Mandelic acid Chemical Properties

Melting point:

131-133 °C(lit.)

alpha 

-150 º (c=2.5, H2O)

Boiling point:

214.6°C (rough estimate)

Density 

1.1677 (rough estimate)

refractive index 

-153.5 ° (C=1, H2O)

Flash point:

>190℃

storage temp. 

Store below +30°C.

solubility 

109.8g/l soluble

form 

Crystalline Powder, Crystals or Flakes

pka

3.37(at 25℃)

color 

White to slightly yellow-beige

PH

3.34(1 mM solution);2.75(10 mM solution);2.22(100 mM solution);

optical activity

[α]25/D 151°, c = 1 in ethanol

Water Solubility 

It is partly soluble in water, freely soluble in isopropyl and ethyl alcohol.

Sensitive 

Light Sensitive

BRN 

2691094

Stability:

Stable, but light sensitive. Combustible. Incompatible with strong bases, strong oxidizing agents.

InChIKey

IWYDHOAUDWTVEP-SSDOTTSWSA-N

LogP

0.550 (est)

CAS DataBase Reference

611-71-2(CAS DataBase Reference)

EPA Substance Registry System

Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.R)- (611-71-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

41-36/37/38

Safety Statements 

22-24/25-36-26-39-37/39

WGK Germany 

1

Hazard Note 

Irritant/Light Sensitive

TSCA 

Yes

HS Code 

29181980

Toxicity

LD50 orally in Rabbit: 5000 mg/kg

MSDS

• Language:English Provider:2-Phenylglycolic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Mandelic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(R)-(-)-Mandelic acid, is used as a antiseptic ingredient particularly against urinary tract infections.Mandelic acid and its derivatives are used to apply the dual activities as an antibacterial agent and as an antiaging agent. It is used as an intermediate for the synthesis of target molecules for other applications.

Uses

(R)-(?)-Mandelic acid can be used:

• As a chiral acid in the separation of diastereomeric salts for the synthesis of chiral pyridoindole based building block.
• In the study of chiral acid selectivity of poly(3,4-ethylenedioxythiophene) (PEDOT) based chiral conducting?polymers.

Uses

Antiseptic (urinary).

Definition

ChEBI: (R)-mandelic acid is the (R)-enantiomer of mandelic acid. It has a role as a human xenobiotic metabolite. It is a conjugate acid of a (R)-mandelate. It is an enantiomer of a (S)-mandelic acid.

Synthesis Reference(s)

The Journal of Organic Chemistry, 33, p. 2565, 1968 DOI: 10.1021/jo01270a105
Synthetic Communications, 18, p. 2141, 1988 DOI: 10.1080/00397918808068285

General Description

(R)-(-)-Mandelic acid, a chiral resolving agent, is also used as a building block to synthesize pharmaceutical drugs such as penicillin and cephalosporin. It can be synthesized from (R,S)-mandelonitrile with high yield and enantioselectivity using nitrilase enzyme.

Flammability and Explosibility

Non flammable

Purification Methods

Purify the mandelic acids by recrystallisation from H2O, *C6H6 or CHCl3. [Roger J Chem Soc 2168 1932,Jamison & Turner J Chem Soc 611 1942.] They have solubilities in H2O of ca 11% at 25o. [Banks & Davies J Chem Soc 73 1938.] The S-benzylisothiuronium salts has m 180o (from H2O) and [] D 25 (+) and (-) 57o (c20, EtOH) [El Masri et al. Biochem J 68 199 1958]. [Beilstein 10 IV 564.]

Mandelic acid(611-71-2)Related Product Information

• Citric acid
• PHENYL VALERATE
• Hyaluronic acid
• 4-Chloromandelic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• Glycolic acid
• CHLOROPHOSPHONAZO III
• Phenylboronic acid
• 5-Pyrazolecarboxylic acid
• Ascoric Acid
• (S)-(+)-Mandelic acid
• 2-Chloromandelic acid
• Benactyzine
• Flurenol-butyl
• 3-Quinuclidinyl benzilate
• (R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid
• Acetic anhydride