660-88-8

Basic information

• Product Name: 5-AMINOVALERIC ACID
• Synonyms: H2N(CH2)4COOH;Pentanoic acid, 5-amino-;Valeric acid, 5-amino-;5-AMINOPENTANOIC ACID;5-AMINO-N-VALERIC ACID;5-AMINO-N-PENTANOIC ACID;5-AMINOVALERIC ACID;DELTA-AMINOVALERIC ACID
• CAS NO: 660-88-8
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.15
• EINECS: 211-544-5
• Product Categories: Amino Acids and Derivatives;Miscellaneous;omega-Aminocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides
• Mol File: 660-88-8.mol

Chemical Properties

• Melting Point: 158-161 °C(lit.)
• Boiling Point: 247.5 °C at 760 mmHg
• Flash Point: 103.5 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.2000 (estimate)
• Refractive Index: 1.4650 (estimate)
• Storage Temp.: Store at 0-5°C
• Solubility: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 4.27(at 25℃)
• BRN: 906833
• CAS DataBase Reference: 5-AMINOVALERIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINOVALERIC ACID(660-88-8)
• EPA Substance Registry System: 5-AMINOVALERIC ACID(660-88-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 660-88-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Aminovaleric Acid is used as an active pharmaceutical ingredient for the development of drugs that help in halting severe types of seizures. Its unique structure and properties make it a promising candidate for the treatment of epilepsy and other seizure disorders.
Used in Solar Energy Industry:
5-Aminovaleric acid (5-AVA) is used in the preparation of (5-AVA)x(MA)1-xPbI3, a perovskite material for fabricating printable mesoscopic perovskite solar cells. This application takes advantage of the compound's ability to form stable and efficient light-absorbing materials, contributing to the advancement of solar energy technology.
Used in Radiopharmaceutical Industry:
5-Aminovaleric acid serves as a spacer in the synthesis of rhenium and technetium-99m labeled insulin. This application leverages the compound's ability to act as a linker between the radioactive isotopes and the insulin molecule, enabling the development of diagnostic agents for imaging and monitoring various medical conditions.
Used in Nanotechnology:
5-Aminovaleric acid is used to synthesize dipeptides that self-assemble to form nanotubes in the solid state as well as in solution over a wide range of pH. These nanotubes have potential applications in various fields, including drug delivery, sensing, and nanotechnology-based devices.
Used in Organic Synthesis:
5-Aminovaleric acid acts as a starting material in the total synthesis of an alkaloid, lycoposerramine Z. This application highlights the compound's versatility and its potential use in the synthesis of complex organic molecules with diverse biological activities.

Purification Methods

Crystallise it from H2O/EtOH. When heated above its melting point, it is converted to 2-piperidone with m 200o. [Wood & Colver J Am Chem Soc 67 654 1945, Beilstein 4 IV 2636.]

InChI:InChI=1/C5H11NO2/c6-4-2-1-3-5(7)8/h1-4,6H2,(H,7,8)

Upstream product

• 675-20-7 piperidin-2-one 
• 124-04-9 Adipic acid 
• 776-75-0 N-benzoylpiperidine 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 105-53-3 diethyl malonate 
• 56-41-7 L-alanin 
• 70-26-8 L-ornithine 
• 157-06-2 D-arginine 
• 74-79-3 L-arginine 
• 59801-88-6 5-chloropentylamine 
• 101719-79-3 (1-phthalimido-propyl)-malonic acid diethyl ester 
• 609-36-9 rac-Pro-OH 
• 147-85-3 L-proline 
• 6317-37-9 5-nitrothiophene-2-carboxylic acid 

Downstream Products

• 1147-76-8 5-(N-phthalimido)pentanoic acid 
• 15647-47-9 5-benzoylaminopentanoic acid 
• 26342-05-2 δ-aminovaleric acid ethyl ester 
• 113551-21-6 5-p-toluoylamino-valeric acid 
• 675-20-7 piperidin-2-one 
• 23645-04-7 4-Aminobutan-2-one 
• 55768-69-9 5-(N'-phenyl-ureido)-valeric acid 
• 23135-50-4 5-(N-benzyloxycarbonylamino)pentanoic acid 
• 55124-91-9 N-Trimethylsilyl-norvalin-trimethylsilylester 
• 63984-03-2 δ-aminovaleric acid tert-butyl ester 
• 89855-60-7 5-(dimethylamino)pentanoic acid 
• 62665-66-1 C₁₈H₁₉NO₃ 
• 62665-99-0 C₁₈H₁₈FNO₃ 
• 27219-07-4 5-(N-tert-butyloxycarbonyl)aminopentanoic acid 

Relevant articles and documents

Cationic–anionic palladium complexes: effect of hydrogen bond character on their stability and biological activity

The solution state of palladium cationic–anionic complexes (AmHn)k[PdCl4] prepared for the first time, where Am is morpholine, methylmorpholine, aminoethylmorpholine, 5-aminovaleric acid, L-1-phenyl-2-methylaminopropanol, and m-xylilenediamine, has been studied by electronic absorption spectroscopy, NMR, and pH measurements. The agreement of obtained results for the state of the complexes in water and NaCl solutions with IR and X-ray diffraction data for these complexes has allowed us to substantiate the principle for designing patent formulation (C5H12NO)2[PdCl4], a new type of palladium complexes, palladium(II) cationic–anionic complexes showing high antitumor and antimetastatic activity. Crystallographic data for six obtained complexes have been presented.

An efficient enzymatic synthesis of 5-aminovaleric acid

The title compound was prepared enzymatically from l-lysine in an excellent yield and under buffer-free conditions. l-Lysine was oxidized by the action of l-lysine α-oxidase from Trichoderma viride followed by spontaneous oxidative decarboxylation of the intermediate 6-amino-2-oxocaproic acid in the reaction medium. l-Lysine α-oxidase was immobilized on an epoxy-activated solid support (Sepabeads EC-EP) and the activity of both solution-based and immobilized enzyme in this reaction was determined.

An Integrated Cofactor/Co-Product Recycling Cascade for the Biosynthesis of Nylon Monomers from Cycloalkylamines

We report a highly atom-efficient integrated cofactor/co-product recycling cascade employing cycloalkylamines as multifaceted starting materials for the synthesis of nylon building blocks. Reactions using E. coli whole cells as well as purified enzymes produced excellent conversions ranging from >80 and 95 % into desired ω-amino acids, respectively with varying substrate concentrations. The applicability of this tandem biocatalytic cascade was demonstrated to produce the corresponding lactams by employing engineered biocatalysts. For instance, ?-caprolactam, a valuable polymer building block was synthesized with 75 % conversion from 10 mM cyclohexylamine by employing whole-cell biocatalysts. This cascade could be an alternative for bio-based production of ω-amino acids and corresponding lactam compounds.

Synthetic studies towards N-substituted 3-vinyl-4-piperidineacetic acid derivatives

The synthesis and full characterization of two new (E)-2-butenyl)-5-amino-2-pentenoates, (Z)-4-[N-(3-buten-1-yl)benzamido]-2-buten-1-ol, and (Z)-1-chloro-4-[N-(3-buten-l-yl)benzamido]-2-butene are reported. These were designed as substrates for a projected thermal ene cyclization leading to the N-substituted 3-vinyl-4-piperidineacetic acid scaffold. Although conditions for this ene-cyclization have not yet been uncovered, the ease of preparation of these ene-cyclization substrates gives promise for their future use.

General Synthesis of Amino Acid Salts from Amino Alcohols and Basic Water Liberating H2

An atom-economical and environmentally friendly method to transform amino alcohols to amino acid salts using just basic water, without the need of pre-protection or added oxidant, catalyzed by a ruthenium pincer complex, is developed. Water is the solvent, the source of the oxygen atom of the carboxylic acid group, and the actual oxidant, with liberation of dihydrogen. Many important and useful natural and unnatural amino acid salts can be produced in excellent yields by applying this new method.

Immunomodulatory peptides

The invention relates to peptides derivatized with a hydrophilic polymer which, in some embodiments, bind to human FcRn and inhibit binding of the Fc portion of an IgG to an FcRn, thereby modulating serum IgG levels. The disclosed compositions and methods may be used in some embodiments, for example, in treating autoimmune diseases and inflammatory disorders. The invention also relates, in further embodiments, to methods of using and methods of making the peptides of the invention.

The chemistry of escapin: Identification and quantification of the components in the complex mixture generated by an L-amino acid oxidase in the defensive secretion of the sea snail Aplysia Californica

Escapin is an L-amino acid oxidase in the ink of a marine snail, the sea hare Aplysia californica, which oxidizes L-lysine (1) to produce a mixture of chemicals which is antipredatory and antimicrobial. The goal of our study was to determine the identity

[2+2] Photocycloadditions with chiral uracil derivatives: Access to all four stereoisomers of 2-aminocyclobutanecarboxylic acid

Starting from a single, chiral, bicyclic derivative of uracil, all four stereoisomers of 2-aminocyclobutanecarboxylic acid have been prepared in enantiomerically pure form, using a synthetic sequence which begins with a key photochemical [2+2] cycloaddition reaction and includes a practical cis to trans β-amino acid isomerisation procedure. Georg Thieme Verlag Stuttgart.

Design and synthesis of novel sulfonamide-containing bradykinin hB 2 receptor antagonists. 2. Synthesis and structure-activity relationships of α,α-cycloalkylglycine sulfonamides

Recently we reported on the design and synthesis of a novel class of selective nonpeptide bradykinin (BK) B2 receptor antagonists (J. Med. Chem. 2006, 3602-3613). This work led to the discovery of MEN 15442, an antagonist with subnanomolar affinity for the human B2 receptor (hB2R), which also displayed significant and prolonged activity in vivo (for up to 210 min) against BK-induced bronchoconstriction in the guinea-pig at a dose of 300 nmol/kg (it), while demonstrating only a slight effect on BK-induced hypotension. Here we describe the further optimization of this series of compounds aimed at maximizing the effect on bronchoconstriction and minimizing the effect on hypotension, with a view to developing topically delivered drugs for airway diseases. The work led to the discovery of MEN 16132, a compound which, after intratracheal or aerosol administration, inhibited, in a dose-dependent manner, BK-induced bronchoconstricton in the airways, while showing minimal systemic activity. This compound was selected as a preclinical candidate for the topical treatment of airway diseases involving kinin B2 receptor stimulation.

15N/14N position-specific isotopic analyses of polynitrogenous amino acids

15N/14N isotope ratios are widely used to study processes and systems involving amino acids. Nitrogen isotope fractionation in biological processes occurs primarily at sites of bond-breaking and formation; the finest discrimination for "isotopic fingerprinting" and studies of isotopic fluxes is thus obtained at the position-specific level. While there are numerous reports of natural intramolecular carbon isotope variability, there are no literature reports of 15N/14N position-specific isotopic analysis (N-PSIA) of biologically relevant molecules. We report a methodology for high-precision N-PSIA of four polynitrogenous α-amino acids (asparagine, glutamine, lysine, histidine) and the first survey of natural intramolecular 15N/14N in these biomolecules. Selective liberation of N-atoms from multiple commercial standards of each parent amino acid was achieved by an appropriate enzymatic reaction or by acid hydrolysis. 15N/14N measurements were performed on N-ethoxycarbonyl ethyl ester derivatives of the parent amino acids and their analogues by gas chromatography combustion isotope ratio mass spectrometry, and the average precision for replicate injections was found to be SD(δ15N) = 0.3‰. Position-specific δ15N values of the parent amino acid were directly observed or indirectly calculated using mass balance. The average precision obtained for directly measured positions was SD(δ15N) = 0.2-0.4‰. The average precision for indirectly obtained positions was SD(δ15N) = 0.6-1.3‰ as a result of propagation of errors. Enrichment in the side chain-N with respect to the peptide-N was observed in nearly all of the amino acid sources, most notably in asparagine (average Δδside-peptide = +11‰), which may be indicative of its method of production. In some cases, it was possible to distinguish commercial sources by N-PSIA that could not be distinguished at the compound-specific level.