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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O3
Molecular Weight 126.11
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXY-6-METHYL-2-PYRONE

SMILES

CC1=CC(O)=CC(=O)O1

InChI

InChIKey=NSYSSMYQPLSPOD-UHFFFAOYSA-N
InChI=1S/C6H6O3/c1-4-2-5(7)3-6(8)9-4/h2-3,7H,1H3

HIDE SMILES / InChI

Molecular Formula C6H6O3
Molecular Weight 126.11
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18007464 | https://www.ncbi.nlm.nih.gov/pubmed/15844878

4-Hydroxy-6-methyl-2-pyrone (also known as triacetic acid lactone) is a precursor of paragloboside contributing to insect and disease resistance of plant Gerbera hybrida and was recently demonstrated to be a potential platform chemical. 4-Hydroxy-6-methyl-2-pyrone is an isolated from the fungus, Hypoxylon investing, in 2014 which has not been extensively investigated for pharmacological activity. 4-Hydroxy-6-methyl-2-pyrone is a useful metabolite for analytical and bioassay dereplication of crude microbial extracts.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.3 mM [Ki]
3.1 mM [Ki]
8.1 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
3,4,6-Trimethyl-1-phenyl-1H-pyrazolo-[3,4-b]pyridine.
2010-07-10
Synthesis and in-vitro cytotoxic evaluation of novel pyridazin-4-one derivatives.
2010-05
Tricyclic pyrone compounds prevent aggregation and reverse cellular phenotypes caused by expression of mutant huntingtin protein in striatal neurons.
2009-07-08
Diastereoselective synthesis of polycyclic acetal-fused pyrano[3,2-c]pyran-5(2H)-one derivatives.
2009-03-06
A unique highly oxygenated pyrano[4,3-c][2]benzopyran-1,6-dione derivative with antioxidant and cytotoxic activities from the fungus Phellinus igniarius.
2005-04-28
Convenient replacement of the hydroxy by an amino group in 4 hydroxycoumarin and 4-hydroxy-6-methyl-2-pyrone under microwave irradiation.
2004-07-31
Direct asymmetric Michael reactions of cyclic 1,3-dicarbonyl compounds and enamines catalyzed by chiral bisoxazoline-copper(II) complexes.
2003-06-27
Gas chromatography/mass spectrometric characterisation of pyrolysis/silylation products of glucose and cellulose.
2002
Syntheses and biological activities of pyranyl-substituted cinnamates.
2001-01
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Mouse macrophage cell line (RAW 264.7) was obtained from Bioresource Collection and Research Center (BCRC 60001) and cultured at 37C in Dulbecco’s Modified Eagle’s Medium (DMEM) supplemented with 10% fetal bovine serum (FBS; Gibco), 4.5 g/l glucose, 4 mm glutamine, penicillin (100 units/ml), and streptomycin (100 mg/ml) in a humidified atmosphere in a 5% CO2 incubator. The cells were treated with 10, 25, and 50 mm natural products (4-Hydroxy-6-methyl-2-pyrone) in the presence of 1 mg/ml LPS (Sigma Aldrich) for 20 h. The concentration of NO in culture supernatants was determined as nitrite, a major stable product of NO, by Griess reagent assay, and cell viabilities were determined using the MTT assay. Levels of IL-6 production were measured in cell culture supernatants with a Mouse IL-6 ELISA Ready-SET-Go ELISA kit (eBiosciencee) according to the manufacturer’s recommendations and quantified with a microplate reader (m-Quant, Bio-Tek Instruments Inc).
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:31:22 GMT 2025
Edited
by admin
on Mon Mar 31 19:31:22 GMT 2025
Record UNII
S1S883S4EE
Record Status Validated (UNII)
Record Version
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Name Type Language
4-HYDROXY-6-METHYL-2-PYRONE
Systematic Name English
NSC-34625
Preferred Name English
6-METHYL-4-HYDROXY-2-PYRONE
Systematic Name English
4-HYDROXY-6-METHYL-2H-PYRAN-2-ONE
Systematic Name English
4-HYDROXY-6-METHYLPYRAN-2-ONE
Systematic Name English
2H-PYRAN-2-ONE, 4-HYDROXY-6-METHYL-
Systematic Name English
4-HYDROXY-6-METHYL-.ALPHA.-PYRONE
Common Name English
HYDROXY-6-METHYL-2-PYRONE, 4-
Systematic Name English
TRIACETIC ACID LACTONE
Common Name English
SORBIC ACID, 3,5-DIHYDROXY-, .DELTA.-LACTONE
Systematic Name English
Code System Code Type Description
PUBCHEM
54675757
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
PRIMARY
NSC
34625
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
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CHEBI
16458
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
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EPA CompTox
DTXSID1060974
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
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CAS
675-10-5
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
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ECHA (EC/EINECS)
211-619-2
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
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FDA UNII
S1S883S4EE
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
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WIKIPEDIA
Triacetic acid lactone
Created by admin on Mon Mar 31 19:31:22 GMT 2025 , Edited by admin on Mon Mar 31 19:31:22 GMT 2025
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