| Identification | Back Directory | [Name]
STIGMATELLIN | [CAS]
91682-96-1 | [Synonyms]
STIGMATELLIN
(e,e,e)-)-8-hydroxy-3-methyl
Stigmatellin
DISCONTINUED. Please see S686780.
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
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- | [Molecular Formula]
C30H42O7 | [MDL Number]
MFCD00077874 | [MOL File]
91682-96-1.mol | [Molecular Weight]
514.65 |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [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 |
| Hazard Information | Back Directory | [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. |
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