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| | STIGMATELLIN Basic information |
| Product Name: | STIGMATELLIN | | Synonyms: | 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;(e,e,e)-)-8-hydroxy-3-methyl;chromone,5,7-dimethoxy-2-(4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrienyl;4H-1-Benzopyran-4-one, 2-(4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrien-1-yl)-8-hydroxy-5,7-dimethoxy-3-methyl-;Stigmatellin
DISCONTINUED. Please see S686780. | | CAS: | 91682-96-1 | | MF: | C30H42O7 | | MW: | 514.65 | | EINECS: | | | 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 |  |
| | STIGMATELLIN Chemical Properties |
| Melting point | 129°C | | Boiling point | 520.22°C (rough estimate) | | density | 1.0924 (rough estimate) | | refractive index | 1.5800 (estimate) | | storage temp. | −20°C | | pka | 8.67±0.40(Predicted) |
| Hazard Codes | T | | Risk 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 |
| | STIGMATELLIN Usage And Synthesis |
| 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. |
| | STIGMATELLIN Preparation Products And Raw materials |
| Raw materials | 4H-1-Benzopyran-2-heptanal, 8-hydroxy-α,γ,5,7-tetramethoxy-β,δ,3-trimethyl-4-oxo-, (αR,βS,δS,γS)--->[(2E,4E)-4-Methyl-2,4-hexadienyl]phosphonic Acid Diethyl Ester |
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