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    Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is usually prepared by the acid-catalysed hydrolysis of mandelonitrile, which is the cyanohydrin of benzaldehyde. Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections. It is also used in skin care products as an alternative to glycolic acid. The drugs cyclandelate and homatropine are esters of mandelic acid.

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    Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is usually prepared by the acid-catalysed hydrolysis of mandelonitrile, which is the cyanohydrin of benzaldehyde. Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections. It is also used in skin care products as an alternative to glycolic acid. The drugs cyclandelate and homatropine are esters of mandelic acid.

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    Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is usually prepared by the acid-catalysed hydrolysis of mandelonitrile, which is the cyanohydrin of benzaldehyde. Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections. It is also used in skin care products as an alternative to glycolic acid. The drugs cyclandelate and homatropine are esters of mandelic acid.

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    16 views3 pages

    New Word 2007 Document

    Uploaded by

    Raman Manhas
    Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is usually prepared by the acid-catalysed hydrolysis of mandelonitrile, which is the cyanohydrin of benzaldehyde. Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections. It is also used in skin care products as an alternative to glycolic acid. The drugs cyclandelate and homatropine are esters of mandelic acid.

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    Mandelic acid

    From Wikipedia, the free encyclopedia


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    Mandelic acid[1]

    IUPAC name[hide]
    2-Hydroxy-2-phenylacetic acid

    Other names[hide]
    Mandelic acid
    Phenylglycolic acid

    Identifiers

    CAS number 90-64-2 

    ChemSpider 1253

    SMILES  [show]

    Properties

    Molecular formula C8H8O3

    Molar mass 152.14 g/mol

    Density 1.30 g/cm3

    119 °C (optically pure: 132 – 135


    Melting point
    °C)
    Solubility in water 15.87 g per 100 mL
    Solubility in chloroform, chloroform 0.12 M, diethyl ether
    diethyl ether, methanol 0.77 M, methanol 3.54 M [2]
    Acidity (pKa) 3.85
    Related compounds
    mandelonitrile, phenylacetic acid,
    Related compounds
    vanillylmandelic acid
       (what is this?)  (verify)
    Except where noted otherwise, data are given for materials in
    their standard state (at 25 °C, 100 kPa)
    Infobox references

    Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula
    C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic
    solvents. It is a useful precursor to various drugs. Since the molecule is chiral, it exists in
    either of two enantiomers as well as the racemic mixture, known as paramandelic acid.

    [edit] Isolation and synthesis


    Mandelic acid was discovered while heating amygdalin, an extract of bitter almonds, with
    diluted hydrochloric acid. It was first reported in 1909 by J. W. Walker and V. K. Krieble.
    The name is derived from the German "Mandel" for "almond". Derivatives of mandelic acid
    are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase
    and catechol-o-methyl transferase.

    It is usually prepared by the acid-catalysed hydrolysis of mandelonitrile,[3] which is the


    cyanohydrin of benzaldehyde. Mandelonitrile can also be prepared by reacting benzaldehyde
    with sodium bisulfite to give the corresponding adduct, forming mandelonitrile with sodium
    cyanide, which is hydrolyzed:[4]

    Alternatively, it arises by base hydrolysis of phenylchloroacetic acid and


    dibromacetophenone.[5] It also arises by heating phenylglyoxal with alkalis.

    [edit] Uses
    Mandelic acid has a long history of use in the medical community as an antibacterial,
    particularly in the treatment of urinary tract infections.[6] It has also been used as an oral
    antibiotic. In skin care, it is also an alternative to glycolic acid in skin care products.
    Mandelic acid is also advantageous in that it possesses antibacterial properties. Its use as a
    skincare modality was pioneered by Dr James E. Fulton, who developed vitamin A acid
    (tretinoin, Retin A) in 1969.[7] On the basis of this research, dermatologists now suggest
    mandelic acid for a wide variety of skin concerns, from acne to wrinkles; it is especially good
    in the treatment of adult acne as it addresses both of these concerns. Mandelic acid is also
    recommended is a pre- and post-laser treatment, reducing the amount and length of irritation
    caused by laser resurfacing.
    The drugs cyclandelate and homatropine are esters of mandelic acid.

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