4-pentynoic acid

pent-4-yn-1-oic acid

CAS: 6089-09-4 C5 H6 O2 MW: 98.10122000

Identification

Name4-pentynoic acid
IUPACpent-4-ynoic acid
CAS Number6089-09-4
EINECS228-028-0
FDA UNIISearch
Molecular FormulaC5 H6 O2
Molecular Weight98.10122000
MDL NumberMFCD00004407
Nikkaji NumberJ69.139I
Beilstein1742047

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 57.70 °C. @ 760.00 mm Hg
Boiling Point 199.20 °C. @ 760.00 mm Hg (est)
Vapor Pressure 0.146000 mmHg @ 25.00 °C. (est)
Flash Point 195.00 °F. TCC ( 90.80 °C. ) (est)
logP (o/w) 0.402 (est)
Soluble in water, 6.239e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintravenous-mouse LD50 28 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#12263']

Safety in Use

Categoryinformation only not used for fragrances or flavors
Recommendation for 4-pentynoic acid usage levels up tonot for fragrance use.
Recommendation for 4-pentynoic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

pent-4-yn-1-oic acid pent-4-ynoic acid propargylacetic acid PubMed: Effective PHIP labeling of bioactive peptides boosts the intensity of the NMR signal. PubMed: Synthesis and evaluation of 2-amino-5-(4-[(18)F]fluorophenyl)pent-4-ynoic acid ([(18)F]FPhPA): a novel (18)F-labeled amino acid for oncologic PET imaging. PubMed: An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards 'clickable' biodegradable polylactide. PubMed: Concise stereoselective total synthesis of (+)-muricatacin and (+)-epi-muricatacin. PubMed: Parahydrogen-induced polarization of carboxylic acids: a pilot study of valproic acid and related structures. PubMed: Synthesis of molecularly encoded oligomers using a chemoselective "AB + CD" iterative approach. PubMed: Versatile on-resin synthesis of high mannose glycosylated asparagine with functional handles. PubMed: Valproic acid and its derivatives enhanced estrogenic activity but not androgenic activity in a structure dependent manner. PubMed: In situ assembly of porous Au-paper electrode and functionalization of magnetic silica nanoparticles with HRP via click chemistry for Microcystin-LR immunoassay. PubMed: Au(I)/Ag(I)-catalyzed cascade approach for the synthesis of benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinones. PubMed: Enantioselective apoptosis induction in histiocytic lymphoma cells and acute promyelocytic leukemia cells. PubMed: Vanadium bromoperoxidase from Delisea pulchra: enzyme-catalyzed formation of bromofuranone and attendant disruption of quorum sensing. PubMed: Preparation of peptide and other biomolecular conjugates through chemoselective ligations. PubMed: Short-time gene expression response to valproic acid and valproic acid analogs in mouse embryonic stem cells. PubMed: Covalent immobilization of redox protein via click chemistry and carbodiimide reaction: direct electron transfer and biocatalysis. PubMed: Preparation, 99mTc-labeling and biodistribution studies of a PNA oligomer containing a new ligand derivative of 2,2'-dipicolylamine. PubMed: Potent neuroprotective effects of novel structural derivatives of valproic acid: potential roles of HDAC inhibition and HSP70 induction. PubMed: Heterogeneous catalysis of a copper-coated atomic force microscopy tip for direct-write click chemistry. PubMed: Cu(I)-catalyzed intramolecular cyclization of alkynoic acids in aqueous media: a "click side reaction". PubMed: Multiple effects of pentyl-4-yn-VPA enantiomers: from toxicity to short-term memory enhancement. PubMed: S-2-pentyl-4-pentynoic hydroxamic acid and its metabolite s-2-pentyl-4-pentynoic acid in the NMRI-exencephaly-mouse model: pharmacokinetic profiles, teratogenic effects, and histone deacetylase inhibition abilities of further valproic acid hydroxamates and amides. PubMed: Increased replication of human cytomegalovirus in retinal pigment epithelial cells by valproic acid depends on histone deacetylase inhibition. PubMed: Differential enantioselective effects of pentyl-4-yn-valproate on spatial learning in the rat, and neurite outgrowth and cyclin D3 expression in vitro. PubMed: Selection of test chemicals for the ECVAM international validation study on in vitro embryotoxicity tests. European Centre for the Validation of Alternative Methods. PubMed: Pharmacological properties of YM-57029, a novel platelet glycoprotein IIb/IIIa antagonist. PubMed: Infrared and Raman Spectra of a Single Resin Bead for Analysis of Solid-Phase Reactions and Use in Encoding Combinatorial Libraries. PubMed: Pentyl-4-yn-valproic acid enhances both spatial and avoidance learning, and attenuates age-related NCAM-mediated neuroplastic decline within the rat medial temporal lobe. PubMed: Prediction of embryotoxic effects of valproic acid-derivatives with molecular in vitro methods. PubMed: 5-[4-(3,3-Dimethylbutoxycarbonyl)phenyl]-4-pentynoic acid and its derivatives inhibit ionotropic gamma-aminobutyric acid receptors by binding to the 4'-ethynyl-4-n-propylbicycloorthobenzoate site. PubMed: Formation of gamma-glutamylpropargylglycylglycine from propargylglycine in human blood and erythrocytes. PubMed: Inhibition effect of propargylglycine on human fibrosarcoma HT-1080 cell invasiveness. PubMed: Studies on the teratogen pharmacophore of valproic acid analogues: evidence of interactions at a hydrophobic centre. PubMed: Evaluation of the Teratogenic Potential of Valproic Acid Analogues in Transgenic Dictyostelium discoideum Strains. PubMed: Cell proliferation, migration and CAM-dependent neurite outgrowth as developmental in vitro endpoints for screening teratogenic potential: Application to valproic acid and related analogues of varying potency. PubMed: Stereoselective dysmorphogenicity of the enantiomers of the valproic acid analogue 2-N-propyl-4-pentynoic acid (4-yn-VPA): cross-species evaluation in whole embryo culture. PubMed: A new metabolite of proglypargylglycine, gamma-glutamylpropargylglycylglycine, in liver of D,L-propargylglycine-administered rats. PubMed: In vivo detoxification of cyanide by cystathionase gamma-lyase. PubMed: Validation of an in vitro teratology system using chiral substances: stereoselective teratogenicity of 4-yn-valproic acid in cultured mouse embryos. PubMed: Mechanisms of interaction of Escherichia coli threonine synthase with substrates and inhibitors. PubMed: The enantiomers of the valproic acid analogue 2-n-propyl-4-pentynoic acid (4-yn-VPA): asymmetric synthesis and highly stereoselective teratogenicity in mice. PubMed: The enantioselective teratogenicity of 2-n-propyl-4-pentynoic acid (4-yn-VPA) is due to stereoselective intrinsic activity and not differences in pharmacokinetics. PubMed: Valproic acid-induced neural tube defects in mouse and human: aspects of chirality, alternative drug development, pharmacokinetics and possible mechanisms. PubMed: Determination of a new blood glucose-lowering agent in biological fluids by capillary gas chromatography using electron-capture detection. PubMed: On the development of alternative antiepileptic drugs. Lack of enantioselectivity of the anticonvulsant activity, in contrast to teratogenicity, of 2-n-propyl-4-pentenoic acid and 2-n-propyl-4-pentynoic acid, analogues of the anticonvulsant drug valproic acid. PubMed: Hepatotoxic action of a poisonous mushroom, Amanita abrupta in mice and its toxic component. PubMed: Affinity labeling of D-amino acid oxidase with an acetylenic substrate. PubMed: Elevation of hepatic tyrosine 2-oxoglutarate aminotransferase in rats by 4-pentynoic acid, a hypoglycemic agent. PubMed: Antimetabolites produced by microorganisms. II. L-2-amino-4-pentynoic acid. PubMed: [Data on acetylenic carboxylic acids. XI. Unsaturated lactones of thio-4-pentynoic acid].