4-hydroxy-6-methyl-2-pyrone
4H-pyran-4-one, 2-hydroxy-6-methyl-
Identification
| Name | 4-hydroxy-6-methyl-2-pyrone |
| IUPAC | 4-hydroxy-6-methylpyran-2-one |
| CAS Number | 675-10-5 |
| EINECS | 211-619-2 |
| FDA UNII | S1S883S4EE |
| Molecular Formula | C6 H6 O3 |
| Molecular Weight | 126.11142000 |
| MDL Number | MFCD00006641 |
| Nikkaji Number | J86H |
| Beilstein | 0113815 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 2.996e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | subcutaneous-mouse LD50 3200 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for 4-hydroxy-6-methyl-2-pyrone usage levels up to | not for fragrance use. |
| Recommendation for 4-hydroxy-6-methyl-2-pyrone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4-
hydroxy-6-methyl-2H-pyran-2-one
2-
hydroxy-6-methyl-4H-pyran-4-one
hydroxy-6-methylpyran-2-one
4H-
pyran-4-one, 2-hydroxy-6-methyl-
triacetic acid lactone
PubMed:
Triacetic acid lactone production in industrial Saccharomyces yeast strains.
PubMed:
Mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase deficiency: urinary organic acid profiles and expanded spectrum of mutations.
PubMed:
Engineering catalyst microenvironments for metal-catalyzed hydrogenation of biologically derived platform chemicals.
PubMed:
Metabolic engineering of Saccharomyces cerevisiae for the production of triacetic acid lactone.
PubMed:
k-OptForce: integrating kinetics with flux balance analysis for strain design.
PubMed:
Screening for enhanced triacetic acid lactone production by recombinant Escherichia coli expressing a designed triacetic acid lactone reporter.
PubMed:
Mechanistic insights into ring-opening and decarboxylation of 2-pyrones in liquid water and tetrahydrofuran.
PubMed:
Polyketide derivatives active against Botrytis cinerea in Gerbera hybrida.
PubMed:
Synthesis and biological evaluation of (+/-)-dinemasone C and analogues.
PubMed:
Synthesis and in-vitro cytotoxic evaluation of novel pyridazin-4-one derivatives.
PubMed:
Crystallization and preliminary X-ray diffraction studies of polyketide synthase-1 (PKS-1) from Cannabis sativa.
PubMed:
Convenient replacement of the hydroxy by an amino group in 4 hydroxycoumarin and 4-hydroxy-6-methyl-2-pyrone under microwave irradiation.
PubMed:
Active site residues governing substrate selectivity and polyketide chain length in aloesone synthase.
PubMed:
Microbial synthesis of triacetic acid lactone.
PubMed:
A unique highly oxygenated pyrano[4,3-c][2]benzopyran-1,6-dione derivative with antioxidant and cytotoxic activities from the fungus Phellinus igniarius.
PubMed:
Rational pathway engineering of type I fatty acid synthase allows the biosynthesis of triacetic acid lactone from D-glucose in vivo.
PubMed:
Direct asymmetric Michael reactions of cyclic 1,3-dicarbonyl compounds and enamines catalyzed by chiral bisoxazoline-copper(II) complexes.
PubMed:
Aromatic and pyrone polyketides synthesized by a stilbene synthase from Rheum tataricum.
PubMed:
Deoxygenation of polyhydroxybenzenes: an alternative strategy for the benzene-free synthesis of aromatic chemicals.
PubMed:
Pyrone and pyridone compounds in the liquid culture of Physisporinus sanguinolentus.
PubMed:
Tolerance and specificity of recombinant 6-methylsalicyclic acid synthase.
PubMed:
A facile and convenient synthesis of 3-alkylamino-5-arylthiophenes with a variety of substituents at C-2 and studies of reaction mechanisms
PubMed:
Effect of NADPH-associated keto-reducing domain on substrate entry into 6-hydroxymellein synthase, a multifunctional polyketide synthetic enzyme involved in phytoalexin biosynthesis in carrot.
PubMed:
Dissociation of dimeric 6-hydroxymellein synthase, a polyketide biosynthetic enzyme in carrot cell extracts, with loss of keto-reducing activity.
PubMed:
Purification and properties of 6-methylsalicylic acid synthase from Penicillium patulum.
PubMed:
Derailment product in NADPH-dependent synthesis of a dihydroisocoumarin 6-hydroxymellein by elicitor-treated carrot cell extracts.
PubMed:
Decarboxylation of malonyl-CoA by lactating bovine mammary fatty acid synthase.
PubMed:
Evidence that the coenzyme A requirement for avian fatty acid synthase is not for the termination reaction.
PubMed:
Synthesis of acetoacetyl-CoA by bovine mammary fatty acid synthase.
PubMed:
Kinetic analysis of the malonyl coenzyme A decarboxylation and the condensation reaction of fatty acid synthesis. Application to the study of malonyl coenzyme A inactivated chicken liver fatty acid synthetase.
PubMed:
Irreversible inactivation of chicken liver fatty acid synthetase by its substrates acetyl and malonyl CoA. Effect of temperature and NADP n fatty acid and triacetic acid lactone synthesis.
PubMed:
Fatty acid synthetase. A steady state kinetic analysis of the reaction catalyzed by the enzyme from pigeon liver.
PubMed:
Further characterization and cellular localization of an ATP: triacetic acid lactone lyase in pigeon liver.
PubMed:
ATP-dependent enzymic splitting of mesitene lactone and triacetic acid lactone.
PubMed:
Triacetic acid lactone, a derailment product of fatty acid biosynthesis.
PubMed:
Synthesis of triacetic acid lactone by the pigeon liver fatty acid synthetase complex.
PubMed:
The isolation of triacetic acid lactone from cultures of Penicillium patulum.
PubMed:
Enzymatic degradation of triacetic acid lactone determined by a spectrophotometric method.