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6-Aminocaproic acid

Description References
Product Name
6-Aminocaproic acid
CAS No.
60-32-2
Chemical Name
6-Aminocaproic acid
Synonyms
6-AMINOHEXANOIC ACID;ACS;Aminocaproic;6-aminohexanoate;EACA;Amicar;H-ACP-OH;Hepin;177 J.D;aminocaproic acid,EACA
CBNumber
CB5223888
Molecular Formula
C6H13NO2
Formula Weight
131.17
MOL File
60-32-2.mol
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6-Aminocaproic acid Property

Melting point:
207-209 °C (dec.) (lit.)
Boiling point:
242.49°C (rough estimate)
Density 
1.042 g/cm3
vapor pressure 
<0.1 hPa (20 °C)
refractive index 
1.4870 (estimate)
Flash point:
207-209°C
storage temp. 
Store below +30°C.
solubility 
H2O: 50 mg/mL
form 
powder
pka
4.373(at 25℃)
color 
white
PH
7.0-7.5 (50g/l, H2O, 20℃)
Odor
Odorless
Water Solubility 
SOLUBLE
Merck 
14,432
BRN 
906872
InChIKey
SLXKOJJOQWFEFD-UHFFFAOYSA-N
CAS DataBase Reference
60-32-2(CAS DataBase Reference)
NIST Chemistry Reference
Hexanoic acid, 6-amino-(60-32-2)
EPA Substance Registry System
Hexanoic acid, 6-amino- (60-32-2)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
2
RTECS 
MO6300000
TSCA 
Yes
HS Code 
29224995
Hazardous Substances Data
60-32-2(Hazardous Substances Data)
Toxicity
LD50 in rats (g/kg): 7.0 i.p.; ~3.3 i.v. (Hallesy)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H320Causes eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.00145
Product name
6-Aminohexanoic acid
Purity
for synthesis
Packaging
5G
Price
$31.8
Updated
2023/01/07
Sigma-Aldrich
Product number
8.00145
Product name
6-Aminohexanoic acid
Purity
for synthesis
Packaging
250g
Price
$73.5
Updated
2023/01/07
Sigma-Aldrich
Product number
8.00145
Product name
6-Aminohexanoic acid
Purity
for synthesis
Packaging
1kg
Price
$265
Updated
2023/01/07
Sigma-Aldrich
Product number
8.00145
Product name
6-Aminohexanoic acid
Purity
for synthesis
Packaging
5kg
Price
$913
Updated
2023/01/07
Sigma-Aldrich
Product number
07260
Product name
6-Aminohexanoic acid
Purity
≥98.5% (NT)
Packaging
100g
Price
$137
Updated
2023/01/07
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6-Aminocaproic acid Chemical Properties,Usage,Production

Description

6-aminocaproic acid (Brand name: Amicar) is a kind of synthetic derivative of lysine. Since it is a analogue of amino acid lysine, it can act as the inhibitor for enzymes that need to bind to that particular lysine residue, e.g. the proteolytic enzyme such as plasmin, which is responsible for fibrinolysis. Therefore, it has anti-fibrinolytic activity. It also competitively inhibits activation of plasminogen, thereby reducing conversion of plasminogen to plasmin. Based on this property, it can be used for the treatment of acute bleeding due to elevated fibrinolytic activity in many clinical situations. It can also indicated by FDA for the prevention of recurrent hemorrhage in patients of traumatic hyphema. It may also act as a prophylactic against the vascular disease due to its inhibitory effect on the formation of lipoprotein which is the risk factor of vascular disease.

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

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.

Uses

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).

Therapeutic Function

Antifibrinolytic

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.

6-Aminocaproic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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6-Aminocaproic acid Suppliers

Zhejiang Semo Pharmaceutical Co. LTD
Tel
15867101671
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310374089@qq.com
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China
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Chengdu Chuanke Fine Chemicals C.,Ltd.
Tel
+86 (28) 68626087
Fax
+86-28-85408898
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customertwo@ckfc.asia
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China
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Chemspon Bio-Tech Co., Ltd
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0571-88937695 13606537248
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0571-88933015 QQ:1423821043
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sales@chemspon.com
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Wuhan Hongde Yuexin Pharmaceutical Technology Co., Ltd
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02783850058 15377551550
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027-83850058
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whhdyxchem027@sina.com
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China
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J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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86-10-82849933
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jkinfo@jkchemical.com
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China
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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18621169121
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86-21-61259102
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market03@meryer.com
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China
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40242
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future industrial shanghai co., ltd
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400-0066400 13621662912
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021-55660885
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sales@jonln.com
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China
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1998
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Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
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China
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30133
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TAIYUAN RHF CO.,LTD.
Tel
+86 351 7031519
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+86 351 7031519
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sales@RHFChem.com
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China
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TCI (Shanghai) Development Co., Ltd.
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021-67121386
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021-67121385
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Sales-CN@TCIchemicals.com
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China
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24540
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View Lastest Price from 6-Aminocaproic acid manufacturers

Hebei Crovell Biotech Co Ltd
Product
6-Aminocaproic Acid 60-32-2
Price
US $10.00/Kg/Drum
Min. Order
1KG
Purity
98%
Supply Ability
10 ton
Release date
2021-07-14
Anhui Rencheng Technology Co., Ltd
Product
6-Aminocaproic acid 60-32-2
Price
US $10.00-100.00/KG
Min. Order
0.5KG
Purity
>99%
Supply Ability
20tons
Release date
2020-12-18
Hebei Guanlang Biotechnology Co., Ltd.
Product
6-Aminocaproic acid 60-32-2
Price
US $100.00/PCS
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2021-03-24

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