Cyclopentanone

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H8O
Molecular Weight	84.1164
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1CCCC1

InChI

InChIKey=BGTOWKSIORTVQH-UHFFFAOYSA-N

InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2

HIDE SMILES / InChI

Molecular Formula	C5H8O
Molecular Weight	84.1164
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
Induction of heme oxygenase-1 expression in murine macrophages is essential for the anti-inflammatory effect of low dose 15-deoxy-Delta 12,14-prostaglandin J2.	2003-05-23	12642589
Oxidative stress causes ERK phosphorylation and cell death in cultured retinal pigment epithelium: prevention of cell death by AG126 and 15-deoxy-delta 12, 14-PGJ2.	2003-03-21	12659653
Cloning of Baeyer-Villiger monooxygenases from Comamonas, Xanthobacter and Rhodococcus using polymerase chain reaction with highly degenerate primers.	2003-03	12588297
Prostaglandin J2 metabolites inhibit aromatase activity by redox-sensitive mechanisms: potential implications for breast cancer therapy.	2003-02-20	12494466
Total synthesis of (+)-4,5-deoxyneodolabelline.	2003-02-19	12580611
Group 6 heteroatom- and non-heteroatom-stabilized carbene complexes. beta,beta'- and alpha,beta,beta'-annulation reactions of cyclic enamines.	2003-02-19	12580610
Biosynthesis of 14,15-dehydro-12-oxo-phytodienoic acid and related cyclopentenones via the phytoprostane D(1) pathway.	2003-02	12620348
The cyclopentenone prostaglandin 15-deoxy-delta(12,14)- PGJ2 attenuates the development of colon injury caused by dinitrobenzene sulphonic acid in the rat.	2003-02	12598422
Electrophilic prostaglandins and lipid aldehydes repress redox-sensitive transcription factors p53 and hypoxia-inducible factor by impairing the selenoprotein thioredoxin reductase.	2003-01-10	12424231
15-PGJ2, but not thiazolidinediones, inhibits cell growth, induces apoptosis, and causes downregulation of Stat3 in human oral SCCa cells.	2002-12-02	12454768
[Cyclopentenone prostaglandin derivatives as neuroprotective compounds].	2002-12	12486935
Prostaglandin A1 inhibits rotenone-induced apoptosis in SH-SY5Y cells.	2002-12	12437580
Role of structure and pH in cyclization of allene oxide fatty acids: implications for the reaction mechanism.	2002-12	12426078
Dual effect of oxidative stress on NF-kappakB activation in HeLa cells.	2002-11-30	12526096
Identification of a jasmonate-regulated allene oxide synthase that metabolizes 9-hydroperoxides of linoleic and linolenic acids.	2002-11-29	12351632
Tandem cyclization-cycloaddition behavior of rhodium carbenoids with carbonyl compounds: stereoselective studies on the construction of novel epoxy-bridged tetrahydropyranone frameworks.	2002-11-15	12423129
Contribution of covalent protein modification to the antiinflammatory effects of cyclopentenone prostaglandins.	2002-11	12485923
15-Deoxy-delta12,14-prostaglandin J2-induced apoptosis does not require PPARgamma in breast cancer cells.	2002-11	12401880
Synthesis and cytotoxicity of some rigid derivatives of methyl 2,5-dihydroxycinnamate.	2002-10	12433188
TX-1123: an antitumor 2-hydroxyarylidene-4-cyclopentene-1,3-dione as a protein tyrosine kinase inhibitor having low mitochondrial toxicity.	2002-10	12150871
Formation of highly reactive A-ring and J-ring isoprostane-like compounds (A4/J4-neuroprostanes) in vivo from docosahexaenoic acid.	2002-09-27	12133837
Human colorectal cancer cells efficiently conjugate the cyclopentenone prostaglandin, prostaglandin J(2), to glutathione.	2002-09-05	12213491
Translational regulation of cyclin D1 by 15-deoxy-delta(12,14)-prostaglandin J(2).	2002-09	12354750
15-deoxy-delta12,14-Prostaglandin J2 inhibits tissue factor expression in human macrophages and endothelial cells: evidence for ERK1/2 signaling pathway blockade.	2002-09	12353085
The cyclopentenone product of lipid peroxidation, 15-A(2t)-isoprostane (8-isoprostaglandin A(2)), is efficiently conjugated with glutathione by human and rat glutathione transferase A4-4.	2002-09	12230403
Cyclopentenone prostaglandins induce caspase activation and apoptosis in dendritic cells by a PPAR-gamma-independent mechanism: regulation by inflammatory and T cell-derived stimuli.	2002-09	12225793
Asymmetric cyclopentannelation: camphor-derived auxiliary.	2002-08-28	12188673
A novel approach to the synthesis of bicyclic lactones via an interrupted Nazarov reaction of gem-divinyl dihydrofurans.	2002-08-22	12182564
In vitro co-metabolism of ethanol and cyclic ketones.	2002-08-15	12135624
TiCl(4)-promoted Baylis-Hillman reactions of substituted 5-isoxazolecarboxaldehydes with cycloalkenones).	2002-08-09	12153281
Development of a new and practical route to chiral 3,4-disubstituted cyclopentanones: asymmetric alkylation and intramolecular cyclopropanation as key C-C bond-forming steps.	2002-08-09	12153248
Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues.	2002-08-05	12113817
Cyclopentenone prostaglandin receptors.	2002-08	12432947
Allene oxide synthases and allene oxides.	2002-08	12432934
Synthesis of 2-indanones via [4 + 1] annulation reactions of (trialkylsilyl)arylketenes.	2002-07-25	12123352
Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size.	2002-07	12087064
Enantioselective synthesis of 12-amino alkylidenecyclopentenone prostaglandins.	2002-06-28	12076134
First total synthesis of A(2) isoprostane.	2002-06-14	12054973
Effect of adjacent chiral tertiary and quaternary centers on the metal-catalyzed allylic substitution reaction.	2002-05-31	12027695
Cobalt-phosphite-catalyzed asymmetric Pauson-Khand reaction.	2002-05-17	12003551
Development of an enantioselective synthetic route to neocarzinostatin chromophore and its use for multiple radioisotopic incorporation.	2002-05-15	11996579
A proinflammatory role for the cyclopentenone prostaglandins at low micromolar concentrations: oxidative stress-induced extracellular signal-regulated kinase activation without NF-kappa B inhibition.	2002-05-15	11994490
Products of the isoprostane pathway: unique bioactive compounds and markers of lipid peroxidation.	2002-05	12088281
Fatty acid-derived signals in plants.	2002-05	11992827
The cyclopentenone prostaglandin 15-deoxy-Delta(12,14)-prostaglandin J(2) attenuates the development of acute and chronic inflammation.	2002-05	11961117
Volatile metabolites from actinomycetes.	2002-04-24	11958631
Cyclopentenone causes cell cycle arrest and represses cyclin D1 promoter activity in MCF-7 breast cancer cells.	2002-03-28	11948404
A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst.	2002-01-18	12491425
Synthesis and antituberculosis activity of cycloalkylidenehydrazide and 4-aza-1-thiaspiro[4.5]decan-3-one derivatives of imidazo[2,1-b]thiazole.	2002	12189781
Roles of prostaglandins and leukotrienes in acute inflammation caused by bacterial infection.	2001-06	11964841

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:57:40 GMT 2025` Edited by `admin` on `Mon Mar 31 18:57:40 GMT 2025`
Record UNII	220W81TN3S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Cyclopentanone

Systematic Name

English

FEMA NO. 3910

Preferred Name

English

NSC-4122

Code

English

ADIPIN KETON

Common Name

English

CYCLOPENTANONE [HSDB]

Common Name

English

CYCLOPENTANONE [MI]

Common Name

English

ADIPIC KETONE

Common Name

English

KETOPENTAMETHYLENE

Common Name

English

DUMASIN

Common Name

English

KETOCYCLOPENTANE

Systematic Name

English

CYCLOPENTANONE [FHFI]

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

CYCLOPENTANONE