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Record Information
Version1.0
Created at2006-08-13 02:57:08 UTC
Updated at2021-10-07 20:41:04 UTC
NP-MRD IDNP0000731
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Heptanone
Description2-Heptanone, also known as butylacetone or heptan-2-one, 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. Thus, 2-heptanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Heptanone is a ketone with the molecular formula C7H14O. 2-Heptanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Heptanone exists in all living species, ranging from bacteria to humans. 2-Heptanone is a sweet, cinnamon, and coconut tasting compound. 2-Heptanone is found, on average, in the highest concentration within a few different foods, such as corns, cow milk, and peppermints. 2-Heptanone has also been detected, but not quantified in several different foods, such as tarragons, blackberries, tortilla chips, ceylon cinnamons, and evergreen blackberries. 2-Heptanone is one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories. 2-Heptanone, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, nonalcoholic fatty liver disease, crohn's disease, and hepatic encephalopathy; 2-heptanone has also been linked to the inborn metabolic disorder celiac disease. It is a colorless to white liquid with a banana-like, fruity odor.
Structure
Thumb
Synonyms
ValueSource
ButylacetoneChEBI
Methyl N-amyl ketoneChEBI
Methyl pentyl ketoneChEBI
N-Amyl methyl ketoneChEBI
N-Pentyl methyl ketoneChEBI
Heptan-2-oneKegg
1-MethylhexanalHMDB
2-OxoheptaneHMDB
Amyl methyl ketoneHMDB
Methyl amyl ketoneHMDB
Methyl N-pentyl ketoneHMDB
Pentyl methyl ketoneHMDB
Methyl-N-amyl ketoneHMDB
2-HeptanoneChEBI
Chemical FormulaC7H14O
Average Mass114.1855 Da
Monoisotopic Mass114.10447 Da
IUPAC Nameheptan-2-one
Traditional Name2-heptanone
CAS Registry Number110-43-0
SMILES
CCCCCC(C)=O
InChI Identifier
InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3
InChI KeyCATSNJVOTSVZJV-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Amorphophallus eichleriLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum foeniculumPlant
Anser anserFooDB
Apis melliferaLOTUS Database
Artemisia dracunculusFooDB
Arum maculatumKNApSAcK Database
Aspalathus linearisLOTUS Database
Averrhoa carambolaKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Capsicum annuum var. annuumFooDB
Carica papaya L.FooDB
Centipeda minimaLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Cinnamomum verumFooDB
Citrullus lanatusFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.Plant
ColumbaFooDB
ColumbidaeFooDB
Daucus carotaLOTUS Database
Dromaius novaehollandiaeFooDB
Elettaria cardamomumFooDB
Equus caballusFooDB
Evernia prunastriLOTUS Database
Foeniculum vulgareKNApSAcK Database
Gallus gallusFooDB
Lagopus mutaFooDB
Laminaria japonicaKNApSAcK Database
LeporidaeFooDB
Lepus timidusFooDB
Mandragora autumnalisKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha x piperitaFooDB
Musa paradisiacaLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
Ontholestes murinusLOTUS Database
Ophrys sphegodesLOTUS Database
Ophrys spp.KNApSAcK Database
OryctolagusFooDB
Ovis ariesFooDB
Pelargonium vitifoliumLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Polygala senegaLOTUS Database
Prunus aviumFooDB
    • J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
Prunus cerasusFooDB
Psidium guajavaKNApSAcK Database
Saccharina japonicaPlant
Sergia lucensLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumKNApSAcK Database
Tricholoma matsutakeLOTUS Database
Trifolium pratenseLOTUS Database
Trigonella foenum-graecumLOTUS Database
Vaccinium angustifoliumFooDB
    • Lugemwa, F. N., Lwande, W., Bentley, M. D., Mendel, M. J., and Alford, A. R. (1989). Volatiles of...
Vitis viniferaLOTUS Database
Zea maysLOTUS Database
Zea mays L.FooDB
    • Carlos Macku, and Takayuki Shibamoto. Headspace volatile compounds formed from heated corn oil an...
Zingiber miogaLOTUS Database
Zingiber officinaleFooDB
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
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-35 °CNot Available
Boiling Point149.00 to 150.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4.3 mg/mL at 25 °CNot Available
LogP1.98Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility2.26 g/LALOGPS
logP1.92ALOGPS
logP2.14ChemAxon
logS-1.7ALOGPS
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 Count4ChemAxon
Refractivity34.62 m³·mol⁻¹ChemAxon
Polarizability14.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003671
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008055
KNApSAcK IDC00001254
Chemspider ID7760
KEGG Compound IDC08380
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Heptanone
METLIN IDNot Available
PubChem Compound8051
PDB IDNot Available
ChEBI ID5672
Good Scents IDrw1002111
References
General References
  1. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. doi: 10.1017/s0022029902005782. [PubMed:12463694 ]
  2. Hansson BS, Larsson MC: Receptor neuron responses to potential sex pheromone components in the caddisfly Rhyacophila nubila (Trichoptera: Rhyacophilidae). J Insect Physiol. 1998 Feb;44(2):189-196. doi: 10.1016/s0022-1910(97)00043-7. [PubMed:12769891 ]
  3. Pionnier E, Chabanet C, Mioche L, Le Quere JL, Salles C: 1. In vivo aroma release during eating of a model cheese: relationships with oral parameters. J Agric Food Chem. 2004 Feb 11;52(3):557-64. doi: 10.1021/jf030544v. [PubMed:14759148 ]
  4. Xu F, Schaefer M, Kida I, Schafer J, Liu N, Rothman DL, Hyder F, Restrepo D, Shepherd GM: Simultaneous activation of mouse main and accessory olfactory bulbs by odors or pheromones. J Comp Neurol. 2005 Sep 5;489(4):491-500. doi: 10.1002/cne.20652. [PubMed:16025460 ]
  5. Resconi VC, Campo MM, Montossi F, Ferreira V, Sanudo C, Escudero A: Relationship between odour-active compounds and flavour perception in meat from lambs fed different diets. Meat Sci. 2010 Aug;85(4):700-6. doi: 10.1016/j.meatsci.2010.03.027. Epub 2010 Mar 21. [PubMed:20416794 ]