mucidin
(E,E,E)-2-(methoxymethylene)-3-methyl-6-phenyl-3,5-hexadienoic acid methyl ester
Identification
| Name | mucidin |
| IUPAC | methyl (2E,3Z,5E)-2-(methoxymethylidene)-3-methyl-6-phenylhexa-3,5-dienoate |
| CAS Number | 52110-55-1 |
| FDA UNII | 15143I0275 |
| Molecular Formula | C16 H18 O3 |
| Molecular Weight | 258.31706000 |
| Nikkaji Number | J9.782I |
| XlogP3 | 3.90 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 13.89 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 250 mg/kg |
| Dermal Toxicity | Not determined |
| 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 | natural substances and extractives |
| Recommendation for mucidin usage levels up to | not for fragrance use. |
| Recommendation for mucidin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
3,5-
hexadienoic acid, 2-(methoxymethylene)-3-methyl-6-phenyl-, methyl ester, (2E,3Z,5E)-
(E,E,E)-2-(
methoxymethylene)-3-methyl-6-phenyl-3,5-hexadienoic acid methyl ester
methyl (2E,3Z,5E)-2-(methoxymethylidene)-3-methyl-6-phenylhexa-3,5-dienoate
PubMed:
Strong lethality and teratogenicity of strobilurins on Xenopus tropicalis embryos: Basing on ten agricultural fungicides.
PubMed:
Assessment of strobilurin fungicides' content in soya-based drinks by liquid micro-extraction and liquid chromatography with tandem mass spectrometry.
PubMed:
Aquatic risk assessment of a novel strobilurin fungicide: A microcosm study compared with the species sensitivity distribution approach.
PubMed:
Design, synthesis, and biological activity of oxime ether strobilurin derivatives containing indole moiety as novel fungicide.
PubMed:
Synthesis and fungicidal activities of novel benzothiophene-substituted oxime ether strobilurins.
PubMed:
Chemosensitization of aflatoxigenic fungi to antimycin A and strobilurin using salicylaldehyde, a volatile natural compound targeting cellular antioxidation system.
PubMed:
Differential effects of mitochondrial Complex I inhibitors on production of reactive oxygen species.
PubMed:
Chemosensitization of fungal pathogens to antimicrobial agents using benzo analogs.
PubMed:
Study of Trichoderma viride metabolism under conditions of the restriction of oxidative processes.
PubMed:
A possible site of superoxide generation in the complex I segment of rat heart mitochondria.
PubMed:
Antibiotics in the chemical communication of fungi.
PubMed:
Cross-resistance to strobilurin fungicides in mitochondrial and nuclear mutants of Saccharomyces cerevisiae.
PubMed:
Architecture of the Qo site of the cytochrome bc1 complex probed by superoxide production.
PubMed:
A strobilurin fungicide enhances the resistance of tobacco against tobacco mosaic virus and Pseudomonas syringae pv tabaci.
PubMed:
The strobilurin fungicides.
PubMed:
Isolation and molecular characterization of the carboxy-terminal pdr3 mutants in Saccharomyces cerevisiae.
PubMed:
Role of the PDR gene network in yeast susceptibility to the antifungal antibiotic mucidin.
PubMed:
Use of mutated PDR3 gene as a dominant selectable marker in transformation of prototrophic yeast strains.
PubMed:
Melithiazols, new beta-methoxyacrylate inhibitors of the respiratory chain isolated from myxobacteria. Production, isolation, physico-chemical and biological properties.
PubMed:
Production of antibiotics by Collybia nivalis, Omphalotus olearis, a Favolaschia and a Pterula species on natural substrates.
PubMed:
The molecular basis for the natural resistance of the cytochrome bc1 complex from strobilurin-producing basidiomycetes to center Qp inhibitors.
PubMed:
Biokinetic properties of BAS 490 F and some related compounds.
PubMed:
Species dependence of mitochondrial respiration inhibition by strobilurin analogues.
PubMed:
The strobilurins, oudemansins, and myxothiazols, fungicidal derivatives of beta-methoxyacrylic acid.
PubMed:
Assay conditions for the mitochondrial NADH:coenzyme Q oxidoreductase.
PubMed:
Roles in inhibitor recognition and quinol oxidation of the amino acid side chains at positions of cyt b providing resistance to Qo-inhibitors of the bc1 complex from Rhodobacter capsulatus.
PubMed:
Interactions of the myxothiazol and mucidin toxophores with cytochrome b.
PubMed:
New tools for mitochondrial genetics of Chlamydomonas reinhardtii: manganese mutagenesis and cytoduction.
PubMed:
Fumaric acid overproduction in yeast mutants deficient in fumarase.
PubMed:
Hyperpolarization and intracellular acidification in Trichoderma viride as a response to illumination.
PubMed:
Structure/function relationships in mitochondrial cytochrome b revealed by the kinetic and circular dichroic properties of two yeast inhibitor-resistant mutants.
PubMed:
Mitochondrial genetics of Chlamydomonas reinhardtii: resistance mutations marking the cytochrome b gene.
PubMed:
Determination of nitrate by conversion to nitrite using Paracoccus denitrificans.
PubMed:
Mutants of ubiquinol-cytochrome c2 oxidoreductase resistant to Qo site inhibitors: consequences for ubiquinone and ubiquinol affinity and catalysis.
PubMed:
Hydroxylamine as an inhibitor and terminal acceptor in the respiratory chain of the bacterium Paracoccus denitrificans.
PubMed:
The cytochrome b of the sea urchin Paracentrotus lividus is naturally resistant to myxothiazol and mucidin.
PubMed:
Mutations conferring resistance to quinol oxidation (Qz) inhibitors of the cyt bc1 complex of Rhodobacter capsulatus.
PubMed:
Molecular basis for resistance to myxothiazol, mucidin (strobilurin A), and stigmatellin. Cytochrome b inhibitors acting at the center o of the mitochondrial ubiquinol-cytochrome c reductase in Saccharomyces cerevisiae.
PubMed:
[A study of the mechanism of cyanide resistant oxidation of succinate from rat liver mitochondria in the presence of menadione].
PubMed:
Separate binding sites for antimycin and mucidin in the respiratory chain of the bacterium Paracoccus denitrificans and their occurrence in other denitrificans bacteria.
PubMed:
Characterisation of binding of the methoxyacrylate inhibitors to mitochondrial cytochrome c reductase.
PubMed:
Superoxide generation by the respiratory chain of tumor mitochondria.
PubMed:
The kinetics of reoxidation of yeast complex III. An evaluation of the Q-cycle.
PubMed:
Is the ubiquinone pool in the respiratory chain of the bacterium Paracoccus denitrificans really unhomogeneous?
PubMed:
Extrachromosomal genetics in the yeast Kluyveromyces lactis. Isolation and characterization of antimycin-resistant mutants.
PubMed:
Mucidin and strobilurin A are identical and inhibit electron transfer in the cytochrome bc1 complex of the mitochondrial respiratory chain at the same site as myxothiazol.
PubMed:
Genetic mapping of nuclear mucidin resistance mutations in Saccharomyces cerevisiae. A new pdr locus on chromosome II.
PubMed:
Effects of bc1-site electron transfer inhibitors on the absorption spectra of mitochondrial cytochromes b.
PubMed:
Localization of a ferricyanide-reactive site of cytochrome b-c1 complex, possibly of cytochrome b or ubisemiquinone, at the outer face of submitochondrial particles.
PubMed:
Effect of electron transfer inhibitors on superoxide generation in the cytochrome bc1 site of the mitochondrial respiratory chain.
PubMed:
Energy-linked spectral shift of ferrocytochrome b in beef heart submitochondrial particles.
PubMed:
[Genetic mapping of the mitochondrial markers of antibiotic resistance in PG-strain Saccharomyces cerevisiae yeasts].
PubMed:
Effect of glucitol on the production of mucidin in Oudemansiella mucida.
PubMed:
Metabolism of aromatic acids in the antibiotic-producing basidiomycete Oudemansiella mucida.
PubMed:
Effect of tryptophan on the production of mucidin in cultures of basidiomycete Oudemansiella mucida.
PubMed:
Spectral properties of cytochrome b-561 and cytochrome b-565 in mucidin-resistant mutants of Saccharomyces cerevisiae.
PubMed:
Oudemansin, strobilurin A, strobilurin B and myxothiazol: new inhibitors of the bc1 segment of the respiratory chain with an E-beta-methoxyacrylate system as common structural element.
PubMed:
Mucidin: its identity with strobilurin A.
PubMed:
Modification of the spectral properties of cytochrome b in mutants of Saccharomyces cerevisiae resistant to 3-(3,4-dichlorophenyl)-1,1-dimethylurea. Mapping at two distinct genetic loci of the split mitochondrial gene of cytochrome b.
PubMed:
Mucidin-nonproducing mutants of oudemansiella mucida.
PubMed:
Mitochondrial translation products of yeast mutants resistant to mucidin.
PubMed:
[Trichophyton violaceum as the causative agent in trichophytosis in the region of North Bohemia, and treatment with mucidin (Mucidermin Spofa) (author's transl)].
PubMed:
Localization of mucidin-resistant locus muc3 on mitochondrial DNA with respect to ubiquinol-cytochrome c reductase deficient box loci. Locus muc3 is allelic to box2.
PubMed:
Genetic localization of diuron- and mucidin-resistant mutants relative to a group of loci of the mitochondrial DNA controlling coenzyme QH2-cytochrome c reductase in Saccharomyces cerevisiae.
PubMed:
Genetic determination of ubiquinol-cytochrome reductase: mitochondrial locus muc3 specifying resistance of Saccharomyces cerevisiae to mucidin.
PubMed:
Biosynthesis of fatty acids and sterols in relation to the antibiotic formation in Oudemansiella mucida.
PubMed:
Mucidin resistance in yeast. Isolation, characterization and genetic analysis of nuclear and mitochondrial mucidin-resistant mutants of Saccharomyces cerevisiae.
PubMed:
Antifungal antibiotic of the Basidiomycete Oudemansiella mucida. III. Nuclei in the hyphae of mono- and dikaryons.
PubMed:
Composition of lipids and production of mucidin in a submerged culture of the basidiomycete Oudemansiella mucida.
PubMed:
Ultrastructural changes, caused by the new antibiotic mucidin in Candida pseudotropicalis.
PubMed:
Mucidin-resistant antimycin A-sensitive mitochondrial mutant of Saccharomyces cerevisiae.
PubMed:
Mode of action of mucidin, a new antifungal antibiotic produced by the basidiomycete Oudemansiella mucida.
PubMed:
Antibiotic mucidin, a new antimycin A-like inhibitor of electron transport in rat liver mitochondria.
PubMed:
Effects of the new antifungal antibiotic mucidin. I. Semiquantitative comparison of the activities of mucidin, nystatin and pimaricin.
PubMed:
Effects of the new antifungal antibiotic mucidin. II. Morphological changes brought about in sensitive test microorganismus.
PubMed:
[Mucidin, the first Czechoslovakian antibiotic].