52110-55-1

Basic information

• Product Name: MUCIDIN
• Synonyms: (E,E,E)-2-(METHOXYMETHYLENE)-3-METHYL-6-PHENYL-3,5-HEXADIENOIC ACID METHYL ESTER;MUCIDERMIN;MUCIDIN;STROBILURIN A;(E,E,E)-2-(methoxymethylene)-3-methyl-6-phenyl-3,5-Hexadienoic acid methyl ester, Mucidermin, Strobilurin A;(3Z,5E)-2-[(E)-Methoxymethylene]-3-methyl-6-phenyl-3,5-hexadienoic acid methyl ester;3,5-Hexadienoic acid, 2-(methoxymethylene)-3-methyl-6-phenyl-, methyl ester, (2E,3Z,5E)-;3,5-Hexadienoic acid, 2-(methoxymethylene)-3-methyl-6-phenyl-, methyl ester, (E,E,E)-
• CAS NO: 52110-55-1
• Molecular Formula: C₁₆H₁₈O₃
• Molecular Weight: 258.31
• Product Categories: Antibiotic
• Mol File: 52110-55-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 414.2°C at 760 mmHg
• Flash Point: 175.9°C
• Appearance: /
• Density: 1.064g/cm³
• Vapor Pressure: 4.52E-07mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: MUCIDIN(CAS DataBase Reference)
• NIST Chemistry Reference: MUCIDIN(52110-55-1)
• EPA Substance Registry System: MUCIDIN(52110-55-1)

Safety Data

• Hazardous Substances Data: 52110-55-1(Hazardous Substances Data)

Usage

Uses

Mucidin (Strobilurin A) is an antifungal antibiotic.

Definition

ChEBI: An enoate ester that is the methyl ester of (2E,3Z,5E)-2-(methoxymethylene)-3-methyl-6-phenylhexa-3,5-dienoic acid.

InChI:InChI=1/C16H18O3/c1-13(15(12-18-2)16(17)19-3)8-7-11-14-9-5-4-6-10-14/h4-12H,1-3H3/b11-7+,13-8-,15-12+

Upstream product

• 55815-92-4 2-Methyl-2-((E)-3-phenyl-allyl)-[1,3]dioxolane 
• 75463-68-2 (3Z,5E)-3-Methyl-6-phenyl-hexa-3,5-dienoic acid methyl ester 
• 111193-99-8 (3E,5E)-2-Dimethoxymethyl-3-methyl-6-phenyl-hexa-3,5-dienoic acid methyl ester 
• 111193-98-7 (3E,5E)-3-Methyl-6-phenyl-hexa-3,5-dienoic acid methyl ester 
• 111193-97-6 2-Oxo-3-(triphenyl-λ⁵-phosphanylidene)-butyric acid methyl ester 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 42762-56-1 (E)-5-phenylpent-4-en-2-one 
• 77-78-1 dimethyl sulfate 
• 56374-74-4 cinnamylidenetriphenylphosphorane 
• 111193-95-4 (3Z,5E)-2-Hydroxy-3-methyl-6-phenyl-hexa-3,5-dienoic acid methyl ester 
• 111193-91-0 ethyl (2Z,4E)-2-methyl-5-phenylpenta-2,4-dienoate 
• 111193-92-1 (2Z,4E)-2-Methyl-5-phenyl-penta-2,4-dienal 
• 54355-96-3 (2Z,4E)-2-methyl-5-phenylpenta-2,4-dien-1-ol 

Downstream Products

• 93440-94-9 2-Methyl-5-phenylbenzoesaeure-methylester 

Relevant articles and documents

Dehydration-type Ti-Claisen Condensation (Carbonhomologation) of α-Heteroatom-substituted Acetates with Alkyl Formates: Utilization as (Z)-Stereodefined Cross-coupling Partners and Application to Concise Synthesis of Strobilurin A

TiCl4?Et3N or ?Bu3N reagent conducted a highly (Z)-stereoselective carbon homologation (dehydration type Ti-Claisen condensation) of alkyl α-heteroatom (halo and sulfonyloxy)-substituted acetates (XCH2CO2R) with alkyl formates (HCO2R) to afford various alkyl β-alkoxy-α-halo or sulfonyloxy-substituted acrylates (24 examples; 51%–91% yield). Stereoretentive Suzuki-Miyaura, Negishi, and Sonogashira cross-couplings using the obtained methyl β-methoxy-α-halo or sulfonyloxy-substituted acrylates proceeded smoothly to produce a variety of β-alkoxy-α-substituted acrylates in moderate to high yield (35 examples; 29%–99% yield). As a successful application, a 3-step straightforward synthesis of strobilurin A was performed utilizing the present reaction sequence (dehydration type Ti-Claisen condensation and Suzuki-Miyaura cross-coupling), wherein the geometry of the three consecutive olefins (2E,3Z,5E) was completely maintained. (Figure presented.).

STEREOCONTROLLED SYNTHESES OF STROBILURIN A AND ITS (9E)-ISOMER

The (E,Z,E)-configuration (1) of the strobilurins has been confirmed by stereocontrolled synthesis.