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Record Information
Version1.0
Creation Date2016-05-19 01:30:59 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003969
Identification
Common Namebeta-Propiolactone
ClassSmall Molecule
DescriptionNot Available
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
1,3-PropiolactoneChEBI
2-OxetanoneChEBI
3-Hydroxypropionic acid beta-lactoneChEBI
3-PropanolideChEBI
beta-Lactone hydracrylic acidChEBI
beta-Propanoic acid lactoneChEBI
beta-PropiolaktonChEBI
beta-PropionolactoneChEBI
BetapronChEBI
BetaproneChEBI
Hydracrylic acid beta-lactoneChEBI
PropanolideChEBI
PropiolactonaChEBI
PropiolactoneChEBI
PropiolactonumChEBI
3-Hydroxypropionate b-lactoneGenerator
3-Hydroxypropionate beta-lactoneGenerator
3-Hydroxypropionate β-lactoneGenerator
3-Hydroxypropionic acid b-lactoneGenerator
3-Hydroxypropionic acid β-lactoneGenerator
b-Lactone hydracrylateGenerator
b-Lactone hydracrylic acidGenerator
beta-Lactone hydracrylateGenerator
β-lactone hydracrylateGenerator
β-lactone hydracrylic acidGenerator
b-Propanoate lactoneGenerator
b-Propanoic acid lactoneGenerator
beta-Propanoate lactoneGenerator
β-propanoate lactoneGenerator
β-propanoic acid lactoneGenerator
b-PropiolaktonGenerator
β-propiolaktonGenerator
b-PropionolactoneGenerator
β-propionolactoneGenerator
Hydracrylate b-lactoneGenerator
Hydracrylate beta-lactoneGenerator
Hydracrylate β-lactoneGenerator
Hydracrylic acid b-lactoneGenerator
Hydracrylic acid β-lactoneGenerator
beta-PropiolactoneMeSH
beta PropiolactoneMeSH
Chemical FormulaC3H4O2
Average Molecular Mass72.063 g/mol
Monoisotopic Mass72.021 g/mol
CAS Registry Number57-57-8
IUPAC Nameoxetan-2-one
Traditional Nameβ propiolactone
SMILESO=C1CCO1
InChI IdentifierInChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2
InChI KeyVEZXCJBBBCKRPI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta propiolactones. These are organic compounds containing a four-member lactone (a cyclic ester).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassBeta propiolactones
Direct ParentBeta propiolactones
Alternative Parents
Substituents
  • Beta_propiolactone
  • Oxetane
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility436.0 mg/mLALOGPS
logP-0.55ALOGPS
logP-0.14ChemAxon
logS0.78ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity15.55 m3·mol-1ChemAxon
Polarizability6.55 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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 IDDB09348
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID2275
ChEBI ID49073
PubChem Compound ID2365
Kegg Compound IDC19297
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Usman A, Razak IA, Fun HK, Chantrapromma S, Zhang Y, Xu JH (2002) 1-Acetyl-3'-(4-bromophenyl)-3'-chlorospiro3H-indole-3,2'-oxetan-2(1H)-one. Acta crystallographica. Section C, Crystal structure communications;Acta Crystallogr C;2002 May;58(Pt 5):o287-8 (PMID: 11983994)
2. Romo D, Harrison PH, Jenkins SI, Riddoch RW, Park K, Yang HW, Zhao C, Wright GD (1998) Synthesis and inhibitory action on HMG-CoA synthase of racemic and optically active oxetan-2-ones (beta-lactones). Bioorganic & medicinal chemistry;Bioorg. Med. Chem.;1998 Aug;6(8):1255-72 (PMID: 9784867)
3. Jeong SY, Jun do Y, Kim YH, Min BS, Min BK, Woo MH (2011) Monoterpenoids from the aerial parts of Aruncus dioicus var. kamtschaticus and their antioxidant and cytotoxic activities. Bioorganic & medicinal chemistry letters;Bioorg. Med. Chem. Lett.;2011 Jun;21(11):3252-6 (PMID: 21546250)
4. Bae S, Hahn HG, Nam KD (2005) Syntheses of 1,3-Imidazoline-2-thione and 2-Phenylimino-1,3-thiazoline combinatorial libraries through different sequences of the same components. Journal of combinatorial chemistry;J Comb Chem;2005 Nov-Dec;7(6):826-36 (PMID: 16283792)
5. Morris BD, Smyth RR, Foster SP, Hoffmann MP, Roelofs WL, Franke S, Francke W (2005) Vittatalactone, a beta-lactone from the striped cucumber beetle, Acalymma vittatum. Journal of natural products;J. Nat. Prod.;2005 Jan;68(1):26-30 (PMID: 15679312)
6. Wuitschik G, Carreira EM, Wagner B, Fischer H, Parrilla I, Schuler F, Rogers-Evans M, Müller K (2010) Oxetanes in drug discovery: structural and synthetic insights. Journal of medicinal chemistry;J. Med. Chem.;2010 Apr;53(8):3227-46 (PMID: 20349959)
7. Breda S, Reva I, Fausto R (2012) UV-Induced unimolecular photochemistry of diketene isolated in cryogenic inert matrices. The journal of physical chemistry. A;J Phys Chem A;2012 Mar;116(9):2131-40 (PMID: 22273010)
8. Jane DE, Hoo K, Kamboj R, Deverill M, Bleakman D, Mandelzys A (1997) Synthesis of willardiine and 6-azawillardiine analogs: pharmacological characterization on cloned homomeric human AMPA and kainate receptor subtypes. Journal of medicinal chemistry;J. Med. Chem.;1997 Oct;40(22):3645-50 (PMID: 9357531)
9. Lamontagne N, Mercier L, Pons M, Thompson EB, Simons SS (1984) Glucocorticoid versus antiglucocorticoid activity: can a single functional group modification of glucocorticoid steroids always convey antiglucocorticoid activity?. Endocrinology;Endocrinology;1984 Jun;114(6):2252-63 (PMID: 6547091)