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all-trans-retinoic acid

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Origin: China

Cas No: 302-79-4

Specification: 99%min

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  • Products Specification
  • Product Description
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    CAS No.: 302-79-4 Formula: C20H28O2 Molecular Weight: 300.43500

    Description

    Retinoic acid is a metabolite of vitamin A (retinol) that mediates the functions of vitamin A required for growth and development. Retinoic acid is required in chordate animals, which includes all higher animals from fish to humans. During early embryonic development, retinoic acid generated in a specific region of the embryo helps determine position along the embryonic anterior/posterior axis by serving as an intercellular signaling molecule that guides development of the posterior portion of the embryo. It acts through Hox genes, which ultimately control anterior/posterior patterning in early developmental stages.
    The key role of retinoic acid in embryonic development mediates the high teratogenicity of retinoid pharmaceuticals, such as isotretinoin used for treatment of cancer and acne. Oral megadoses of pre-formed vitamin A (retinyl palmitate), and retinoic acid itself, also have teratogenic potential by this same mechanism.

    Basic Info

    Chemical Name all-trans-retinoic acid
    Synonyms

    (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid;
    retin-a;
    ATRA;
    13-cis-retinoic acid;
    aknoten;
    all-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid;
    Tretinoin;
    [3H]-Retinoic Acid;
    13-trans-Retinoic acid;
    Atragen;
    effederm;
    (all-e);
    all-trans-Retinoic Acid;
    Vitamin A Acid;
    aberel;
    eudyna;
    Retinoic acid;
    all-trans tretinoin;
    all-trans-vitamin A acid;
    tretinm;
    all-trans retinoic acid;

    CAS No. 302-79-4
    Molecular Formula C20H28O2
    Molecular Weight 300.43500
    PSA 37.30000
    LogP 5.60260

    Properties

    Appearance & Physical State Yellow-orange powder
    Density 1.011 g/cm3
    Boiling Point 462.8ºC at 760 mmHg
    Melting Point 179-184ºC
    Flash Point 350.6ºC

    Safety Info

    Safety Statements S36/37-S45
    HS Code 2916209090
    Risk Statements R22; R38; R63
    Hazard Codes Xn
    Symbol GHS07
    Caution Statement P301 + P312 + P330
    Hazard Declaration H302
    Signal Word Warning

    Synthesis Route

    acide carboxy-14-retinoiqueisotretinoin+all-trans-retinoic acid
    ethyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoateisotretinoin+all-trans-retinoic acid
    5-Hydroxy-4-Methyl-2(5H)Furanone+[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)penta-2,4-dienyl]-triphenylphosphanium,chlorideisotretinoin+all-trans-retinoic acid

    Toxicity

    Exposure Route Type of Test Species Observed Dose/Duration Toxic Effects
    Administration onto the skin Standard Draize test Human 525 mg/21D (Intermittent) -
    Oral LD50 - Lethal dose, 50 percent kill Rodent - rat >200 mg/kg 1.Details of toxic effects not reported other than lethal dose value
    Intraperitoneal LD50 - Lethal dose, 50 percent kill Rodent - rat 96 mg/kg 1.Spinal Cord-other degenerative changes
    2.Behavioral-ataxia
    3.Blood-normocytic anemia

    Precursor

    ethyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
    (2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl fluoride
    all-trans-Retinol
    acide carboxy-14-retinoique

    Downstream Product

    isotretinoin
    all-trans-4-oxoretinoic acid
    Benzoyl peroxide
    all-trans-4-hydroxyretinoic acid

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