HMDB
Isoeugenol, (e)-isomer	MeSH, HMDB
Isoeugenol	MeSH
(E)-2-Methoxy-4-(1-propenyl)phenol	HMDB
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenol	HMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propene	HMDB
2-Methoxy-4(E)-1-propenylphenol	HMDB
2-Methoxy-4-(1-propen-1-yl)phenol	HMDB
2-Methoxy-4-(1E)-1-propen-1-ylphenol	HMDB
2-Methoxy-4-[(E)-1-propenyl]phenol	HMDB
3-Methoxy-4-hydroxy-1-propenylbenzene	HMDB
4-(1-Propenyl) Guaiacol	HMDB
4-Hydroxy-3-methoxy-beta-methylstyrene	HMDB
4-Hydroxy-3-methoxy-β-methylstyrene	HMDB
4-Propenylguaiacol	HMDB
iso-Eugenol	HMDB
trans-4-Propenylguaiacol	HMDB
trans-p-Propenylguaiacol	HMDB

Molecular Formula

C₁₀H₁₂O₂

Average Mass

164.2011

Monoisotopic Mass

164.083729628

IUPAC Name

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

Traditional Name

isoeugenol

CAS Registry Number

5932-68-3

SMILES

COC1=CC(\C=C\C)=CC=C1O

InChI Identifier

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

InChI Key

BJIOGJUNALELMI-ONEGZZNKSA-N

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	24421258

External Links

HMDB ID

HMDB0005802

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isoeugenol

METLIN ID

Not Available

PubChem Compound

853433

PDB ID

Not Available

ChEBI ID

50545

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
White IR, Johansen JD, Arnau EG, Lepoittevin JP, Rastogi S, Bruze M, Andersen KE, Frosch PJ, Goossens A, Menne T: Isoeugenol is an important contact allergen: can it be safely replaced with isoeugenyl acetate? Contact Dermatitis. 1999 Nov;41(5):272-5. doi: 10.1111/j.1600-0536.1999.tb06160.x. [PubMed:10554062 ]
Atsumi T, Fujisawa S, Tonosaki K: A comparative study of the antioxidant/prooxidant activities of eugenol and isoeugenol with various concentrations and oxidation conditions. Toxicol In Vitro. 2005 Dec;19(8):1025-33. doi: 10.1016/j.tiv.2005.04.012. Epub 2005 Jun 17. [PubMed:15964168 ]

Showing metabocard for E-4-Propenyl-2-methoxyphenol (MMDBc0033627)

MOL for #<Metabolite:0x00007f12415849b8>

3D MOL for #<Metabolite:0x00007f12415849b8>

3D SDF for #<Metabolite:0x00007f12415849b8>

3D-SDF for #<Metabolite:0x00007f12415849b8>

PDB for #<Metabolite:0x00007f12415849b8>

3D PDB for #<Metabolite:0x00007f12415849b8>

SMILES for #<Metabolite:0x00007f12415849b8>

INCHI for #<Metabolite:0x00007f12415849b8>

Structure for #<Metabolite:0x00007f12415849b8>

3D Structure for #<Metabolite:0x00007f12415849b8>