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Merck

P6273

2-Propylpentanoic acid

Synonym(s):

Valproic acid

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About This Item

Linear Formula:
(CH3CH2CH2)2CHCO2H
CAS Number:
99-66-1
Molecular Weight:
144.21
NACRES:
NA.25
PubChem Substance ID:
24898751
UNSPSC Code:
12352211
EC Number:
202-777-3
MDL number:
MFCD00002672

InChI key

NIJJYAXOARWZEE-UHFFFAOYSA-N

InChI

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

SMILES string

CCCC(C(O)=O)CCC

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

Quality Level

200

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

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Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB4958
STBK9557
STBK2010
STBJ6639
STBJ0425

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3-Heptanone as a potential new marker for valproic acid therapy
Erhart S, et al.
Journal of Breath Research, 3(1), 016004-016004 (2009)
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)
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
Jakob Christensen et al.
JAMA, 309(16), 1696-1703 (2013-04-25)
Valproate is used for the treatment of epilepsy and other neuropsychological disorders and may be the only treatment option for women of childbearing potential. However, prenatal exposure to valproate may increase the risk of autism. To determine whether prenatal exposure
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