Sodium phenylbutyrate

Base Information

• Chemical Name: Sodium phenylbutyrate
• CAS No.: 1716-12-7
• Molecular Formula: C10H11NaO2
• Molecular Weight: 186.186
• Hs Code.: 29163990
• UNII: NT6K61736T
• DSSTox Substance ID: DTXSID7040948
• Nikkaji Number: J783.828J
• Wikipedia: Sodium_phenylbutyrate
• Wikidata: Q7553358
• NCI Thesaurus Code: C1440
• RXCUI: 214837
• ChEMBL ID: CHEMBL1746
• Mol file: 1716-12-7.mol

Synonyms:4-phenylbutyrate;4-phenylbutyric acid;4-phenylbutyric acid, calcium salt;4-phenylbutyric acid, sodium salt;Ammonaps;Buphenyl;sodium 4-phenylbutanoate;sodium 4-phenylbutyrate;sodium phenylbutyrate

Chemical Property of Sodium phenylbutyrate

Chemical Property:

• Vapor Pressure: 0.00288mmHg at 25°C
• Melting Point: 207°C (dec.)(lit.)
• Boiling Point: 290.7 °C at 760 mmHg
• Flash Point: 187.9 °C
• PSA: 40.13000
• Density: 1.095g/cm3
• LogP: 0.75920
• Storage Temp.: Desiccate at -20°C
• Solubility.: H2O: ≥5mg/mL
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 186.06567387
• Heavy Atom Count: 13
• Complexity: 142

Purity/Quality:

99% ^*data from raw suppliers

Sodium 4-Phenylbutyrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCCC(=O)[O-].[Na+]
• Recent ClinicalTrials: Role of BCAA in Glucose Homeostasis
• Recent EU Clinical Trials: A Phase IIIb, Open Label Extension Study Evaluating The Safety And Tolerability of AMX0035 Up To 108 Weeks In Adult Participants with Amyotrophic Lateral Sclerosis (ALS) Previously Enrolled In Study A35-004 (PHOENIX)
• Description: Sodium 4-phenylbutyrate (4-PBA sodium) is an inhibitor of HDAC and endoplasmic reticulum (ER) stress, used in cancer and infection research.Sodium phenylbutyrate stimulates urinary nitrogen excretion. It is a prodrug, which undergoes β-oxidation to phenylacetate. Sodium phenylbutyrate is used to treat urea cycle disorder. It might be associated with menstrual dysfunction, amenorrhea and painful mucositis of the esophagus and stomach.Sodium phenylbutyrate has been used as an endoplasmic reticulum (ER) stress inhibitor to study the role of ER stress in the expression of betatrophin. Sodium 4-phenylbutyrate is a chemical chaperone that has been shown to rescue the trafficking of misfolded proteins. It also weakly blocks histone deacetylase activity (IC50 = 0.4 mM), which results in cell cycle arrest, differentiation, and/or apoptosis of various tumors. Formulations containing sodium 4-phenylbutyrate have been used for the treatment of urea cycle disorders.
• Uses: ACE inhibitor, antihypertensive, Inhibitor of histone deacetylase (HDAC). Anti-neoplastic agent and transcriptional regulator. Also acts as an inducer of tumor cytostasis and differentiation.Sodium 4-phenylbutyrate is a chemical chaperone that has been shown to rescue the trafficking of misfolded proteins.It also weakly blocks histone deacetylase activity (IC50 = 0.4 mM), which results in cell cycle arrest, differentiation, and/or apoptosis of various tumors.Formulations containing sodium 4-phenylbutyrate have been used for the treatment of urea cycle disorders. Sodium 4-Phenylbutyrate is a histone-deacetylase inhibitor. Sodium phenylbutyrate has been used as an endoplasmic reticulum (ER) stress inhibitor to study the role of ER stress in the expression of betatrophin.

Technology Process of Sodium phenylbutyrate

There total 5 articles about Sodium phenylbutyrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-phenyl-N-(quinolin-8-yl)butanamide (1449300-08-6) → Ammonaps (1716-12-7)

Guidance literature:

With sodium hydroxide; In ethanol; for 12h; Reflux;

Reference yield: 96.0%

4-Phenylbutyric acid (1821-12-1) → Ammonaps (1716-12-7)

Guidance literature:

With sodium hydroxide; In water;

Reference yield:

bromobenzene (108-86-1,52753-63-6) → Ammonaps (1716-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1: bis(η3-allyl-μ-chloropalladium(II)); N–phenyl–2–(dicyclohexylphosphino)pyrrole; water; lithium acetate; 2.3-butanediol / 18 h / 130 °C / Inert atmosphere; Schlenk technique; Sealed tube

2: sodium hydroxide / ethanol / 14 h / 130 °C / Sealed tube

With bis(η3-allyl-μ-chloropalladium(II)); lithium acetate; water; sodium hydroxide; N–phenyl–2–(dicyclohexylphosphino)pyrrole; 2.3-butanediol; In ethanol;

DOI:10.1021/acs.orglett.9b04474

upstream raw materials:

4-Phenylbutyric acid

4-phenyl-N-(quinolin-8-yl)butanamide

bromobenzene

8-amino quinoline

Refernces

• 1、 -. "Preparation method of sodium phenylbutyrate". Paragraph 0014; 0028-0032. . Retrieved 2019/10/22.
• 2、 -. "Use of 4-phenylbutyric acid and/or salts thereof for enhancing stress tolerance in plants". Page/Page column 3. . Retrieved 2012/04/05.