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Biosynthesis of Mandelic acid

Mar 10，2022

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. The molecule is chiral. The racemic mixture is known as paramandelic acid.

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Benefits

Mandelic acid is a type of alpha hydroxy acid (AHA) that's derived from bitter almonds. It's a powerful ingredient which can help to supercharge your skincare routine when it needs a boost. Like other types of AHAs it works by exfoliating the skin. It's gentler compared to glycolic acid because its molecule size is twice as big, so it takes longer to penetrate the skin and is therefore less likely to cause irritation. Finally, like all acids, mandelic has the tendency to make skin sensitive to UVA rays, so wearing an SPF during the day is non-negotiable if you want to keep hold of your glow.

Uses

Mandelic acid can be used to treat three major skin concerns: signs of ageing, acne and enlarged pores, as well as pigmentation that is the result of excess sun exposure, acne scarring, taking hormonal contraceptives and pregnancy. It targets these concerns by speeding up cell turnover that slows with age.

Biosynthesis

Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway. Mandelate racemase interconverts the two enantiomers via a pathway that involves cleavage of the alpha-CH bond. Mandelate dehydrogenase is yet another enzyme on this pathway.Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated.Phenylpyruvic acid is another precursor to 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 biotechnological production of 4-hydroxy-mandelic acid and mandelic acid on the basis of glucose was demonstrated with a genetically modified yeast Saccharomyces cerevisiae, in which the hydroxymandelate synthase naturally occurring in the bacterium Amycolatopsis was incorporated into a wild-type strain of yeast, partially altered by the exchange of a gene sequence and expressed.

It also arises from the biodegradation of styrene, as detected in urine.

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