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P6273

Sigma-Aldrich

2-Propylpentanoic acid

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Synonym(s):
Valproic acid
Linear Formula:
(CH3CH2CH2)2CHCO2H
CAS Number:
99-66-1
Molecular Weight:
144.21
EC Number:
202-777-3
MDL number:
MFCD00002672
PubChem Substance ID:
24898751
NACRES:
NA.25

refractive index

n20/D 1.425 (lit.)

bp

220 °C (lit.)

solubility

H2O: slightly soluble
alcohol: soluble

density

0.9 g/mL at 25 °C (lit.)

lipid type

saturated FAs

SMILES string

CCCC(C(O)=O)CCC

InChI

1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)

InChI key

NIJJYAXOARWZEE-UHFFFAOYSA-N

Gene Information

human ... ALDH5A1(7915) , CYP1A2(1544)
mouse ... Hdac1(433759)
rat ... Slc6a1(79212)

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Application

2-Propylpentanoic acid has been used as a supplement in mouse embryonic fibroblast - conditioned medium (MEF-CM) to feed the cells.

Biochem/physiol Actions

2-Propylpentanoic acid is a short-chain fatty acid and potentially inhibits histone deacetylase action. It is known to promote tumor cell toxicity and increase susceptibility to radiation. 2-Propylpentanoic acid elevates the levels of γ-aminobutyric acid in the brain. Reduced central nervous system action is observed in overdosage of 2-propylpentanoic acid. It enhance the inhibitory action of γ-aminobutyric acid (GABA) by blocking voltage-dependent sodium channel.
Anticonvulsant that also has efficacy as a mood stabilizer in bipolar disorder

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 1A - Skin Irrit. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

231.8 °F - closed cup

Flash Point(C)

111 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Efficient generation of nonhuman primate induced pluripotent stem cells
Zhong B, et al.
Stem Cells and Development, 20(5), 795-807 (2010)
Histone deacetylase inhibitor, 2-propylpentanoic acid, increases the chemosensitivity and radiosensitivity of human glioma cell linesin vitro
Cuijie S, et al.
Chinese Medical Journal (English Edition), 125(24), 4338-4343 (2012)
3-Heptanone as a potential new marker for valproic acid therapy
Erhart S, et al.
Journal of Breath Research, 3(1), 016004-016004 (2009)
Xi Chen et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(21), 9202-9213 (2013-05-24)
Progranulin (PGRN) is a secreted glycoprotein expressed in neurons and glia that is implicated in neuronal survival on the basis that mutations in the GRN gene causing haploinsufficiency result in a familial form of frontotemporal dementia (FTD). Recently, a direct
P C Ho et al.
The pharmacogenomics journal, 3(6), 335-342 (2003-11-05)
The present study investigated the effect of cytochrome P450 2C9 (CYP2C9) genetic polymorphism on the biotransformation of valproic acid (VPA) to its hepatotoxic metabolite, 4-ene-VPA, and compared that to the formation of the inactive 4-OH-VPA and 5-OH-VPA. cDNA-expressed CYP2C9(*)2 and
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