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Showing metabocard for 4-Methyl-3-heptene (HMDB0061911)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:57:10 UTC
Update Date2022-03-07 03:17:49 UTC
HMDB IDHMDB0061911
Secondary Accession Numbers
  • HMDB61911
Metabolite Identification
Common Name4-Methyl-3-heptene
Description4-Methyl-3-heptene belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. 4-Methyl-3-heptene is possibly neutral.
Structure
Data?1563866246
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061911 (4-Methyl-3-heptene)


  Mrv0541 10081412352D          

  9  8  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    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
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
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3D MOL for HMDB0061911 (4-Methyl-3-heptene)

HMDB0061911
     RDKit          3D
4-Methyl-3-heptene
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.1701    0.7664    0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2815   -0.1979   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8540    0.1446   -0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -0.6942    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664   -2.0032    0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.4168    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8388    0.9311   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3265    1.1784   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    1.7653    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4209    0.3683    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1397    0.8550   -0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5620   -0.2887   -1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4230   -1.2055   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4730    1.1038   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437   -2.5979   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3448   -2.5942    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987   -1.7893    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570   -1.2335   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7095   -0.3986    1.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6127    0.8875   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2441    1.7375    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864    0.7007   -1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6300    0.7138    0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5320    2.2674   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  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
  2 13  1  0
  3 14  1  0
  5 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 HMDB0061911 (4-Methyl-3-heptene)


  Mrv0541 10081412352D          

  9  8  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    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
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061911

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CC)=C(\C)CCC

> <INCHI_IDENTIFIER>
InChI=1S/C8H16/c1-4-6-8(3)7-5-2/h6H,4-5,7H2,1-3H3/b8-6+

> <INCHI_KEY>
KKVVJQGDNYIIMN-SOFGYWHQSA-N

> <FORMULA>
C8H16

> <MOLECULAR_WEIGHT>
112.2126

> <EXACT_MASS>
112.125200512

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
15.416286274169048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-4-methylhept-3-ene

> <ALOGPS_LOGP>
4.33

> <JCHEM_LOGP>
3.4571461726666666

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
39.4078

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-heptene, 4-methyl-

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0061911 (4-Methyl-3-heptene)

HMDB0061911
     RDKit          3D
4-Methyl-3-heptene
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.1701    0.7664    0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2815   -0.1979   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8540    0.1446   -0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -0.6942    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664   -2.0032    0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.4168    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8388    0.9311   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3265    1.1784   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7273    1.7653    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4209    0.3683    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1397    0.8550   -0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5620   -0.2887   -1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4230   -1.2055   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4730    1.1038   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437   -2.5979   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3448   -2.5942    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987   -1.7893    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570   -1.2335   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7095   -0.3986    1.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6127    0.8875   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2441    1.7375    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864    0.7007   -1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6300    0.7138    0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5320    2.2674   -0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  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
  2 13  1  0
  3 14  1  0
  5 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
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PDB for HMDB0061911 (4-Methyl-3-heptene)

HEADER    PROTEIN                                 08-OCT-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-14         0                                  
HETATM    1  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770   1.334   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      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    8                                                            
CONECT    4    1    6                                                       
CONECT    5    2    7                                                       
CONECT    6    4    8    9                                                  
CONECT    7    5    8                                                       
CONECT    8    3    6    7                                                  
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0061911 (4-Methyl-3-heptene)

COMPND    HMDB0061911
HETATM    1  C1  UNL     1      -3.170   0.766   0.192  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.281  -0.198  -0.545  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.854   0.145  -0.471  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.012  -0.694   0.062  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.466  -2.003   0.595  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.466  -0.417   0.171  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.839   0.931  -0.396  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.326   1.178  -0.269  1.00  0.00           C  
HETATM    9  H1  UNL     1      -2.727   1.765   0.307  1.00  0.00           H  
HETATM   10  H2  UNL     1      -3.421   0.368   1.203  1.00  0.00           H  
HETATM   11  H3  UNL     1      -4.140   0.855  -0.357  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.562  -0.289  -1.621  1.00  0.00           H  
HETATM   13  H5  UNL     1      -2.423  -1.205  -0.112  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.473   1.104  -0.857  1.00  0.00           H  
HETATM   15  H7  UNL     1      -0.944  -2.598  -0.222  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.345  -2.594   1.060  1.00  0.00           H  
HETATM   17  H9  UNL     1      -1.199  -1.789   1.404  1.00  0.00           H  
HETATM   18  H10 UNL     1       2.057  -1.234  -0.279  1.00  0.00           H  
HETATM   19  H11 UNL     1       1.710  -0.399   1.254  1.00  0.00           H  
HETATM   20  H12 UNL     1       1.613   0.887  -1.488  1.00  0.00           H  
HETATM   21  H13 UNL     1       1.244   1.738   0.036  1.00  0.00           H  
HETATM   22  H14 UNL     1       3.886   0.701  -1.088  1.00  0.00           H  
HETATM   23  H15 UNL     1       3.630   0.714   0.708  1.00  0.00           H  
HETATM   24  H16 UNL     1       3.532   2.267  -0.265  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4    4   14
CONECT    4    5    6
CONECT    5   15   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8   22   23   24
END
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SMILES for HMDB0061911 (4-Methyl-3-heptene)

[H]\C(CC)=C(\C)CCC
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INCHI for HMDB0061911 (4-Methyl-3-heptene)

InChI=1S/C8H16/c1-4-6-8(3)7-5-2/h6H,4-5,7H2,1-3H3/b8-6+
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC8H16
Average Molecular Weight112.2126
Monoisotopic Molecular Weight112.125200512
IUPAC Name(3E)-4-methylhept-3-ene
Traditional Name3-heptene, 4-methyl-
CAS Registry NumberNot Available
SMILES
[H]\C(CC)=C(\C)CCC
InChI Identifier
InChI=1S/C8H16/c1-4-6-8(3)7-5-2/h6H,4-5,7H2,1-3H3/b8-6+
InChI KeyKKVVJQGDNYIIMN-SOFGYWHQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassBranched unsaturated hydrocarbons
Direct ParentBranched unsaturated hydrocarbons
Alternative Parents
Substituents
  • Branched unsaturated hydrocarbon
  • 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 Solubility0.41 g/LALOGPS
logP4.33ALOGPS
logP3.46ChemAxon
logS-2.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity39.41 m³·mol⁻¹ChemAxon
Polarizability15.42 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]+125.67131661259
DarkChem[M-H]-121.61131661259
DeepCCS[M+H]+132.16530932474
DeepCCS[M-H]-129.62730932474
DeepCCS[M-2H]-165.58830932474
DeepCCS[M+Na]+140.32530932474
AllCCS[M+H]+128.832859911
AllCCS[M+H-H2O]+124.532859911
AllCCS[M+NH4]+132.932859911
AllCCS[M+Na]+134.132859911
AllCCS[M-H]-134.332859911
AllCCS[M+Na-2H]-137.732859911
AllCCS[M+HCOO]-141.432859911

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, 2022.6.09 minutes32390414
Predicted by Siyang on May 30, 202218.0589 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.18 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2231.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid681.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid261.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid468.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid298.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid721.6 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 Acid758.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)148.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1467.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid547.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1429.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid549.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid441.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate504.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA603.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water25.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Methyl-3-heptene[H]\C(CC)=C(\C)CCC936.1Standard polar33892256
4-Methyl-3-heptene[H]\C(CC)=C(\C)CCC774.0Standard non polar33892256
4-Methyl-3-heptene[H]\C(CC)=C(\C)CCC779.6Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5364638
PDB IDNot Available
ChEBI ID88853
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. Kadota S, Tezuka Y, Prasain JK, Ali MS, Banskota AH: Novel diarylheptanoids of Alpinia blepharocalyx. Curr Top Med Chem. 2003;3(2):203-25. [PubMed:12570774 ]
  2. Yan FL, Wang AX, Jia ZJ: Three new polymeric isopropenyl benzofurans from Ligularia stenocephala. Pharmazie. 2005 Feb;60(2):155-9. [PubMed:15739908 ]
  3. Giang PM, Son PT, Matsunami K, Otsuka H: New diarylheptanoids from Alpinia pinnanensis. Chem Pharm Bull (Tokyo). 2005 Oct;53(10):1335-7. [PubMed:16204997 ]
  4. Olafsdottir G, Jonsdottir R, Lauzon HL, Luten J, Kristbergsson K: Characterization of volatile compounds in chilled cod (Gadus morhua) fillets by gas chromatography and detection of quality indicators by an electronic nose. J Agric Food Chem. 2005 Dec 28;53(26):10140-7. [PubMed:16366707 ]
  5. Suzuki Y, Yasumoto T, Mashima K, Okuda J: Hafnocene catalysts for selective propylene oligomerization: efficient synthesis of 4-methyl-1-pentene by beta-methyl transfer. J Am Chem Soc. 2006 Oct 4;128(39):13017-25. [PubMed:17002399 ]
  6. Moularat S, Robine E, Ramalho O, Oturan MA: Detection of fungal development in closed spaces through the determination of specific chemical targets. Chemosphere. 2008 May;72(2):224-32. doi: 10.1016/j.chemosphere.2008.01.057. Epub 2008 Mar 10. [PubMed:18329690 ]
  7. Maurizio Foglio, Antonino Suarato, Paolo Masi, Giovanni Franceschi, Giorgio Palamidessi, Luigi Bernardi, U.S. Patent US4077970, issued December, 1975. [Link]
  8. George Preti, 'Method for detecting bovine estrus by determining methyl heptanol concentrations in vaginal secretions.' U.S. Patent US4467814, issued October, 1978. [Link]
  9. Dariush Davalian, Cheng-I Lin, Edwin F. Ullman, '2-methyl-4-hexene- and 2-methyl-4-heptene-1,2-diol derivatives.' U.S. Patent US5089390, issued February, 1988. [Link]
  10. Dariush Davalian, Cheng-I Lin, Edwin F. Ullman, '2-methyl-4-hexene-and 3-methyl-5-heptene-1,2-diol derivatives.' U.S. Patent US5401649, issued September, 1988. [Link]