1716-12-7 Usage
Description
Different sources of media describe the Description of 1716-12-7 differently. You can refer to the following data:
1. 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.
2. 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
Different sources of media describe the Uses of 1716-12-7 differently. You can refer to the following data:
1. 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.
2. Sodium 4-Phenylbutyrate is a histone-deacetylase inhibitor.
3. Sodium phenylbutyrate has been used as an endoplasmic reticulum (ER) stress inhibitor to study the role of ER stress in the expression of betatrophin.
Definition
ChEBI: The organic sodium salt of 4-phenylbutyric acid. A prodrug for phenylacetate, it is used to treat urea cycle disorders.
Brand name
Buphenyl (Medicis).
General Description
An antineoplastic agent that demonstrates potent differentiating capacity in multiple hematopoietic and solid tumor cell lines. Acts as an inducer of tumor cytostasis and differentiation as well as of peroxisomal proliferation. A more effective inhibitor of histone deacetylase and inducer of histone acetylation than its structural analogs including 2- and 3-phenylbutyrate. Acts as a transcriptional regulator and improve the targeting of δF508-CFTR (cystic fibrosis transmembrane regulator) for ubiquitination and degradation by reducing the expression of HSC70 in epithelial cells. Also, reported to increase fetal hemoglobin production in vitro and in vivo.
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
Check Digit Verification of cas no
The CAS Registry Mumber 1716-12-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,1 and 6 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1716-12:
(6*1)+(5*7)+(4*1)+(3*6)+(2*1)+(1*2)=67
67 % 10 = 7
So 1716-12-7 is a valid CAS Registry Number.
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
1716-12-7Relevant articles and documents
Intermolecular Reductive Heck Reaction of Unactivated Aliphatic Alkenes with Organohalides
Zheng, Kewang,Xiao, Guanlin,Guo, Tao,Ding, Yalan,Wang, Chengdong,Loh, Teck-Peng,Wu, Xiaojin
, p. 694 - 699 (2020/01/31)
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
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Paragraph 0084; 0089, (2017/06/29)
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
Hopkins Hatzopoulos, Marios,Eastoe, Julian,Dowding, Peter J.,Grillo, Isabelle,Deme, Bruno,Rogers, Sarah E.,Heenan, Richard,Dyer, Robert
experimental part, p. 9332 - 9340 (2012/09/22)
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.
