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D(-)-Isovaline

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Origin: China

Cas No: 3059-97-0

Specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 100 mt/month

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

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  • Products Specification
  • Product Description

  • Property

    CAS No.: 3059-97-0 Formula: C5H11NO2 Molecular Weight: 117.14600

    Description

    Isovaline is a rare amino acid transported to earth by the Murchison meteorite, which landed in Australia in 1969. The discovery of isovaline in the biosphere demonstrates an extraterrestrial origin of amino acids and has been linked to the homochirality of life on earth suggesting a role in the origin of life.
    The structure of isovaline is similar to the amino acids GABA and glycine, the chief inhibitory neurotransmitters in the mammalian central nervous system. Isovaline acts as an analgesic in mice by activating peripheral GABAB receptors. In a mouse model of osteoarthritis isovaline restored mobility, suggesting inhibition of nociception by isovaline in the synovial membrane of the mouse knee.
    Isovaline does not cross the blood-brain barrier and does not enter into the brain or spinal cord. Drugs such as opioids cross the blood-brain barrier to produce analgesia but often produce confusion, sedation and addiction.
    Isovaline acts downstream to the cyclooxygenase system that NSAIDs inhibit, suggesting a means to avoid adverse effects such as irritation of the gastrointestinal system.
    This novel first-in-class compound has potential for treatment of acute and chronic pain, without the negative side effects associated with other commonly used analgesics.

    Basic Info

    Chemical Name D(-)-Isovaline
    Synonyms

    D-Isovaline;

    CAS No. 3059-97-0
    Molecular Formula C5H11NO2
    Molecular Weight 117.14600
    PSA 63.32000
    LogP 0.89870

    Properties

    Appearance & Physical State White powder
    Density 1.07 g/cm3
    Boiling Point 213.6ºC at 760 mmHg
    Melting Point 276-278ºC (lit.)
    Flash Point 83ºC
    Refractive Index 1.465

    Safety Info

    Safety Statements S24/25
    HS Code 2922499990

    Synthesis Route

    (RS)-2-amino-2-methylbutanamide→D(-)-Isovaline+L(+)-Isovaline monohydrate
    benzyl (R)-2-azido-2-methylbutanoate→D(-)-Isovaline
    (R)-tert-butyl 2-methyl-2-((3S,4R)-2-oxo-3-phenoxy-4-phenylazetidin-1-yl)butanoate→D(-)-Isovaline

    Precursor

    benzyl (R)-2-azido-2-methylbutanoate
    N-chloroacetyl-D-isovaline
    (+/-)-2-amino-4-(benzylthio)-2-methylbutanoic acid
    (2R)-2-benzamido-2-methylbutanoic acid

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