Encyclopedia / Pharmaceutical / Pharmaceutical Intermediates / Organic Intermediate

6-Aminocaproic acid

CAS：60-32-2
MW:131.17292
MF：C6H13NO2

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. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: 6-Aminocaproic acid

1.2 Synonyms: 177 J.D; 177 J.D.; 177j.d.; 177jd; 4-04-00-02695; 4-04-00-02695 (Beilstein Handbook Reference); 4-aminobutyltrimethoxysilane; 6-(((Benzyloxy)carbonyl)amino)hexanoic acid; 6-[(phenylmethoxy)carbonylamino]hexanoic acid; 6-[N-(Benzyloxycarbonyl)amino]hexanoic acid; 6-{[(Benzyloxy)carbonyl]amino}hexanoic acid; 6-amino hexanoic acid; 6-Aminohexanoic acid; 6-amino-hexanoic acid; 6-amino-hexanoicaci; 6-amino-n-caproic acid; 6-amino-n-hexanoic acid; 6-N-Cbz-aminohexanoic acid; Acepramin; Acepramine; acido aminocaproico; Acidum Aminocaproicum; ACS; AMICAR; aminobutyltrimethoxysilane; Aminocaproic acid; Aminohexanoic acid; Cbz-ε- Aminocaproic acid; Cbz-ε-Ahx-OH; EINECS 200-469-3; H-6-Aca-OH; H-6-Ahx-OH; H-EAhx-OH; Hexanoic acid, 6-[[(phenylmethoxy)carbonyl]amino]-; Hexanoic acid, 6-amino-; HEXANOIC ACID,6-AMINO; H-ε-Acp-OH; MFCD00008238; N-(Benzyloxycarbonyl)-6-aminohexanoic acid; N-Benzyloxycarbonyl-6-aminocaproic Acid; N-benzyloxycarbonyl-6-aminohexanoic acid; N-Carbobenzoxy-6-aminohexanoic Acid; N-Carbobenzoxy-ε-aminocaproic Acid; N-Cbz-6-aminocaproic acid; N-Cbz-6-aminohexanoic Acid; N-Cbz-ε-aminocaproic Acid; w-Aminocaproic acid; w-Aminohexanoic acid; Z-6-Aminohexanoic acid; ε-aminocaproic acid; ε-aminohexanoic acid; ε-Amino-n-caproic acid;

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1.3 CAS No.: 60-32-2

1.4 CID: 564

1.5 EINECS: 200-469-3

1.6 Molecular Formula: C6H13NO2

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

1.8 InChkey: SLXKOJJOQWFEFD-UHFFFAOYSA-N

1.9 Canonical Smiles: C(CCC(=O)O)CCN

1.10 Isomers Smiles: C(CCC(=O)O)CCN

2. Properties

2.1 Solubility: H2O: 50?mg/mL

2.2 Appearance: white crystalline powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: white crystalline powder

2.5 Color/Form: FINE, WHITE, CRYSTALLINE POWDER
LEAVES FROM ETHER

2.6 Odor: ODORLESS, OR NEARLY SO

2.7 PH: 7.0-7.5 (50g/l, H2O, 20℃)

2.8 pKa: 4.373(at 25℃)

2.9 Water Solubility: SOLUBLE

2.10 Spectral Properties: SADTLER REF NUMBER: 15194 (IR, PRISM)
IR: 1903 (Coblentz Society Spectral Collection)
NMR: 4445 (Sadtler Research Laboratories Spectral Collection)

2.11 Stability: STABLE IN LIGHT & AIR

2.12 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Definition: ChEBI: An amino-acid anion that is the conjugate base of 6-aminohexanoic acid.

3.2 Description: 6-Aminocaproic acid (CAS 60-32-2) is a white crystalline powder that is commonly used in various fields. Its basic structure consists of a six-carbon chain with an amino group (-NH2) and a carboxylic acid group (-COOH) attached. This compound is highly soluble in water, forming a clear and colorless solution. It has a molecular weight of 131.17 g/mol and a melting point of 205-209°C.

Applicable Fields
Pharmaceutical Industry: 6-Aminocaproic acid is widely used in the pharmaceutical industry as a hemostatic agent. Its mechanism of action involves inhibiting the activation of plasmin, an enzyme responsible for breaking down blood clots. By preventing the excessive breakdown of blood clots, it helps in controlling bleeding.

Storage Conditions
Store in a cool and dry place.

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3.3 Usage: hemostatic

4. Safety and Handling

4.1 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,.

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4.2 Formulations/Preparations: ...AVAILABLE AS INJECTION (250 MG/ML), SYRUP (250 MG/ML) & TABLETS (500 MG).

4.3 Report: Reported in EPA TSCA Inventory.

4.4 Safety: Moderately toxic by intravenous route. Human systemic effects by ingestion: changes in tubules (including 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 NO_x.
Hazard Codes?:?Xi
Risk Statements?: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:? 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
WGK Germany:2

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4.5 Specification: ? 6-Aminocaproic acid (CAS NO.60-32-2), its Synonyms are Aminocaproic acid ; Hexanoic acid, 6-amino- ; epsilon-Aminocaproic acid ; Eaca kabi ; Epsamon ; Epsicapron ; Epsikapron ; Epsilcapramin ; Epsilon S ; Epsilon-Aminocapronsaeure ; Epsilon-aminocaproic acid ; Epsilon-aminocapronzuur ; Hemocaprol ; Hemopar ; Hepin ; Hexanoic acid, 6-amino- . It is white crystalline powder.

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4.6 Toxicity

1.	???	eye-rbt 500?mg/24H MLD	???	28ZPAK ?? Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.:?1972,128.
2.	???	orl-man TDLo:1778?mg/kg/8D-I:SYS	???	AJKDDP ?? American Journal of Kidney Diseases. 8 (1986),441.
3.	???	mul-man TDLo:14,400?mg/kg/59D-I	???	BJURAN ?? Journal of Urology. 60 (1987),81.
4.	???	ipr-rat LD50:7000?mg/kg	???	PHMCAA ?? Pharmacologist. 3 (1961),62.
5.	???	ivn-rat LD50:3300?mg/kg	???	PHMCAA ?? Pharmacologist. 3 (1961),62.
6.	???	orl-mus LD50:14,300?mg/kg	???	NIIRDN ?? “Drugs in Japan. Ethical Drugs, 6 (1982),79.
7.	???	ivn-mus LD50:4900?mg/kg AAREAV 22,481,65
8.	???	ivn-dog LDLo:2150?mg/kg	???	PHMCAA ?? Pharmacologist. 3 (1961),62.
9.	???	ivn-gpg LDLo:19,800?mg/kg AAREAV 22,481,65

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : 400 MHz in D2O

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

Raman : 4880 A,200 M,powder

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

60-32-2Total: 42 Synthesis Route

57-08-9 33 Suppliers

60-32-2 273 Suppliers

57-08-9 33 Suppliers

105-60-2 266 Suppliers

60-32-2 273 Suppliers

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8. Precursor and Product

precursor:

928-81-4

1947-00-8

371-34-6

57-08-9

996-82-7

5515-01-5

100-64-1

105-60-2

product:

2780-89-4

928-81-4

373-04-6

956-09-2

1926-80-3

462-94-2

407-91-0

3633-17-8

5264-33-5

105-60-2

9. Computed Properties

Molecular Weight：131.17292g/mol
Molecular Formula：C₆H₁₃NO₂
Compound Is Canonicalized：True
XLogP3-AA：131.094628657
Monoisotopic Mass：131.094628657
Complexity：83.1
Rotatable Bond Count：5
Hydrogen Bond Donor Count：2
Hydrogen Bond Acceptor Count：3
Topological Polar Surface Area：63.3
Heavy Atom Count：：9
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBiMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAACADBgAQACABAAgAIAACQCAAAAAAAAAAAAIEAAAAAABIAgAAAQAAEEAAAAAGYSAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Usage: 6-Aminohexanoic acid is used as an intermediate in the polymerization of Nylon-6. It is involved in the extraction of aldehydes from the reaction mixture as well as to improve the solubilization of membrane proteins in electrophoresis. It acts as an inhibitor of fibrinolysis.

Merck: 14,432

BRN: 906872

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.

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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

Originator: Epsilon,Roche,W. Germany,1962

Uses: hemostatic

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.

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Uses: Propylparaben Food preservative

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.

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Definition: ChEBI: An amino-acid anion that is the conjugate base of 6-aminohexanoic acid.

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.

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Brand name: Amicar (Xanodyne).

Therapeutic Function: Antifibrinolytic

General Description: Aminocaproic acid is a synthetic inhibitor of fibrinolysis and is utilized for the control of excessive bleeding in patients with amegakaryocytic thrombocytopenia.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

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11. Toltal 252 Suppliers View more

Baoji Guokang Healthchem co.,ltd

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High purity 6-Aminocaproic acid 98% TOP1 supplier in ChinaCAS NO.: 60-32-2

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Manufacturer supply 6-Aminocaproic acid CAS 60-32-2 of USP/EP standard

Wuhan Fortuna Chemical Co., Ltd.

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12. Related Questions

: What Role Does 6-Aminocaproic Acid Play in Advancing Cancer Diagnostics and Therapeutics?General Description 6-Aminocaproic acid is a key component in improving cancer diagnostic and therapeutic techniques by enhancing the stability and efficacy of indocyanine green (ICG) in the developme..; What is the application and preparation method of 6-Aminocaproic acid?6-Aminocaproic acid is used in the synthesis of polyurethane material nylon 6, which is widely used in industries such as machinery, chemical, instrumentation, automotive manufacturing, medical, and t..; How is 6-Aminocaproic Acid Prepared and Used as an Antifibrinolytic Agent?Title: How is 6-Aminocaproic Acid Prepared and Used as an Antifibrinolytic Agent? Introduction: 6-Aminocaproic acid, with the molecular formula C6H13O2N, NH2(CH2)5COOH, is a white crystalline powder t..; Proton NMR spectrum of aminocaproic acid I have completely unpacked the NMR spectrum for the drug aminocaproic acid (structure below) and have found a peak that I myself can not explain. The signals for the drug are simple to understand wha..

13. Realated Product Infomation