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myriocin

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Origin: China

Cas No: 35891-70-4

Specification: 99%min

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  • Products Specification
  • Product Description

  • Property

    CAS No.: 35891-70-4 Formula: C21H39NO6 Molecular Weight: 401.53700

    Description

    Myriocin, also known as antibiotic ISP-1 and thermozymocidin, is an atypical amino acid and an antibiotic derived from certain thermophilic fungi. Among the producing strains are Mycelia sterilia.
    Myriocin is a very potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Due to this property, it is used in biochemical research as a tool for depleting cells of sphingolipids.
    Myriocin was shown to inhibit the proliferation of an IL-2-dependent mouse cytotoxic T cell line.
    Myriocin possesses immunosuppressant activity. It is reported to be 10- to 100-fold more potent than ciclosporin.
    The multiple sclerosis drug fingolimod was derived from myriocin by using structure–activity relationship studies to determine the parts of the molecule important to its activity.

    Basic Info

    Chemical Name myriocin
    Synonyms

    ISP-1;
    thermozymocidin;
    Myriocin,Mycelia sterilia;
    (E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid;
    ISP-I;
    Myriocin from Mycelia sterilia;
    Myriocin;

    CAS No. 35891-70-4
    Molecular Formula C21H39NO6
    Molecular Weight 401.53700
    PSA 141.08000
    LogP 3.00930

    Properties

    Density 1.123g/cm3
    Boiling Point 636.7ºC at 760 mmHg
    Flash Point 338.8ºC
    Refractive Index 1.521
    Storage Condition 2-8ºC

    Safety Info

    RIDADR UN 2811 6.1/PG 3
    Risk Statements R22
    Hazard Codes Xi; Xn

    Synthesis Route

    (2S,3R,4R)-2-acetamido-3-acetoxy-2-acetoxymethyl-4-[(E)-10'-oxohexadec-2'-en-1'-yl]-4-butanolide→myriocin
    (1S,5R,6R)-1-hydroxymethyl-6-[(E)-10-oxohexadec-2-en-1-yl]-2-aza-4,7-dioxabicyclo[3.3.0]octane-3,8-dione→myriocin
    2-benzoylamino-2-benzoyloxymethyl-2,5-dideoxy-3-O-benzoyl-5-(E)-9-oxopentadec-1-enyl-D-lyxono-1,4-lactone→myriocin

    Toxicity

    Exposure Route Type of Test Species Observed Dose/Duration Toxic Effects
    Intraperitoneal LD50 - Lethal dose, 50 percent kill Rodent - rat 2 mg/kg 1.Details of toxic effects not reported other than lethal dose value
    Oral LD50 - Lethal dose, 50 percent kill Rodent - mouse 300 mg/kg 1.Details of toxic effects not reported other than lethal dose value
    Intraperitoneal LD50 - Lethal dose, 50 percent kill Rodent - mouse 5 mg/kg 1.Details of toxic effects not reported other than lethal dose value

    Precursor

    (2S,3R,4R)-2-acetamido-3-acetoxy-2-acetoxymethyl-4-[(E)-10'-oxohexadec-2'-en-1'-yl]-4-butanolide
    (1S,5R,6R)-1-hydroxymethyl-6-[(E)-10-oxohexadec-2-en-1-yl]-2-aza-4,7-dioxabicyclo[3.3.0]octane-3,8-dione
    N-benzoylanhydromyriocin
    (4S,5R)-methyl 5-formyl-4-((methoxymethoxy)methyl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

    Downstream Product

    (E)-2-amino-3,4,14-trihydroxy-2-(hydroxymethyl)icos-6-enoic acid

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