Names | |||
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Preferred IUPAC name Hydroxy(phenyl)acetic acid | |||
Other names 2-Hydroxy-2-phenylacetic acid Mandelic acid Phenylglycolic acid α-Hydroxyphenylacetic acid | |||
Identifiers | |||
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3D model (JSmol) | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.001.825 | ||
EC Number |
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PubChem CID | |||
RTECS number |
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UNII |
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CompTox Dashboard (EPA) | |||
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Properties | |||
C8H8O3 | |||
Molar mass | 152.149 g·mol−1 | ||
Appearance | White crystalline powder | ||
Density | 1.30 g/cm3 | ||
Melting point | 119 °C (246 °F; 392 K) optically pure: 132 to 135 °C (270 to 275 °F; 405 to 408 K) | ||
Boiling point | 321.8 °C (611.2 °F; 595.0 K) | ||
15.87 g/100 mL | |||
Solubility | soluble in diethyl ether, ethanol, isopropanol | ||
Acidity (pKa) | 3.41 [2] | ||
Refractive index (nD) | 1.5204 | ||
Thermochemistry | |||
Std enthalpy of formation (ΔfH⦵298) | 0.1761 kJ/g | ||
Pharmacology | |||
B05CA06 ( WHO ) J01XX06 ( WHO ) | |||
Hazards | |||
Flash point | 162.6 °C (324.7 °F; 435.8 K) | ||
Related compounds | |||
Related compounds | mandelonitrile, phenylacetic acid, vanillylmandelic acid | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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.
Mandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler (1801–1868) while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. The name is derived from the German "Mandel" for "almond". [3]
Mandelic acid is usually prepared by the acid-catalysed hydrolysis of mandelonitrile, [4] 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: [5]
Alternatively, it can be prepared by base hydrolysis of phenylchloroacetic acid as well as dibromacetophenone. [6] It also arises by heating phenylglyoxal with alkalis. [7] [8]
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. [9] Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated. [10] 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. [11]
It also arises from the biodegradation of styrene [12] and ethylbenzene, as detected in urine.
Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections. [13] It has also been used as an oral antibiotic, and as a component of chemical face peels analogous to other alpha hydroxy acids. [14]
The drugs cyclandelate and homatropine are esters of mandelic acid.
Cystine is the oxidized derivative of the amino acid cysteine and has the formula (SCH2CH(NH2)CO2H)2. It is a white solid that is poorly soluble in water. As a residue in proteins, cystine serves two functions: a site of redox reactions and a mechanical linkage that allows proteins to retain their three-dimensional structure.
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.
Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word furfur, meaning bran, referring to its usual source. Furfural is only derived from dried biomass. In addition to ethanol, acetic acid, and sugar, furfural is one of the oldest organic chemicals available readily purified from natural precursors.
Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet bitter almond odour. It is mainly used as a precursor to the resin benzoguanamine.
The Kolbe–Schmitt reaction or Kolbe process is a carboxylation chemical reaction that proceeds by treating phenol with sodium hydroxide to form sodium phenoxide, then heating sodium phenoxide with carbon dioxide under pressure, then treating the product with sulfuric acid. The final product is an aromatic hydroxy acid which is also known as salicylic acid.
The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid.
Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.
In organic chemistry, the benzoin addition is an addition reaction involving two aldehydes. The reaction generally occurs between aromatic aldehydes or glyoxals, and results in formation of an acyloin. In the classic example, benzaldehyde is converted to benzoin.
Benzoin ( or ) is an organic compound with the formula PhCH(OH)C(O)Ph. It is a hydroxy ketone attached to two phenyl groups. It appears as off-white crystals, with a light camphor-like odor. Benzoin is synthesized from benzaldehyde in the benzoin condensation. It is chiral and it exists as a pair of enantiomers: (R)-benzoin and (S)-benzoin.
Hippuric acid is a carboxylic acid and organic compound. It is found in urine and is formed from the combination of benzoic acid and glycine. Levels of hippuric acid rise with the consumption of phenolic compounds. The phenols are first converted to benzoic acid, and then to hippuric acid and excreted in urine.
The Reimer–Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols. with the simplest example being the conversion of phenol to salicylaldehyde. The reaction was first reported by Karl Reimer and Ferdinand Tiemann.
Nikolay Nikolaevich Zinin was a Russian organic chemist.
The Erlenmeyer–Plöchl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform an N-acyl glycine to various other amino acids via an oxazolone.
In organic chemistry, the Claisen–Schmidt condensation is the reaction between an aldehyde or ketone having an α-hydrogen with an aromatic carbonyl compound lacking an α-hydrogen. It can be considered as a specific variation of the aldol condensation. This reaction is named after two of its pioneering investigators Rainer Ludwig Claisen and J. Gustav Schmidt, who independently published on this topic in 1880 and 1881. An example is the synthesis of dibenzylideneacetone ( -1,5-diphenylpenta-1,4-dien-3-one).
In enzymology, a mandelate 4-monooxygenase (EC 1.14.16.6) is an enzyme that catalyzes the chemical reaction
In enzymology, (S)-mandelate dehydrogenase (MDH), is an enzyme that catalyzes the chemical reaction.
The enzyme (R)-mandelonitrile lyase (EC 4.1.2.10, (R)-HNL, (R)-oxynitrilase, (R)-hydroxynitrile lyase) catalyzes the chemical reaction
Mellitic anhydride, the anhydride of mellitic acid, is an organic compound with the formula C12O9.
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful.
(R)-prunasin is a cyanogenic glycoside related to amygdalin. Chemically, it is the glucoside of (R)-mandelonitrile.