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Mandelic acid

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Identification
Molecular formula
C8H8O3
CAS number
90-64-2
IUPAC name
2-hydroxy-2-phenyl-propanoic acid
State
State
At room temperature, mandelic acid is a solid. It is commonly available as both its optical isomers and racemic mixture, all of which are crystalline.
Melting point (Celsius)
119.00
Melting point (Kelvin)
392.15
Boiling point (Celsius)
360.00
Boiling point (Kelvin)
633.15
General information
Molecular weight
152.15g/mol
Molar mass
152.1470g/mol
Density
1.3000g/cm3
Appearence

Mandelic acid manifests as a white crystalline solid. Its crystals are often seen as colorless rhomboidal forms. The compound is known for being optically active.

Comment on solubility

Solubility of 2-hydroxy-2-phenyl-propanoic acid (C8H8O3)

The solubility of 2-hydroxy-2-phenyl-propanoic acid, commonly known as a compound possessing both hydroxyl and carboxylic acid functional groups, can be quite interesting. This compound is typically expected to demonstrate moderate solubility in certain polar solvents.

Key Points about Solubility:

  • Polarity: Due to the presence of the hydroxyl (-OH) group, the compound exhibits polar characteristics.
  • Solvent Interaction: It tends to be soluble in alcohols and warm aqueous solutions owing to hydrogen bonding capabilities.
  • Limited Solubility in Non-Polar Solvents: On the contrary, its solubility in non-polar solvents, such as hydrocarbons, is much lower.

In general, the solubility behavior can be attributed to its structure, where the hydroxyl group enhances interaction with water, while the phenyl group contributes to hydrophobic characteristics. As a result, it can be expressed that:

“The balance between hydrophilic and hydrophobic components dictates the overall solubility.”

For practical applications, understanding this solubility is crucial, as it impacts formulation in various chemical and pharmaceutical contexts.

Interesting facts

Interesting Facts About 2-Hydroxy-2-phenyl-propanoic Acid

2-Hydroxy-2-phenyl-propanoic acid, commonly known as benzylic acid, is a fascinating compound with diverse applications and characteristics that capture the interest of chemists.

Chemical and Physical Properties

This compound features a unique structure with a phenyl group attached to a propanoic acid unit, which contributes to its interesting chemical behavior. Here are a few notable aspects:

  • Reactivity: The presence of the hydroxyl group (-OH) makes this compound a potential candidate for various chemical reactions, including esterification and substitution reactions.
  • Acidity: The carboxylic acid part of the compound imparts acidic properties, which can be leveraged in synthesis and pH adjustments in various chemical processes.

Applications

2-Hydroxy-2-phenyl-propanoic acid serves important roles in several fields:

  • Pharmaceuticals: Due to its structural features, this compound can be utilized as a pharmaceutical intermediate or in drug formulations.
  • Cosmetics: It is often found in cosmetic products due to its antioxidant properties, which help in skin protection.
  • Synthesis: This compound is a valuable building block in organic synthesis, enabling the creation of a variety of derivatives.

Scientific Significance

One of the most remarkable aspects of 2-hydroxy-2-phenyl-propanoic acid is its relevance in the study of structure-activity relationships. Researchers often investigate how slight modifications to its structure can influence biological activity and efficacy in medicinal chemistry.

In summary, 2-hydroxy-2-phenyl-propanoic acid is not just a simple chemical compound; it is a versatile participant in numerous industrial and research applications, showcasing the intersection of chemistry and practical utility in everyday life. As John Dalton once said, “All matter is composed of atoms,” and compounds like this remind us of the complexity and beauty inherent within these atomic structures.

Synonyms
2-Hydroxy-2-phenylpropanoic acid
Atrolactic acid
515-30-0
2-Phenyllactic acid
2-Hydroxy-2-phenylpropionic acid
phenyllactic acid
alpha-Methylmandelic acid
2-Phenyl-2-hydroxypropionic acid
Atrolactic acid hydrate
Benzeneacetic acid, .alpha.-hydroxy-.alpha.-methyl-
4607-38-9
Mandelic acid, .alpha.-methyl-
.alpha.-Phenyllactic acid
DL-Atrolactic acid
(+/-)-2-phenyllactic acid
DL-.alpha.-Phenyllactic acid
NSC 128998
NSC 401846
UNII-3709C1T8IF
alpha-Hydroxy-alpha-phenylpropionic acid
3709C1T8IF
ATROLACTINIC ACID
DL-2-Phenyllactic acid
EINECS 208-196-1
EINECS 225-014-6
Hydroxyphenylpropionic acid
(1)-2-Phenyllactic acid
NSC-128998
NSC-401846
ATROLACTIC ACID [MI]
alpha-hydroxy-alpha-methylbenzeneacetic acid
ATROLACTIC ACID DL-FORM
ATROLACTIC ACID ANHYDROUS
.alpha.-Hydroxy-.alpha.-phenylpropionic acid
CHEBI:50392
DTXSID10862090
ATROLACTIC ACID, (+/-)-
Mandelic acid, alpha-methyl-, DL-
DL-.ALPHA.-METHYLMANDELIC ACID
Benzeneacetic acid, alpha-hydroxy-alpha-methyl-
(+/-)-2-HYDROXY-2-PHENYLPROPIONIC ACID
a-Phenyllactic acid
2-hydroxy-2-phenyl-propionic acid
DL-alpha-Phenyllactic acid
MFCD00067699
MFCD00067700
phenyl lactic acid
Phenyl-lactic acid
Mandelic acid, DL-
alpha-Phenyllactic acid
hydroxymethylmandelic acid
(+/-)-atrolactic acid
Maybridge3_003173
(+/-)-Phenyllactic acid
Cambridge id 5152365
Oprea1_696321
Mandelic acid, alpha-methyl-
SCHEMBL153694
(+-)-ATROLACTIC ACID
2-Hydroxy-2-phenylpropanoicacid
DTXCID60810905
DL-ALPHA-METHYLMANDELIC ACID
NAA11371
NSC128998
NSC152653
NSC401846
(S)-2-hydroxy-2-phenylpropionic acid
AKOS005265787
NSC-152653
SDCCGMLS-0064676.P001
IDI1_014560
AS-60955
SY036080
SY036081
Mandelic acid, alpha-methyl-, DL-(8CI)
DB-042003
DB-049460
A1035
CS-0435032
NS00043616
2-Hydroxy-2-phenylpropanoic acid hemi hydrate
EN300-69840
T70989
AR-360/42760319
Q27122051
Z336127660