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N-Acetyl-L-proline

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N-Acetyl-L-proline Basic information

Product Name:
N-Acetyl-L-proline
Synonyms:
  • N-AN-Acetyl-L-prolineN-Acetyl-L-prolinecetyl-L-proline
  • (2S)-1-acetyl-2-pyrrolidinecarboxylate
  • (S)-N-Acetylproline
  • L-N-Acetylproline
  • NSC 280718
  • N-Ac-Pro-OH
  • ASINEX-REAG BAS 16579166
  • ACETYL-L-PROLINE
CAS:
68-95-1
MF:
C7H11NO3
MW:
157.17
EINECS:
200-698-9
Product Categories:
  • A - H
  • Amino Acids
  • chiral
  • Amino Acid Derivatives
  • Amino Acids
  • Modified Amino Acids
  • ACETYLGROUP
  • PYRROLE
  • pharmacetical
  • N-Acetyl-Amino acid series
  • amino
  • bc0001
Mol File:
68-95-1.mol
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N-Acetyl-L-proline Chemical Properties

Melting point:
115-117 °C
alpha 
-86 º (c=1 EtOH)
Boiling point:
366.2±35.0 °C(Predicted)
Density 
1.274±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
pka
3.69±0.20(Predicted)
form 
Powder
color 
White to off-white
BRN 
83200
InChI
InChI=1S/C7H11NO3/c1-5(9)8-4-2-3-6(8)7(10)11/h6H,2-4H2,1H3,(H,10,11)/t6-/m0/s1
InChIKey
GNMSLDIYJOSUSW-LURJTMIESA-N
SMILES
C(O)(=O)[C@@H]1CCCN1C(C)=O
CAS DataBase Reference
68-95-1(CAS DataBase Reference)
NIST Chemistry Reference
L-proline, 1-acetyl-(68-95-1)
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Safety Information

Hazard Codes 
Xi
Safety Statements 
24/25
WGK Germany 
3
HazardClass 
IRRITANT
HS Code 
29339900

MSDS

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N-Acetyl-L-proline Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

N-Acetyl-L-proline is an aminoacid used in the synthesis of pharmaceutical compounds useful in preventing and treating disorders and syndromes associated with the nervous, vascular, musculoskeletal, o r cutaneous systems.

Definition

ChEBI: N-acetyl-L-proline is a N-acetyl-L-amino acid, a N-acylpyrrolidine, a pyrrolidinemonocarboxylic acid and a L-proline derivative.

Biochem/physiol Actions

N-acetyl-L-proline is an analog of the COOH-terminal dipeptide portion of preferred substrates of angiotensin-converting enzyme (ACE). It may be used in studies of the binding of substrates and inhibitors by ACE and to differentiate the specificities of various aminoacylases.

References

[1] Jingxuan Qiu. “Solubility Behavior and Polymorphism of N-Acetyl-l-proline in 16 Individual Solvents from 283.15 to 323.15 K.” Journal of Chemical & Engineering Data 66 3 (2021): 1533–1542.

Description

N-Acetyl-L-proline (NALP) is an N-acetyl derivative of L-proline, which has wide application in medicine and is commonly utilized as a biologically active supplement. It can also act as an intermediate for synthesizing pharmaceuticals for preventing and treating some disorders and syndromes associated with the nervous, vascular, musculoskeletal, or cutaneous systems. In laboratories, it could play the role of a simple model for the secondary structure of proline-containing peptides. NALP can be acetylated from L-proline via a standard method, in the environment of acetic acid, or by the action of acetic anhydride on aqueous solutions of the products of the alkaline hydrolysis of gelatin followed by extraction. However,  these methods may result in the production of many byproducts[1]. 

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