68-95-1

Basic information

• Product Name: N-Acetyl-L-proline
• Synonyms: N-ACETYL-L-PROLINE (N-AC-L-PRO);N-alpha-Actetyl-L-proline;N-Acethyl-L-proline;N-ACETYL-L-PROLINE (USP);(+/-)-(3-Methoxy-4-hydroxyphenyl)-2-isopropylaminoethanol hydrochloride;Benzenemethanol, 4-hydroxy-3-methoxy-a-[[(1-methylethyl)amino]methyl]-, hydrochloride;Vanillyl alcohol, a-[(isopropylamino)methyl]-, hydrochloride;(2S)-1-Acetylpyrrolidine-2α-carboxylic acid
• CAS NO: 68-95-1
• Molecular Formula: C₇H₁₁NO₃
• Molecular Weight: 157.17
• EINECS: 200-698-9
• Product Categories: chiral;Amino Acid Derivatives;Amino Acids;N-Acetyl-Amino acid series;A - H;Amino Acids;Modified Amino Acids;amino;PYRROLE;ACETYLGROUP;pharmacetical
• Mol File: 68-95-1.mol
• Article Data: 34

Chemical Properties

• Melting Point: 115-117 °C
• Boiling Point: 366.2 °C at 760 mmHg
• Flash Point: 175.3 °C
• Appearance: White to off-white/Powder
• Density: 1.274 g/cm³
• Vapor Pressure: 2.31E-06mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 3.69±0.20(Predicted)
• BRN: 83200
• CAS DataBase Reference: N-Acetyl-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-L-proline(68-95-1)
• EPA Substance Registry System: N-Acetyl-L-proline(68-95-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 68-95-1(Hazardous Substances Data)

Usage

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.

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.

InChI:InChI=1/C7H11NO3/c1-5(9)8-4-2-3-6(8)7(10)11/h6H,2-4H2,1H3,(H,10,11)/p-1/t6-/m0/s1

Upstream product

• 147-85-3 L-proline 
• 132090-10-9 N-acetyl-L-proline benzyl ester 
• 830-03-5 4-nitrophenol acetate 
• 147-85-3 L-proline 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 75-36-5 acetyl chloride 
• 2812-47-7 pyrrolidine-2-carboxylic acid amide 
• 2311-25-3 N-acetyl-L-proline methyl ester 
• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 64-19-7 acetic acid 
• 108-05-4 vinyl acetate 
• 94740-40-6 N-(N'-acetyl-L-prolyl)-N-nitrosoglycine 
• 94740-41-7 N-(N'-acetyl-L-prolyl)-N-nitroso-L-alanine 
• 108-24-7 acetic anhydride 

Downstream Products

• 94740-35-9 N-(N'-acetyl-L-prolyl)glycine benzyl ester 
• 915762-97-9 N-[1-(1-acetyl-L-prolyl)piperidin-4-yl]-5-(phenylsulfonyl)-2-(trifluoromethyl)benzenesulfonamide 
• 1215172-62-5 C₂₃H₂₆N₄O₄ 
• 16395-58-7 N-acetyl-L-prolinamide 
• 1403959-04-5 (S)-1-acetyl-N-tosylpyrrolidine-2-carboxamide 
• 1403959-05-6 C₁₃H₁₅N₃O₆S 
• 23037-82-3 (S)-ethyl 1-acetylpyrrolidine-2-carboxylate 
• 74214-36-1 N-(N'-acetyl-L-prolyl)-L-alanine benzyl ester 
• 19701-85-0 N-acetyl-L-proline-N'-methylamide 

Relevant articles and documents

n-Pentyl N-acetylprolinate. A new skin penetration enhancer

The activity of n-pentyl N-acetylprolinate (PNAP) as a transdermal penetration enhancer was investigated. PNAP was synthesized from L-proline by acetylation with acetic anhydride, followed by acid-catalyzed esterification with 1-pentanol. Structure confirmation was accomplished by IR and NMR spectroscopy and elemental analysis. Benzoic acid (BA) was used as a model drug, and the effect of PNAP on the flux of BA through human cadaver skin was evaluated. The central nervous system (CNS) toxicity of PNAP was evaluated by comparing the effects of intraperitoneal administration of PNAP to mice with those of laurocapram (Azone), a known penetration enhancer. Based on preliminary studies, PNAP appears to be an effective transdermal penetration enhancer, is nontoxic at tow doses, and exhibits dose-related CNS toxicity at higher doses.

Bioinspired Synthesis of (?)-PF-1018

The combination of electrocyclizations and cycloadditions accounts for the formation of a range of fascinating natural products. Cascades consisting of 8π electrocyclizations followed by a 6π electrocyclization and a cycloaddition are relatively common. We now report the synthesis of the tetramic acid PF-1018 through an 8π electrocyclization, the product of which is immediately intercepted by a Diels–Alder cycloaddition. The success of this pericyclic cascade was critically dependent on the substitution pattern of the starting polyene and could be rationalized through DFT calculations. The completion of the synthesis required the instalment of a trisubstituted double bond by radical deoxygenation. An unexpected side product formed through 4-exo-trig radical cyclization could be recycled through an unprecedented triflation/fragmentation.

(4-HYDROXYPYRROLIDIN-2-YL)-HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure relates to bifunctional compounds of formula (I), which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands of formula (III).

Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media

The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Br?nsted dependence and revealed linear correlation between rate constant logarithm and the energy difference of the frontier orbitals of α-amino acids anions.