2H-PYRAN-2-ONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H4O2
Molecular Weight	96.0841
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1OC=CC=C1

InChI

InChIKey=ZPSJGADGUYYRKE-UHFFFAOYSA-N

InChI=1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H

HIDE SMILES / InChI

Molecular Formula	C5H4O2
Molecular Weight	96.0841
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
Novel alpha-pyrones produced by a marine Pseudomonas sp. F92S91: taxonomy and biological activities.	2003 Dec	15015731
Kinetic study of the oxidation of quercetin by mushroom tyrosinase.	2003 Dec 17	14664545
Rhenium-catalyzed coupling of propargyl alcohols and allyl silanes.	2003 Dec 24	14677963
[Studies on flavonoids of Anaphalis sinica].	2003 Jun	15015333
Synthesis and photochemistry of isothiocoumarins fused to an additional pyranone or thiopyranone ring.	2003 Nov	14690238
Studies on K2CO3-catalyzed 1,4-addition of 1,2-allenic ketones with diethyl malonate: controlled selective synthesis of beta,gamma-unsaturated enones and alpha-pyrones.	2003 Nov 14	14604373
Viridepyronone, a new antifungal 6-substituted 2H-pyran-2-one produced by Trichoderma viride.	2003 Nov 19	14611154
Design, synthesis, and biological evaluation of 6-substituted-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones: a novel class of diarylheterocyclic selective cyclooxygenase-2 inhibitors.	2003 Nov 6	14584938
Placidenes C-F, novel alpha-pyrone propionates from the Mediterranean sacoglossan Placida dendritica.	2003 Oct	14575447
Influence of iodide and iodolactones on thyroid apoptosis. Evidence that apoptosis induced by iodide is mediated by iodolactones in intact porcine thyroid follicles.	2003 Sep	14520597
Dietary flavonoids and cancer risk: evidence from human population studies.	2004	15572291
Zooxanthellamide B, a novel large polyhydroxy metabolite from a marine dinoflagellate of Symbiodinium sp.	2004 Apr	15118333
Formal total synthesis of (-)-apicularen A via transannular conjugate addition.	2004 Apr 15	15070319
Inhibition of pancreatic cholesterol esterase reduces cholesterol absorption in the hamster.	2004 Apr 19	15096274
X-ray investigations of bicyclic alpha-methylene-delta-valerolactones. II. (4aS,8aS)-4a-methyl-3-methyleneperhydrochromen-2-one.	2004 Dec	15579977
Furocoumarins in medicinal chemistry. Synthesis, natural occurrence and biological activity.	2004 Dec	15579011
Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton.	2004 Dec 10	15575759
Analysis of anal secretions from phlaeothripine thrips.	2004 Feb	15112732
Four new stilbenoids from the lianas of Gnetum montanum f. megalocarpum.	2004 Feb	14994195
Structure of macrophomate synthase.	2004 Jul	15213379
New beginnings for matrix metalloproteinase inhibitors: identification of high-affinity zinc-binding groups.	2004 Jul 14	15237990
Design, synthesis, and structure-activity relationship studies of 3,4,6-triphenylpyran-2-ones as selective cyclooxygenase-2 inhibitors.	2004 Jul 29	15267236
Interconvertions between delta-lactam and delta-lactone derivatives initiated by unique transannular interactions of the rigid cyclohexane boat structure in pentacycloundecane.	2004 Jul 9	15230619
Stereocontrolled synthesis of the C21-C38 fragment of the unnatural enantiomer of the antibiotic nystatin A1.	2004 Mar 19	15034898
Cytotoxic flavonoids and alpha-pyrones from Cryptocarya obovata.	2004 May	15165150
Facile one-step synthesis of beta-alkoxy lactone via sequential lactonization and 1,4-addition of alkoxide group: total synthesis of all stereoisomers of dihydrokawain-5-ol.	2004 May 14	15132552
Structure-activity relationships of derivatives of fusapyrone, an antifungal metabolite of Fusarium semitectum.	2004 May 19	15137845
(4R,4aR,6S,7S,7aS)-6-Hydroxy-7-hydroxymethyl-4-methylperhydrocyclopenta[c]pyran-1-one chloroform solvate from Valeriana laxiflora.	2004 Nov	15528817
Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation: a one-step synthesis of (S)-(+)-dihydrokawain.	2004 Nov 19	15487027
Precise structural elucidation of dehydroaltenusin, a specific inhibitor of mammalian DNA polymerase alpha.	2004 Oct 15	15388163
The chafer pheromone buibuilactone and ant pyrazines are also produced by marine bacteria.	2005 Apr	16124260
Synthesis of the putative structure of tridachiahydropyrone.	2005 Apr 14	15816757
Stereoselective synthesis of c3-c12 dihydropyran portion of antitumor laulimalide using copper-catalyzed oxonium ylide formation-[2,3] shift.	2005 Aug	16079533
Synthesis of the aglycones of altromycins and kidamycin from a common intermediate.	2005 Aug 18	16092833
A gamma-lactone form nafuredin, nafuredin-gamma, also inhibits helminth complex I.	2005 Jan	15813180
1H chemical shifts in NMR. Part 21--prediction of the 1H chemical shifts of molecules containing the ester group: a modelling and ab initio investigation.	2005 Jan	15390026
Exploiting the reaction flexibility of a type III polyketide synthase through in vitro pathway manipulation.	2005 Jan 12	15631450
Koniamborine, the first pyrano[3,2-b]indole alkaloid and other secondary metabolites from Boronella koniambiensis.	2005 Jul	16038554
Aurovertin E, a new polyene pyrone from the basidiomycete Albatrellus confluens.	2005 Jun	16156519
2-Pyrone natural products and mimetics: isolation, characterisation and biological activity.	2005 Jun	16010346
Macrophomate synthase: QM/MM simulations address the Diels-Alder versus Michael-Aldol reaction mechanism.	2005 Mar 16	15755179
Applications of the amino-Cope rearrangement: synthesis of tetrahydropyran, delta-lactone and piperidine targets.	2005 Mar 7	15731867
Diastereoselective annulation of 4-hydroxypyran-2H-ones with enantiopure 2,3-dideoxy-alpha,beta-unsaturated sugar aldehydes derived from respective glycals.	2005 May 23	15854598
Covalent attachment of the plant natural product naringenin to small glass and ceramic beads.	2005 Oct 10	16216122
Potent, selective pyrone-based inhibitors of stromelysin-1.	2005 Oct 19	16218585
Preclinical pharmacokinetics and metabolism of a novel prototype DNA-PK inhibitor NU7026.	2005 Oct 31	16249792
On the pyrolysis mechanism of 2-pyranones and 2-pyranthiones: thermally induced ground electronic state chemistry of pyran-2-thione.	2005 Sep 16	16149802
Novel and stereocontrolled synthesis of (+/-)-tetrodotoxin from myo-inositol.	2005 Sep 16	16149776
Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models.	2005 Sep-Oct	15882092
Experimental study on the thermal oxidation of 2-chlorophenol in air over the temperature range 450-900 degrees C.	2006 Mar	16213547

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:03:17 GMT 2023` Edited by `admin` on `Fri Dec 15 18:03:17 GMT 2023`
Record UNII	8WW45I202V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2H-PYRAN-2-ONE

Systematic Name

English

Code System Code Type Description

CAS

504-31-4