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Showing NP-Card for Acetophenone (NP0001122)

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Record Information
Version1.0
Created at2012-09-11 18:41:07 UTC
Updated at2021-08-19 23:58:48 UTC
NP-MRD IDNP0001122
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetophenone
DescriptionAcetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances. Acetophenone is found in chicory. Acetophenone is a flavouring ingredient used in fruit flavours. Acetophenone is a raw material for the synthesis of some pharmaceuticals and is also listed as an approved excipient by the U.S. FDA. In a 1994 report released by five top cigarette companies in the U.S., Acetophenone was listed as one of the 599 additives to cigarettes.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001122 (Acetophenone)


  Mrv1652303202019002D          

  9  9  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
  4  9  1  0  0  0  0
M  END
Download

3D MOL for NP0001122 (Acetophenone)

HMDB0033910
     RDKit          3D
Acetophenone
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.6594    0.5281   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664   -0.5542   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -1.7422   -0.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309   -0.3212    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2678    0.9697    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    1.1746    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    0.1158    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -1.1689    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613   -1.3632    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    0.9064    0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5990    0.1589   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    1.3856   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067    1.8293   -0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    2.2014    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    0.2730    0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477   -1.9802    0.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3310   -2.4131    0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0001122 (Acetophenone)


  Mrv1652303202019002D          

  9  9  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001122

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3

> <INCHI_KEY>
KWOLFJPFCHCOCG-UHFFFAOYSA-N

> <FORMULA>
C8H8O

> <MOLECULAR_WEIGHT>
120.1485

> <EXACT_MASS>
120.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.05282053698111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-phenylethan-1-one

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.5308933346666667

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.099925039370238

> <JCHEM_PKA_STRONGEST_BASIC>
-7.3885191025078125

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
36.460800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetophenone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001122 (Acetophenone)

HMDB0033910
     RDKit          3D
Acetophenone
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.6594    0.5281   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6664   -0.5542   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -1.7422   -0.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309   -0.3212    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2678    0.9697    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6413    1.1746    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    0.1158    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -1.1689    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613   -1.3632    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    0.9064    0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5990    0.1589   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    1.3856   -0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067    1.8293   -0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    2.2014    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6058    0.2730    0.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477   -1.9802    0.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3310   -2.4131    0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

PDB for NP0001122 (Acetophenone)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0001122 (Acetophenone)

COMPND    HMDB0033910
HETATM    1  C1  UNL     1      -2.659   0.528  -0.054  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.666  -0.554  -0.027  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.073  -1.742  -0.027  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.231  -0.321   0.001  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.268   0.970   0.002  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.641   1.175   0.029  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.536   0.116   0.054  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.033  -1.169   0.053  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.661  -1.363   0.026  1.00  0.00           C  
HETATM   10  H1  UNL     1      -2.867   0.906   0.979  1.00  0.00           H  
HETATM   11  H2  UNL     1      -3.599   0.159  -0.516  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.330   1.386  -0.709  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.407   1.829  -0.017  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.009   2.201   0.029  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.606   0.273   0.075  1.00  0.00           H  
HETATM   16  H7  UNL     1       2.748  -1.980   0.073  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.331  -2.413   0.027  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    4
CONECT    4    5    5    9
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   17
END
Download

SMILES for NP0001122 (Acetophenone)

CC(=O)C1=CC=CC=C1
Download

INCHI for NP0001122 (Acetophenone)

InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3
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View in JSmolView NMR Assignments
Synonyms
ValueSource
1-PhenylethanoneChEBI
AcetylbenzeneChEBI
Benzoyl methideChEBI
Methyl phenyl ketoneChEBI
Phenyl methyl ketoneChEBI
1-Phenyl-1-ethanoneHMDB
1-Phenyl-ethanoneHMDB
1-Phenylethan-1-oneHMDB
1-Phenylethanone (acetophenone)HMDB
1-Phenylethanone, 9ciHMDB
AcetofenonHMDB
AcetophenonHMDB
Acetyl-benzeneHMDB
AcetylbenzolHMDB
alpha-AcetophenoneHMDB
BenzoylmethideHMDB
DymexHMDB
FEMA 2009HMDB
HypnonHMDB
HypnoneHMDB
Ketone, methyl phenylHMDB
Methyl phenyl-ketoneHMDB
MethylphenylketoneHMDB
Nchem.180-comp5HMDB
PhenylHMDB
PhenylethanoneHMDB
PhenylmethylketoneHMDB
Chemical FormulaC8H8O
Average Mass120.1485 Da
Monoisotopic Mass120.05751 Da
IUPAC Name1-phenylethan-1-one
Traditional Nameacetophenone
CAS Registry Number98-86-2
SMILES
CC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3
InChI KeyKWOLFJPFCHCOCG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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 NMR1H NMR Spectrum (1D, 1000 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 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 NMR1H NMR Spectrum (1D, 300 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 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 NMR1H NMR Spectrum (1D, 500 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 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 NMR1H NMR Spectrum (1D, 700 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, 800 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, 900 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
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acca sellowianaKNApSAcK Database
Amorphophallus cicatriciferLOTUS Database
Apis mellifera (Propolis)KNApSAcK Database
Apium graveolensFooDB
Artemisia xanthochroaLOTUS Database
Aspalathus linearisLOTUS Database
Averrhoa carambolaLOTUS Database
Basella albaLOTUS Database
Bellis perennisLOTUS Database
Camellia sinensisLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Castanopsis cuspidataLOTUS Database
Cichorium intybusFooDB
Cistus creticusKNApSAcK Database
Cistus ladaniferusKNApSAcK Database
Citrullus lanatusFooDB
Daphne odoraLOTUS Database
Dittrichia graveolensKNApSAcK Database
Elsholtzia blandaLOTUS Database
Elsholtzia ciliataLOTUS Database
Eruca vesicaria subsp. SativaFooDB
Euphorbia cyparissiasLOTUS Database
Evernia prunastriLOTUS Database
Feijoa sellowianaPlant
Gossypium hirsutumLOTUS Database
Hypericum hyssopifoliumLOTUS Database
Jatropha multifidaKNApSAcK Database
Malpighia emarginataLOTUS Database
Medicago sativaKNApSAcK Database
Mentha spicataFooDB
Musa paradisiacaLOTUS Database
Nepeta nepetellaLOTUS Database
Nepeta racemosaLOTUS Database
Ophrys x splendidaLOTUS Database
Opuntia ficus-indicaLOTUS Database
Paeonia lactifloraLOTUS Database
Paeonia suffruticosaLOTUS Database
Photinia melanocarpaLOTUS Database
Piper nigrum L.FooDB
Polygala senegaLOTUS Database
Populus balsamiferaKNApSAcK Database
Prunus salcina Lindl. (Blackamber)KNApSAcK Database
Sauromatum venosumLOTUS Database
Scutellaria baicalensisLOTUS Database
Stirlingia latifoliaKNApSAcK Database
Syzygium aromaticumFooDB
Tamarix aphyllaLOTUS Database
Taxus baccataPlant
Theobroma cacaoLOTUS Database
Tricholoma matsutakeLOTUS Database
Trifolium pratenseLOTUS Database
Urtica dioicaKNApSAcK Database
Vaccinium macrocarponLOTUS Database
Vitis viniferaLOTUS Database
Species Where Detected
Species NameSourceReference
Orthodon linalooliferumKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Acetophenone
  • Aryl alkyl ketone
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point20 °CNot Available
Boiling Point202.00 to 203.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility6.13 mg/mL at 25 °CNot Available
LogP1.58Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP1.65ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)16.1ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.46 m³·mol⁻¹ChemAxon
Polarizability13.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033910
DrugBank IDDB04619
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012106
KNApSAcK IDC00002685
Chemspider ID7132
KEGG Compound IDC07113
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetophenone
METLIN IDNot Available
PubChem Compound7410
PDB IDAC0
ChEBI ID27632
Good Scents IDrw1000131
References
General References
  1. Gul HI, Ojanen T, Vepsalainen J, Gul M, Erciyas E, Hanninen O: Antifungal activity of some mono, bis and quaternary Mannich bases derived from acetophenone. Arzneimittelforschung. 2001 Jan;51(1):72-5. [PubMed:11215330 ]
  2. Zhao Y, DeLancey GB: Transmembrane distribution of substrate and product during the bioreduction of acetophenone with resting cells of Saccharomyces cerevisiae. Biotechnol Bioeng. 1999 Aug 20;64(4):434-41. doi: 10.1002/(sici)1097-0290(19990820)64:4<434::aid-bit6>3.0.co;2-1. [PubMed:10397882 ]
  3. Raspotnig G, Schaider M, Stabentheiner E, Leis HJ, Karaman I: On the enigmatic scent glands of dyspnoan harvestmen (Arachnida, Opiliones): first evidence for the production of volatile secretions. Chemoecology. 2014;24:43-55. doi: 10.1007/s00049-014-0146-5. Epub 2014 Jan 31. [PubMed:24634568 ]
  4. Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Patient Version. 2002. [PubMed:34403226 ]
  5. Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:28876831 ]
  6. Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
  7. Authors unspecified: Adult Soft Tissue Sarcoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389481 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .