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Mandelic acid information


Mandelic acid[1]
Structural formula of mandelic acid
Ball-and-stick model of the mandelic acid molecule
Names
Preferred IUPAC name
Hydroxy(phenyl)acetic acid
Other names
2-Hydroxy-2-phenylacetic acid
Mandelic acid
Phenylglycolic acid
α-Hydroxyphenylacetic acid
Identifiers
CAS Number
  • 90-64-2 checkY
  • 611-71-2 (R) checkY
  • 17199-29-0 (S) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:35825 checkY
ChEMBL
  • ChEMBL1609 checkY
ChemSpider
  • 1253 checkY
ECHA InfoCard 100.001.825 Edit this at Wikidata
EC Number
  • 202-007-6
PubChem CID
  • 1292
RTECS number
  • OO6300000
UNII
  • NH496X0UJX checkY
  • PPL7YW1M9W (R) checkY
  • L0UMW58G3T (S) checkY
CompTox Dashboard (EPA)
  • DTXSID6023234 Edit this at Wikidata
InChI
  • InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11) checkY
    Key: IWYDHOAUDWTVEP-UHFFFAOYSA-N checkY
  • InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)
    Key: IWYDHOAUDWTVEP-UHFFFAOYAD
SMILES
  • O=C(O)C(O)c1ccccc1
Properties
Chemical formula
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)
Solubility in water
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 fH298)
0.1761 kJ/g
Pharmacology
ATC code
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).
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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. The molecule is chiral. The racemic mixture is known as paramandelic acid.

  1. ^ Merck Index, 11th Edition, 5599.
  2. ^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.

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Mandelic acid

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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...

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Alpha hydroxycarboxylic acid

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acids, where the functional groups are separated by two carbon atoms. Notable AHAs include glycolic acid, lactic acid, mandelic acid, and citric acid...

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Vanillylmandelic acid

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Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)" (PDF). Journal of Research of the National Bureau of...

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Mandelonitrile

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In organic chemistry, mandelonitrile is the nitrile of mandelic acid, or the cyanohydrin derivative of benzaldehyde. Small amounts of mandelonitrile occur...

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Styrene oxide

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sufficient, acid-catalyzed isomerization for phenylacetaldehyde will occur. Styrene oxide in the body is metabolized to mandelic acid, phenylglyoxylic acid, benzoic...

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Benzaldehyde

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synthesis of mandelic acid starts with the addition of hydrocyanic acid to benzaldehyde: The resulting cyanohydrin is hydrolysed to mandelic acid. (The scheme...

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Phenylglyoxylic acid

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of 64–66 °C and is moderately acidic (pKa = 2.15). Phenylglyoxylic acid can be synthesized by oxidation of mandelic acid with potassium permanganate. An...

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Chiral auxiliary

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with chiral 8-phenylmenthol and by Barry Trost in 1980 with chiral mandelic acid. The menthol compound is difficult to prepare and as an alternative...

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Glyoxylic acid

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Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic...

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Microbacterium paraoxydans

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Microbacterium paraoxydans metabolize (RS)-mandelonitrile to (R)-(-)mandelic acid. Microbacterium paraoxydans is a plant growth-promoting bacteria. Laffineur...

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Kinetic resolution

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ester derived from (+)-mandelic acid to be quicker than the formation of the ester from (−)-mandelic acid. The unreacted acid was observed to have a slight...

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Electrophilic aromatic substitution

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Glyoxylate: A Simple Procedure for the Synthesis of Optically Active Aromatic Mandelic Acid Esters Nicholas Gathergood, Wei Zhuang, and Karl Anker Jrgensen J. Am...

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C8H8O3

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Hydroxyphenylacetic acid 2-Hydroxyphenylacetic acid 3-Hydroxyphenylacetic acid 4-Hydroxyphenylacetic acid Isovanillin Mandelic acid Methylparaben Methyl...

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Fischer oxazole synthesis

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more specific example of Fischer oxazole synthesis involves reacting mandelic acid nitrile with benzaldehyde to give 2,5-diphenyl-oxazole. Fischer developed...

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Hexamethylenetetramine

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processes, and fireproof materials. As the mandelic acid salt (methenamine mandelate) or the hippuric acid salt (methenamine hippurate), it is used for...

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Chiral resolution

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optically active (S)-mandelic acid 3. The alcohol (S)-enantiomer forms an insoluble diastereomeric salt with the mandelic acid and can be filtered from...

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Manganate

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1039/JR9560003373 Lee, Donald G.; Chen, Tao (1993), "Reduction of manganate(VI) by mandelic acid and its significance for development of a general mechanism of dationoxin...

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Guaiacol

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condensation reaction of glyoxylic acid with guaiacol to give mandelic acid, which is oxidized to produce phenylglyoxylic acid. This acid undergoes a decarboxylation...

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Ethylvanillin

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give guaethol (1). This ether condenses with glyoxylic acid to give the corresponding mandelic acid derivative (2), which by oxidation (3) and decarboxylation...

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Vanillin

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Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)". Journal of Research of the National Bureau of Standards...

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Cyanohydrin

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Yeaw, J. S. (1941). "Mandelic Acid". Organic Syntheses; Collected Volumes, vol. 1, p. 336. William Bauer, Jr. "Methacrylic Acid and Derivatives" in Ullmann's...

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Piperonal

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Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)". Journal of Research of the National Bureau of Standards...

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Amygdalin

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D-glucose, benzaldehyde, and prussic acid; while hydrochloric acid gives mandelic acid, D-glucose, and ammonia. In 1845 amygdalin was used as a cancer...

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Permanganate

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 52. Lee, Donald G.; Chen, Tao (1993), "Reduction of manganate(VI) by mandelic acid and its significance for development of a general mechanism of oxidation...

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Cosmetics

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exfoliants include azelaic acid, citric acid, acetic acid, malic acid, mandelic acid, glycolic acid, lactic acid, salicylic acid, papain, and bromelain....

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