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4-Bromo-DL-mandelic acid for synthesis

Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C8H8O3

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Search results for Mandelic acid at Sigma-Aldrich

An easy access to substituted ()-3-hydroxy-3-phenyloxindoles, ()-benzylic acids, and benzophenones is described. The reaction of the lithium enolate of the (2,5)--1,3-dioxolan-4-one derived from optically active ()mandelic acid and pivalaldehyde with several - and -halonitrobenzenes proceeds readily to give the corresponding arylation products in good yields and diastereoselectivities. The reduction of the nitro group with Zn/HCl/EtOH in the -nitro arylation products with concomitant intramolecular aminolysis of the dioxolanone moiety leads directly to enantiomerically pure ()-3-hydroxy-3-phenyloxindoles. On the other hand the basic hydrolysis of the dioxolanone moiety in all the arylation products (ortho and para) leads to enantiomerically pure substituted ()-benzylic acids. The oxidative decarboxylation of these latter with oxygen as terminal oxidant in the presence of pivalaldehyde and the Co(III)-Me2opba complex as catalyst gives substituted nitrobenzophenones.

Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula CHCH(OH)COH

Mandelic acid and its derivatives are used to apply the dual activities as an antibacterial agent and as an antiaging agent (AHA activity) similar to glycolic acid.

Showing metabocard for Mandelic acid (HMDB0000703)

Showing metabocard for Mandelic acid ..

Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-o-methyl transferase.

The simple esters of these alkyl-substituted phenols (Nos. 698-705) are expected to undergo hydrolysis in vivo, followed by conjugation and excretion as sulfate and glucuronic acid conjugates. -Tolyl acetate (No. 698) was 60% hydrolysed in vitro after incubation with pancreatin for 2 h at 37 °C (Grundschober, 1977). -Vinylphenol (No. 711), a metabolite of styrene, was excreted as the glucuronic acid conjugate of -vinylphenol or as a mandelic acid derivative formed by oxidation of the vinyl group (Pfäffli et al., 1981).

Synthesis of polyhydroxylated aromatic mandelic acid amides and ..

Synthesis of hydroxymandelic acid ..

No chromosomal aberrations were induced when Chinese hamster ovary cells were incubated with phenol at 600-800 µg/ml without metabolic activation (Ivett et al., 1989) or 2-phenylphenol at 60-80 µg/ml with and without metabolic activation (National Toxicology Program, 1986). However, positive results were reported when a metabolic activation system was added and the phenol concentration was increased to 2000-3000 µg/ml (Ivett et al., 1989). The authors did not determine the cytotoxic threshold or the pH of the test media. Mammalian cells rely on complex regulatory mechanisms to maintain homeostatic conditions, and those in culture are not equipped to respond to environmental changes. The pH of the culture media used in mammalian cell assays must be maintained at approximately 6.8-7.5, because lower values or changes in osmolality due to acidic or ionizing test substances (e.g. phenol) may result in false-positive results, especially with metabolic activation systems. Acidity facilitates the breakdown of the components of such systems into mutagenic agents (Brusick, 1986). Micronuclei were not induced in human lymphocytes exposed to phenol at a concentration of 94 µg/ml without metabolic activation (Robertson et al., 1991).

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  • PDF Downloads : Oriental Journal of Chemistry

    A crystalline para form of aminobenzoic acid that is part of the vitamin B complex, sometimes used in sunscreens.

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