1716-12-7

Basic information

• Product Name: Sodium 4-phenylbutyrate
• Synonyms: SPB;SODIUM 4-PHENYLBUTYRATE;SODIUM PHENYLBUTYRATE;PBNA;PHENYL N-BUTYRATE SODIUM SALT;4-PHENYLBUTYRATE, NA;4-PHENYLBUTYRIC ACID SODIUM;4-PHENYLBUTYRIC ACID SODIUM SALT
• CAS NO: 1716-12-7
• Molecular Formula: C₁₀H₁₁O₂*Na
• Molecular Weight: 186.18
• EINECS: 1308068-626-2
• Product Categories: VASOTEC
• Mol File: 1716-12-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 290.7 °C at 760 mmHg
• Flash Point: 187.9 °C
• Appearance: white to beige/
• Density: 1.095g/cm3
• Vapor Pressure: 0.00288mmHg at 25°C
• Storage Temp.: Desiccate at -20°C
• Solubility: H2O: ≥5mg/mL
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: Sodium 4-phenylbutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium 4-phenylbutyrate(1716-12-7)
• EPA Substance Registry System: Sodium 4-phenylbutyrate(1716-12-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• RTECS: CY9057220
• Hazardous Substances Data: 1716-12-7(Hazardous Substances Data)

Usage

Description

Sodium 4-phenylbutyrate (4-PBA sodium) is an organic sodium salt of 4-phenylbutyric acid, acting as a prodrug for phenylacetate. It serves as a chemical chaperone, rescuing the trafficking of misfolded proteins, and weakly inhibits histone deacetylase activity. This results in cell cycle arrest, differentiation, and/or apoptosis of various tumors. It is also used in the treatment of urea cycle disorders and has been studied for its role in endoplasmic reticulum (ER) stress.

Uses

Used in Pharmaceutical Industry:
Sodium 4-phenylbutyrate is used as an antineoplastic agent for its potent differentiating capacity in multiple hematopoietic and solid tumor cell lines. It acts as an inducer of tumor cytostasis and differentiation, as well as a transcriptional regulator, improving the targeting of δF508-CFTR for ubiquitination and degradation by reducing the expression of HSC70 in epithelial cells.
Used in Cancer Research:
Sodium 4-phenylbutyrate is used as a histone-deacetylase inhibitor, which has been shown to increase fetal hemoglobin production in vitro and in vivo. It is also used as an endoplasmic reticulum (ER) stress inhibitor to study the role of ER stress in the expression of betatrophin.
Used in Urea Cycle Disorder Treatment:
Sodium 4-phenylbutyrate is used as a treatment for urea cycle disorders, where it stimulates urinary nitrogen excretion and is formulated under the brand name Buphenyl (Medicis).
Used in Infection Research:
Sodium 4-phenylbutyrate is used in cancer and infection research due to its inhibitory effects on various tumors and its role in ER stress.

Biological Activity

Sodium 4-Phenylbutyrate is a histone deacetylase inhibitor that displays anticancer activity. Inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. Also inhibits protein isoprenylation, depletes plasma glutamine, increases production of fetal hemoglobin through transcriptional activation of the γ-globin gene and affects hPPARγ activation.

Biochem/physiol Actions

Sodium phenylbutyrate is a histone deacetylase inhibitor.

References

1) Engelhard et al. (1998), Inhibitory effects of phenylbutyrate on the proliferation, morphology, migration and invasiveness of malignant glioma cells; J. Neuro-Oncol., 37 97 2) Appelskog et al. (2004), Histone deacetylase inhibitor 4-phenylbutyrate suppresses GAPDH mRNA expression in glioma cells; Int. J. Oncol., 24 1419

InChI:InChI=1/C10H12O2.Na/c1-2-9(10(11)12)8-6-4-3-5-7-8;/h3-7,9H,2H2,1H3,(H,11,12);/q;+1/p-1

Upstream product

• 1449300-08-6 4-phenyl-N-(quinolin-8-yl)butanamide 
• 578-66-5 8-amino quinoline 
• 108-86-1 bromobenzene 
• 1821-12-1 4-Phenylbutyric acid 

Relevant articles and documents

Intermolecular Reductive Heck Reaction of Unactivated Aliphatic Alkenes with Organohalides

A general intermolecular reductive Heck reaction of organohalides with both terminal and internal unactivated aliphatic alkenes has been first realized in high yield with complete anti-Markovnikov selectivity. The challenging vinyl bromides, aryl chlorides, and polysubstituted internal alkenes were first applied. More than 100 remote carbofunctionalized alkyl carboxylic acid derivatives were rapidly synthesized from easily accessible starting materials. The synthesis of drug molecules has further demonstrated the wide synthetic utility of this scalable strategy. Preliminary mechanistic studies are consistent with the proposed catalytic cycle.

Preparation method for sodium phenylbutyrate

The invention discloses a preparation method for sodium phenylbutyrate. The method comprises the following steps: (1) purification of 4-phenylbutyric acid: 1) under the catalysis of a catalyst, reacting industrial grade phenylbutyric acid in alcoholic solvents, and treating a reacted system to obtain the 4-phenylbutyric acid; 2) in the existence of an alkali catalyst or an acidic catalyst, performing hydrolysis reaction on the 4-phenylbutyric acid in a solvent to obtained purified phenylbutyric acid, namely, the industrial grade phenylbutyric acid is purified; (2) preparation of the sodium phenylbutyrate: enabling the phenylbutyric acid which is purified by the step 1) to react with a sodium reagent to obtain the sodium phenylbutyrate. According to the preparation method disclosed by the invention, alcohols (methyl alcohol and ethyl alcohol) serve as reaction solvents, so that the preparation method is more environmentally -friendly and green compared with a synthesis method in the prior art; the preparation of high-purity methyl alcohol is realized through a three-step conventional reaction; the purity of the sodium phenylbutyrate prepared by the preparation method reaches 99.5 percent or above, and single impurities are controlled to be within 0.1 percent.

Effects of structure variation on solution properties of hydrotropes: Phenyl versus cyclohexyl chain tips

The physicochemical behavior of the phenyl-n-alkanoate (PhenCx) and cyclohexyl-n-alkanoate (CyclohexCx) series has been investigated, supporting previous work on the understanding of hydrotropes (Hopkins Hatzopoulos, M.; Eastoe, J.; Dowding, P.J.; Rogers, S. E.; Heenan, R.; Dyer, R. Langmuir2011, 27, 12346-12353). Electrical conductivity, surface tension, 1H NMR, and small-angle neutron scattering (SANS) were used to study adsorption and aggregation in terms of critical aggregation concentration (cac). The PhenCx series exhibited very similar d log(cac)/dn to n-alkylbenzoates (CnBenz), exhibiting two branches of behavior, with a common inflection point at four linear carbons, whereas the CyclohexCx series showed no break point. Electrical conductivity and 1H NMR concentration scans indicate a difference in physicochemical behavior between higher and lower homologues in both the PhenCx and CyclohexCx series. Surface tension measurements with compounds belonging to either group gave typical Gibbs adsorption profiles, having d log(cac)/dn curves consistent with limiting headgroup areas in the region of (35-55 A2) indicating monolayer formation. SANS profiles showed no evidence for aggregates below the electrical conductivity determined cac values, inferring an "on-off" mode of aggregation. Analyses of SANS profiles was consistent with charged ellipsoidal aggregates, persisting from lower through to higher homologues in both the PhenCx and CyclohexCx series.