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Showing metabocard for 2-Methyltetrahydrofuran-3-one (HMDB0031178)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:28 UTC
Update Date2023-02-21 17:19:58 UTC
HMDB IDHMDB0031178
Secondary Accession Numbers
  • HMDB31178
Metabolite Identification
Common Name2-Methyltetrahydrofuran-3-one
Description2-Methyltetrahydrofuran-3-one, also known as coffee furanone, is a member of the class of compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. 2-Methyltetrahydrofuran-3-one is soluble (in water) and an extremely weak acidic compound (based on its pKa). 2-Methyltetrahydrofuran-3-one is a flavouring agent and is a volatile constituent of coffee and coffee products. 2-Methyltetrahydrofuran-3-one is present in many foods.
Structure
Data?1676999998
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031178 (2-Methyltetrahydrofuran-3-one)


  Mrv1652304091819092D          

  7  7  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
M  END
Download

3D MOL for HMDB0031178 (2-Methyltetrahydrofuran-3-one)

HMDB0031178
     RDKit          3D
2-Methyltetrahydrofuran-3-one
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.0692   -0.1400   -0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6608   -0.3496    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1380   -0.9531   -0.7538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4423   -0.6185   -0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4608    0.5746    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334    0.9258    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649    1.9956    0.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615    0.7083   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3831   -1.0937   -0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7166    0.0481    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6619   -0.9168    1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692   -1.4996   -0.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -0.3365   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1090    1.3920    0.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8642    0.2633    1.3993 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  2  0
  6  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
M  END
Download

3D SDF for HMDB0031178 (2-Methyltetrahydrofuran-3-one)


  Mrv1652304091819092D          

  7  7  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031178

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OCCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3

> <INCHI_KEY>
FCWYQRVIQDNGBI-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.216214659356119

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyloxolan-3-one

> <ALOGPS_LOGP>
-0.23

> <JCHEM_LOGP>
0.43926426733333346

> <ALOGPS_LOGS>
0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.138793781552508

> <JCHEM_PKA_STRONGEST_BASIC>
-4.197835501119555

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
25.2824

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coffee furanone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0031178 (2-Methyltetrahydrofuran-3-one)

HMDB0031178
     RDKit          3D
2-Methyltetrahydrofuran-3-one
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.0692   -0.1400   -0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6608   -0.3496    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1380   -0.9531   -0.7538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4423   -0.6185   -0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4608    0.5746    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334    0.9258    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649    1.9956    0.6250 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0615    0.7083   -1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3831   -1.0937   -0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7166    0.0481    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6619   -0.9168    1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692   -1.4996   -0.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -0.3365   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1090    1.3920    0.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8642    0.2633    1.3993 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  2  0
  6  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
M  END
Download

PDB for HMDB0031178 (2-Methyltetrahydrofuran-3-one)

HEADER    PROTEIN                                 09-APR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-18         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    3    5                                                       
CONECT    3    2    7                                                       
CONECT    4    1    5    7                                                  
CONECT    5    2    4    6                                                  
CONECT    6    5                                                            
CONECT    7    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0031178 (2-Methyltetrahydrofuran-3-one)

COMPND    HMDB0031178
HETATM    1  C1  UNL     1       2.069  -0.140  -0.314  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.661  -0.350   0.212  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.138  -0.953  -0.754  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.442  -0.618  -0.511  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.461   0.575   0.411  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.033   0.926   0.447  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.465   1.996   0.625  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.062   0.708  -1.015  1.00  0.00           H  
HETATM    9  H2  UNL     1       2.383  -1.094  -0.771  1.00  0.00           H  
HETATM   10  H3  UNL     1       2.717   0.048   0.565  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.662  -0.917   1.166  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.969  -1.500  -0.065  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.001  -0.336  -1.444  1.00  0.00           H  
HETATM   14  H7  UNL     1      -2.109   1.392   0.049  1.00  0.00           H  
HETATM   15  H8  UNL     1      -1.864   0.263   1.399  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    6   11
CONECT    3    4
CONECT    4    5   12   13
CONECT    5    6   14   15
CONECT    6    7    7
END
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SMILES for HMDB0031178 (2-Methyltetrahydrofuran-3-one)

CC1OCCC1=O
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INCHI for HMDB0031178 (2-Methyltetrahydrofuran-3-one)

InChI=1S/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
FEMA 3373HMDB
tetrahydro-2-Methyl-3-furanoneHMDB
Coffee furanoneHMDB
Dihydro-2-methyl-3(2H)-furanoneHMDB
2-Methyl-2H-furan-3-oneHMDB
2-Methyl-3-ketotetrahydrofuranHMDB
2-Methyl-3-oxotetrahydrofuranHMDB
2-Methyldihydrofuran-3(2H)-oneHMDB
2-Methyldihydrofuran-3-oneHMDB
2-Methyloxolan-3-oneHMDB
2-Methyltetrahydrofuran-3-ketoneHMDB
Dihydro-2-methyl-3-furanoneHMDB
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name2-methyloxolan-3-one
Traditional Namecoffee furanone
CAS Registry Number3188-00-9
SMILES
CC1OCCC1=O
InChI Identifier
InChI=1S/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3
InChI KeyFCWYQRVIQDNGBI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • 3-furanone
  • Tetrahydrofuran
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point138.00 to 139.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP-0.563 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility285 g/LALOGPS
logP-0.23ALOGPS
logP0.44ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.28 m³·mol⁻¹ChemAxon
Polarizability10.22 ųChemAxon
Number of Rings1ChemAxon
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]+119.00431661259
DarkChem[M-H]-113.95931661259
DeepCCS[M+H]+130.19930932474
DeepCCS[M-H]-127.40130932474
DeepCCS[M-2H]-163.95530932474
DeepCCS[M+Na]+138.46130932474
AllCCS[M+H]+120.232859911
AllCCS[M+H-H2O]+115.232859911
AllCCS[M+NH4]+124.932859911
AllCCS[M+Na]+126.332859911
AllCCS[M-H]-119.832859911
AllCCS[M+Na-2H]-122.932859911
AllCCS[M+HCOO]-126.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methyltetrahydrofuran-3-oneCC1OCCC1=O1253.1Standard polar33892256
2-Methyltetrahydrofuran-3-oneCC1OCCC1=O783.3Standard non polar33892256
2-Methyltetrahydrofuran-3-oneCC1OCCC1=O807.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methyltetrahydrofuran-3-one,1TMS,isomer #1CC1=C(O[Si](C)(C)C)CCO11075.6Semi standard non polar33892256
2-Methyltetrahydrofuran-3-one,1TMS,isomer #1CC1=C(O[Si](C)(C)C)CCO11143.2Standard non polar33892256
2-Methyltetrahydrofuran-3-one,1TMS,isomer #2CC1OCC=C1O[Si](C)(C)C1026.1Semi standard non polar33892256
2-Methyltetrahydrofuran-3-one,1TMS,isomer #2CC1OCC=C1O[Si](C)(C)C1111.2Standard non polar33892256
2-Methyltetrahydrofuran-3-one,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)CCO11309.2Semi standard non polar33892256
2-Methyltetrahydrofuran-3-one,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)CCO11373.9Standard non polar33892256
2-Methyltetrahydrofuran-3-one,1TBDMS,isomer #2CC1OCC=C1O[Si](C)(C)C(C)(C)C1258.6Semi standard non polar33892256
2-Methyltetrahydrofuran-3-one,1TBDMS,isomer #2CC1OCC=C1O[Si](C)(C)C(C)(C)C1268.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyltetrahydrofuran-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-e3f8793e49d60fd017062017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyltetrahydrofuran-3-one 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 - 2-Methyltetrahydrofuran-3-one 10V, Positive-QTOFsplash10-0udi-1900000000-292e7d61f2837f8a2bdb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 20V, Positive-QTOFsplash10-0udi-4900000000-edfea591ca0bfab8dc642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 40V, Positive-QTOFsplash10-0pb9-9000000000-068b28f9e446c64e3b112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 10V, Negative-QTOFsplash10-0002-9000000000-9dafb9e0683d4e36c3532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 20V, Negative-QTOFsplash10-0002-9000000000-5c82778d6e8d3cd09ce12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 40V, Negative-QTOFsplash10-0gb9-9000000000-4516d0e13d4cac50eae82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 10V, Negative-QTOFsplash10-0002-9000000000-6b7b6e2d789a127b33b22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 20V, Negative-QTOFsplash10-052f-9000000000-602d2c535477cf76300c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 40V, Negative-QTOFsplash10-0a4l-9000000000-40b5b0507d39ed00397d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 10V, Positive-QTOFsplash10-0kai-9300000000-b2550620d1a80612d33d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 20V, Positive-QTOFsplash10-0a4i-9000000000-92cd62df0927dfd89bf62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyltetrahydrofuran-3-one 40V, Positive-QTOFsplash10-052b-9000000000-80f39eb55338a8d2bcb02021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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 IDFDB003197
KNApSAcK IDNot Available
Chemspider ID17494
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoffee furanone
METLIN IDNot Available
PubChem Compound18522
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1036001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .