Mandelic acid

Identification

Molecular formula

C₈H₈O₃

CAS number

90-64-2

IUPAC name

2-hydroxy-2-phenyl-acetic acid

State

At room temperature, mandelic acid is typically found in solid form. It exists as a crystalline powder that is slightly soluble in water but more soluble in organic solvents like ethanol and methanol.

Melting point (Celsius)

119.00

Melting point (Kelvin)

392.00

Boiling point (Celsius)

321.70

Boiling point (Kelvin)

594.80

General information

Molecular weight

152.15g/mol

Molar mass

152.1520g/mol

Density

1.3000g/cm³

Appearence

Mandelic acid is a white crystalline solid that appears as a colorless or white crystalline powder. It is often used in its powder form in various chemical applications and can sometimes be found in solution form in cosmetic products.

Comment on solubility

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

2-hydroxy-2-phenyl-acetic acid, also known as mandelic acid, exhibits distinctive solubility characteristics owing to its unique structure. This compound is a white crystalline solid that is generally known for its moderate solubility in various solvents. Here’s a closer look at its solubility properties:

Aqueous Solubility: It shows good solubility in water, especially at higher temperatures. This characteristic makes it versatile for various chemical applications.
Organic Solvents: 2-hydroxy-2-phenyl-acetic acid is also soluble in organic solvents such as ethanol and methanol, which highlights its compatibility in organic synthesis processes.
pH Dependence: The solubility can be influenced by pH levels, as the ionic form of the molecule tends to be more soluble in basic conditions due to enhanced dissociation.

These solubility traits underscore the importance of 2-hydroxy-2-phenyl-acetic acid in chemical formulations and pharmaceuticals. As one might observe:

“The dissolution of a compound is a critical aspect that determines its reactivity and application in solution-based reactions.”

Exploring the solubility of this compound allows for a deeper understanding of its potential uses in both industrial and laboratory settings.

Interesting facts

Interesting Facts about 2-Hydroxy-2-phenyl-acetic acid

2-Hydroxy-2-phenyl-acetic acid, often referred to as mandelic acid, is a compound that exhibits fascinating properties and applications in various fields:

Historical Context: This compound was first isolated from Almonds and has been utilized in traditional medicine for its beneficial properties.
Pharmaceutical Significance: Mandelic acid is known for its antimicrobial effects, making it useful in the development of antibiotics and skin care products.
Chirality: It is a chiral molecule, which means it can exist in two different forms. This chirality plays a significant role in its biological activity, with each enantiomer often exhibiting different effects.
Environmental Impact: Mandelic acid is considered more environmentally friendly compared to other chemical compounds due to its natural origins and biodegradable properties.
Cosmetic Use: This compound is frequently utilized in skincare formulations, particularly for its ability to enhance exfoliation and improve skin tone.
Synthesis: 2-Hydroxy-2-phenyl-acetic acid can be synthesized through several methods, including the hydrolysis of benzyl cyanide, providing considerable flexibility for chemists in laboratory settings.

Moreover, its multifunctional properties extend to the fields of organic chemistry and biochemistry, where it serves as a crucial intermediate in various reactions. As a student of chemistry or a scientist, understanding compounds like 2-hydroxy-2-phenyl-acetic acid opens up pathways for innovative research and practical applications across multiple industries.

Synonyms

MANDELIC ACID

dl-Mandelic acid

90-64-2

2-hydroxy-2-phenylacetic acid

611-72-3

Phenylglycolic acid

Amygdalic acid

Paramandelic acid

Racemic mandelic acid

Uromaline

Almond acid

p-Mandelic acid

(RS)-Mandelic acid

2-Phenylglycolic acid

Hydroxy(phenyl)acetic acid

Phenylhydroxyacetic acid

Glycolic acid, phenyl-

Acido mandelico

Kyselina mandlova

(+-)-Mandelic acid

alpha-Hydroxyphenylacetic acid

2-Phenyl-2-hydroxyacetic acid

alpha-Hydroxy-alpha-toluic acid

(+/-)-alpha-Hydroxyphenylacetic acid

2-Hydroy-2-phenylacetic acid

DL-Hydroxy(phenyl)acetic acid

Benzeneacetic acid, alpha-hydroxy-

NSC 7925

(+-)-alpha-Hydroxybenzeneacetic acid

alpha-Hydroxybenzeneacetic acid

(+/-)-mandelic acid

2-hydroxy-2-phenyl-acetic acid

(+-)-2-Hydroxy-2-phenylethanoic acid

alpha-Toluic acid, alpha-hydroxy-

DL-2-Hydroxy-2-phenylacetic acid

Kyselina 2-fenyl-2-hydroxyethanova

UNII-NH496X0UJX

NSC-7925

(+-)-alpha-Hydroxyphenylacetic acid

EINECS 202-007-6

EINECS 210-277-1

NH496X0UJX

Benzeneacetic acid, .alpha.-hydroxy-

alpha-Hydroxybenzeneacetic acid, (+-)-

.alpha.-Hydroxyphenylacetic acid

CHEBI:35825

AI3-06293

(+/-)-alpha-Hydroxybenzeneacetic acid

DTXSID6023234

2-Hydroxy-2-phenylethanoic acid

.alpha.-Hydroxy-.alpha.-toluic acid

.alpha.-Toluic acid, .alpha.-hydroxy-

(+)-Mandelate, XXI

Benzeneacetic acid, .alpha.-hydroxy-, (.+/-.)-

mandelic-acid

MANDELIC ACID (MART.)

MANDELIC ACID [MART.]

MANDELIC ACID (USP-RS)

MANDELIC ACID [USP-RS]

Mandelic acid [USP]

DL-Amygdalic Acid

DL-Mandelicacid

Acido mandelico [Italian]

Kyselina mandlova [Czech]

GLYCOPYRRONIUM BROMIDE IMPURITY C (EP IMPURITY)

GLYCOPYRRONIUM BROMIDE IMPURITY C [EP IMPURITY]

HOMATROPINE HYDROBROMIDE IMPURITY C (EP IMPURITY)

HOMATROPINE HYDROBROMIDE IMPURITY C [EP IMPURITY]

HOMATROPINE METHYLBROMIDE IMPURITY C (EP IMPURITY)

HOMATROPINE METHYLBROMIDE IMPURITY C [EP IMPURITY]

Mandelsaeure

Kyselina 2-fenyl-2-hydroxyethanova [Czech]

Benzoglycolic acid

Phenylacetic acid, alpha-hydroxy-

NCGC00166022-01

l(+)mandelic acid

(+) mandelic acid

(+)-mandelic acid

SAMMA

hyroxyphenylacetic acid

l (+)-mandelic acid

Mandelic acid, 99%

(-)-Mandelate, XX

hydroxyphenyl acetic acid

81432-25-9

Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.R)-

Mandelic acid (Standard)

Pregabalin EP Impurity C

WLN: QYR&VQ

hydroxy-phenyl-acetic acid

Mandelic acid, >=99%

DL-Mandelic acid, 99%

MANDELIC ACID [MI]

SCHEMBL1050

(.+/-.)-Mandelic acid

CHEMBL1609

2-Hydroxy-2-phenylaceticacid

MLS001074208

DTXCID203234

MANDELIC ACID [WHO-DD]

.alpha.-Phenylhydroxyacetic acid

BDBM92715

NSC7925

2-oxidanyl-2-phenyl-ethanoic acid

HMS2230F19

HMS3371M20

HMS3373A03

acetic acid, 2-hydroxy-2-phenyl-

(2rs)-hydroxy(phenyl)ethanoic acid

HY-W015591R

VCA83871

BBL028097

MFCD00064250

s3363

STL283951

AKOS000118795

AKOS016050628

CS-W016307

DB13218

HY-W015591

KS-1423

NCGC00166023-01

NCGC00166269-01

PHENYLACETIC ACID, alpha--HYDROXY-

(.+/-.)-alpha-Hydroxybenzeneacetic acid

AC-12228

SMR000653543

SY001645

SY001670

DB-016128

DB-016158

DS-000887

M0038

NS00001311

Benzeneacetic acid, .alpha.-hydroxy-, ( )-

Benzeneacetic acid, .alpha.-hydroxy-, (S)-

EN300-19482

PHENYLACETIC ACID, .ALPHA.--HYDROXY-

DL-Mandelic acid, analytical reference material

MLS-0090887.0001

A833072

AE-562/40233036

Q412293

(2RS)-2-Hydroxy-2-phenylacetic Acid (Mandelic Acid)

BRD-A91448670-001-06-4

Mandelic Acid ((2RS)-2-Hydroxy-2-phenylacetic Acid)

14A53E4A-8315-42A7-9D60-DE06CCBB1AF9

F2191-0202

Z104473974

Mandelic acid, United States Pharmacopeia (USP) Reference Standard

D-2-Hydroxy-2-phenylacetic acid; (S)-(+)-alpha-Hydroxyphenylacetic acid

202-007-6

32518-00-6

a-Hydroxy-benzeneacetic acid; Hydroxy(phenyl)acetic acid; 2-Phenylglycolic acid; 2-Hydroxy-2-phenylacetic acid; alpha-Hydroxyphenylacetic acid;R(-)-Mandelic acid

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

Interesting Facts about 2-Hydroxy-2-phenyl-acetic acid

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