Hypaphorine

Base Information

• Chemical Name: Hypaphorine
• CAS No.: 487-58-1
• Deprecated CAS: 12673-47-1,63767-89-5,97045-39-1
• Molecular Formula: C₁₄H₁₈N₂O₂
• Molecular Weight: 246.309
• European Community (EC) Number: 803-882-2
• UNII: GJ3358U63L
• DSSTox Substance ID: DTXSID70964100
• Wikidata: Q27106905
• Metabolomics Workbench ID: 49923
• ChEMBL ID: CHEMBL2235164
• Mol file: 487-58-1.mol

Synonyms:hypaforin;hypaphorine;lenticin;lenticin nitrate

Chemical Property of Hypaphorine

Chemical Property:

• Melting Point: 255℃ (decomposition)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 55.92000
• Density: g/cm³
• LogP: 0.53510
• Storage Temp.: -20°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 246.136827821
• Heavy Atom Count: 18
• Complexity: 306

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Hypaphorine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+](C)(C)C(CC1=CNC2=CC=CC=C21)C(=O)[O-]
• Isomeric SMILES: C[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C21)C(=O)[O-]

Technology Process of Hypaphorine

There total 7 articles about Hypaphorine 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: 24.0%

O-Methyl-N,N'-diisopropylisourea (54648-79-2) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → α-N,N,N-trimethyltryptophan betaine (64363-86-6,487-58-1,12673-47-1,97045-39-1)

Guidance literature:

In methanol; for 408h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89759-3

Reference yield:

S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N,N-α-dimethyl-L-tryptophan (2812-40-0) + α-N,N,N-trimethyltryptophan betaine (64363-86-6,487-58-1,12673-47-1,97045-39-1) + L-abrine (526-31-8)

Guidance literature:

With adenine deaminase; recombinant (SAM)-dependent tryptophan methyltransferase from Psilocybe serbica FSU₁₂₄₁₆; SAH-nucleosidase; In aq. buffer; at 25 ℃; for 4h; pH=8; Catalytic behavior; Enzymatic reaction;

DOI:10.1002/cbic.201800336

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + methyl iodide (74-88-4) → α-N,N,N-trimethyltryptophan betaine (64363-86-6,487-58-1,12673-47-1,97045-39-1)

Guidance literature:

With potassium carbonate; In methanol; for 6h; Heating;

upstream raw materials:

O-Methyl-N,N'-diisopropylisourea

L-Tryptophan

methyl iodide

L-abrine

Downstream raw materials:

indole

trimethylamine

Refernces

• 1、 Blei, Felix,Fricke, Janis,Wick, Jonas,Slot, Jason C.,Hoffmeister, Dirk. "Iterative l-Tryptophan Methylation in Psilocybe Evolved by Subdomain Duplication". . p. 2160 - 2166. Retrieved 2018/10/09.
• 2、 Naresh Chary,Dinesh Kumar, Ch.,Vairamani,Prabhakar. "Characterization of amino acid-derived betaines by electrospray ionization tandem mass spectrometry". experimental part. p. 79 - 88. Retrieved 2012/05/04.