NP-MRD: Showing NP-Card for Methoxyeugenol (NP0000695)

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Record Information

Version

2.0

Created at

2012-09-12 02:51:36 UTC

Updated at

2024-09-03 04:15:58 UTC

NP-MRD ID

NP0000695

Natural Product DOI

https://doi.org/10.57994/0476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methoxyeugenol

Description

Methoxyeugenol, also known as 4-allylsyringol, 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. Methoxyeugenol is a sweet, bacon, and burnt tasting compound. Methoxyeugenol has been detected, but not quantified, in herbs and spices. This could make methoxyeugenol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305271900202D          

 14 14  0  0  0  0            999 V2000
   15.1821  -14.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1823  -13.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8980  -15.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4678  -15.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8997  -13.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4665  -13.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6123  -14.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9024  -15.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6139  -13.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7522  -13.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1851  -16.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3252  -13.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0376  -13.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7503  -13.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000695

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC=C)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3

> <INCHI_KEY>
FWMPKHMKIJDEMJ-UHFFFAOYSA-N

> <FORMULA>
C11H14O3

> <MOLECULAR_WEIGHT>
194.2271

> <EXACT_MASS>
194.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.53726426167309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.4529086959999997

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.335852773119273

> <JCHEM_PKA_STRONGEST_BASIC>
-4.603104312142213

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
55.25260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      28.340 -27.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.340 -25.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.676 -28.242   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.007 -28.234   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      29.679 -25.153   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      27.004 -25.148   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      31.010 -27.473   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      29.684 -29.785   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      31.013 -25.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.671 -25.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.346 -30.556   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.340 -25.159   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.670 -25.924   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.001 -25.150   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1                                                            
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3    9                                                       
CONECT    8    3   11                                                       
CONECT    9    5   12    7                                                  
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
2,6-Dimethoxy-4-(2-propenyl)-phenol	HMDB
2,6-Dimethoxy-4-(2-propenyl)phenol, 9ci	HMDB
2,6-Dimethoxy-4-allylphenol	HMDB
2,6-Dimethoxychavicol	HMDB
4-(2-Propenyl)-2,6-dimethoxyphenol	HMDB
4-Allyl-2,6-dimethoxy-phenol	HMDB
4-Allyl-2,6-dimethoxyphenol	HMDB
4-Allyl-2,6-dimethoxyphenol, 8ci	HMDB
4-Allyl-2,6-dimetoxyphenol	HMDB
4-Allylsyringol	HMDB
4-Hydroxy-3,5-dimethoxyallylbenzene	HMDB
N-Allylcyclohexylamine	HMDB
Phenol, 2,6-dimethoxy-4-(2-propenyl)- (9ci)	HMDB
Phenol, 4-(2-propenyl)-2,6-dimethoxy	HMDB
Phenol, 4-allyl-2,6-dimethoxy- (8ci)	HMDB
2,6-Dimethoxy-4-(2-propenyl)phenol	MeSH
6-Methoxyeugenol	MeSH

Chemical Formula

C₁₁H₁₄O₃

Average Mass

194.2271 Da

Monoisotopic Mass

194.09429 Da

IUPAC Name

2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

Traditional Name

2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

CAS Registry Number

6627-88-9

SMILES

COC1=CC(CC=C)=CC(OC)=C1O

InChI Identifier

InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3

InChI Key

FWMPKHMKIJDEMJ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.33, CDCl₃, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Asarum asperum		LOTUS database
Cinnamomum glanduiferum	Plant	KNApSAcK
Cocculus orbiculatus		LOTUS database
fragrans		Not Available
Illicium dunnianum		LOTUS database
Illicium verum	FooDB	PHYTOHUB
Musa acuminata	FooDB	PHYTOHUB
Myristica fragrans	Plant	KNApSAcK
Pimenta racemosa		LOTUS database
Piper aduncum		LOTUS database
Piper auritum		LOTUS database
Sassafras albidum	Plant	KNApSAcK
Spathiphyllum cannifolium		LOTUS database

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

M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
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:86562 )
phenylpropanoid (CHEBI:86562 )
dimethoxybenzene (CHEBI:86562 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.59 g/L	ALOGPS
logP	2.23	ALOGPS
logP	2.45	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.25 m³·mol⁻¹	ChemAxon
Polarizability	20.54 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

External Links

HMDB ID

HMDB0041194

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021092

KNApSAcK ID

Not Available

Chemspider ID

196968

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

226486

PDB ID

Not Available

ChEBI ID

86562

Good Scents ID

Not Available

References

General References

Xiao WW, Zhang HL, Wang CF, Chen Y, Zhan R, Li D, Shao LD: Chemical Synthesis Enables the Configurational Determination of Myristriol, a Highly Oxygenated Phenylpropanoid from Myristica fragrans Houtt. Chem Biodivers. 2023 Mar;20(3):e202201075. doi: 10.1002/cbdv.202201075. Epub 2023 Feb 20. [PubMed:36762483 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Methoxyeugenol (NP0000695)

MOL for NP0000695 (Methoxyeugenol)

3D MOL for NP0000695 (Methoxyeugenol)

3D SDF for NP0000695 (Methoxyeugenol)

3D-SDF for NP0000695 (Methoxyeugenol)

PDB for NP0000695 (Methoxyeugenol)

3D PDB for NP0000695 (Methoxyeugenol)

SMILES for NP0000695 (Methoxyeugenol)

INCHI for NP0000695 (Methoxyeugenol)

Structure for NP0000695 (Methoxyeugenol)

3D Structure for NP0000695 (Methoxyeugenol)