Mandelic acid: Difference between revisions

From WikiMD's Wellness Encyclopedia

CSV import
Tags: mobile edit mobile web edit
 
CSV import
 
Line 1: Line 1:
'''Mandelic Acid'''
{{Short description|Overview of mandelic acid}}


'''Mandelic Acid''' is an [[alpha hydroxy acid (AHA)]] derived from bitter almonds. It is a white crystalline solid that is soluble in water and other organic solvents. Mandelic acid is used in the medical field, skincare industry, and in the synthesis of other chemicals.
== Mandelic Acid ==
[[File:Preparation_of_mandelic_acid.png|thumb|right|Synthesis of mandelic acid]]
'''Mandelic acid''' is an [[aromatic]] [[alpha hydroxy acid]] (AHA) with the formula C_H_CH(OH)CO_H. It is a white crystalline solid that is soluble in water and polar organic solvents. Mandelic acid is used in various applications, including as an intermediate in the synthesis of other compounds and in [[cosmetic]] products for its exfoliating properties.


== History ==
== Structure and Properties ==
Mandelic acid consists of a [[benzene]] ring with a [[carboxylic acid]] group and a [[hydroxyl group]] attached to the alpha carbon. This structure gives it both acidic and alcohol-like properties. The presence of the hydroxyl group classifies it as an alpha hydroxy acid, which is known for its ability to promote [[exfoliation]] of the skin.


Mandelic acid was first isolated in 1831 by the German pharmacist [[Friedrich Wöhler]] and was named after the German word for almond (''Mandel''). It was one of the first alpha hydroxy acids to be used in skincare, with its use dating back to the 1940s.
== Synthesis ==
Mandelic acid can be synthesized through several methods. One common method involves the [[hydrolysis]] of [[mandelonitrile]], which is derived from the reaction of [[benzaldehyde]] with [[hydrogen cyanide]]. The hydrolysis of mandelonitrile yields mandelic acid and [[ammonia]].


== Properties and Synthesis ==
Another method involves the oxidation of [[phenylglycine]] using [[potassium permanganate]] or other oxidizing agents. This process converts the amino acid into the corresponding alpha hydroxy acid.


Mandelic acid is a chiral molecule, with two [[enantiomers]]. The (R)-enantiomer is naturally occurring and has a sweet taste, while the (S)-enantiomer has a bitter taste. The synthesis of mandelic acid involves the hydrolysis of [[mandelonitrile]], which is derived from benzaldehyde and hydrogen cyanide.
== Applications ==
Mandelic acid is widely used in the [[pharmaceutical]] and [[cosmetic]] industries. In cosmetics, it is valued for its ability to improve skin texture and tone by promoting the shedding of dead skin cells. It is often used in [[chemical peels]] and other skin care products.


== Uses ==
In the pharmaceutical industry, mandelic acid serves as an intermediate in the synthesis of various drugs. Its derivatives are used in the production of [[antibiotics]] and other therapeutic agents.


=== Medical Uses ===
== Safety and Handling ==
 
Mandelic acid should be handled with care, as it can cause irritation to the skin and eyes. Appropriate [[personal protective equipment]] (PPE) such as gloves and goggles should be worn when handling the compound.
In the medical field, mandelic acid is used as an [[antibiotic]], particularly in the treatment of urinary tract infections. It is also used as an oral antibiotic in the treatment of [[acne]].
 
=== Skincare Uses ===
 
In the skincare industry, mandelic acid is used as a chemical peel. It is less irritating and has a larger molecular size than other AHAs, which makes it penetrate the skin more slowly and cause less irritation. It is used to treat acne, melasma, and photoaging.
 
=== Chemical Synthesis ===
 
Mandelic acid is also used in the synthesis of other chemicals, including the anti-Parkinson's drug [[Levodopa]].
 
== Safety and Side Effects ==
 
While generally safe for use, mandelic acid can cause skin irritation, redness, and peeling, particularly at higher concentrations. It is recommended to use sunscreen when using products containing mandelic acid, as it can increase the skin's sensitivity to the sun.
 
== See Also ==


== Related Pages ==
* [[Alpha hydroxy acid]]
* [[Alpha hydroxy acid]]
* [[Benzaldehyde]]
* [[Chemical peel]]
* [[Chemical peel]]
* [[Acne]]
* [[Exfoliation (cosmetology)]]
* [[Levodopa]]
 
== References ==
 
<references />


[[Category:Organic compounds]]
[[Category:Alpha hydroxy acids]]
[[Category:Alpha hydroxy acids]]
[[Category:Chemical compounds]]
[[Category:Cosmetic chemicals]]
[[Category:Skincare]]
[[Category:Medicine]]
{{Chem-stub}}
{{Medicine-stub}}

Latest revision as of 05:21, 16 February 2025

Overview of mandelic acid


Mandelic Acid[edit]

Synthesis of mandelic acid

Mandelic acid is an aromatic alpha hydroxy acid (AHA) with the formula C_H_CH(OH)CO_H. It is a white crystalline solid that is soluble in water and polar organic solvents. Mandelic acid is used in various applications, including as an intermediate in the synthesis of other compounds and in cosmetic products for its exfoliating properties.

Structure and Properties[edit]

Mandelic acid consists of a benzene ring with a carboxylic acid group and a hydroxyl group attached to the alpha carbon. This structure gives it both acidic and alcohol-like properties. The presence of the hydroxyl group classifies it as an alpha hydroxy acid, which is known for its ability to promote exfoliation of the skin.

Synthesis[edit]

Mandelic acid can be synthesized through several methods. One common method involves the hydrolysis of mandelonitrile, which is derived from the reaction of benzaldehyde with hydrogen cyanide. The hydrolysis of mandelonitrile yields mandelic acid and ammonia.

Another method involves the oxidation of phenylglycine using potassium permanganate or other oxidizing agents. This process converts the amino acid into the corresponding alpha hydroxy acid.

Applications[edit]

Mandelic acid is widely used in the pharmaceutical and cosmetic industries. In cosmetics, it is valued for its ability to improve skin texture and tone by promoting the shedding of dead skin cells. It is often used in chemical peels and other skin care products.

In the pharmaceutical industry, mandelic acid serves as an intermediate in the synthesis of various drugs. Its derivatives are used in the production of antibiotics and other therapeutic agents.

Safety and Handling[edit]

Mandelic acid should be handled with care, as it can cause irritation to the skin and eyes. Appropriate personal protective equipment (PPE) such as gloves and goggles should be worn when handling the compound.

Related Pages[edit]