N,N,N-Trimethyl-Histidine

Base Information

• Chemical Name: N,N,N-Trimethyl-Histidine
• CAS No.: 534-30-5
• Molecular Formula: C9H16N3O2+
• Molecular Weight: 197.237
• DSSTox Substance ID: DTXSID40968054
• Nikkaji Number: J2.996.113A,J3.568.054C
• Wikidata: Q27135608
• Metabolomics Workbench ID: 78605
• Mol file: 534-30-5.mol

Synonyms:N,N,N-Trimethyl-Histidine;Nalpha,Nalpha,Nalpha-Trimethyl-L-histidine;N(alpha),N(alpha),N(alpha)-trimethyl-L-histidinium(1+);[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]trimethylazanium;AVJ;C05575;SCHEMBL2926302;SCHEMBL17308657;CHEBI:67049;DTXSID40968054;Q27135608;[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]-trimethylazanium;(1S)-1-carboxy-2-(1H-imidazol-4-yl)-N,N,N-trimethylethanaminium;(1S)-1-carboxy-2-(1H-imidazol-5-yl)-N,N,N-trimethylethanaminium;1-Carboxy-2-(1H-imidazol-5-yl)-N,N,N-trimethylethan-1-aminium

Chemical Property of N,N,N-Trimethyl-Histidine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 198.124251762
• Heavy Atom Count: 14
• Complexity: 213

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+](C)(C)C(CC1=CN=CN1)C(=O)O
• Isomeric SMILES: C[N+](C)(C)[C@@H](CC1=CN=CN1)C(=O)O

Technology Process of N,N,N-Trimethyl-Histidine

There total 15 articles about N,N,N-Trimethyl-Histidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

N,N-dimethylhistidine hydrochloride + methyl iodide (74-88-4) → α-N,N,N-trimethylhistidine (534-30-5)

Guidance literature:

With ammonium hydroxide; In methanol; at 20 - 30 ℃; for 18h; pH=9; Reagent/catalyst;

Reference yield: 73.0%

L-histidine hydrochloride + methyl iodide (74-88-4) → α-N,N,N-trimethylhistidine (534-30-5)

Guidance literature:

With potassium hydroxide; In methanol; water; at 25 - 35 ℃; for 18h; pH=9 - 13; Reagent/catalyst;

Reference yield: 36.0%

N,N-dimethyl-L-histidine hydrochloride (17451-63-7) + methyl iodide (74-88-4) → α-N,N,N-trimethylhistidine (534-30-5)

Guidance literature:

N,N-dimethyl-L-histidine hydrochloride; With ammonia; In methanol; water; pH=9;

methyl iodide; In methanol; water; at 20 ℃;

DOI:10.1021/ol402275t

upstream raw materials:

methyl iodide

(2S)-3-(2-thioxo-1,3-dihydroimidazol-4-yl)-2-(trimethylammonio) propanoate

L-histidine

N,N-dimethyl-L-histidine hydrochloride

Downstream raw materials:

(2S)-3-(2-thioxo-1,3-dihydroimidazol-4-yl)-2-(trimethylammonio) propanoate

L-cysteinesulfinic acid

Refernces

• 1、 Song, Heng,Leninger, Maureen,Lee, Norman,Liu, Pinghua. "Regioselectivity of the oxidative C-S bond formation in ergothioneine and ovothiol biosyntheses". . p. 4854 - 4857. Retrieved 2013.
• 2、 Lim, David,Gründemann, Dirk,Seebeck, Florian P.. "Total Synthesis and Functional Characterization of Selenoneine". supporting information. p. 15026 - 15030. Retrieved 2019/09/12.
• 3、 -. "METHOD FOR PRODUCING PURE L-HERCYNINE". Paragraph 0071-0080. . Retrieved 2017/10/23.