6-Aminocaproic acid

Iupac Name：6-aminohexanoic acid

CAS No.: 60-32-2

Molecular Weight：131.17292

Modify Date.: 2022-11-05 21:12

Introduction: 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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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

1.3 CAS No.: 60-32-2

1.4 CID: 564

1.5 EINECS(EC#): 200-469-3

1.6 Molecular Formula: C6H13NO2 (isomer)

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 Density: 1.042

2.1 Melting point: 204-209℃

2.1 Boiling point: 255.6°C at 760 mmHg

2.1 Refractive index: 1.4870 (estimate)

2.1 Flash Point: 108.4°C

2.1 Precise Quality: 131.09500

2.1 PSA: 63.32000

2.1 logP: 1.29040

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 Usage: hemostatic

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S36

4.1 RIDADR: NONH for all modes of transport

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,.

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

4.3 WGK Germany: 2

4.3 RTECS: MO6300000

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

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.

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

View all

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 34 Suppliers

60-32-2 269 Suppliers

Literatures:
Pharmaceutical Chemistry Journal, , vol. 14, # 1 p. 60 - 63 Khimiko-Farmatsevticheskii Zhurnal, , vol. 14, # 1 p. 73 - 75
Yield: null

57-08-9 34 Suppliers

105-60-2 260 Suppliers

60-32-2 269 Suppliers

Literatures:
WO2010/41943 A2, ; Page/Page column 10-11 ;
Yield: null

928-81-4 1 Suppliers

60-32-2 269 Suppliers

Literatures:
BASF Aktiengesellschaft Patent: US4730040 A1, 1988 ;
Yield: ~79%

View all

8. Precursor and Product

precursor:

1468-42-4

1947-00-8

74760-66-0

14660-52-7

89490-49-3

56403-09-9

371-34-6

2432-74-8

57-08-9

2677-33-0

4450-39-9

5515-01-5

928-81-4

6404-29-1

98553-02-7

4224-70-8

996-82-7

100-64-1

105-60-2

1888-91-1

10269-96-2

5264-33-5

View all

product :

373-04-6

1468-42-4

5834-63-9

1577-22-6

462-94-2

3633-17-8

71510-39-9

4321-58-8

4224-70-8

407-91-0

79778-41-9

6954-30-9

2780-89-4

6621-60-9

59178-92-6

1947-00-8

5612-13-5

1700-05-6

5776-78-3

61714-42-9

1926-80-3

5100-36-7

5107-12-0

50347-17-6

5514-98-7

View all

9. Other Information

9.0 Merck: 14,432

9.1 BRN: 906872

9.2 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.

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

9.4 Chemical Properties: white crystalline powder

9.5 Originator: Epsilon,Roche,W. Germany,1962

9.6 Uses: hemostatic

9.7 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.

9.8 Uses: Propylparaben Food preservative

9.9 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.

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

9.11 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.

9.12 Brand name: Amicar (Xanodyne).

9.13 Therapeutic Function: Antifibrinolytic

9.14 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.

9.15 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.

10. Computational chemical data

Molecular Weight: 131.17292g/mol
Molecular Formula: C₆H₁₃NO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 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==

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CAS：60-32-2 6-Aminocaproic acid