2-N-HEXYL-4-PENTYNOIC ACID Chemical Properties

Boiling point:

287.1±23.0 °C(Predicted)

Density 

0.94

refractive index 

1.4450-1.4510

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).

pka

4.24±0.21(Predicted)

form 

oil

color 

Colorless

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2916.19.3000

2-N-HEXYL-4-PENTYNOIC ACID Usage And Synthesis

Description

2-hexyl-4-Pentynoic acid is a derivative of valproic acid , an inhibitor of histone deacetylases (HDACs). It inhibits HDAC activity more potently (IC₅₀ = 13 μM) than valproic acid (IC₅₀ = 398 μM). 2-hexyl-4-Pentynoic acid induces histone hyperacetylation in cerebellar granule cells significantly at 5 μM. It also induces the expression of heat shock proteins Hsp70-1a and Hsp70-1b and protects cerebellar granule cells from glutamate-induced excitotoxicity when used at a concentration of 50 μM.

Uses

2-Hexyl-4-pentynoic acid ((±)-2-Hexyl-4-pentynoic acid), valproic acid (VPA) derivative, exhibits potential roles of HDAC inhibition (IC50=13 μM) and HSP70 induction. Potent neuroprotective effects. 2-Hexyl-4-pentynoic acid causes histone hyperacetylation and protect against glutamate-induced excitotoxicity in cultured neurons[1]. 2-Hexyl-4-pentynoic acid is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

References

[1] DANIEL EIKEL  Heinz N  Alfonso Lampen. Teratogenic Effects Mediated by Inhibition of Histone Deacetylases: Evidence from Quantitative Structure Activity Relationships of 20 Valproic Acid Derivatives[J]. Chemical Research in Toxicology, 2006, 19 2: 272-278. DOI:10.1021/tx0502241
[2] YAN LENG . Potent neuroprotective effects of novel structural derivatives of valproic acid: Potential roles of HDAC inhibition and HSP70 induction[J]. Neuroscience Letters, 2010, 476 3: Pages 127-132. DOI:10.1016/j.neulet.2010.04.013

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