| Common Name |
Erythrono-1,4-lactone
| Description |
Erythrono-1,4-lactone has been identified as a lactone of tetronic acid in the urine from normal adlits and neonates. The formation of this compound may be a consequence of lactonization of erythronic acid during the extraction/isolation process. Lactonization is a potential problem when measuring acids that contain a hydroxyl group at the number 4 carbon, as lactones are formed under acidic conditions. Evidence indicates that most 4-hydroxy acids do not normally exist to any appreciable extent as lactones in urine. (PMID 1192581 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
D-ErythronolactoneChEBI
Erythronic acid gamma-lactoneChEBI
Erythronate g-lactoneGenerator
Erythronate gamma-lactoneGenerator
Erythronate γ-lactoneGenerator
Erythronic acid g-lactoneGenerator
Erythronic acid γ-lactoneGenerator
(3R,4R)-dihydro-3,4-Dihydroxy-threono-1,4-lactone 2(3H)-furanoneHMDB
(3R,4R)-Rel-dihydro-3,4-dihydroxy-2(3H)-furanoneHMDB
3,4-dihydroxydihydro-2(3H)-FuranoneHMDB
D-Erythronic acid gamma-lactoneHMDB
delta-Erythronic acid gamma-lactoneHMDB
dihydro-3,4-Dihydroxy-cis-2(3H)-furanoneHMDB
| Chemical Formlia |
C4H6O4
| Average Molecliar Weight |
118.088
| Monoisotopic Molecliar Weight |
118.02660868
| IUPAC Name |
(3R,4R)-3,4-dihydroxyoxolan-2-one
| Traditional Name |
erythrono-1,4-lactone
| CAS Registry Number |
17675-99-9
| SMILES |
O[C@@H]1COC(=O)[C@@H]1O
| InChI Identifier |
InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1
| InChI Key |
SGMJBNSHAZVGMC-PWNYCUMCSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as gamma butyrolactones. These 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Lactones
| Direct Parent |
Gamma butyrolactones
| Alternative Parents |
Oxolanes
Secondary alcohols
Carboxylic acid esters
1,2-diols
Oxacyclic compounds
Monocarboxylic acids and derivatives
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Gamma butyrolactone
Oxolane
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
| Molecliar Framework |
Aliphatic heteromonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility1240.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.85 m3·mol-1ChemAxon
Polarizability9.84 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-0udi-1920000000-8bf103e6bad44eb52cacView in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm (predicted from logP)
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021972
| KNApSAcK ID |
Not Available
| Chemspider ID |
4483398
| KEGG Compound ID |
Not Available
| BioCyc ID |
CPD-8574
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00349
| Metagene Link |
HMDB00349
| METLIN ID |
5338
| PubChem Compound |
5325915
| PDB ID |
Not Available
| ChEBI ID |
290972
Product: BMS-779788
References |
| Synthesis Reference |
Isaac, I.; Aizel, G.; Stasik, I.; Wadouachi, A.; Beaupere, D. A new efficient access to glycono 1,4-lactones by oxidation of unprotected itols by catalytic hydrogen transfer with RhH(PPh3)4-benzalacetone system. Synlett (1998), (5), 475-476. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Thompson JA, Markey SP, Fennessey PV: Gas-chromatographic/mass-spectrometric identification and quantitation of tetronic and deoxytetronic acids in urine from normal adults and neonates. Clin Chem. 1975 Dec;21(13):1892-8. [PubMed:1192581 ]
|
PMID: 23381899