Record Information
Version1.0
Creation date2010-04-08 22:12:32 UTC
Update date2019-11-26 03:13:30 UTC
Primary IDFDB016604
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGalanolactone
DescriptionGalanolactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Galanolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Galanolactone has been detected, but not quantified in, gingers and herbs and spices. This could make galanolactone a potential biomarker for the consumption of these foods.
CAS Number115753-79-2
Structure
Thumb
Synonyms
SynonymSource
Galanolactonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
logP3.81ALOGPS
logP4.24ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.37 m³·mol⁻¹ChemAxon
Polarizability36.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H30O3
IUPAC name(3Z)-3-(2-{5,5,8a-trimethyl-octahydro-1H-spiro[naphthalene-2,2'-oxirane]-1-yl}ethylidene)oxolan-2-one
InChI IdentifierInChI=1S/C20H30O3/c1-18(2)9-4-10-19(3)15(18)7-11-20(13-23-20)16(19)6-5-14-8-12-22-17(14)21/h5,15-16H,4,6-13H2,1-3H3/b14-5-
InChI KeyMBPTXJNHCBXMBP-RZNTYIFUSA-N
Isomeric SMILESCC1(C)CCCC2(C)C(C\C=C3\CCOC3=O)C3(CO3)CCC12
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
Classification
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 75.43%; H 9.49%; O 15.07%DFC
Melting PointMp 125.5-126°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +28 (c, 0.26 in CHCl3)DFC
Spectroscopic UV Data[neutral] lmax 226 (e 11400) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGalanolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-0691000000-76ff2be2a471bb872fd2Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1079000000-1752926143446e156771Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fsj-2192000000-34665ab35024bcaec03bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-8920000000-9070c224eeba82a073c6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1019000000-c8e6f08fa9a4c772c41eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-3095000000-9f4bfe9957ad918fccc7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-4090000000-bec7fcb4c3d0c3bfeb83Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC17498
Pubchem Compound ID57457805
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37523
CRC / DFC (Dictionary of Food Compounds) IDKRS12-J:KRS13-K
EAFUS IDNot Available
Dr. Duke IDGALANOLACTONE
BIGG IDNot Available
KNApSAcK IDC00034848
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGalanolactone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti 5-hydroxytryptamine48279 Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.DUKE
anti emetic50919 A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.DUKE
anti thromboxane35222 A substance that diminishes the rate of a chemical reaction.DUKE
gastrostimulant55324 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).