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Showing metabocard for Isoeugenol (HMDB0005802)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-01-22 22:53:28 UTC
Update Date2023-02-21 17:17:08 UTC
HMDB IDHMDB0005802
Secondary Accession Numbers
  • HMDB05802
Metabolite Identification
Common NameIsoeugenol
DescriptionIsoeugenol 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
Data?1676999828
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005802 (Isoeugenol)


  Mrv1652309042000312D          

 12 12  0  0  0  0            999 V2000
 9999.652410000.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.366710000.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.793310000.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.222110000.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.507710000.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5077 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2221 9998.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9366 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.936610000.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.081310000.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.078610000.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7932 9998.9783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1  9  1  0  0  0  0
  5  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  6 12  1  0  0  0  0
M  END
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3D MOL for HMDB0005802 (Isoeugenol)

HMDB0005802
     RDKit          3D
Isoeugenol
 24 24  0  0  0  0  0  0  0  0999 V2000
   -4.0998   -0.7656    0.9030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -0.1940    0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988   -0.4208    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008    0.0856   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217    0.8724   -1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.3373   -1.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    1.0225   -1.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0415    1.4654   -1.9630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129    0.2313   -0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579   -0.0928    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -0.8951    1.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -0.2272    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1819   -1.8180    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271   -0.7233    1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268   -0.2522    0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949    0.4151   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768   -1.0432    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4731    1.1394   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5962    1.9620   -2.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    2.0410   -2.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5998   -1.7604    1.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522   -1.2631    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0578   -0.2722    2.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -0.8439    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
 11 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

3D SDF for HMDB0005802 (Isoeugenol)


  Mrv1652309042000312D          

 12 12  0  0  0  0            999 V2000
 9999.652410000.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.366710000.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.793310000.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.222110000.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.507710000.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5077 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2221 9998.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9366 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.936610000.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.081310000.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.078610000.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7932 9998.9783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1  9  1  0  0  0  0
  5  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  6 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005802

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C10H12O2

> <MOLECULAR_WEIGHT>
164.2011

> <EXACT_MASS>
164.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.29788150152988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.6353462913333328

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.013922795139589

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8937792336789006

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
49.8619

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoeugenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0005802 (Isoeugenol)

HMDB0005802
     RDKit          3D
Isoeugenol
 24 24  0  0  0  0  0  0  0  0999 V2000
   -4.0998   -0.7656    0.9030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -0.1940    0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988   -0.4208    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008    0.0856   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217    0.8724   -1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.3373   -1.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    1.0225   -1.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0415    1.4654   -1.9630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129    0.2313   -0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579   -0.0928    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -0.8951    1.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -0.2272    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1819   -1.8180    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271   -0.7233    1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268   -0.2522    0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949    0.4151   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768   -1.0432    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4731    1.1394   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5962    1.9620   -2.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    2.0410   -2.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5998   -1.7604    1.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522   -1.2631    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0578   -0.2722    2.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -0.8439    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
 11 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

PDB for HMDB0005802 (Isoeugenol)

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
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3D PDB for HMDB0005802 (Isoeugenol)

COMPND    HMDB0005802
HETATM    1  C1  UNL     1      -4.100  -0.766   0.903  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.931  -0.194   0.139  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.699  -0.421   0.518  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.501   0.086  -0.151  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.522   0.872  -1.276  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.620   1.337  -1.888  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.865   1.023  -1.383  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.041   1.465  -1.963  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.913   0.231  -0.252  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.158  -0.093   0.267  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.323  -0.895   1.419  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.761  -0.227   0.351  1.00  0.00           C  
HETATM   13  H1  UNL     1      -4.182  -1.818   0.569  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.927  -0.723   1.982  1.00  0.00           H  
HETATM   15  H3  UNL     1      -5.027  -0.252   0.578  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.095   0.415  -0.738  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.577  -1.043   1.412  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.473   1.139  -1.699  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.596   1.962  -2.781  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.960   2.041  -2.788  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.600  -1.760   1.362  1.00  0.00           H  
HETATM   22  H10 UNL     1       4.352  -1.263   1.523  1.00  0.00           H  
HETATM   23  H11 UNL     1       3.058  -0.272   2.301  1.00  0.00           H  
HETATM   24  H12 UNL     1       0.784  -0.844   1.233  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3   16
CONECT    3    4   17
CONECT    4    5    5   12
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8    9
CONECT    8   20
CONECT    9   10   12   12
CONECT   10   11
CONECT   11   21   22   23
CONECT   12   24
END
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SMILES for HMDB0005802 (Isoeugenol)

COC1=CC(\C=C\C)=CC=C1O
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INCHI for HMDB0005802 (Isoeugenol)

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(e)-2-Methoxy-4-(prop-1-enyl)phenolChEBI
2-Methoxy-4-[(1E)-1-propenyl]phenolChEBI
2-Methoxy-4-propenylphenolChEBI
3-Methoxy-4-hydroxy-1-propen-1-ylbenzeneChEBI
3-Methoxy-4-hydroxypropenylbenzeneChEBI
4-Hydroxy-3-methoxy-1-propenylbenzeneChEBI
Iso-eugenol 2ChEBI
Isoeugenol (I)ChEBI
Isoeugenol eChEBI
Isoeugenol trans-formChEBI
PropenylgualacolChEBI
trans-2-Methoxy-4-(1-propenyl)phenolChEBI
trans-2-Methoxy-4-propenylphenolChEBI
trans-4-PropenylgualacolChEBI
trans-p-PropenylquaiacolChEBI
2-Methoxy-4-(prop-1-en-1-yl)phenolKegg
(e)-2-Methoxy-4- (1-propenyl)-phenolHMDB
(e)-2-Methoxy-4-(1-propenyl)-phenolHMDB
(e)-2-Methoxy-4-propenyl-phenolHMDB
(E)-IsoeugenolHMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propaneHMDB
1-Hydroxy-2-methoxy-4-propen-1-ylbenzeneHMDB
2-Methoxy-4-(1-propenyl)-phenolHMDB
2-Methoxy-4-(1-propenyl)phenolHMDB
2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0)HMDB
2-Methoxy-4-propenyl-phenolHMDB
2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenolHMDB
4-Hydroxy-3-methoxy-1-propen-1-ylbenzeneHMDB
4-Hydroxy-3-methoxypropenylbenzeneHMDB
trans-IsoeugenolHMDB
Isoeugenol, (e)-isomerMeSH, HMDB
IsoeugenolMeSH
(E)-2-Methoxy-4-(1-propenyl)phenolHMDB
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenolHMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propeneHMDB
2-Methoxy-4(E)-1-propenylphenolHMDB
2-Methoxy-4-(1-propen-1-yl)phenolHMDB
2-Methoxy-4-(1E)-1-propen-1-ylphenolHMDB
2-Methoxy-4-[(E)-1-propenyl]phenolHMDB
3-Methoxy-4-hydroxy-1-propenylbenzeneHMDB
4-(1-Propenyl) GuaiacolHMDB
4-Hydroxy-3-methoxy-beta-methylstyreneHMDB
4-Hydroxy-3-methoxy-β-methylstyreneHMDB
4-PropenylguaiacolHMDB
iso-EugenolHMDB
trans-4-PropenylguaiacolHMDB
trans-p-PropenylguaiacolHMDB
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol
Traditional Nameisoeugenol
CAS Registry Number5932-68-3
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 KeyBJIOGJUNALELMI-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-10 °CNot Available
Boiling Point125.00 to 126.00 °C. @ 14.00 mm HgThe Good Scents Company Information System
Water Solubility165.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.04GRIFFIN,S ET AL. (1999)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP2.79ALOGPS
logP2.64ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.86 m³·mol⁻¹ChemAxon
Polarizability18.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.65931661259
DarkChem[M-H]-137.52431661259
DeepCCS[M+H]+137.76430932474
DeepCCS[M-H]-135.26230932474
DeepCCS[M-2H]-171.25530932474
DeepCCS[M+Na]+146.5130932474
AllCCS[M+H]+134.232859911
AllCCS[M+H-H2O]+129.732859911
AllCCS[M+NH4]+138.432859911
AllCCS[M+Na]+139.632859911
AllCCS[M-H]-134.832859911
AllCCS[M+Na-2H]-135.832859911
AllCCS[M+HCOO]-137.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.17 minutes32390414
Predicted by Siyang on May 30, 202212.3535 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.62 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1929.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid365.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid152.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid220.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid172.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid543.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid457.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)99.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1167.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid423.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid990.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid336.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid413.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate390.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA293.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water28.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsoeugenolCOC1=CC(\C=C\C)=CC=C1O2277.2Standard polar33892256
IsoeugenolCOC1=CC(\C=C\C)=CC=C1O1399.2Standard non polar33892256
IsoeugenolCOC1=CC(\C=C\C)=CC=C1O1425.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isoeugenol,1TMS,isomer #1C/C=C/C1=CC=C(O[Si](C)(C)C)C(OC)=C11591.2Semi standard non polar33892256
Isoeugenol,1TBDMS,isomer #1C/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C11856.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Isoeugenol EI-B (Non-derivatized)splash10-03di-5900000000-d5e9036e83fd9c1033b02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoeugenol EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc0413362622017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoeugenol EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c49782017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoeugenol EI-B (Non-derivatized)splash10-03di-5900000000-d5e9036e83fd9c1033b02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoeugenol EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc0413362622018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Isoeugenol EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c49782018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoeugenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ds-1900000000-54cb7bf6efac012f1f932016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoeugenol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7790000000-39afffdef59235ab22a42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoeugenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ik9-7900000000-d378eaa3d6e1b33ea92e2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol n/a 11V, positive-QTOFsplash10-0019-0900000000-95d2bb40c1282fcc841b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol n/a 11V, positive-QTOFsplash10-0a4i-0900000000-66bdcdfc1f3c9d7059ef2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol n/a 11V, positive-QTOFsplash10-0a4i-2900000000-1eef4e3fa8cc372a7bd02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol Orbitrap 3V, positive-QTOFsplash10-000i-0900000000-568dabede3d6d65eef272020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol Orbitrap 4V, positive-QTOFsplash10-000i-0900000000-704d8c207b799f62a1652020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol Orbitrap 5V, positive-QTOFsplash10-0079-1900000000-dc5eb5b27b41f37fff512020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol Orbitrap 6V, positive-QTOFsplash10-00du-6900000000-724fc19b181ae95ed7f02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol Orbitrap 7V, positive-QTOFsplash10-0006-9400000000-e33fcab9c4877cbfaaa82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol Orbitrap 9V, positive-QTOFsplash10-00kf-9100000000-7581434dd013744b10fe2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol Orbitrap 11V, positive-QTOFsplash10-014l-9000000000-a332174b204c08062e142020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol Orbitrap 14V, positive-QTOFsplash10-014i-9000000000-eca4e980b9dcfbfa0d882020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol 40V, Negative-QTOFsplash10-0006-9100000000-51b1ddd89b75760804fb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol 20V, Negative-QTOFsplash10-0002-0900000000-59e54fb66a534d3ff6dc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoeugenol 10V, Negative-QTOFsplash10-0002-0900000000-92bea35f22ee86583e9f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 10V, Positive-QTOFsplash10-014i-0900000000-976746f8642ed9cede8f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 20V, Positive-QTOFsplash10-014i-2900000000-aeeef8533840707861152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 40V, Positive-QTOFsplash10-0f6x-9400000000-28c3454817ba3f9187002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 10V, Negative-QTOFsplash10-03di-0900000000-ba4c51d900ead0baa7412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 20V, Negative-QTOFsplash10-03di-0900000000-b71be30e0aefb9374dd32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 40V, Negative-QTOFsplash10-0535-4900000000-dc2d63615991af22ecd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 10V, Positive-QTOFsplash10-0159-0900000000-6f75a3780b4d03c3f78f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 20V, Positive-QTOFsplash10-00m3-2900000000-f418214add56c19743ea2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 40V, Positive-QTOFsplash10-00or-9000000000-95268ee51bd407edd9b82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 10V, Negative-QTOFsplash10-03di-0900000000-8db47caa9667c101bd0f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoeugenol 20V, Negative-QTOFsplash10-03ds-0900000000-c240e3167c4ef90295d02021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012403
KNApSAcK IDC00000620
Chemspider ID21106129
KEGG Compound IDC10469
BioCyc IDISOEUGENOL
BiGG IDNot Available
Wikipedia LinkIsoeugenol
METLIN IDNot Available
PubChem Compound853433
PDB IDNot Available
ChEBI ID50545
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006911
References
Synthesis ReferenceMannich, C.; Schmitt, Frida. Synthesis of amino alcohols from isosafrole, isoeugenol and anethole. Arch. Pharm. (1928), 266 73-84. CAN 22:39242 AN 1928:39242
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. Epub 2005 Jun 17. [PubMed:15964168 ]
  2. 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 ]
  3. 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 ]