36097-48-0

Basic information

• Product Name: AC-HIS-OME
• Synonyms: AC-HIS-OME;ACETYL-L-HISTIDINE METHYL ESTER;N-ALPHA-ACETYL-L-HISTIDINE METHYL ESTER;N-ACETYL-L-HISTIDINE METHYL ESTER;N-BENZOYL-L-HISTIDINE METHYL ESTER;Methyl (2S)-2-acetaMido-3-(1H-iMidazol-4-yl)propanoate;(S)-Methyl 2-acetaMido-3-(1H-iMidazol-4-yl)propanoate;L-Histidine, N-acetyl-, Methyl ester
• CAS NO: 36097-48-0
• Molecular Formula: C₉H₁₃N₃O₃
• Molecular Weight: 211.22
• Mol File: 36097-48-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 508.5 °C at 760 mmHg
• Flash Point: 261.4 °C
• Appearance: /
• Density: 1.245±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.84E-10mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: AC-HIS-OME(CAS DataBase Reference)
• NIST Chemistry Reference: AC-HIS-OME(36097-48-0)
• EPA Substance Registry System: AC-HIS-OME(36097-48-0)

Safety Data

• Hazardous Substances Data: 36097-48-0(Hazardous Substances Data)

Usage

Description

AC-HIS-OME, or N-Acetyl-L-histidine Methyl Ester, is the N-acetylated methyl ester of L-Histidine, an essential amino acid. It plays a crucial role in various biological processes and has potential applications in different industries due to its unique properties.

Uses

Used in Pharmaceutical Industry:
AC-HIS-OME is used as a pharmaceutical compound for its potential therapeutic effects. As a derivative of L-Histidine, it may have implications in the treatment of various health conditions, including those related to the immune system and cellular metabolism.
Used in Nutritional Supplements:
AC-HIS-OME is used as an ingredient in nutritional supplements for its potential benefits in enhancing overall health and well-being. Its role in cellular metabolism and immune function makes it a valuable addition to dietary supplements.
Used in Research and Development:
AC-HIS-OME is used as a research compound for studying the properties and potential applications of L-Histidine and its derivatives. This can lead to the development of new drugs, therapies, and supplements that leverage the unique characteristics of AC-HIS-OME.
Used in Cosmetics Industry:
AC-HIS-OME may be used as an ingredient in the cosmetics industry for its potential benefits in skin health and rejuvenation. Its role in cellular metabolism could contribute to the development of products that promote skin regeneration and overall skin health.

InChI:InChI=1/C9H13N3O3/c1-6(13)12-8(9(14)15-2)3-7-4-10-5-11-7/h4-5,8H,3H2,1-2H3,(H,10,11)(H,12,13)/t8-/m0/s1

Upstream product

• 67-56-1 methanol 
• 2497-02-1 N-acetyl-L-histidine 
• 71-00-1 L-histidine 
• 917484-74-3 (1R,2R)-N-acetyl-1,2-bis(trifluoromethanesulfonamido) cyclohexane 
• 1499-46-3 L-Histidine methyl ester 
• 71-00-1 L-histidine 
• 75-36-5 acetyl chloride 

Downstream Products

• 154061-60-6 N^α-Acetyl-N^τ-(p-nitrophenyl)-L-histidine methyl ester 
• 406470-83-5 1-o-allyloxyphenyl(acetyl)-L-histidine methyl ester 
• 955134-23-3 methyl N-acetyl-5-phenyl-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate 
• 955134-10-8 methyl N-acetyl-5-phenyl-3-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate 
• 955134-24-4 methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate 
• 955134-11-9 methyl N-acetyl-5-(2-methoxy-5-methylphenyl)-3-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate 
• 955134-26-6 methyl N-acetyl-5-(2-methoxyphenyl)-1-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate 
• 955134-12-0 methyl N-acetyl-5-(2-methoxyphenyl)-3-[2-(trimethylsilyl)ethoxymethyl]-L-histidinate 

Relevant articles and documents

Determination of Acid Dissociation Constants of Histidine-Containing Peptides by Proton Magnetic Resonance Spectroscopy

The acid dissociation constant of the imidazolium ring of the decapeptide luliberin has been determined by 1H NMR-followed titration in D2O.The normal procedure for the analysis of the titration curve, i. e. direct use of the Henderson-Haselbalch equation, is still applicable in this case, but for more complex peptides a modified calculation procedure is proposed.Results obtained when both methods were applied to luliberin are compared.The influence of D2O when used as the solvent in this type of determination has been studied using Nα-acetyl-L-histidine methyl ester as a model compound.The difference between the acid dissociation constant of this molecule determined in H2O and in D2O implies that a correction of -0.25 unit is needed for those pKa values calculated by plotting the chemical shifts in D2O vs the apparent pH meter readings.The pKa found for Nα-acetyl-L-histidine methyl ester, 6.30 +/- 0.04, can be taken as a standard value for histidine-containing peptides.

Selective Photoredox Trifluoromethylation of Tryptophan-Containing Peptides

For application in drug discovery and biomedicine, it is crucial to develop new biocompatible methods to modify polypeptides. Herein, a visible-light-induced photoredox trifluoromethylation of tryptophan-containing peptides is reported. Under a mild, biocompatible, and straightforward condition, this strategy could incorporate the trifluoromethyl group into tryptophan residue with excellent chemo- and site-selectivity. The use of lower photocatalyst loading in 2 mol-% and cheap CF3SO2Na salt represents a great catalytic activity and economic CF3 source. This direct trifluoromethylation strategy allows the ready study of fluorinated peptides exploiting 19F-NMR. Additionally, the development of this protocol enables the study of biochemical systems and potentially modulates the function of biomolecules. Careful mechanistic studies (Stern-Volmer fluorescence quenching, EPR, and radical inhibition/trapping experiments) indicate that the reaction would proceed with a radical–radical cross-coupling procedure.

Nanomole-scale assignment of configuration for primary amines using a kinetic resolution strategy

The absolute configurations of primary amines were assigned using a kinetic resolution strategy with Mioskowski's enantioselective 1-(R,R) and 2-(S,S) acylating agents. A simple mnemonic was developed to determine the configuration. A pseudoenantiomeric pair of reagents, 1-(R,R) and 2-(S,S)-d 3, was prepared and used to assay primary amines on a micromolar scale. The ESI-MS readout of the resulting acetamide products reproduced the selectivity factors from kinetic experiments. The method can be used on mixtures of amines and was validated with amine samples as small as 50 nmol.