Np mrd loader

Showing NP-Card for 2-Undecanone (NP0044967)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-03-10 18:51:58 UTC
Updated at2022-03-10 22:17:06 UTC
NP-MRD IDNP0044967
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Undecanone
Description2-Undecanone, also known as undecan-2-one or rue ketone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). 2-Undecanone is a ketone, also known as methyl nonyl ketone (MNK). Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a base. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide. 2-Undecanone is a very hydrophobic molecule, practically insoluble in water but it is soluble in ethanol, benzene, chloroform, and acetone. 2-Undecanone is found in cloves and one of several ketones that are known in cannabis plants (PMID: 6991645 ). 2-Undecanone is found in palm kernel oil and soya bean oil. 2-Undecanone is an important constituent of rue oil (Ruta graveolens) and found in many other essential oils. Also found in black currant buds, raspberry, black berry peach and other fruits. 2-Undecanone is used in flavourings It is found naturally in bananas, cloves, ginger, guava, strawberries, and wild-grown tomatoes. 2-Undecanone is used in the perfumery and flavoring industries, but because of its strong odor it is primarily used as an insect repellent or animal repellent.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044967 (2-Undecanone)

UOC
  Mrv1652303202019002D          

 12 11  0  0  0  0            999 V2000
   -3.1158    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9723   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2578    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0294    0.2362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -1.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0044967 (2-Undecanone)

     RDKit          3D

 34 33  0  0  0  0  0  0  0  0999 V2000
   -4.6579   -0.1708   -0.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4155   -0.9859   -0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6165   -0.4065    0.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1716    1.0162    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091    1.0650   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0597    0.2555   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8259    0.7180    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803   -0.1166    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9311   -0.0669   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1160   -0.9259   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -0.3564    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881   -2.1352   -0.3011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3338    0.7626   -0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2699   -0.7976   -1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2205    0.0035    0.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7805   -1.9893    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8167   -1.1054   -1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -1.0733    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2659   -0.3776    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    1.5900    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149    1.4917    1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8920    0.6829   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    2.1229   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263    0.4442   -1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2519   -0.8145   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0260    1.7880    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2488    0.5188    1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7668   -1.1895    0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029    0.1494    1.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879    0.9683   -0.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936   -0.3624   -1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9944   -1.1154    0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0034   -0.1673   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542    0.5794    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
M  END
Download

3D SDF for NP0044967 (2-Undecanone)

UOC
  Mrv1652303202019002D          

 12 11  0  0  0  0            999 V2000
   -3.1158    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6868    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9723   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2578    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -0.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0294    0.2362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -1.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3

> <INCHI_KEY>
KYWIYKKSMDLRDC-UHFFFAOYSA-N

> <FORMULA>
C11H22O

> <MOLECULAR_WEIGHT>
170.2918

> <EXACT_MASS>
170.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
22.6599784859607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
undecan-2-one

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
3.918796310333334

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.64344776069631

> <JCHEM_PKA_STRONGEST_BASIC>
-7.270866249933755

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
53.0287

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
undecan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0044967 (2-Undecanone)

Download
PDB for NP0044967 (2-Undecanone)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: UOC                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -5.816   0.441   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.483  -0.329   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.149   0.441   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.815  -0.329   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.481   0.441   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.853  -0.329   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.186   0.441   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.520  -0.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.854   0.441   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.188  -0.329   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.522   0.441   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.188  -1.869   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Download
3D PDB for NP0044967 (2-Undecanone)
Download
SMILES for NP0044967 (2-Undecanone)
CCCCCCCCCC(C)=O
Download
INCHI for NP0044967 (2-Undecanone)
InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
Download
View in JSmol
Synonyms
ValueSource
2-HendecanoneChEBI
Methyl nonyl ketoneChEBI
Rue ketoneChEBI
Undecan-2-oneKegg
2-OxoundecaneHMDB
EnodylHMDB
FEMA 3093HMDB
Ketone, methyl nonylHMDB
LuparoneHMDB
Methyl N-nonyl ketoneHMDB
Methyl-N-nonylketoneHMDB
MethylnonylketoneHMDB
MGK Dog AMP MNKHMDB
Nonyl methyl ketoneHMDB
UndecanoneHMDB
Undecanone-(2)HMDB
BioUDHMDB
2-UndecanoneChEBI
Chemical FormulaC11H22O
Average Mass170.2918 Da
Monoisotopic Mass170.16707 Da
IUPAC Nameundecan-2-one
Traditional Nameundecan-2-one
CAS Registry Number112-12-9
SMILES
CCCCCCCCCC(C)=O
InChI Identifier
InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
InChI KeyKYWIYKKSMDLRDC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acca sellowianaLOTUS Database
Adelanthus decipiensLOTUS Database
Alpinia zerumbetLOTUS Database
Azadirachta indicaLOTUS Database
Cannabis sativaNULL
      Not Available
Capsicum annuum var. annuumFooDB
Citrus medicaLOTUS Database
Commiphora rostrataLOTUS Database
Crocus sativusFooDB
Cucumis sativus L.FooDB
    • Ancheng Zhou and Roger F. McFeeters. Volatile Compounds in Cucumbers Fermented in Low-Salt Condit...
Curcuma longaPlant
Curcuma manggaPlant
Curcuma phaeocaulisPlant
Curcuma pierreanaLOTUS Database
Etlingera elatiorLOTUS Database
Eupatorium capillifoliumLOTUS Database
Evernia prunastriLOTUS Database
Feijoa sellowianaPlant
Frullania solanderianaPlant
Ganoderma lucidumFungi
Geum heterocarpumLOTUS Database
Hamamelis virginianaLOTUS Database
Hedychium spicatumLOTUS Database
Houttuynia cordataPlant
Houttuynia emeiensisPlant
Humulus lupulusPlant
Kaempferia galangaLOTUS Database
Lippia albaLOTUS Database
Litsea glaucescensLOTUS Database
Ophrys sphegodesLOTUS Database
Origanum vulgareFooDB
Pilocarpus pauciflorusLOTUS Database
Pilocarpus spicatusLOTUS Database
Pinus mugo subsp. MugoPlant
Pinus sibiricaPlant
Piper fimbriulatumPlant
Piper nigrum L.FooDB
Pistacia lentiscusLOTUS Database
Polygala senegaLOTUS Database
Primula halleriPlant
Ruta angustifoliaLOTUS Database
Ruta graveolensPlant
Ruta montanaLOTUS Database
Sauromatum venosumLOTUS Database
Scolochloa festucaceaLOTUS Database
Solanum agrimoniifoliumLOTUS Database
Solanum habrochaitesLOTUS Database
Spongiporus leucomallellus (Murril)-
Strobilanthes crispusPlant
Syzygium aromaticumFooDB
Terminalia chebulaLOTUS Database
Vaccinium corymbosumLOTUS Database
Vitis viniferaLOTUS Database
Zanthoxylum armatumLOTUS Database
Zanthoxylum hawaiienseLOTUS Database
Zea maysLOTUS Database
Zea mays L.FooDB
Zingiber miogaLOTUS Database
Zingiber officinaleFooDB
Zingiber officinale ROSC.Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentKetones  
Alternative Parents
Substituents
  • Ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.25ALOGPS
logP3.92ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity53.03 m³·mol⁻¹ChemAxon
Polarizability22.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033713  
DrugBank IDDB08688  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011831  
KNApSAcK IDC00030758  
Chemspider ID7871  
KEGG Compound IDC01875  
BioCyc ID2-UNDECANONE  
BiGG IDNot Available
Wikipedia Link2-Undecanone  
METLIN IDNot Available
PubChem Compound8163  
PDB IDUOC  
ChEBI ID17700  
Good Scents IDNot Available
References
General References
  1. Castaneda F, Zimmermann D, Nolte J, Baumbach JI: Role of undecan-2-one on ethanol-induced apoptosis in HepG2 cells. Cell Biol Toxicol. 2007 Nov;23(6):477-85. doi: 10.1007/s10565-007-9009-y. Epub 2007 Apr 24. [PubMed:17453350  ] 
  2. Yang L, Zhang Y, Yi H, Yang H, Zhang Q: [Determination of methyl nonyl ketone in volatile oil from herbs of Houttuynia cordata by GC-MS]. Zhongguo Zhong Yao Za Zhi. 2010 Aug;35(15):1987-9. doi: 10.4268/cjcmm20101516. [PubMed:20931852  ] 
  3. Bisht D, Chanotiya CS: 2-undecanone rich leaf essential oil from Zanthoxylum armatum. Nat Prod Commun. 2011 Jan;6(1):111-4. [PubMed:21366058  ] 
  4. Grant AJ, Dickens JC: Functional characterization of the octenol receptor neuron on the maxillary palps of the yellow fever mosquito, Aedes aegypti. PLoS One. 2011;6(6):e21785. doi: 10.1371/journal.pone.0021785. Epub 2011 Jun 30. [PubMed:21738794  ] 
  5. Fischer D, Imholt C, Prokop A, Jacob J: Efficacy of methyl nonyl ketone as an in-soil repellent for common voles (Microtus arvalis). Pest Manag Sci. 2013 Mar;69(3):431-6. doi: 10.1002/ps.3426. Epub 2013 Jan 3. [PubMed:23292923  ]