60-32-2

Basic information

• Product Name: 6-Aminocaproic acid
• Synonyms: 177 J.D;177 J.D.;177j.d.;177jd;6-amino-hexanoicaci;Acepramin;Acepramine;ACS
• CAS NO: 60-32-2
• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.17
• EINECS: 200-469-3
• Product Categories: Amino Acids;Organic acids;omega-Aminocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Fibrinogen/Thrombin;AMICAR;Pharmaceutical raw materials
• Mol File: 60-32-2.mol

Chemical Properties

• Melting Point: 207-209 °C (dec.)(lit.)
• Boiling Point: 242.49°C (rough estimate)
• Flash Point: 207-209°C
• Appearance: white/powder
• Density: 1.03 g/mL at 20 °C
• Vapor Pressure: 0.00495mmHg at 25°C
• Refractive Index: 1.4870 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL
• PKA: 4.373(at 25℃)
• Water Solubility: SOLUBLE
• Merck: 14,432
• BRN: 906872
• CAS DataBase Reference: 6-Aminocaproic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Aminocaproic acid(60-32-2)
• EPA Substance Registry System: 6-Aminocaproic acid(60-32-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: MO6300000
• TSCA: Yes
• Hazardous Substances Data: 60-32-2(Hazardous Substances Data)

Usage

References

https://pubchem.ncbi.nlm.nih.gov/compound/6-aminohexanoic_acid#section=Pharmacology-and-Biochemistry https://en.wikipedia.org/wiki/Aminocaproic_acid

Chemical Properties

white crystalline powder. Leaf crystals were obtained from ether. Odorless, bitter taste. Melting point 202 ~ 207 ℃ (decomposition). Soluble in water, slightly soluble in methanol, insoluble in ethanol, ether and chloroform.

Originator

Epsilon,Roche,W. Germany,1962

Uses

Different sources of media describe the Uses of 60-32-2 differently. You can refer to the following data:
1. EACA is directly soluble in water at 25 mg/ml. As an inhibitor of plasmin it is has been utilized in the clotting buffer for fibrinogen assays. This buffer is 10 mM potassium and sodium phosphate, pH 6.4, with 0.20 g CaCl2, 5 g 6-Aminohexanoic acid, 1 g sodium azide, and 9 g NaCl in 1 liter. The buffer is stable indefinitely at room temperature.
2. 6-Aminohexanoic Acid is a reagent commonly used for the extraction of aldehydes from reaction mixtures. 6-Aminohexanoic Acid has also been shown to improve solubilization of membrane proteins in elect rophoresis. Studies suggest that 6-Aminohexanoic Acid inhibits the activation of the first component of the complement system.

Definition

ChEBI: 6-aminohexanoic acid is an epsilon-amino acid comprising hexanoic acid carrying an amino substituent at position C-6. Used to control postoperative bleeding, and to treat overdose effects of the thrombolytic agents streptokinase and tissue plasminogen activator. It has a role as an antifibrinolytic drug, a hematologic agent and a metabolite. It is an epsilon-amino acid and an omega-amino fatty acid. It derives from a hexanoic acid. It is a conjugate acid of a 6-aminohexanoate. It is a tautomer of a 6-aminohexanoic acid zwitterion.

Application

6-Aminohexanoic acid was used as a biochemical reagent. It is also used as a hemostatic agent. 6-aminocaproic acid has a significant effect on some severe bleeding caused by increased fibrinolytic activity. It is suitable for oozing or local bleeding during various surgical operations. 6-aminocaproic acid is used for hemoptysis, gastrointestinal bleeding and bleeding disorders in obstetrics and gynecology.6-Aminocaproic acid is an anti-fibrinolytic drug with a similar chemical structure to lysine. It can qualitatively inhibit the binding of plasminogen to fibrin and prevent its activation, thereby inhibiting fibrinolysis and achieving hemostasis. Aminocaproic acid is a monoaminocarboxylic acid, which can inhibit the conversion of plasminogen into plasmin and its binding to fibrin. For severe bleeding caused by hyperfibrinolysis caused by increased activation of plasminogen, can have therapeutic effect.

Preparation

6-aminocaproic acid is obtained by hydrolysis of 6-(N-benzoylamino)capronitrile in the presence of hydrochloric acid, or by hydrolysis of caprolactam in the presence of hydrochloric acid, and then treated with ammonium hydroxide.

Manufacturing Process

5 kg of caprolactam were heated with 40 liters of water in a pressure vessel at 250°C for a period of four hours. These quantities of reactants correspond to a water:lactam molecular ratio of 50:1. After cooling, the small quantity of the nonsoluble substance that is formed is filtered off, and the filtrate is evaporated as far as possible. The resulting concentrate is mixed with three times its volume of strong alcohol, thereby causing the desired product, epsilon-aminocaproic acid (6-aminohexanoic acid), to crystallize out. After separating the crystalline product thus obtained, a further quantity of epsilonaminocaproic acid can be obtained from the mother liquid if desired.

Brand name

Amicar (Xanodyne).

General Description

6-Aminocaproic acid is a synthetic inhibitor of fibrinolysis and is utilized for the control of excessive bleeding in patients with amegakaryocytic thrombocytopenia. It also is a protease inhibitor that displays anticancer activity but is limited by cytotoxicity.

Biochem/physiol Actions

Lysine analog. Promotes rapid dissociation of plasmin, thereby inhibiting the activation of plasminogen and subsequent fibrinolysis. Reported to inhibit plasminogen binding to activated platelets. An early report indicated that it inhibits the activation of the first component of the complement system. Binds and inactivates Carboxypeptidase B.

Mechanism of action

Because binding of plasminogen or plasmin to fibrinogen or fibrin is mediated by lysine groups that are part of the structures of fibrin and fibrinogen, aminocaproic acid, which is a structural analog of lysine that only differs in that it has one less amino group, acts as a competitive inhibitor for binding of plasmin(ogen) to fibrin. Aminocaproic acid shifts the homeostatic balance on the side of coagulation, thus restoring fibrinolytic mechanism activity. Aminocaproic acid, which is not a procoagulant, such as those used during surgical intervention and various pathological conditions, is accompanied by an elevation in fibrinolytic activity of blood and tissue. It is used to stop bleeding.

Safety Profile

Moderately toxic by intravenous route. Human systemic effects by ingestion: changes in tubules (includmg acute renal failure, acute tubular necrosis), hematuria, and increased body temperature. Experimental reproductive effects. An eye irritant. When heated to decomposition it emits toxic fumes such as NOx,.

Synthesis

Aminocaproic acid (24.4.1) is synthesized by hydrolyzing ε -caprolactam at high temperature.

Veterinary Drugs and Treatments

Aminocaproic acid has been used as a treatment to degenerative myelopathy (seen primarily in German shepherds), but no controlled studies documenting its efficacy were located. There is interest in evaluating aminocaproic acid for adjunctive treatment of thrombocytopenia in dogs, but efficacy and safety for this purpose remains to be investigated. In humans, it is primarily used for treating hyperfibrinolysis-induced hemorrhage.

InChI:InChI=1/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)/p-1

Upstream product

• 105-60-2 caprolactam 
• 5264-33-5 5-cyanopentanoic acid 
• 2432-74-8 1-amino-5-cyanopentane 
• 89490-49-3 6,6-dichloro-hex-5-enylamine 
• 4224-70-8 6-bromohexanoic acid 
• 371-34-6 ethyl 6-aminohexanoate 
• 4450-39-9 ethyl 5-cyanovalerate 
• 24552-57-6 6-hydroxyimino-hexanoic acid 
• 79598-53-1 6-azidohexanoic acid 
• 70288-80-1 6-methoxycarbonylaminohexanoic acid methyl ester 
• 1888-91-1 N-acetylcaprolactam 
• 57-08-9 6-(acetylamino)hexanoic acid 
• 96594-16-0 6-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(Z)-ylidene]-amino}-hexanoic acid 
• 61625-05-6 6-{[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-hexanoic acid 

Downstream Products

• 4443-26-9 6-phthalimidohexanoic acid 
• 10466-72-5 N-(2,4-dinitrophenyl)-ε-amino-n-caproic acid 
• 6659-35-4 ε-guanidinocaproic acid 
• 956-09-2 6-(benzoylamino)hexanoic acid 
• 46949-54-6 N-(4-chlorobenzenesulfonyl)-ε-aminocaproic acid 
• 7336-15-4 hexahydro-1-(2'-cyanoethyl)-2H-azepin-2-one 
• 108875-83-8 6-(N'-benzoyl-thioureido)-hexanoic acid 
• 61714-42-9 6-(benzenesulfonamido) hexanoic acid 
• 78521-39-8 Tosyl-ε-aminocapronsaeure 
• 1468-42-4 6-ureidohexanoic acid 
• 1072-09-9 N,N-dimethyl-ε-aminohexanoic acid 
• 407-91-0 6-(trifluoroacetamido)hexanoic acid 
• 49701-55-5 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid 
• 60760-70-5 6-[6-(6-benzyloxycarbonylamino-hexanoylamino)-hexanoylamino]-hexanoic acid 

Relevant articles and documents

The pharmacophore of a peptoid VEGF receptor 2 antagonist includes both side chain and main chain residues

Here we identify the pharmacophore in a peptoid that antagonizes Vascular Endothelial Growth Factor Receptor-2 (VEGFR2) in vitro and in vivo. Only three of the side chains in the peptoid are required for activity. Surprisingly, however, main chain atoms also form critical interactions with the receptor.

Activation of Water at the Active-Site Cavity of Zinc Phthalocyanine with Tris(pentafluorophenyl)borane

Activation of water bound with Zn2+ has attracted much attention as an artificial model of natural enzymes. Despite many attempts, water activation accompanied with a change in the coordination geometry of Zn2+ in complexes remains a challenge. In this study, we discover a new structure that is composed of partially protonated zinc phthalocyanine (ZnPc), hydroxide ion, and tris(pentafluorophenyl)borane (TPFB). The coordination of TPFB with water bounded with ZnPc results in the dissociation of water, and the dissociated proton from water moves to one nitrogen atom of the phthalocyanine ring through the intramolecular proton transfer. On the basis of this reaction, the coordination geometry transforms from a five-coordinated to a distorted tetrahedral species. The Zn2+-bound hydroxide nucleophile in the ZnPc-TPFB complex attacks amide of ε-caprolactam to produce hydrolyzed 6-aminohexanoic acid in toluene.

Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading

Acceptorless dehydrogenative coupling (ADC) of alcohols and water/hydroxides is an emergent and graceful approach to produce carboxylic acids. Therefore, it is of high demand to develop active and practical catalysts/catalytic systems for this attractive transformation. Herein, we designed and fabricated a series of cyclometallated N-heterocyclic carbene-Ru (NHC-Ru) complexes via ligand tuning of [Ru-1], the superior complex in our previous work. Gratifyingly, gram-scale synthesis of carboxylic acids was efficiently enabled at an ultralow Ru loading (62.5 ppm) in open air. Moreover, effects of distinct ancillary NHC ligands and other parameters on this catalytic process were thoroughly studied, while further systematic studies were carried out to provide rationales for the activity trend of [Ru-1]-[Ru-7]. Finally, determination of quantitative green metrics illustrated that the present work exhibited superiority over representative literature reports. Hopefully, this study could provide valuable input for researchers who are engaging in metal-catalyzed ADC reactions.

Preparation method of 6-aminocaproic acid

The invention discloses a preparation method of 6-aminocaproic acid, which comprises the following steps: by using caprolactam as a raw material, carrying out alkaline hydrolysis, neutralization treatment, desalination treatment and refining treatment to obtain the 6-aminocaproic acid, wherein the alkaline hydrolysis is carried out on caprolactam, sodium hydroxide and water at a certain temperature and under a certain pressure, a certain temperature is 115-125 DEG C, a certain pressure is 0.15-0.3 MPa, and the reaction time of alkaline hydrolysis does not exceed 1.5 hours. According to the alkaline hydrolysis method disclosed by the invention, the hydrolysis time is shortened through pressurization, so that the generation of by-products can be effectively inhibited under the condition of ensuring complete hydrolysis, and therefore, the alkaline hydrolysis method not only has relatively high reaction yield, but also has relatively high product purity.

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.

Method for preparing aminocaproic acid

The invention discloses a method for preparing aminocaproic acid. The method comprises the following steps: in the presence of heteropolyacid or concentrated sulfuric acid, carrying out hydrolysis reaction on caprolactam and water at 70-80 DEG C for 6-15 hours, sequentially carrying out adsorption by virtue of a cationic resin exchange column and an anionic resin exchange column, and carrying outrefining, so as to obtain the product. According to the method for preparing aminocaproic acid provided by the invention, the maximum feeding scale is 300kg of caprolactam, and the yield of the finally obtained aminocaproic acid is about 99% relative to caprolactam.

IMPROVED PROCESS FOR THE PREPARATION OF 6-AMINOHEXANOIC ACID

The present invention relates to highly pure 6-aminohexanoic acid of formula-1 which is free of organic volatile impurities, caprolactam impurity and improved process for its preparation thereof. The present invention also relates to an improved process for the preparation of caprolactam of formula-2 which is used for the preparation of 6-aminohexanoic acid of formula-1.

Highly active bidentate N-heterocyclic carbene/ruthenium complexes performing dehydrogenative coupling of alcohols and hydroxides in open air

Eight bidentate NHC/Ru complexes, namely [Ru]-1-[Ru]-8, were designed and prepared. In particular, [Ru]-2 displayed extraordinary performance even in open air for the dehydrogenative coupling of alcohols and hydroxides. Notably, an unprecedentedly low catalyst loading of 250 ppm and the highest TON of 32 800 and TOF of 3200 until now were obtained.

Generation of amine dehydrogenases with increased catalytic performance and substrate scope from ε-deaminating L-Lysine dehydrogenase

Amine dehydrogenases (AmDHs) catalyse the conversion of ketones into enantiomerically pure amines at the sole expense of ammonia and hydride source. Guided by structural information from computational models, we create AmDHs that can convert pharmaceutically relevant aromatic ketones with conversions up to quantitative and perfect chemical and optical purities. These AmDHs are created from an unconventional enzyme scaffold that apparently does not operate any asymmetric transformation in its natural reaction. Additionally, the best variant (LE-AmDH-v1) displays a unique substrate-dependent switch of enantioselectivity, affording S- or R-configured amine products with up to >99.9% enantiomeric excess. These findings are explained by in silico studies. LE-AmDH-v1 is highly thermostable (Tm of 69 °C), retains almost entirely its catalytic activity upon incubation up to 50 °C for several days, and operates preferentially at 50 °C and pH 9.0. This study also demonstrates that product inhibition can be a critical factor in AmDH-catalysed reductive amination.

Method for preparing 6-aminocaproic acid

The invention discloses a method for preparing 6-aminocaproic acid. The method includes the steps: (1) dissolving caprolactam in acidic water solution with the concentration of 5-15%, stirring mixturefor 2-10 hours at the temperature of 80-120 DEG C, and distilling the mixture in a pressure reduction manner to obtain white solid; (2) adding a polar solvent until the solid is completely dissolved,slowly leading in ammonia gas until reaction is completed, or dripping organic amine, continuing to stir mixture for 1-12 hours at the temperature of 0-80 DEG C after dripping is completed, and filtering the mixture to obtain an aminocaproic acid crude product; (3) washing the crude product to obtain the 6-aminocaproic acid the purity higher than 99.0%. The molar ratio of the led in ammonia gas or amidogen in the organic amine to the caprolactam is (1-4.5):1. The method has the advantages of low cost, environmental friendliness, high product quality, simplicity and easiness in operation, mildreaction condition and the like, reaction materials can be easily recovered, and a process is more suitable for mass production.