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Mandelic acid[1]
Mandelic acid.png
IUPAC name
Other names Mandelic acid
Phenylglycolic acid
Identifiers
CAS number 90-64-2 Yes check.svgY
SMILES
ChemSpider ID 1253
Properties
Molecular formula C8H8O3
Molar mass 152.14 g/mol
Density 1.30 g/cm3
Melting point

119 °C

Solubility in water 1 g per 6.3 mL
Solubility in chloroform, diethyl ether, methanol chloroform 0.12 M, diethyl ether 0.77 M, methanol 3.54 M [2]
Acidity (pKa) 3.37
Related compounds
Related compounds mandelonitrile, phenylacetic acid, vanillylmandelic acid
 Yes check.svgY (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 C8H8O3. It is a white crystalline solid that is soluble in water and most common organic solvents.

Contents

Discovery and name

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".

Chemistry

It is an isomer of cresotinic acid (2-hydroxy-3-methylbenzoic acid) and 2-methoxybenzoic acid. 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 also present in certain skin care products, is an intermediate molecule in the production of other biochemicals, may be used as an analytical reagent and is a precursor in the manufacture of dyes.

Since the molecule contains a chiral carbon atom, the acid exists in either of two optically active forms. The racemic mixture of the two is known as paramandelic acid.

It may be prepared by the action of hydrochloric acid on mandelonitrile, the addition compound of benzaldehyde and hydrocyanic acid; by boiling phenylchloroacetic acid with alkalis; by heating benzoyl formaldehyde with alkalis; or by the action of dilute alkalis on ω-dibromacetophenone.

Preparation

Mandelonitrile may be prepared by reacting benzaldehyde with sodium bisulfite to give the corresponding adduct, forming mandelonitrile with sodium cyanide, which is hydrolyzed:[3]

Preparation of mandelic acid.png

Uses

Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections.[4] It has also been used as an oral antibiotic. Lately, Mandelic acid has gained popularity as a topical skin care treatment for adult acne. It is also used as an alternative to glycolic acid in skin care products. Mandelic acid is a larger molecule than glycolic acid which makes it better tolerated on the skin. Mandelic acid is also advantageous in that it possesses antibacterial properties, whereas glycolic acid does not.

Its use as a skincare modality was pioneered by Dr James E. Fulton, who developed vitamin A acid (tretinoin, Retin A) in 1969.[5] On the basis of this research, dermatologists now suggest mandelic acid as an appropriate treatment 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.

References

  1. ^ Merck Index, 11th Edition, 5599.
  2. ^ Solubility of mandelic acid in non-aqueous solvents
  3. ^ Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941), "Mandelic Acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0336  ; Coll. Vol. 1: 336  
  4. ^ Putten, P. L. (1979). "Mandelic acid and urinary tract infections". Antonie van Leeuwenhoek 45: 622. doi:10.1007/BF00403669.  
  5. ^ Taylor, MB. (1999). "Summary of mandelic acid for the improvement of skin conditions". Cosmetic Dermatology 21: 26–28.  
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Mandelic acid[1]
File:Kwas migdał
Identifiers
CAS number 90-64-2 Y
ChemSpider 1253
SMILES
Properties
Molecular formula C8H8O3
Molar mass 152.14 g/mol
Density 1.30 g/cm3
Melting point

119 °C (optically pure: 132 – 135 °C)

Solubility in water 15.87 g per 100 mL
Solubility in chloroform, diethyl ether, methanol chloroform 0.12 M, diethyl ether 0.77 M, methanol 3.54 M [2]
Acidity (pKa) 3.85
Related compounds
Related compounds mandelonitrile, phenylacetic acid, vanillylmandelic acid
 Y (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.

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.

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.

References

  1. ^ Merck Index, 11th Edition, 5599.
  2. ^ Solubility of mandelic acid in non-aqueous solvents
  3. ^ Edwin Ritzer and Rudolf Sundermann “Hydroxycarboxylic Acids, Aromatic” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a13_519
  4. ^ Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941), "Mandelic Acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0336 ; Coll. Vol. 1: 336 
  5. ^ J. G. Aston, J. D. Newkirk, D. M. Jenkins, and Julian Dorsky (1952), "Mandelic Acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0538 ; Coll. Vol. 3: 538 
  6. ^ Putten, P. L. (1979). [Expression error: Unexpected < operator "Mandelic acid and urinary tract infections"]. Antonie van Leeuwenhoek 45: 622. doi:10.1007/BF00403669. 
  7. ^ Taylor, MB. (1999). [Expression error: Unexpected < operator "Summary of mandelic acid for the improvement of skin conditions"]. Cosmetic Dermatology 21: 26–28. 
  •  This article incorporates text from a publication now in the public domainChisholm, Hugh, ed (1911). Encyclopædia Britannica (Eleventh ed.). Cambridge University Press. 


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