4-hydroxy-6-methyl-2-pyrone

4H-pyran-4-one, 2-hydroxy-6-methyl-

CAS: 675-10-5 C6 H6 O3 MW: 126.11142000

Identification

Name4-hydroxy-6-methyl-2-pyrone
IUPAC4-hydroxy-6-methylpyran-2-one
CAS Number675-10-5
EINECS211-619-2
FDA UNIIS1S883S4EE
Molecular FormulaC6 H6 O3
Molecular Weight126.11142000
MDL NumberMFCD00006641
Nikkaji NumberJ86H
Beilstein0113815

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 SDSView
Oral/Parenteral ToxicityNot determined
Dermal Toxicitysubcutaneous-mouse LD50 3200 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryinformation only not used for fragrances or flavors
Recommendation for 4-hydroxy-6-methyl-2-pyrone usage levels up tonot for fragrance use.
Recommendation for 4-hydroxy-6-methyl-2-pyrone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

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.