2(5H)-FURANONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H4O2
Molecular Weight	84.0734
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1OCC=C1

InChI

InChIKey=VIHAEDVKXSOUAT-UHFFFAOYSA-N

InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2

HIDE SMILES / InChI

Molecular Formula	C4H4O2
Molecular Weight	84.0734
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Furanones as potential anti-bacterial coatings on biomaterials.	2004-09	15109862
(5Z)-4-bromo-5-(bromomethylene)-3-butyl-2(5H)-furanone reduces corrosion from Desulfotomaculum orientis.	2004-05	15049927
Total synthesis of the nonadjacently linked bis-tetrahydrofuran acetogenin bullatanocin (squamostatin C).	2004-04-30	15104456
Highly efficient and diastereoselective synthesis of (+)-lineatin.	2004-04-29	15101764
New beta-caryophyllene-derived terpenoids from the soft coral Sinularia nanolobata.	2004-04	15104488
Development of novel chiral urea catalysts for the hetero-Michael reaction.	2004-04	15056971
Butenolides from a cultured microfungus, Acremonium sp.	2004-04	14984081
Synthesis and inhibitory action of novel acetogenin mimics with bovine heart mitochondrial complex I.	2004-03-30	15035635
Stereoselective approach to C-aryl pyranoside synthesis which addresses the problem of C7-substitution in blepharocalyxin E.	2004-03-19	15058975
Abilities of 3,4-diarylfuran-2-one analogs of combretastatin A-4 to inhibit both proliferation of tumor cell lines and growth of relevant tumors in nude mice.	2004-03-16	15015595
Further insights on the structural aspects of PLA(2) inhibition by gamma-hydroxybutenolide-containing natural products: a comparative study on petrosaspongiolides M-R.	2004-03-15	15018920
Synthesis of gamma,delta-unsaturated and delta,epsilon-unsaturated alpha-amino acids from fragmentation of gamma- and delta-lactones.	2004-02-06	14750809
Lambertellols A and B, novel 3,4-dihydronaphthalen-1(2H)-ones with spiro-butenolide produced by Lambertella sp.1346.	2004-01-22	14723517
Analysis of Fusarium graminearum mycotoxins in different biological matrices by LC/MS.	2004-01	15008354
Plakolide A, a new gamma-lactone from the marine sponge Plakortis sp.	2004-01	14738400
Synthesis and supramolecular properties of conformationally restricted and flexible phospholipids.	2003-12-26	14682702
Synthesis of the cyclobutanone core of solanoeclepin A intramolecular allene butenolide photocycloaddition.	2003-12-21	14685306
Effect of cyclooxygenase-2 (COX-2) inhibitors on prostate cancer cell proliferation.	2003-12-12	14666698
Hydroperoxide and endoperoxide lactones from photooxygenation of 3-alkylidenedihydrofuran-2,4-diones.	2003-12-12	14656117
Novel alpha-pyrones produced by a marine Pseudomonas sp. F92S91: taxonomy and biological activities.	2003-12	15015731
Alpha-pyrones and a 2(5H)-furanone from Hyptis pectinata.	2003-12	14599529
Enantioselective synthesis of bicyclo[6.1.0]nonane-9-carboxylic acids via Me2AlOTf-promoted intramolecular Friedel-Crafts alkylation of arenes with the gamma-lactone moiety of 3-oxabicyclo[3.1.0]hexan-2-ones.	2003-11-28	14629177
Inhibitory effects on mitochondrial complex I of semisynthetic mono-tetrahydrofuran acetogenin derivatives.	2003-11-17	14592516
Enhancement of the antiplasmodial activity of quassin by transformation into a gamma-lactone.	2003-11	14640524
Physiological significance of 2-buten-4-olide (2-B4O), an endogenous satiety substance increased in the fasted state.	2003-11	14610253
Design, synthesis, and anticancer activity of phosphonic acid diphosphate derivative of adenine-containing butenolide and its water-soluble derivatives of paclitaxel with high antitumor activity.	2003-10-01	13129566
Synthesis and evaluation of 5-arylated 2(5H)-furanones and 2-arylated pyridazin-3(2H)-ones as anti-cancer agents.	2003-09	14604469
New monascus metabolites with a pyridine structure in red fermented rice.	2003-08-27	12926903
Novel autoxidation and Michael addition of a butenolide-containing sugar leading to a C-branched-chain glucopyranosidulose, and X-ray structure of intermediates.	2003-08-12	12892940
Attenuation of Pseudomonas aeruginosa virulence by quorum sensing inhibitors.	2003-08-01	12881415
Iridoids from Kigelia pinnata DC. fruits.	2003-08	12895535
Synthesis and inhibitory activity of ubiquinone-acetogenin hybrid inhibitor with bovine mitochondrial complex I.	2003-07-21	12824040
A GaCl3-catalyzed [4+1] cycloaddition of alpha,beta-unsaturated carbonyl compounds and isocyanides leading to unsaturated gamma-lactone derivatives.	2003-07-02	12822994
A cytotoxic butenolide, two new dolabellane diterpenoids, a chroman and a benzoquinol derivative formosan Casearia membranacea.	2003-07	12898426
New taxane diterpenoids from Taiwanese Taxus sumatrana.	2003-07	12843599
Isolation and characterization of kallosin A, a novel rearranged pseudopterane diterpenoid from the Caribbean sea plume Pseudopterogorgia kallos (Bielschowsky).	2003-06-13	12790615
First asymmetric synthesis of (-)-lintetralin via intramolecular Friedel-Crafts-type cyclization.	2003-06	12774291
Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of alpha-hydroxy epoxides.	2003-05-30	12762747
Inhibitory activities of three annonaceous acetogenins on NADH oxidase of chicken liver mitochondria.	2003-05	12736522
Total synthesis of a cytotoxic acetogenin, pyranicin.	2003-04-17	12688757
Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes.	2003-04-04	12658646
Synthetic studies on himbacine, a potent antagonist of the muscarinic M2 subtype receptor. Part 2: synthesis and muscarinic M2 subtype antagonistic activity of the novel himbacine congeners modified at the C-3 position of lactone moiety.	2003-04-03	12628644
C2-Symmetric enantiopure ethanotethered bis(alpha,beta-butenolides) as templates for asymmetric synthesis. Application to the synthesis of (+)-grandisol.	2003-03-21	12636414
Palladium catalyzed kinetic and dynamic kinetic asymmetric transformations of gamma-acyloxybutenolides. Enantioselective total synthesis of (+)-Aflatoxin B1 and B2a.	2003-03-12	12617676
Efficient desymmetrization of "pseudo"-C2-symmetric substrates: illustration in the synthesis of a disubstituted butenolide from arabitol.	2003-03-07	12608797
Total synthesis and structure confirmation of the annonaceous acetogenins 30(S)-hydroxybullatacin, uvarigrandin a, and 5(R)-uvarigrandin a (narumicin I?).	2003-03-07	12608791
A modular synthesis of annonaceous acetogenins.	2003-03-07	12608790
Two novel ravenelones from the edible mushroom Pulveroboletus ravenelii.	2003-03	12612423
In vitro antitumor structure-activity relationships of threo/trans/threo mono-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex I.	2003	14760863
NMR determination of absolute configuration of butenolides of annonaceous type.	2002-12-16	12693047

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:35:01 GMT 2025` Edited by `admin` on `Mon Mar 31 19:35:01 GMT 2025`
Record UNII	8KXK25H388
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FEMA NO. 4138

Preferred Name

English

2(5H)-FURANONE

Systematic Name

English

2,5-DIHYDROFURANONE

Systematic Name

English

CRATONE

Common Name

English

2-OXO-2,5-DIHYDROFURAN

Systematic Name

English

4-HYDROXY-2-BUTENOIC ACID .GAMMA.-LACTONE [FHFI]

Common Name

English

.BETA.-CROTONOLACTONE

Common Name

English

4-HYDROXY-2-BUTENOIC ACID LACTONE

Common Name

English

5-OXO-2,5-DIHYDROFURAN-3-YL ESTER

Common Name

English

CROTONIC ACID, 4-HYDROXY-, .GAMMA.-LACTONE

Common Name

English

NSC-197009

Code

English

2-BUTEN-4-OLIDE

Common Name

English

2-BUTENOIC ACID, 4-HYDROXY-, .GAMMA.-LACTONE

Common Name

English

ISOCROTONOLACTONE

Common Name

English

.DELTA.,.ALPHA.,.BETA.-BUTENOLIDE

Common Name

English

Code System Code Type Description

WIKIPEDIA

2-Furanone