96017-59-3

Basic information

• Product Name: 2-N-HEXYL-4-PENTYNOIC ACID
• Synonyms: 2-(2-PROPYNYL)OCTANOIC ACID;2-N-HEXYL-4-PENTYNOIC ACID;2-PROPARGYLOCTANOIC ACID;2-Hexyl-4-pentynoic Acid;2-Propargyloctanoic Acid 2-(2-Propynyl)octanoic Acid
• CAS NO: 96017-59-3
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.26
• Product Categories: Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives
• Mol File: 96017-59-3.mol

Chemical Properties

• Boiling Point: 287.1°Cat760mmHg
• Flash Point: 138.7°C
• Appearance: /
• 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).
• 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
• CAS DataBase Reference: 2-N-HEXYL-4-PENTYNOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-HEXYL-4-PENTYNOIC ACID(96017-59-3)
• EPA Substance Registry System: 2-N-HEXYL-4-PENTYNOIC ACID(96017-59-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 96017-59-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-N-HEXYL-4-PENTYNOIC ACID is used as a histone deacetylase inhibitor for its ability to potently inhibit HDAC activity, making it a potential candidate for the development of therapeutic agents targeting various diseases associated with HDAC dysregulation.
Used in Neuroprotective Applications:
In the field of neuroprotection, 2-N-HEXYL-4-PENTYNOIC ACID is used as a neuroprotective agent for its capacity to induce histone hyperacetylation and protect cerebellar granule cells from glutamate-induced excitotoxicity, which may have implications for the treatment of neurodegenerative disorders.
Used in Heat Shock Protein Induction:
2-N-HEXYL-4-PENTYNOIC ACID is utilized as an inducer of heat shock proteins Hsp70-1a and Hsp70-1b, which are crucial for cellular stress response and protection against various forms of cellular damage, suggesting its potential use in conditions where heat shock protein expression is beneficial.

References

1) Eikel et al. (2006), Teratogenic effects mediated by inhibition of histone deacetylases: evidence from quantitative structure activity relationships of 20 valproic acid derivatives; Chem. Res. Toxicol., 19 272 2) Leng et al. (2010), Potent neuroprotective effects of novel structural derivatives of valproic acid: potential roles of HDAC inhibition and HSP70 induction; Neurosci. Lett., 476 127

Upstream product

• 716316-58-4 2-hexyl-2-propargylmalonic acid 
• 716316-63-1 2-hexyl-2-propargylmalonic acid diethyl ester 
• 17920-23-9 diethyl propargylmalonate 

Relevant articles and documents

Direct β- and γ-C(sp3)?H Alkynylation of Free Carboxylic Acids**

In this study we report the identification of a novel class of ligands for palladium-catalyzed C(sp3)?H activation that enables the direct alkynylation of free carboxylic acid substrates. In contrast to previous synthetic methods, no introduction/removal of an exogenous directing group is required. A broad scope of acids including both α-quaternary and challenging α-non-quaternary can be used as substrates. Additionally, the alkynylation in the distal γ-position is reported. Finally, this study encompasses preliminary findings on an enantioselective variant of the title transformation as well as synthetic applications of the products obtained.

Design, synthesis, and structure-activity relationships of haloenol lactones: Site-directed and isozyme-selective glutathione S-transferase inhibitors

Overexpression of glutathione S-transferase (GST), particularly the GST-π isozyme, has been proposed to be one of the biochemical mechanisms responsible for drug resistance in cancer chemotherapy, and inhibition of overexpressed GST has been suggested as an approach to combat GST-induced drug resistance. 3-Cinnamyl-5(E)-bromomethylidenetetrahydro-2-furanone (1a), a lead compound of site-directed GST-π inactivator, has been shown to potentiate the cytotoxic effect of cisplatin on tumor cells. As an initial step to develop more potent and more selective haloenol lactone inactivators of GST-π, we examined the relationship between the chemical structures of haloenol lactone derivatives and their GST inhibitory activity. A total of 16 haloenol lactone derivatives were synthesized to probe the effects of (1) halogen electronegativity, (2) electron density of aromatic rings, (3) molecular size and rigidity, (4) lipophilicity, and (5) aromaticity on the potency of GST-π inactivation. The inhibitory potency of each compound was determined by time-dependent inhibition tests, and recombinant human GST-π was used to determine their inhibitory activity. Our structure-activity relationship studies demonstrated that (1) reactivity of the halide leaving group plays a weak role in GST inactivation by the haloenol lactones, (2) aromatic electron density may have some influence on the potency of GST inactivation, (3) high rigidity likely disfavors enzyme inhibition, (4) lipophilicity is inversely proportional to enzyme inactivation, and (5) an unsaturated system may be important for enzyme inhibition. This work facilitated understanding of the interaction of GST-π with haloenol lactone derivatives as site-directed and isozyme-selective inactivators, possibly potentiating cancer chemotherapy.

Antiproliferative and neurotrophic molecules

Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate are provided. These compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.

Antiproliferative and neurotrophic molecules

Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate are provided. These compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.