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P21005

4-Phenylbutyric acid

99%

Synonym(s):

γ-Phenylbutanoic acid, ψ-Phenylbutanoic acid, 4-Phenyl-n-butyric acid, 4-Phenylbutanoic acid, Benzenebutyric acid

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25 G

$72.50

100 G

$176.00

$72.50


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About This Item

Linear Formula:
C6H5(CH2)3COOH
CAS Number:
Molecular Weight:
164.20
Beilstein/REAXYS Number:
638180
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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assay

99%

form

crystals

bp

165 °C/10 mmHg (lit.)

mp

49-51 °C (lit.)

SMILES string

OC(=O)CCCc1ccccc1

InChI

1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)

InChI key

OBKXEAXTFZPCHS-UHFFFAOYSA-N

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1 of 4

This Item
279889P20955116807
assay

99%

assay

99%

assay

98%

assay

98%

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

bp

165 °C/10 mmHg (lit.)

bp

98-100 °C/0.3 mmHg (lit.)

bp

270-272 °C (lit.)

bp

170-172 °C/20 mmHg (lit.)

mp

49-51 °C (lit.)

mp

-

mp

39-42 °C (lit.)

mp

35-38 °C (lit.)

form

crystals

form

-

form

crystals

form

solid

General description

4-Phenylbutyric acid (4-PBA) is used in the treatment of urea cycle disorders.[1]

Application

4-PBA has been used as a selective inhibitor of endoplasmic reticulum stress (ERS).[2]
It can also be used as a reactant in the synthesis of:
  • 1-Tetralone using Lewis acid catalyst.[3]
  • 4,N-diphenylbutyramide.[4]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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The therapeutic effects of 4-phenylbutyric acid in maintaining proteostasis.
Kolb PS, et al.
The International Journal of Biochemistry & Cell Biology, 61, 45-52 (2015)
Synthesis of 1-tetralones by intramolecular Friedel?Crafts reaction of 4-arylbutyric acids using Lewis acid catalysts
Cui DM, et al.
Tetrahedron Letters, 44(21), 4007-4010 (2003)
Clean, reusable and low cost heterogeneous catalyst for amide synthesis
Comerford JW, et al.
Chemical Communications (Cambridge, England), 18(21), 2562-2564 (2009)
Min Han Kim et al.
Clinical and experimental otorhinolaryngology, 12(2), 181-189 (2018-10-20)
Endoplasmic reticulum (ER) stress is known to be associated with inflammatory airway diseases, and three major transmembrane receptors: double-stranded RNA-activated protein kinase-like ER kinase, inositol requiring enzyme 1, and activating transcription factor 6 (ATF6) play important roles in ER stress-related
Induction of apoptosis coupled to endoplasmic reticulum stress through regulation of CHOP and JNK in bone marrow mesenchymal stem cells from patients with systemic lupus erythematosus
Guo G, et al.
Journal of immunology research (2015)

Questions

1–6 of 6 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. How to conserve the powder ?

    1 answer
    1. This material is quite stable in the original sealed container. As listed in the Safety Data Sheet, under SECTION 7, the product may be stored at ambient temperature, tightly sealed, and in a dry environment.

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  4. What is the solubility of the product 4-Phenylbutyric acid, P21005?

    1 answer
    1. The water solubility of 4-phenylbutyric acid at 40 ºC is 5.3 g/L.

      Helpful?

  5. Hello, this reference is suitable for cell culture experiments?

    1 answer
    1. This product is not specified for cell culture use. Kindly review the following citation in which it was cited to treat cells in culture:
      Eigner K, Filik Y, Mark F, Schütz B, Klambauer G, Moriggl R, Hengstschläger M, Stangl H, Mikula M, Röhrl C. The unfolded protein response impacts melanoma progression by enhancing FGF expression and can be antagonized by a chemical chaperone. Sci Rep. 2017 Dec 13;7(1):17498. doi: 10.1038/s41598-017-17888-9. PMID: 29235576; PMCID: PMC5727496.

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  6. Hi, what is the solubility and in what?

    1 answer
    1. This product is not tested for solubility, however, various literature sources cite the following:
      0.010M in water
      3.670M in toluene
      4.800M in methanol
      4.130M in diethyl ether
      4.040M in chloroform
      0.500M in 1-hexanol
      This information has not been validated.

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