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Chemical Structure| 1821-12-1 Chemical Structure| 1821-12-1
Chemical Structure| 1821-12-1

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4-Phenylbutanoic acid is an inhibitor of HDAC which can regulate gene transcription with anti-tumor and neuroprotective effects.

Synonyms: 4-PBA; Benzenebutyric acid

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Product Citations

Product Citations

Griffin, Matthew E. ; Tsukidate, Taku ; Hang, Howard C. ;

Abstract: The characterization of microbiota mechanisms in health and disease has reinvigorated pattern recognition receptors as prominent targets for immunotherapy. Notably, our recent studies on Enterococcus species revealed peptidoglycan remodeling and activation of NOD2 as key mechanisms for microbiota enhancement of immune checkpoint inhibitor therapy. Inspired by this work and other studies of NOD2 activation, we performed in silico ligand screening and developed N-arylpyrazole dipeptides as novel NOD2 agonists. Importantly, our N-arylpyrazole NOD2 agonist is enantiomer-specific and effective at promoting immune checkpoint inhibitor therapy and requires NOD2 for activity in vivo. Given the significant functions of NOD2 in innate and adaptive immunity, these next-generation agonists afford new therapeutic leads and adjuvants for a variety of NOD2-responsive diseases.

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Product Details of 4-Phenylbutyric acid

CAS No. :1821-12-1
Formula : C10H12O2
M.W : 164.20
SMILES Code : O=C(O)CCCC1=CC=CC=C1
Synonyms :
4-PBA; Benzenebutyric acid
MDL No. :MFCD00004403
InChI Key :OBKXEAXTFZPCHS-UHFFFAOYSA-N
Pubchem ID :4775

Safety of 4-Phenylbutyric acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-Phenylbutyric acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1821-12-1 ]
  • Downstream synthetic route of [ 1821-12-1 ]

[ 1821-12-1 ] Synthesis Path-Upstream   1~2

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YieldReaction ConditionsOperation in experiment
42% With sulfuric acid; iodine; acetic acid; periodic acid In water at 70℃; for 19 h; A mixture of 4-phenylbutanoic acid (20.0 g, 121.8 mmol), H5IO6 (5.56 g, 24.4 mmol), iodine (13.30 g, 52.4 mmol), 10 M H2SO4 (5.0 mL), water (36 mL) and acetic acid (166 mL) was heated at 70° C. for 19 h.
The reaction mixture was cooled and evaporated to dryness.
The residue was dissolved in EtOAc (300 mL) and washed with aqueous Na2S2O3 (2*200 mL), brine (2*200 mL), dried over Na2SO4, filtered, and evaporated to leave a yellow solid.
The crude product was precipitated from EtOAc/hexane at 0° C. to afford product as light yellow solid (15.0 g, 42percent).
1H NMR (400 MHz, CDCl3) δ 11.0 (brs, 1H), 7.61 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.0 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H), 2.38 (t, J=7.6 Hz, 2H).
References: [1] Mendeleev Communications, 2015, vol. 25, # 2, p. 111 - 113.
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5919 - 5924.
[3] Patent: US2018/66298, 2018, A1, . Location in patent: Paragraph 0172; 0173; 0174.
[4] Journal of the American Chemical Society, 1943, vol. 65, p. 1273,1274.
[5] Patent: US2348231, 1940, , .
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  • [ 27913-58-2 ]
References: [1] Tetrahedron, 2004, vol. 60, # 32, p. 6945 - 6958.
[2] Phytochemistry, 2013, vol. 96, p. 223 - 234.
 

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