oxolan-2-one

• ChemBase ID: 4252
• Molecular Formular: C4H6O2
• Molecular Mass: 86.08924
• Monoisotopic Mass: 86.03677943
• SMILES: O=C1CCCO1
• Canonical SMILES: O=C1CCCO1
• InChI: InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
• InChIKey: YEJRWHAVMIAJKC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: oxolan-2-one
• IUPAC Traditional name: 4-butyrolactone; butyrolactone
• Synonyms: γ-Butyrolactone; 4-Hydroxybutanoic acid lactone; Dihydro-2(3H)-furanone; 1,4-Butanolide; 1-Oxacyclopentan-2-one; 2,3,4,5-Tetrahydro-2-furanone; 2-Oxotetrahydrofuran; γ-Butyryllactone; γ-Butyrolactone; dihydrofuran-2(3h)-one; 1,4-Lactone; 4-Butyrolactone; GBL; butyrolactonL; 1,4-lactonL; 4-butyrolactonL; 4-hydroxybutyric acid lactonL; gamma-hydroxybutyric acid lactonL; and oxolan-2-one; Gamma-Butyrolactone; gamma-Butyrolactone; γ-Hydroxybutyric acid lactone; 4-Hydroxybutyric acid lactone; γ-Butyrolactone; Dihydrofuran-2(3H)-one; γ-丁内酯; 4-羟基丁酸内酯; γ-羟基丁酸内酯; 4-羟基丁酸内酯; γ-丁内酯

Database IDs

• CAS Number: 96-48-0; 187997-16-6
• EC Number: 202-509-5
• MDL Number: MFCD00005386
• Beilstein Number: 105248
• PubChem SID: 24891553; 46508619; 160967684; 24901615
• PubChem CID: 7302
• CHEBI ID: 42639
• CHEMBL: 95681
• Chemspider ID: 7029
• DrugBank ID: DB04699
• FEMA ID: 3291
• KEGG ID: C01770
• Unique Ingredient Identifier: OL659KIY4X
• Wikipedia Title: Gamma-Butyrolactone
• Council of Europe Number: 615
• Flavis Number: 10.006

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.1495513
• LogD (pH = 7.4): 0.1495513
• Log P: 0.1495513
• Molar Refractivity: 20.3081 cm^3
• Polarizability: 8.181739 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.11
• LOG S: 0.44
• Solubility (Water): 2.38e+02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Miscible in water; soluble in CCl₄, methanol, ethanol, acetone, benzene, ethyl ether
• Apperance: Clear Colorless Liquid; Colorless oily liquid
• Melting Point: -43.53°C; -45 °C(lit.)
• Boiling Point: 204°C; 204-205 °C(lit.)
• Flash Point: 208.4 °F; 98 °C; 98 °C (closed cup)
• Auto Ignition Point: 851 °F
• Density: 1.12 g/mL at 25 °C(lit.); 1.1286 g/mL (15 °C), 1.1296 g/mL (20 °C)
• Refractive Index: 1.435, 1.4341 (20 °C); n20/D 1.436; n20/D 1.436(lit.); n20/D 1.437
• Vapor Pressure: 1.5 mmHg ( 20 °C)
• Vapor Density: 3 (vs air)
• pKa: 4.5
• Viscosity: 1.7 cp (25 °C)
• Organoleptic: caramel

Safety Information

• Storage Condition: Refrigerator
• RTECS: LU3500000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22-41-67; R22 R36
• Safety Statements: 26-39; S26 S36
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• Main Hazard: Harmful
• LD50: 17.2 mL/kg (orally, rat)
• Explode Limits: 16 %
• GHS Hazard statements: H302-H318-H336
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C
• Regulation Compliance: FCC

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥98%; ≥98.0% (GC); ≥99%; ≥99% (GC); ≥99.0% (GC); ≥99.5%; 95+%
• Grade: Kosher; NI; puriss.; purum; ReagentPlus®; SAJ first grade
• Empirical Formula (Hill Notation): C4H6O2

DETAILS

DrugBank - DB04699

• Drug Groups: experimental
• Description: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent. [PubChem]

Sigma Aldrich - H7629

Biochem/physiol Actions
Precursor of γ-hydroxybutyric acid (GHB). It blocks dopamine release by blocking impulse flow in dopaminergic neurons. Pretreatment with γ-butyrolactone allows detection of autoreceptor-induced dopamine release.

Sigma Aldrich - W329118

Packaging
1 kg in glass bottle
1 sample in glass bottle
10, 25 kg in poly drum
500 lb in comp drum
Biochem/physiol Actions
Precursor of γ-hydroxybutyric acid (GHB). It blocks dopamine release by blocking impulse flow in dopaminergic neurons. Pretreatment with γ-butyrolactone allows detection of autoreceptor-induced dopamine release.

Sigma Aldrich - B103608

Packaging
2.5 kg in glass bottle
20 kg in VerSA-Flow™
25, 500 g in glass bottle
Application
For the introduction of 3-carboxypropyl side chain.1 Used as a component of electrolyte solutions in batteries and capacitors.2
Biochem/physiol Actions
Precursor of γ-hydroxybutyric acid (GHB). It blocks dopamine release by blocking impulse flow in dopaminergic neurons. Pretreatment with γ-butyrolactone allows detection of autoreceptor-induced dopamine release.
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 20740

Biochem/physiol Actions
Precursor of γ-hydroxybutyric acid (GHB). It blocks dopamine release by blocking impulse flow in dopaminergic neurons. Pretreatment with γ-butyrolactone allows detection of autoreceptor-induced dopamine release.

Sigma Aldrich - 20741

Biochem/physiol Actions
Precursor of γ-hydroxybutyric acid (GHB). It blocks dopamine release by blocking impulse flow in dopaminergic neurons. Pretreatment with γ-butyrolactone allows detection of autoreceptor-induced dopamine release.

Sigma Aldrich - 03-5330

Biochem/physiol Actions
Precursor of γ-hydroxybutyric acid (GHB). It blocks dopamine release by blocking impulse flow in dopaminergic neurons. Pretreatment with γ-butyrolactone allows detection of autoreceptor-induced dopamine release.

Toronto Research Chemicals - B760995

Solvent for polyacrylonitrile, cellulose acetate, methyl methacrylate polymers, polystyrene. Constituent of paint removers, textile aids, drilling oils.

REFERENCES

• Moon, J., et al.: J. Agric. Food Chem., 58, 5465 (2010)
• Rodriguez-Bencomo, J., et al.: Eur. Food Res. Technol., 230, 485 (2010)
• Mahalingam, A., et al.: J. Med. Chem., 53, 607 (2010)