ChemicalBook CAS DataBase List 1821-12-1

1821-12-1

Name	4-Phenylbutyric acid
CAS	1821-12-1
EINECS(EC#)	217-341-8
Molecular Formula	C10H12O2
MDL Number	MFCD00004403
Molecular Weight	164.2
MOL File	1821-12-1.mol

Synonyms

4-PHENYLBUTANOIC ACID 4-PHENYLBUTYRIC ACID 4-PHENYL-N-BUTYRIC ACID AKOS BBS-00003749 GAMA-PHENYLBUTYRIC ACID GAMMA-PHENYL-N-BUTYRIC ACID PHENYLBUTYRATE PHENYLBUTYRIC-4 ACID PHENYLBUTYRIC ACID RARECHEM AL BO 0178 TIMTEC-BB SBB008452 Benzenebutanoic acid benzenebutanoicacid Benzenebutyric acid Butyric acid, 4-phenyl- gamma-Phenylbutyric acid omega-Phenylbutanoic acid 4-PHENYBUTYTIC ACID 4-PhenylButyricAcid99% 4-Phenyl Butyric Acid 99%

Chemical Properties

Appearance	white to slightly yellowish crystalline powder
Melting point	49-51 °C(lit.)
Boiling point	165 °C10 mm Hg(lit.)
density	1.0326 (rough estimate)
refractive index	1.5405 (estimate)
Fp	>230 °F
storage temp.	Sealed in dry,Room Temperature
solubility	5.3g/l
form	Crystalline Powder
pka	4.76(at 25℃)
color	White to slightly yellow
Water Solubility	5.3 g/L at 40 ºC
BRN	638180
InChI	1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)
InChIKey	OBKXEAXTFZPCHS-UHFFFAOYSA-N
SMILES	OC(=O)CCCc1ccccc1
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	1821-12-1(EPA Substance)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H335-H315-H319
Precautionary statements	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes	Xi
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . less more
Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . S36:Wear suitable protective clothing . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . less more
WGK Germany	3
Hazard Note	Irritant
TSCA	Yes
HS Code	29163900
Storage Class	11 - Combustible Solids

Raw materials And Preparation Products

Hazard Information

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.

Uses

4-Phenylbutyric acid is used as organic intermediates.

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.

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

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

storage

Store at RT

Purification Methods

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

Material Safety Data Sheet(MSDS)

Spectrum Detail

Well-known Reagent Company Product Information

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