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Showing NP-Card for coffee furanone (NP0244784)

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Record Information
Version2.0
Created at2022-09-07 05:39:29 UTC
Updated at2022-09-07 05:39:29 UTC
NP-MRD IDNP0244784
Secondary Accession NumbersNone
Natural Product Identification
Common Namecoffee furanone
Description2-Methyltetrahydrofuran-3-one, also known as fema 3373 or tetrahydro-2-methyl-3-furanone, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. 2-Methyltetrahydrofuran-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methyltetrahydrofuran-3-one is a sweet, bread, and buttery tasting compound. Outside of the human body,. Coffee furanone is less odorous than furfuryl mercaptan, which with an odor threshold of 0.005 Ppb was the first high impact aroma chemical, but has a very pleasant sweet caramel character, with some nuttiness. Coffee furanone (2-methyltetrahydrofuran-3-one) is a pleasant smelling liquid furan derivative which is a volatile constituent of the aroma complex of roasted coffee. The synthetic version of this natural flavorant and odorant is used in a variety of food and beverage applications, including coffee, nuts, cocoa, brandy, meat sauces and as a general food flavorant at a typical dosage (about 5-20 ppm), similar to the natural concentration (30 ppm) of coffee furanone in roasted coffee. Coffee furanone has also been prepared via the condensation of ethyl lactate and methyl acrylate in DMSO solution and (under phase transfer conditions) in ionic liquids. Further approaches to the synthesis of coffee furanone involved the hydrolysis of the corresponding dithioketals and the oxidation of 2-methyltetrahydrofuran employing lithium hypochlorite in the presence of ruthenium catalysts. This compound has also been prepared in acceptable yield via oxidative hydroxylation of the 2-acetylbutyrolactone. Coffee furnone was synthesized in 1963 by Wynberg via acid-catalyzed ring closure of β-alkoxy diazoketones. coffee furanone is found in Aloe africana. A related lactic acid synthesis was described as having the advantages of a simple process, high conversion rate, low pollution, and low cost.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0244784 (coffee furanone)


  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
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3D MOL for NP0244784 (coffee furanone)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.0048   -0.5438   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5665   -0.4567    0.2555 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2940   -0.9010   -0.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334   -0.3604   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3366    0.9201    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    0.9304    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8064    1.8721    0.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3506   -1.5816    0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6706    0.1681    0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559   -0.4230   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4012   -1.0970    1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273   -0.0475   -1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1597   -1.0926    0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9014    0.8026    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    1.8102   -0.2386 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  1
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
M  END
Download

3D SDF for NP0244784 (coffee furanone)


  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>
NP0244784

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0244784 (coffee furanone)

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PDB for NP0244784 (coffee furanone)
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 NP0244784 (coffee furanone)
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SMILES for NP0244784 (coffee furanone)
CC1OCCC1=O
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INCHI for NP0244784 (coffee furanone)
InChI=1S/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3
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View in JSmol
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 Mass100.1158 Da
Monoisotopic Mass100.05243 Da
IUPAC Name2-methyloxolan-3-one
Traditional Namecoffee furanone
CAS Registry NumberNot Available
SMILES
CC1OCCC1=O
InChI Identifier
InChI=1S/C5H8O2/c1-4-5(6)2-3-7-4/h4H,2-3H2,1H3
InChI KeyFCWYQRVIQDNGBI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
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
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
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
HMDB IDHMDB0031178  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]