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STIGMATELLIN

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Origin: China

Cas No: 91682-96-1

Specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 80 mt/month

Lead time: 7 days for OEM, 3 days for ready goods

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  • Products Specification
  • Product Description

  • Property

    CAS No.: 91682-96-1 Formula: C30H42O7 Molecular Weight: 514.65000

    Description

    Stigmatellin is a potent inhibitor of the quinol oxidation (Qo) site of the cytochrome bc1 complex in mitochondria and the cytochrome b6f complex of thylakoid membranes.
    Stigmatellin is isolated from the myxobacterium Stigmatella aurantica, and contains a 5,7-dimethoxy-8-hydroxychromone aromatic headgroup with a hydrophobic alkenyl chain in position 2 . Crystal structures for stigmatellin-inhibited bovine and yeast (Saccharomyces cerevisiae) bc1 complex are available. Stigmatellin binds at the cytochrome b Qo site in the '(heme) bl distal' position, and associates with the Rieske iron-sulfur protein via a hydrogen bond to histidine residue 181 (His-181), a ligand to the [2Fe2S] iron-sulfur cluster of this subunit. This association raises the midpoint potential of the iron-sulfur cluster from 290 to 540 mV and restricts movement of the cytoplasmic domain of the Rieske protein.

    Basic Info

    Chemical Name STIGMATELLIN
    Synonyms

    Stigmatellin A;

    CAS No. 91682-96-1
    Molecular Formula C30H42O7
    Molecular Weight 514.65000
    PSA 87.36000
    LogP 6.13760

    Properties

    Density 1.081g/cm3
    Boiling Point 635ºC at 760mmHg
    Melting Point 82-89ºC /Technical grade 82-90% purity/
    Flash Point 198.1ºC
    Refractive Index 1.527
    Storage Condition -20ºC

    Safety Info

    Hazard Class 6.1(a)
    Packing Group II
    RIDADR UN 2811 6.1/PG 2
    Risk Statements R25
    Hazard Codes T

    Synthesis Route

    (2E,4E)-4-Methylhexa-2,4-dienylphosphonic acid diethylester+(2R,3S,4S,5S)-7-[8-hydroxy-5,7-dimethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanal→STIGMATELLIN
    1-(2,3-Dihydroxy-4,6-dimethoxyphenyl)propan-1-one→STIGMATELLIN
    3,5-Dimethoxyphenol→STIGMATELLIN

    Toxicity

    Exposure Route Type of Test Species Observed Dose/Duration Toxic Effects
    Oral LD50 - Lethal dose, 50 percent kill Rodent - mouse 30 mg/kg 1.Details of toxic effects not reported other than lethal dose value
    Subcutaneous LD50 - Lethal dose, 50 percent kill Rodent - mouse 2 mg/kg 1.Details of toxic effects not reported other than lethal dose value
    - Mutation test systems - not otherwise specified - 3300 ug/L -

    Precursor

    (2R,3S,4S,5S)-7-[8-hydroxy-5,7-dimethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanal
    3,5-Dimethoxyphenol
    (2E,4E)-4-Methylhexa-2,4-dienylphosphonic acid diethylester
    1-(2,3-Dihydroxy-4,6-dimethoxyphenyl)propan-1-one

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