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2-Furanone

Names

Preferred IUPAC name

Furan-2(5H)-one

Other names

Furan-2-one, γ-crotonolactone, butenolide, 5H-furan-2-one

Identifiers

CAS Number

497-23-4^Y

3D model (JSmol)

Interactive image

Beilstein Reference

383585

ChEBI

CHEBI:38118^Y

ChEMBL

ChEMBL166223^Y

ChemSpider

9917^Y

ECHA InfoCard

100.007.128

EC Number

207-839-3

Gmelin Reference

773828

KEGG

C17601^Y

MeSH

butenolide

PubChem CID

10341

UNII

8KXK25H388^Y

CompTox Dashboard (EPA)

DTXSID7075422

InChI

InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2^Y
Key: VIHAEDVKXSOUAT-UHFFFAOYSA-N^Y
InChI=1/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
Key: VIHAEDVKXSOUAT-UHFFFAOYAD

SMILES

O=C\1OC/C=C/1

Properties

C₄H₄O₂

84.07336

1.185 g/cm³, liquid

4 to 5 °C (39 to 41 °F; 277 to 278 K)^[1]

Boiling point

86 to 87 °C (187 to 189 °F; 359 to 360 K) 12 mm Hg^[1]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ^YN ?)

Infobox references

2-Furanone is a heterocyclic organic compound. It is also known as γ-crotonolactone (GCL), as it is formally the lactone derived from γ-hydroxyisocrotonic acid. The chemical is colloquially called "butenolide", and is the parent structure for the butenolide class of compounds. It is a colourless liquid.

Synthesis and reactions

2-Furanone is prepared by oxidation of furfural:^[2]

It exists in equilibrium with the tautomer 2-hydroxyfuran, which serves as an intermediate in the interconversion between the β- and α-furanones.^{[further explanation needed]} The β form is the more stable. The interconversion is catalyzed by base.

2-Furanones can be converted to furans by a two-step process of reduction followed by dehydration.

Furanone is thought to contribute to the unique taste of Maple syrup.

References

^ ^a ^b Sigma-Aldrich Chemicals Product detail
^ Näsman, Jan H. (1990). "3-Methyl-2(5H)-furanone". Organic Syntheses. 68: 162. doi:10.15227/orgsyn.068.0162.

GHB receptor modulators

Receptor
(ligands)

GHBR

Agonists: Main site: 1,4-BD
3-HPA
Aceburic acid (GHB acetate)
BDDA (DABD)
EAB
GBL
GCL
GHB
GHBAL
GHV (4-methyl-GHB)
GVL
HOCHCA
HOCPCA
MAB
NCS-356
NCS-435
Sodium oxybate
T-HCA (GHC)
THF
UMB58
UMB66
UMB68
UMB72
UMB73
UMB86; Positive allosteric modulators: (+)-Catechin
Monastrol

Antagonists: Main site: Gabazine (SR-95531)
NCS-382

Unknown/unsorted: Main site: 2-HPA
3-Methyl-GHB
3-Methyl-THCA
4-Benzyl-GHB
4-HPBA
4-Methyl-THCA
4-Phenyl-GHB
4-Phenyl-THCA
Amisulpride
azido-BnOPh-GHB
BnOPh-GHB
DHV
DVL
GTBL
Levosulpiride
NCS-400
Prochlorperazine
Sulpiride
Sultopride
UMB108
UMB109
UMB119

GABA_B

See here instead.

Transporter
(blockers)

MCTsTooltip Monocarboxylate transporters	α-Ketoisocaproate Acetoacetic acid AR-C155858 Atorvastatin Benzoic acid BHB Butyric acid CHCA DBDS DIDS Hexanoic acid Lactic acid Luteolin Niflumic acid NPPB Phenylpyruvic acid Phloretin Probenecid Pyruvic acid Quercetin Salicylic acid Simvastatin Sodium valproate Valproic acid
SMCTsTooltip Sodium-coupled monocarboxylate transporters	Benzoic acid BHB Butyric acid Fenoprofen Ibuprofen Ketoprofen Mesalazine (5-ASA) Naproxen Nicotinic acid Probenecid Propionic acid Pyruvic acid Salicyclic acid
VIATTTooltip Vesicular inhibitory amino acid transporter	β-Alanine Bafilomycin A1 Butyric acid Evans blue GABA Glycine Nigericin Nipecotic acid Valinomycin Vigabatrin

Enzyme
(inhibitors)

SSRTooltip Succinic semialdehyde reductase	Quercetin
GHBDHTooltip 4-Hydroxybutyrate dehydrogenase	α-Ketoisocaproic acid Ethosuximide Phenylacetate Salicylic acid Valproic acid Enhancers: D-Glucuronic acid
HOTTooltip Hydroxyacid-oxoacid transhydrogenase	Cyanide Phenanthroline
ADHTooltip Alcohol dehydrogenase	Cimetidine Ethanol Fomepizole (4-methylpyrazole) Pyrazole
ALDHTooltip Aldehyde dehydrogenase	Acetaldehyde Cimetidine Cyanamide Disulfiram Prunetin

See also: Receptor/signaling modulators; GABA receptor modulators; Glutamate receptor modulators; Glycine receptor modulators

Categories:

Hidden categories:

Synthesis and reactions

See also

References