91682-96-1

Basic information

• Product Name: STIGMATELLIN
• Synonyms: (e,e,e)-)-8-hydroxy-3-methyl;chromone,5,7-dimethoxy-2-(4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrienyl;2-(4,6-Dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrienyl)-8-hydroxy-5,7-dimethoxy-3-methyl-4H-1-benzopyran-4-one;STIGMATELLIN
• CAS NO: 91682-96-1
• Molecular Formula: C₃₀H₄₂O₇
• Molecular Weight: 514.65
• Product Categories: Antibiotics;Antibiotics A to;Antibiotics by Application;Antibiotics N-SAntibiotics;AntifungalAntibiotics;Antineoplastic and Immunosuppressive AntibioticsAntibiotics;Chemical Structure Class;Inhibits an EnzymeAntibiotics;Mechanism of Action;Miscellaneous;Spectrum of Activity
• Mol File: 91682-96-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 129°C
• Boiling Point: 520.22°C (rough estimate)
• Flash Point: 198.1°C
• Appearance: /
• Density: 1.0924 (rough estimate)
• Vapor Pressure: 1.01E-16mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: −20°C
• PKA: 8.67±0.40(Predicted)
• CAS DataBase Reference: STIGMATELLIN(CAS DataBase Reference)
• NIST Chemistry Reference: STIGMATELLIN(91682-96-1)
• EPA Substance Registry System: STIGMATELLIN(91682-96-1)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: GB7972000
• F: 8-10-23
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 91682-96-1(Hazardous Substances Data)

Usage

Uses

Stigmatellin is a cytochrome bc1 complex inhibitor.

Definition

ChEBI: A member of the class of chromones that is isolated from Stigmatella aurantiaca Sg a15.

Purification Methods

Stigmatellin A is stable in aqueous solution at neutral pH but decomposes at pH <5. It is purified by recrystallisation from toluene/hexane. It has UV max: nm () 248sh (4,100), 258 (59,500), 267 (65,500)max: 3550m, 1645chs, 1635ss, 1620ss, 1590s, 1510m and 905m cm-1. It gives colour reactions at 110o with vanillin/H2SO4 (grey), Ce(IV)/(NH4)2SO4 (yellow) and phosphomolybdate (blue-grey). [H.fle et al. Justus Liebigs Ann Chem 1882 1984.] It inhibits electron transport [Jagow & Link Methods Enzymol 126 253 1986, Robertson et al. Biochemistry 32 1310 1933], and has antibiotic properties [Kunze et al. J Antibiot 37 454 1984]. The 7t,9t,11c-isomer is Stigmatellin B.

InChI:InChI=1/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10-

Upstream product

• 293744-13-5 8-Benzyloxy-5,7-dimethoxy-2-((3S,4S,5R)-4-methoxy-3,5-dimethyl-6-triisopropylsilanyloxy-hexyl)-3-methyl-chromen-4-one 
• 293743-92-7 (4S,5S,6R)-5-Methoxy-4,6-dimethyl-7-triisopropylsilanyloxy-heptanoic acid 2-benzyloxy-3,5-dimethoxy-6-propionyl-phenyl ester 
• 293744-14-6 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one 
• 293744-03-3 1-(3-benzyloxy-2-hydroxy-4,6-dimethoxy-phenyl)-propan-1-one 
• 293744-09-9 (4S,5S,6R)-5-Methoxy-4,6-dimethyl-7-triisopropylsilanyloxy-heptanoic acid methyl ester 
• 293744-10-2 (4S,5S,6R)-5-Methoxy-4,6-dimethyl-7-triisopropylsilanyloxy-heptanoyl chloride 
• 293743-93-8 (4S,5S,6R)-5-Methoxy-4,6-dimethyl-7-triisopropylsilanyloxy-heptanoic acid 
• 293744-02-2 propionic acid 2,4-dimethoxy-6-propionyloxy-phenyl ester 
• 293743-95-0 methyl 7-hydroxy-2-phenylbenzo[d][1,3]dioxole-5-carboxylate 
• 293743-98-3 7-methoxy-2-phenyl-benzo[1,3]dioxole-5-carboxylic acid methyl ester 

Downstream Products

• 94190-80-4 2,4-Dimethoxy-3,5-dimethyl-1,8-octandisaeure-bis(p-bromphenacylester) 

Relevant articles and documents

Asymmetric synthesis of stigmatellin and crocacin C

The crystalline sulfone 18 (X-ray analysis), prepared from the monoacetate product [i.e., (+)-12; 98.2% ee] of the lipase PS-catalyzed acetylation of anti,anti-2,4-dimethyl-1,3,5-pentantriol (19a), has been elaborated either to crocacin C (10) or stigmatellin (1), thereby providing a convenient divergent access to these two natural antibiotics.

Diastereo- and enantioselective total synthesis of stigmatellin A

Stigmatellin A (1) isolated from the myxobacterium Stigmatella aurantiaca is a powerful inhibitor of electron transport in mitochondria and chloroplasts. The first highly diastereo- and enantioselective total synthesis of this important natural product is