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Showing metabocard for Safrole (HMDB0033591)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:20:11 UTC
Update Date2023-02-21 17:23:27 UTC
HMDB IDHMDB0033591
Secondary Accession Numbers
  • HMDB0002333
  • HMDB02333
  • HMDB33591
Metabolite Identification
Common NameSafrole
DescriptionSafrole, also known as shikimol, is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil, or synthesized from other related methylenedioxy compounds. It is the principal component of brown camphor oil, and is found in small amounts in a wide variety of plants, where it functions as a natural pesticide. Safrole is found in anise and nutmeg. Banned by FDA for use in food. Safrole is formerly used as a food flavour It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide and the recreational drug MDMA ("Ecstacy"). Safrole is a natural plant constituent, found in oil of sassafras and certain other essential oils. It is a member of the methylenedioxybenzene group of compounds, many of which (e.g. piperonyl butoxide) are extensively used as insecticide synergists. Safrole is a major source of human exposure to safrole is through consumption of spices, such as nutmeg, cinnamon and black pepper, in which safrole is a constituent. Safrole is also present in root beer, and has been used as an additive in chewing gum, toothpaste, soaps and certain pharmaceutical preparations. Safrole is a weak hepatocarcinogen and it is a matter of considerable interest whether the ally1 moiety or the methylenedioxy group, or both, are involved in the mechanism of its carcinogenesis. Safrole is extensively metabolized, giving rise to a large number of metabolites. Metabolism involves essentially two major routes, oxidation of the ally1 side chain, and oxidation of the methylenedioxy group with subsequent cleavage to form the catechol. Safrole undergoes oxidation of the allylic group to yield the 2, 3-epoxide (safrole epoxide). The dihydrodiol is one of the metabolites of safrole, and presumably arises from the hydration of the 2, 3-epoxide. The principal route of metabolism of safrole is through cleavage of the methylenedioxy group, the major metabolites being allylcatechol and its isomer, propenylcatechol. Eugenol and its isomer I-methoxy- 2-hydroxy-4-allylbenzene have been detected as minor metabolites in rat, mouse and human (PMID:6719936 ). The Ocotea cymbarum oil made of the Ocotea pretiosa, a plant growing in Brazil, and sassafras oil made of Sassafras albidum, a tree growing in eastern North America, are the main natural sources for safrole. It has a characteristic "candy-shop" aroma
Structure
Data?1677000207
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033591 (Safrole)

Safrole
  Mrv1652305201900042D          

 12 13  0  0  0  0            999 V2000
    2.7420    0.6639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7420   -0.6639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5228    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5228   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6662    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2605    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3808    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0953    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1 10  1  0  0  0  0
  2  5  1  0  0  0  0
  2 10  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  2  0  0  0  0
 11 12  2  0  0  0  0
M  END
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3D MOL for HMDB0033591 (Safrole)

HMDB0033591
     RDKit          3D
Safrole
 22 23  0  0  0  0  0  0  0  0999 V2000
    3.8633    0.0068   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8118    0.6676   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0309    0.1866    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047   -0.1006    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120   -1.3475    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152   -1.6009   -0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0716   -0.6122   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968    0.6365    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661    0.8751    0.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8448    1.4160    0.3013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9953    0.5951    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4365   -0.5713   -0.3966 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1717   -0.8897   -0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4280    0.3596   -1.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.5660   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632    1.0021    1.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.7291    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -2.1057    0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -2.5775   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934    1.8563    0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779    0.3331    1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8035    1.0337   -0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  9  4  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  9 20  1  0
 11 21  1  0
 11 22  1  0
M  END
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3D SDF for HMDB0033591 (Safrole)

Safrole
  Mrv1652305201900042D          

 12 13  0  0  0  0            999 V2000
    2.7420    0.6639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7420   -0.6639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5228    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5228   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6662    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9517   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2372   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2605    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3808    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0953    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1 10  1  0  0  0  0
  2  5  1  0  0  0  0
  2 10  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  2  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033591

> <DATABASE_NAME>
hmdb

> <SMILES>
C=CCC1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2

> <INCHI_KEY>
ZMQAAUBTXCXRIC-UHFFFAOYSA-N

> <FORMULA>
C10H10O2

> <MOLECULAR_WEIGHT>
162.1852

> <EXACT_MASS>
162.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.236884252439626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(prop-2-en-1-yl)-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.6950500166666664

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.741508932190474

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
46.11220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sassafras

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0033591 (Safrole)

HMDB0033591
     RDKit          3D
Safrole
 22 23  0  0  0  0  0  0  0  0999 V2000
    3.8633    0.0068   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8118    0.6676   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0309    0.1866    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047   -0.1006    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120   -1.3475    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152   -1.6009   -0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0716   -0.6122   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968    0.6365    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661    0.8751    0.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8448    1.4160    0.3013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9953    0.5951    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4365   -0.5713   -0.3966 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1717   -0.8897   -0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4280    0.3596   -1.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.5660   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632    1.0021    1.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.7291    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -2.1057    0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161   -2.5775   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934    1.8563    0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779    0.3331    1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8035    1.0337   -0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  9  4  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  9 20  1  0
 11 21  1  0
 11 22  1  0
M  END
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PDB for HMDB0033591 (Safrole)

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Safrole                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  O   UNK     0       5.118   1.239   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.118  -1.239   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.243   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.576   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.576  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.909   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.577   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.243  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.909  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.220   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.911   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.245   1.540   0.000  0.00  0.00           C+0
CONECT    1    4   10                                                       
CONECT    2    5   10                                                       
CONECT    3    6    7    8                                                  
CONECT    4    1    5    6                                                  
CONECT    5    2    4    9                                                  
CONECT    6    3    4                                                       
CONECT    7    3   11                                                       
CONECT    8    3    9                                                       
CONECT    9    5    8                                                       
CONECT   10    1    2                                                       
CONECT   11    7   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for HMDB0033591 (Safrole)

COMPND    HMDB0033591
HETATM    1  C1  UNL     1       3.863   0.007  -0.640  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.812   0.668  -0.226  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.031   0.187   0.934  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.605  -0.101   0.561  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.212  -1.348   0.118  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.115  -1.601  -0.225  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.072  -0.612  -0.131  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.697   0.637   0.308  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.366   0.875   0.647  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.845   1.416   0.301  1.00  0.00           O  
HETATM   11  C10 UNL     1      -3.995   0.595   0.210  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.437  -0.571  -0.397  1.00  0.00           O  
HETATM   13  H1  UNL     1       4.172  -0.890  -0.145  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.428   0.360  -1.483  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.506   1.566  -0.725  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.063   1.002   1.713  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.445  -0.729   1.381  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.981  -2.106   0.054  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.416  -2.578  -0.570  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.093   1.856   0.988  1.00  0.00           H  
HETATM   21  H9  UNL     1      -4.278   0.333   1.251  1.00  0.00           H  
HETATM   22  H10 UNL     1      -4.804   1.034  -0.372  1.00  0.00           H  
CONECT    1    2    2   13   14
CONECT    2    3   15
CONECT    3    4   16   17
CONECT    4    5    5    9
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8   12
CONECT    8    9    9   10
CONECT    9   20
CONECT   10   11
CONECT   11   12   21   22
END
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SMILES for HMDB0033591 (Safrole)

C=CCC1=CC2=C(OCO2)C=C1
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INCHI for HMDB0033591 (Safrole)

InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,2-Methylenedioxy-4-allylbenzeneChEBI
1-Allyl-3,4-methylenedioxybenzeneChEBI
3,4-(Methylenedioxy)allylbenzeneChEBI
3-(3,4-Methylenedioxyphenyl)prop-1-eneChEBI
4-Allyl-1,2-methylenedioxybenzeneChEBI
4-Allylpyrocatechol formaldehyde acetalChEBI
5-(2-Propenyl)-1,3-benzodioxoleChEBI
5-Allyl-benzo[1,3]dioxoleChEBI
Allylcatechol methylene etherChEBI
m-Allylpyrocatechin methylene etherChEBI
SafrolChEBI
ShikimolChEBI
ShikimoleChEBI
(1,2-(Methylenedioxy)-4-allyl)benzeneHMDB
(Allyldioxy)benzene methylene etherHMDB
(e)5-1-Propenyl]-1,3-benzodioxoleHMDB
1, 2-(Methylenedioxy)-4-allylbenzeneHMDB
1,2-(Methylenedioxy)-4-propenylbenzeneHMDB
1,2-Methylenedioxy-4-allyl-benzeneHMDB
1-Allyl,3,4-methylenedioxy benzeneHMDB
3, 4-(Methylenedioxy)allylbenzeneHMDB
3,4-(Methylenedioxy)-1-propenylbenzeneHMDB
3,4-Methylenedioxy-allybenzeneHMDB
3,4-MethylenedioxyallylbenzeneHMDB
4-Allyl-1, 2-(methylenedioxy)benzeneHMDB
4-Allyl-1,2-(methylenedioxy)benzene, 8ciHMDB
4-AllylpyrocatecholHMDB
4-Propenyl-1,2-methylenedioxybenzeneHMDB
4-Propenylcatechol methylene etherHMDB
5-(1-Propenyl)-1,3-benzodioxoleHMDB
5-(2-Propenyl)-1,3-benzodioxole, 9ciHMDB
5-Allyl-1,3-benzodioxolerlet DS baseHMDB
5-Prop-2-enyl-1,3-benzodioxoleHMDB
6-(1-Propenyl)-1,3-benzodioxoleHMDB
Allyldioxybenzene methylene etherHMDB
Allylpyrocatechol methylene etherHMDB
IsosafrolHMDB
IsosafroleHMDB
IzosafrolHMDB
ShikomolHMDB
4 Allyl 1,2 methylenedioxybenzeneMeSH
4-Allyl-1,2-methylenedioxybenzenesMeSH
SafrolesMeSH
ShikimolsMeSH
SafrolsMeSH
Chemical FormulaC10H10O2
Average Molecular Weight162.1852
Monoisotopic Molecular Weight162.068079564
IUPAC Name5-(prop-2-en-1-yl)-2H-1,3-benzodioxole
Traditional Namesassafras
CAS Registry Number94-59-7
SMILES
C=CCC1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2
InChI KeyZMQAAUBTXCXRIC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Benzenoid
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Environmental roleIndustrial applicationBiological roleIndirect biological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point11.2 °CNot Available
Boiling Point232–234 °CNot Available
Water Solubility1.08 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available138.573http://allccs.zhulab.cn/database/detail?ID=AllCCS00001146
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.24 g/LALOGPS
logP2.23ALOGPS
logP2.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.11 m³·mol⁻¹ChemAxon
Polarizability17.24 ųChemAxon
Number of Rings2ChemAxon
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]+136.60631661259
DarkChem[M-H]-132.93131661259
DeepCCS[M+H]+133.90430932474
DeepCCS[M-H]-130.46830932474
DeepCCS[M-2H]-167.91730932474
DeepCCS[M+Na]+143.45530932474
AllCCS[M+H]+132.732859911
AllCCS[M+H-H2O]+128.032859911
AllCCS[M+NH4]+137.032859911
AllCCS[M+Na]+138.332859911
AllCCS[M-H]-133.732859911
AllCCS[M+Na-2H]-134.332859911
AllCCS[M+HCOO]-134.932859911

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, 2022.6.0 minutes32390414
Predicted by Siyang on May 30, 202215.6238 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.29 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid36.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2008.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid556.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid211.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid376.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid269.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid594.8 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 Acid664.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)184.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1366.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid484.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1442.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid471.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid414.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate542.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA487.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water49.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SafroleC=CCC1=CC2=C(OCO2)C=C11832.9Standard polar33892256
SafroleC=CCC1=CC2=C(OCO2)C=C11314.0Standard non polar33892256
SafroleC=CCC1=CC2=C(OCO2)C=C11295.7Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011672
KNApSAcK IDC00002771
Chemspider ID13848731
KEGG Compound IDC10490
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSafrole
METLIN IDNot Available
PubChem Compound5144
PDB IDNot Available
ChEBI ID8994
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1619951
References
Synthesis ReferenceNguyen, Duc Tao; Le, Huyen; Pham, Van Tin. Study on the preparation of isosafrol from essential oil of Xa Xi. Tap Chi Duoc Hoc (1998), (1), 9-10.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ioannides C, Lum PY, Parke DV: Cytochrome P-448 and the activation of toxic chemicals and carcinogens. Xenobiotica. 1984 Jan-Feb;14(1-2):119-37. [PubMed:6719936 ]
  2. Hung SL, Chen YL, Chen YT: Effects of safrole on the defensive functions of human neutrophils. J Periodontal Res. 2003 Apr;38(2):130-4. [PubMed:12608906 ]
  3. Zhao J, Miao J, Zhao B, Zhang S, Yin D: Safrole oxide inhibits angiogenesis by inducing apoptosis. Vascul Pharmacol. 2005 Jun;43(1):69-74. [PubMed:15936989 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .