2-amino-3-(1,3,3-trimethyl-2H-imidazol-3-ium-4-yl)propanoate

Base Information

• Chemical Name: 2-amino-3-(1,3,3-trimethyl-2H-imidazol-3-ium-4-yl)propanoate
• CAS No.: 507-29-9
• Molecular Formula: C₉H₁₅N₃O₂
• Molecular Weight: 197.237
• DSSTox Substance ID: DTXSID80964939
• Mol file: 507-29-9.mol

Synonyms:Erzinine;507-29-9;2-amino-3-(1,3,3-trimethyl-2H-imidazol-3-ium-4-yl)propanoate;Ammonium, (alpha-carboxy-1H-imidazol-4-ylethyl)trimethyl-, inner salt;1H-Imidazole-4-ethanaminium, alpha-carboxy-N,N,N-trimethyl-, hydroxide, inner salt;DTXSID80964939;2-Amino-3-(1,3,3-trimethyl-2,3-dihydro-1H-imidazol-3-ium-4-yl)propanoate

Chemical Property of 2-amino-3-(1,3,3-trimethyl-2H-imidazol-3-ium-4-yl)propanoate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 199.132076794
• Heavy Atom Count: 14
• Complexity: 268

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C[N+](C(=C1)CC(C(=O)[O-])N)(C)C

Technology Process of 2-amino-3-(1,3,3-trimethyl-2H-imidazol-3-ium-4-yl)propanoate

There total 11 articles about 2-amino-3-(1,3,3-trimethyl-2H-imidazol-3-ium-4-yl)propanoate 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:

His (4998-57-6,26062-48-6,90081-11-1) + methyl iodide (74-88-4) → hercynine (507-29-9)

Guidance literature:

With potassium hydrogencarbonate; In methanol; at 20 ℃;

DOI:10.1016/j.freeradbiomed.2014.11.017

Reference yield:

spithioneine A → bohemamine C + Hercynine (507-29-9,534-30-5)

Guidance literature:

With Raney-Nickel; In ethanol; water; at 20 ℃; for 2h;

DOI:10.1021/acs.orglett.5b01328

Reference yield:

(2S)-3-(2-thioxo-1,3-dihydroimidazol-4-yl)-2-(trimethylammonio) propanoate (4756-85-8,497-30-3) → Hercynine (507-29-9,534-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / water / 48 h / 20 °C

2: Raney-Nickel / ethanol; water / 2 h / 20 °C

With sodium carbonate; In ethanol; water;

DOI:10.1021/acs.orglett.5b01328

upstream raw materials:

2-chloro-3-(1H-imidazol-4-yl)propanoic acid

trimethylamine

D,L-histidine

methyl iodide

Downstream raw materials:

urocanic Acid

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

Refernces

• 1、 Fu, Peng,Macmillan, John B.. "Spithioneines A and B, Two New Bohemamine Derivatives Possessing Ergothioneine Moiety from a Marine-Derived Streptomyces spinoverrucosus". . p. 3046 - 3049. Retrieved 2015.
• 2、 Lim, David,Gründemann, Dirk,Seebeck, Florian P.. "Total Synthesis and Functional Characterization of Selenoneine". supporting information. p. 15026 - 15030. Retrieved 2019/09/12.