Sodium Phenylbutyrate Powder CAS 1716-12-7

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Sodium phenylbutyrate powder, formerly known as sodium 4-phenylbutyrate, also known as sodium phenylbutyrate, is a white crystal powder used as pharmaceutical intermediates and other fine chemicals. Sodium 4-phenylbutyrate is an organic compound that exists in the form of colorless or white solid crystals. The chemical formula is C10H11NaO2, with a corresponding molecular weight of 186.19 g/mol, usually without obvious odor. Has good solubility in water. It can also dissolve in some organic solvents, such as methanol, ethanol, chloroform, etc. Relatively stable at high temperatures. However, if heated for a long time, it may undergo decomposition. The aqueous solution is alkaline and has a high pH value. It is a flammable substance that can burn under open flames, producing carbon dioxide, water, and organic gases. It has been widely used in some cosmetics and beauty products. It has moisturizing, antioxidant, and antibacterial properties, which can be used to improve skin texture, delay skin aging, and prevent skin problems such as acne. There are also other application areas, such as neuroprotection, anti epilepsy, and the treatment of angiotensin converting enzyme deficiency. In addition, it is also used as a laboratory reagent and plays a role in biomedical research.

Storage condition room temp, Solubility H2O: ≥ 5 mg/ml, White to slightly yellow solid, Color white to Beige, InChIKeyOBKXEAXTFZPCHS-UHFFFAOYSA-N, Hazard symbol (GHS) ghs07, Warning word, Hazard description h319, Precautions p305 + P351 + P338, Dangerous goods sign Xi, Hazard category code 36, Safety instructions 26, WGK Germany 3, RTECS No.: cy9057220.

Sodium 4-phenylbutyrate (CAS number: 1716-12-7), as a multifunctional organic compound, has shown wide application value in the fields of medicine, scientific research, industry, and food due to its unique chemical properties and biological activity.

Medical field: from metabolic disease treatment to anti-tumor research

 

1. Effective treatment for urea cycle disorders
It is a classic medication for treating urea cycle disorders (UCD). This disease is caused by liver enzyme defects leading to abnormal ammonia metabolism, causing hyperammonemia, brain edema, and even death. Its mechanism of action is:
Accelerated ammonia clearance: As a precursor of phenylacetic acid, it is converted into phenylacetylglutamine in the body, which combines with ammonia to form non-toxic phenylacetylglutamine, which is excreted through urine and reduces blood ammonia concentration.

 

Clinical efficacy: Long term use can significantly reduce the frequency of hyperammonemia attacks and improve neurocognitive function. For example, a clinical study on children with UCD showed that after 6 months of continuous treatment, blood ammonia levels decreased by 60% and the number of epileptic seizures decreased by 75%.

2. Synergistic enhancement of anti-tumor therapy
As a histone deacetylase (HDAC) inhibitor, it inhibits tumor cell proliferation and induces apoptosis by regulating epigenetic modifications:
Mechanism analysis: Reversible inhibition of class I/II HDAC enzymes, increased histone acetylation levels, relaxed chromatin structure, activated pro apoptotic genes (such as p21, Bax) expression, while inhibiting the synthesis of anti apoptotic proteins (such as Bcl-2).

 

Combination therapy case:

Prostate cancer: When combined with ionizing radiation, the apoptosis rate of tumor cells increases by 2.3 times compared to radiotherapy alone. The mechanism involves downregulating the expression of DNA dependent protein kinase (DNA-PK) and inhibiting DNA damage repair.
Non small cell lung cancer (NSCLC): Inhibits A549 cell line proliferation at a concentration of 2mM, with an IC50 value of 1.8mM. The synergistic effect is significant when combined with promethazine.
African swine fever virus (ASFV) infection: 0-5mM dose-dependent inhibition of virus late stage protein synthesis, disruption of virus induced H3K9/K14 hypoacetylation state, and complete elimination of virus replication when combined with enrofloxacin.

 

3. Potential treatments for neurodegenerative diseases
In animal models, neural function is improved by regulating epigenetic and inflammatory pathways
Amyotrophic lateral sclerosis (ALS): In the G93A transgenic mouse model, continuous administration can prolong survival by 30%, induce NF - κ B p50 expression, and downregulate cytochrome c and caspase-3 levels.
Huntington's disease (HD): In transgenic mouse brain tissue, histone acetylation levels increased by 40% and methylation levels decreased by 25%, while activating the ubiquitin proteasome pathway and reducing abnormal protein aggregation.

Research field: Tool compounds for epigenetics and cellular stress

 

1. Model tools for epigenetic research
As an HDAC inhibitor, sodium 4-phenylbutyrate is widely used in the study of chromatin remodeling mechanisms
Gene expression regulation: In HEK293 cells, 24-hour treatment can increase histone H3 acetylation levels by 2.8 times and CpG island demethylation rate in the promoter region by 15%.
Drug screening platform: As a positive control compound, it is used for high-throughput screening of novel HDAC inhibitors. When combined with trichostatin A (TSA), it can distinguish the specificity of class I/class II HDAC enzymes.

 

2. Regulators of endoplasmic reticulum stress (ER stress)
To study cellular stress pathways by inhibiting the unfolded endoplasmic reticulum protein response (UPR):
Neuroprotective mechanism: In a rat traumatic brain injury model, reducing the expression level of GRP78/p-PERK/CHOP protein by 30% -50% and decreasing neuronal apoptosis.
Autophagy regulation research: In the LPS induced bone loss model, inhibition of LC3II accumulation reduces autophagosome formation rate by 40%, while reversing p62 protein degradation disorder.

 

3. Intervention methods for viral infection research
To develop antiviral strategies targeting epigenetic regulation in the lifecycle of viruses:
ASFV infection inhibition: Blocking late stage protein synthesis of the virus at a concentration of 0.5mM, the virus titer decreased by 5 logarithmic orders when combined with enrofloxacin.
Activation of HIV latent pool: In the J-Lat cell line, the combination of PKC agonists can induce a threefold increase in the replication rate of latent HIV virus compared to stimulation alone.

Industrial and Food Fields: From Catalysts to Additives

 

1. Synthesis intermediates in fine chemicals
Preparation of ester derivatives: Nucleophilic substitution reaction occurs with alkyl halide compounds in dimethyl sulfoxide (DMSO) to generate 4-phenylbutyrate ester derivatives, which are used for the synthesis of polymer plasticizers.
Polymer catalysis: As an alkaline catalyst, it promotes the ring opening polymerization of epoxy resin, doubling the reaction rate and narrowing the molecular weight distribution of the product.

 

2. Functional additives in the food industry
Flavor enhancer: Adding 0.05% -0.1% to fruit juice drinks can mask the metallic ion odor, while synergistically providing a refreshing sour taste with citric acid.
Antioxidant preservation: By compounding 0.02% tea polyphenols in meat products, the induction period of lipid oxidation can be extended to 2.5 times that of the control group, and the shelf life can be extended from 7 days to 18 days.
Microbial control: In canned food, the inhibition rate of Escherichia coli and Staphylococcus aureus reaches 90% at a concentration of 0.1%, which meets the national food safety standard GB 2760-2014.

Special Medical Scenarios and Frontier Exploration

 

1. Intervention for bone metabolism diseases
In the LPS induced bone loss model, improving bone quality through multi-target regulation:
Bone density improvement: After continuous administration for 3 weeks, the bone mineral density (BMD) of the distal femur increased by 12%, and the bone volume fraction (BV/TV) increased by 18%.
Inflammatory cytokine inhibition: reduces serum MCP-1 levels by 40%, blocks NF - κ B pathway activation, and reduces osteoclast differentiation.

 

2. Development of orphan drugs for rare disease treatment
For organic acidemia such as propionic acidemia, sodium 4-phenylbutyrate improves symptoms through alternative metabolic pathways:
Metabolic bypass activation: induces the expression of propionic acid metabolism related enzymes (such as ACAT1, MUT), reducing blood propionic acid concentration by 50%.
Clinical case: An open label trial involving 15 patients with propionic acidemia showed that continuous treatment for one year resulted in a 70% decrease in seizure frequency and a 40% improvement in quality of life score.

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Sodium 4-phenylbutyrate is an organic compound that can be prepared through various synthetic methods. The following are several common synthesis methods:

1. In situ generation method

This method generates 4-phenylsodium phenylbutyrate in situ through a reaction.

-Reaction step: Benzoic acid and bromobutane are added to the reactor for condensation reaction in the presence of alkali to generate 4-phenylbutyrate. Then, 4-phenylester of phenylbutyrate is reacted with sodium hydroxide to form 4-phenylsodium phenylbutyrate.

C₇H₆O₂+C₄H₉Br → 4-phenylbutyrate

4-phenylbutyrate+NaOH → C₁₀H₁₃NaO₂

2. Reaction method

-Reaction step: 4-phenylbutyric acid is reacted with a base (such as sodium hydroxide or sodium carbonate) in an appropriate solvent to produce 4-phenylsodium phenylbutyrate.

C₁₀H₁₂O₂ + NaOH → C₁₀H₁₃NaO₂

3. Ammoniation method

-Reaction step: 4-phenylbutyric acid is reacted with ammonia gas in the presence of an appropriate catalyst to produce 4-phenylammonium phenylbutyrate.

C₁₀H₁₂O₂ + NH₃ → C₁₀H₁₃NaO₂

4. Photocatalytic method

-Reaction step: 4-phenylbutyric acid is reacted with an appropriate photosensitive catalyst (such as a derivative of styrene) under ultraviolet light to generate 4-phenylsodium phenylbutyrate.

C₁₀H₁₂O₂ + photosensitive catalyst+light irradiation → C₁₀H₁₃NaO₂

It should be noted that when conducting the above synthesis method, the experimental operation needs to follow safety regulations and select reaction conditions, solvents, and catalysts within the applicable range. At the same time, it is recommended to refer to relevant scientific literature and manuals for more detailed operating procedures and specific experimental conditions.

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