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4-Hydroxy-6-methyl-2-pyrone Sale

(Synonyms: 4-羟基-6-甲基-2-吡喃酮) 目录号 : GC41375

A fungal metabolite

4-Hydroxy-6-methyl-2-pyrone Chemical Structure

Cas No.:675-10-5

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5mg
¥668.00
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25mg
¥2,673.00
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产品描述

4-Hydroxy-6-methyl-2-pyrone is a fungal metabolite that has been isolated from H. investians.

Chemical Properties

Cas No. 675-10-5 SDF
别名 4-羟基-6-甲基-2-吡喃酮
Canonical SMILES O=C1OC(C)=CC(O)=C1
分子式 C6H6O3 分子量 126.1
溶解度 DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:10): 0.09 mg/ml,Ethanol: 20 mg/ml 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 7.9302 mL 39.6511 mL 79.3021 mL
5 mM 1.586 mL 7.9302 mL 15.8604 mL
10 mM 0.793 mL 3.9651 mL 7.9302 mL
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Research Update

Biosynthesis of phlorisovalerophenone and 4-hydroxy-6-isobutyl-2-pyrone in Escherichia coli from glucose

Microb Cell Fact 2016 Aug 30;15(1):149.PMID:27577056DOI:10.1186/s12934-016-0549-9.

Background: Type III polyketide synthases (PKSs) contribute to the synthesis of many economically important natural products, which are typically produced by direct extraction from plants or synthesized chemically. For example, humulone and lupulone (Fig. 1a) in hops (Humulus lupulus) account for the characteristic bitter taste of beer and display multiple pharmacological effects. 4-Hydroxy-6-methyl-2-pyrone is a precursor of parasorboside contributing to insect and disease resistance of plant Gerbera hybrida, and was recently demonstrated to be a potential platform chemical. Fig. 1 Examples of phloroglucinols (a) and 2-pyrones (b) synthesized by type III PKS. PIBP phlorisobutyrophenone; PIVP phlorisovalerophenone; TAL 4-Hydroxy-6-methyl-2-pyrone (triacetic acid lactone); HIPP 4-hydroxy-6-isopropyl-2-pyrone; HIBP 4-hydroxy-6-isobutyl-2-pyrone Results: In this study, we achieved simultaneous biosynthesis of phlorisovalerophenone, a key intermediate of humulone biosynthesis and 4-hydroxy-6-isobutyl-2-pyrone in Escherichia coli from glucose. First, we constructed a biosynthetic pathway of isovaleryl-CoA via hydroxy-3-methylglutaryl CoA followed by dehydration, decarboxylation and reduction in E. coli. Subsequently, the type III PKSs valerophenone synthase or chalcone synthase from plants were introduced into the above E. coli strain, to produce phlorisovalerophenone and 4-hydroxy-6-isobutyl-2-pyrone at the highest titers of 6.4 or 66.5 mg/L, respectively. Conclusions: The report of biosynthesis of phlorisovalerophenone and 4-hydroxy-6-isobutyl-2-pyrone in E. coli adds a new example to the list of valuable compounds synthesized in E. coli from renewable carbon resources by type III PKSs.

tert-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1 H)-ones with 4-hydroxycoumarins, 4-Hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions

Org Biomol Chem 2020 Aug 26;18(33):6537-6548.PMID:32789325DOI:10.1039/d0ob01304h.

We report an efficient and atom-economical method of C-3 functionalization of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-Hydroxy-6-methyl-2-pyrone, and 2-hydroxy-1,4-naphthoquinone via the free radical cross-coupling pathway under metal-free conditions. tert-Butylhydroperoxide (TBHP) smoothly promotes the reaction furnishing the cross-dehydrogenative coupling (CDC) products in very good to excellent yields. The protocol neither uses any toxic reagents nor metal catalysts to carry out the reaction, and all the products have been obtained without column chromatography purification. Different radical trapping experiments with 2,2,6,6-tetramethylpiperidine-1-oxyl, butylated hydroxytoluene, and diphenyl ethylene confirm the involvement of radicals.

Correction: tert-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-Hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions

Org Biomol Chem 2020 Sep 21;18(35):6965-6966.PMID:32936196DOI:10.1039/d0ob90117b.

Correction for 'tert-Butylhydroperoxide (TBHP) mediated oxidative cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with 4-hydroxycoumarins, 4-Hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone under metal-free conditions' by Suraj Sharma et al., Org. Biomol. Chem., 2020, 18, 6537-6548, DOI: .

Convenient replacement of the hydroxy by an amino group in 4 hydroxycoumarin and 4-Hydroxy-6-methyl-2-pyrone under microwave irradiation

Molecules 2004 Jul 31;9(8):627-31.PMID:18007464DOI:10.3390/90800627.

The reaction of 4-hydroxycoumarin (1) with some primary amines 2a-h and morpholine (2i) under microwave irradiation occurred without opening of the lactone ring to give N-substituted 4-aminocoumarins 3a-i in excellent yields. Under the same experimental conditions, 4-Hydroxy-6-methyl-2-pyrone (4) reacted with benzylamine (2e) or 2-phenyl- ethylamine (2f) to give the corresponding N,N'-disubstituted 4-amino-6-methyl-2-pyridones 5e,f. The main advantages of this procedure are dramatically shortened reaction times, higher amine utilization and considerably improved yields.

Mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase deficiency: urinary organic acid profiles and expanded spectrum of mutations

J Inherit Metab Dis 2015 May;38(3):459-66.PMID:25511235DOI:10.1007/s10545-014-9801-9.

Mitochondrial 3-hydroxy-3-methylglutaryl CoA synthase (HMCS2) deficiency results in episodes of hypoglycemia and increases in fatty acid metabolites. Metabolite abnormalities described to date in HMCS2 deficiency are nonspecific and overlap with other inborn errors of metabolism, making the biochemical diagnosis of HMCS2 deficiency difficult. Urinary organic acid profiles from periods of metabolic decompensation were studied in detail in HMCS2-deficient patients from four families. An additional six unrelated patients were identified from clinical presentation and/or qualitative identification of abnormal organic acids. The diagnosis was confirmed by sequencing and deletion/duplication analysis of the HMGCS2 gene. Seven related novel organic acids were identified in urine profiles. Five of them (3,5-dihydroxyhexanoic 1,5 lactone; trans-5-hydroxyhex-2-enoate; 4-Hydroxy-6-methyl-2-pyrone; 5-hydroxy-3-ketohexanoate; 3,5-dihydroxyhexanoate) were identified by comparison with synthesized or commercial authentic compounds. We provisionally identified trans-3-hydroxyhex-4-enoate and 3-hydroxy-5-ketohexanoate by their mass spectral characteristics. These metabolites were found in samples taken during periods of decompensation and normalized when patients recovered. When cutoffs of adipic >200 and 4-Hydroxy-6-methyl-2-pyrone >20 μmol/mmol creatinine were applied, all eight samples taken from five HMCS2-deficient patients during episodes of decompensation were flagged with a positive predictive value of 80% (95% confidence interval 35-100%). Some ketotic patients had increased 4-Hydroxy-6-methyl-2-pyrone. Molecular studies identified a total of 12 novel mutations, including a large deletion of HMGCS2 exon 1 in two families, highlighting the need to perform quantitative gene analyses. There are now 26 known HMGCS2 mutations, which are reviewed in the text. 4-Hydroxy-6-methyl-2-pyrone and related metabolites are markers for HMCS2 deficiency. Detection of these metabolites will streamline the biochemical diagnosis of this disorder.