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Showing metabocard for (E)-2-Octene (HMDB0061904)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:57:01 UTC
Update Date2022-03-07 03:17:49 UTC
HMDB IDHMDB0061904
Secondary Accession Numbers
  • HMDB61904
Metabolite Identification
Common Name(E)-2-Octene
Description(E)-2-Octene belongs to the class of organic compounds known as unsaturated aliphatic hydrocarbons. These are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. These compounds contain one or more double or triple bonds (E)-2-Octene is possibly neutral. Outside of the human body, (E)-2-Octene has been detected, but not quantified in, corns and mango. This could make (e)-2-octene a potential biomarker for the consumption of these foods.
Structure
Data?1563866245
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061904 ((E)-2-Octene)


  Mrv0541 02241220542D          

  8  7  0  0  0  0            999 V2000
   -0.9059   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  8  1  4  0  0  0
M  END
Download

3D MOL for HMDB0061904 ((E)-2-Octene)

HMDB0061904
     RDKit          3D
(E)-2-Octene
 24 23  0  0  0  0  0  0  0  0999 V2000
    2.4255    0.8522   -1.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2984   -0.5878   -1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.9903    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656   -0.0041    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146   -0.1215    1.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8468    0.1008    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150   -0.0161    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1932   -0.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0839    1.3503   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123    1.3099   -1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085    1.0471   -2.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799   -1.3000   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7712   -2.0777    0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    1.0039    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1164   -0.2101    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -1.0363    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860    0.7366    2.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5896   -0.6007   -0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840    1.1498   -0.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4870   -1.0251    1.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4727    0.7508    1.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9250   -0.6616   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907    1.0795   -0.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6163    0.3591   -1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
M  END
Download

3D SDF for HMDB0061904 ((E)-2-Octene)


  Mrv0541 02241220542D          

  8  7  0  0  0  0            999 V2000
   -0.9059   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  8  1  4  0  0  0
M  END
> <DATABASE_ID>
HMDB0061904

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC=CC

> <INCHI_IDENTIFIER>
InChI=1S/C8H16/c1-3-5-7-8-6-4-2/h3,5H,4,6-8H2,1-2H3

> <INCHI_KEY>
ILPBINAXDRFYPL-UHFFFAOYSA-N

> <FORMULA>
C8H16

> <MOLECULAR_WEIGHT>
112.2126

> <EXACT_MASS>
112.125200512

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
15.570997419068362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
oct-2-ene

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
3.6583535659999997

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
39.7268

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-octene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0061904 ((E)-2-Octene)

HMDB0061904
     RDKit          3D
(E)-2-Octene
 24 23  0  0  0  0  0  0  0  0999 V2000
    2.4255    0.8522   -1.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2984   -0.5878   -1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.9903    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656   -0.0041    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146   -0.1215    1.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8468    0.1008    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150   -0.0161    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337    0.1932   -0.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0839    1.3503   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123    1.3099   -1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085    1.0471   -2.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799   -1.3000   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7712   -2.0777    0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    1.0039    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1164   -0.2101    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -1.0363    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860    0.7366    2.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5896   -0.6007   -0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840    1.1498   -0.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4870   -1.0251    1.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4727    0.7508    1.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9250   -0.6616   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907    1.0795   -0.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6163    0.3591   -1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
M  END
Download

PDB for HMDB0061904 ((E)-2-Octene)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.691  -2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.311  -2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.025  -1.334   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    1                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0061904 ((E)-2-Octene)

COMPND    HMDB0061904
HETATM    1  C1  UNL     1       2.426   0.852  -1.443  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.298  -0.588  -1.150  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.849  -0.990   0.010  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.466  -0.004   1.035  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.015  -0.121   1.440  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.847   0.101   0.228  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.315  -0.016   0.628  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.234   0.193  -0.528  1.00  0.00           C  
HETATM    9  H1  UNL     1       3.084   1.350  -0.700  1.00  0.00           H  
HETATM   10  H2  UNL     1       1.412   1.310  -1.319  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.808   1.047  -2.469  1.00  0.00           H  
HETATM   12  H4  UNL     1       2.580  -1.300  -1.901  1.00  0.00           H  
HETATM   13  H5  UNL     1       1.771  -2.078   0.184  1.00  0.00           H  
HETATM   14  H6  UNL     1       1.634   1.004   0.672  1.00  0.00           H  
HETATM   15  H7  UNL     1       2.116  -0.210   1.932  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.213  -1.036   1.995  1.00  0.00           H  
HETATM   17  H9  UNL     1      -0.186   0.737   2.140  1.00  0.00           H  
HETATM   18  H10 UNL     1      -0.590  -0.601  -0.584  1.00  0.00           H  
HETATM   19  H11 UNL     1      -0.684   1.150  -0.101  1.00  0.00           H  
HETATM   20  H12 UNL     1      -2.487  -1.025   1.047  1.00  0.00           H  
HETATM   21  H13 UNL     1      -2.473   0.751   1.418  1.00  0.00           H  
HETATM   22  H14 UNL     1      -3.925  -0.662  -0.712  1.00  0.00           H  
HETATM   23  H15 UNL     1      -3.891   1.079  -0.380  1.00  0.00           H  
HETATM   24  H16 UNL     1      -2.616   0.359  -1.443  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3   12
CONECT    3    4   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8   22   23   24
END
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SMILES for HMDB0061904 ((E)-2-Octene)

CCCCCC=CC
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INCHI for HMDB0061904 ((E)-2-Octene)

InChI=1S/C8H16/c1-3-5-7-8-6-4-2/h3,5H,4,6-8H2,1-2H3
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC8H16
Average Molecular Weight112.2126
Monoisotopic Molecular Weight112.125200512
IUPAC Nameoct-2-ene
Traditional Name2-octene
CAS Registry NumberNot Available
SMILES
CCCCCC=CC
InChI Identifier
InChI=1S/C8H16/c1-3-5-7-8-6-4-2/h3,5H,4,6-8H2,1-2H3
InChI KeyILPBINAXDRFYPL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as unsaturated aliphatic hydrocarbons. These are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. These compounds contain one or more double or triple bonds.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassUnsaturated aliphatic hydrocarbons
Direct ParentUnsaturated aliphatic hydrocarbons
Alternative Parents
Substituents
  • Unsaturated aliphatic hydrocarbon
  • Olefin
  • Alkene
  • Acyclic olefin
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.005 g/LALOGPS
logP4.59ALOGPS
logP3.66ChemAxon
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.73 m³·mol⁻¹ChemAxon
Polarizability15.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.99631661259
DarkChem[M-H]-123.05431661259
DeepCCS[M+H]+133.88930932474
DeepCCS[M-H]-131.87730932474
DeepCCS[M-2H]-167.35830932474
DeepCCS[M+Na]+142.0530932474
AllCCS[M+H]+129.232859911
AllCCS[M+H-H2O]+124.832859911
AllCCS[M+NH4]+133.332859911
AllCCS[M+Na]+134.432859911
AllCCS[M-H]-135.532859911
AllCCS[M+Na-2H]-138.732859911
AllCCS[M+HCOO]-142.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(E)-2-OcteneCCCCCC=CC876.7Standard polar33892256
(E)-2-OcteneCCCCCC=CC798.5Standard non polar33892256
(E)-2-OcteneCCCCCC=CC794.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (E)-2-Octene GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9000000000-10dd3d0c85b08bc53d402017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-2-Octene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 10V, Positive-QTOFsplash10-03di-0900000000-1e1bd2540e4bc3208ae82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 20V, Positive-QTOFsplash10-03di-3900000000-3a2903f299afe84956f72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 40V, Positive-QTOFsplash10-0006-9000000000-2612ea4af9ecf601dd152015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 10V, Negative-QTOFsplash10-03di-0900000000-28cb15d99b12140ddd3f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 20V, Negative-QTOFsplash10-03di-0900000000-1f26e6fa41fd6e589e9a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 40V, Negative-QTOFsplash10-03di-9400000000-f01aa403661e4fad46b52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 10V, Negative-QTOFsplash10-03di-0900000000-11928ed622f3341a1add2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 20V, Negative-QTOFsplash10-03di-0900000000-11928ed622f3341a1add2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 40V, Negative-QTOFsplash10-0gb9-9000000000-1acec013fc6a9d7be7222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 10V, Positive-QTOFsplash10-0a4i-9100000000-d4aac1c5a22528b4711e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 20V, Positive-QTOFsplash10-0a4l-9000000000-50b30953b673a14f7a402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-2-Octene 40V, Positive-QTOFsplash10-0a4l-9000000000-d569c35779dce87027972021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005971
KNApSAcK IDNot Available
Chemspider ID7834
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5364448
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Srivastava PC, Callahan AP, Cunningham EB, Knapp FF Jr: Potential cerebral perfusion agents: synthesis and evaluation of a radioiodinated vinylalkylbarbituric acid analogue. J Med Chem. 1983 May;26(5):742-6. [PubMed:6842514 ]
  2. Qian H, Widenhoefer RA: Mechanism of the palladium-catalyzed intramolecular hydroalkylation of 7-octene-2,4-dione. J Am Chem Soc. 2003 Feb 26;125(8):2056-7. [PubMed:12590527 ]
  3. Takabe K, Mase N, Hashimoto H, Tsuchiya A, Ohbayashi T, Yoda H: Chemoenzymatic synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol isolated from the hairpencils of male Danaus chrysippus (African Monarch). Bioorg Med Chem Lett. 2003 Jun 16;13(12):1967-9. [PubMed:12781175 ]
  4. Kranjc K, Polanc S, Kocevar M: Diels-Alder reactions of fused pyran-2-ones with maleimides: efficient syntheses of benz[e]isoindoles and related systems. Org Lett. 2003 Aug 7;5(16):2833-6. [PubMed:12889886 ]
  5. Aschmann SM, Atkinson R: Rate constants for the gas-phase reactions of OH radicals with E-7-tetradecene, 2-methyl-1-tridecene and the C(7)-C(14) 1-alkenes at 295 +/- 1 K. Phys Chem Chem Phys. 2008 Jul 28;10(28):4159-64. doi: 10.1039/b803527j. Epub 2008 Jun 2. [PubMed:18612520 ]
  6. Li YG, Chen HF, Tu MZ, Zhang PZ, Wang XY, Yuan JB, Yang WL: Identification, synthesis and quantification of process-related impurities in auraptene. J Pharm Biomed Anal. 2011 Sep 10;56(2):191-9. doi: 10.1016/j.jpba.2011.05.011. Epub 2011 May 19. [PubMed:21705169 ]
  7. Maurizio Francesco Velati, Andrea Busca, Cristina Manfrotto, Marco Nicolini, Claudio Gianluca Pozzoli, 'Process for the preparation of mivacurium chloride.' U.S. Patent US20070293534, issued December 20, 2007. [Link]
  8. Maurizio Francesco Velati, Andrea Busca, Cristina Manfrotto, Marco Nicolini, Claudio Gianluca Pozzoli, 'Process for the preparation of mivacurium chloride.' U.S. Patent US07872137, issued January 18, 2011. [Link]