4-Phenylbutyric acid Chemical Properties

Melting point:

49-51 °C(lit.)

Boiling point:

165 °C10 mm Hg(lit.)

Density 

1.0326 (rough estimate)

refractive index 

1.5405 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

5.3g/l. Almost insoluble in water, soluble in alcohol and oils

form 

Crystalline Powder

pka

4.76(at 25℃)

color 

White to slightly yellow

Water Solubility 

5.3 g/L at 40 ºC

BRN 

638180

InChIKey

OBKXEAXTFZPCHS-UHFFFAOYSA-N

LogP

2.420

CAS DataBase Reference

1821-12-1(CAS DataBase Reference)

NIST Chemistry Reference

4-Phenylbutanoic acid(1821-12-1)

EPA Substance Registry System

4-Phenylbutyric acid (1821-12-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29163900

MSDS

• Language:English Provider:4-Phenylbutanoic acid
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4-Phenylbutyric acid Usage And Synthesis

Chemical Properties

4-Phenylbutyric acid is white to slightly yellowish crystalline powder. It is slightly soluble in chloroform and methanol. Its solubility in water is 5.3 g/l (at 40 °C).

Uses

4-Phenylbutyric acid is used as a chemical chaperone involved in protein-folding disorders. It is involved in the synthesis of dyes and an active pharmaceutical ingredient intermediate.

Preparation

4-phenylbutyric acid is obtained by the reaction of benzene with butyrolactone in the presence of aluminum chloride, followed by neutralization with base.
Synthesis of 4-phenylbutyric acid

Application

4-Phenylbutyric acid (4-PBA) is used in the treatment of urea cycle disorders under the trade name Buphenyl. 4-PBA has been used as a selective inhibitor of endoplasmic reticulum stress (ERS).
4-Phenylbutyric acid is used as organic intermediates. It can also be used as a reactant in the synthesis of:
1-Tetralone using Lewis acid catalyst.
4,N-diphenylbutyramide.

Definition

4-Phenylbutyric acid is a monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apopto is in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 3309, 1991 DOI: 10.1016/S0040-4039(00)92693-5

General Description

4-Phenylbutyric acid (4-PBA) is a small-molecular-weight fatty acid with a terminal aromatic group, and its sodium salt (sodium 4-phenyl butyrate) has been used for the treatment of urea cycle disorders. This molecule is also used for the treatment of sickle cell diseases and thalassemia owing to its ability to activate β-globin transcription. Moreover, 4-PBA is employed as an orally bioavailable agent for the treatment of spinal muscular atrophy (SMA) and tumors.
Neuroprotective Effects of 4-phenylbutyric Acid and Its Derivatives: Possible Therapeutics for Neurodegenerative Diseases

Purification Methods

Crystallise the acid from pet ether (b 40-60o). [Beilstein 9 IV 1811.]

4-Phenylbutyric acid(1821-12-1)Related Product Information

• Hydrocortisone-17-butyrate
• 4-Aminobutyric acid
• Indole-3-butyric acid
• Isobutyric acid
• Butyric Acid
• 4-Phenylbutanol
• Chlorambucil
• (E)-1-HEXENE-1,2-DIBORONIC ACID BIS(PINACOL) ESTER
• N-TETRADECYLBORONIC ACID
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• FERROCENEBORONIC ACID
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• 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)HEPTENE
• 4-(4-Aminophenyl)butyric acid
• CYCLOPENTEN-1-YLBORONIC ACID
• 1-Octylboronic acid
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• (R)-(-)-2-HYDROXY-4-PHENYLBUTYRIC ACID