Threonolactone (CHEM035002)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:24:35 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM035002
Identification
Common NameThreonolactone
ClassSmall Molecule
DescriptionA butan-4-olide that is dihydrofuran-2-one substituted at C-3 and C-4 by hydroxy groups (the 3R,4S-diastereomer).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
L-Threonic acid-1,4-lactoneChEBI
Threonic acid-1,4-lactoneChEBI
L-Threonate-1,4-lactoneGenerator
Threonate-1,4-lactoneGenerator
3,4-Bis[(trimethylsilyl)oxy]dihydro-cis-2(3H)-furanoneHMDB
Bis-TMS-threono-1,4-lactoneHMDB
cis-Dihydro-3,4-bis[(trimethylsilyl)oxy]-2(3H)-furanoneHMDB
Di-TMS-threono-1,4-lactoneHMDB
Chemical FormulaC4H6O4
Average Molecular Mass118.088 g/mol
Monoisotopic Mass118.027 g/mol
CAS Registry Number21730-93-8
IUPAC Name(3R,4S)-3,4-dihydroxyoxolan-2-one
Traditional Name(3R,4S)-3,4-dihydroxyoxolan-2-one
SMILESO[C@H]1COC(=O)[C@@H]1O
InChI IdentifierInChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3+/m0/s1
InChI KeySGMJBNSHAZVGMC-STHAYSLISA-N
Chemical Taxonomy
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
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1240 g/LALOGPS
logP-1.7ALOGPS
logP-1.5ChemAxon
logS1.02ALOGPS
pKa (Strongest Acidic)11.66ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.85 m³·mol⁻¹ChemAxon
Polarizability9.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-63c53760143cd2044873Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fki-9430000000-f0cfa4e00daeb540aee7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-1900000000-d7d529471e146551a470Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-1900000000-7e70d7eac9b72e1cbd36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9100000000-7a95b8e64f0d366b4101Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-c877a9861f0a9e0fa947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-8900000000-874d13e11592fe389a74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-295d5454144b0a74cb00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9100000000-ccaaa47150cc978a00b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9000000000-07ca8b081361da8d614eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-846eebab9a9caa26cce6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-6900000000-fde995765993269b5d05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-9100000000-11a72527d4f24a67775bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-f1bef05a855750753132Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000940
FooDB IDFDB022328
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5888
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID2006913
ChEBI ID71176
PubChem Compound ID2724794
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
2. Nakaminami, Gen; Edo, Haruo; Nakagawa, Masazumi. Syntheses of L-threose and methyl di-O-acetyl-L-threuronate from (+)-tartaric acid. Bulletin of the Chemical Society of Japan (1973), 46(1), 266-9.
3. Kurata, T; Miyake, N; Otsuka, Y. Formation of L-threonolactone and oxalic acid in the autoxidation reaction of L-ascorbic acid - Possible involvement of singlet oxygen. Bioscience, Biotechnology, and Biochemistry, Volume 60, Issue 7, pp. 1212-1214.