D-Octopine

Base Information

• Chemical Name: D-Octopine
• CAS No.: 34522-32-2
• Molecular Formula: C9H18 N4 O4
• Molecular Weight: 246.266
• Hs Code.: 2925290090
• Mol file: 34522-32-2.mol

Synonyms:D-Octopine;C9H18N4O4;C9-H18-N4-O4;Arginine, N2-(1-carboxyethyl)-, L-;N2-((1R)-1-Carboxyethyl)-L-arginine;N2-[(1R)-1-carboxyethyl]-L-Arginine;L-Arginine, N2-[(1R)-1-carboxyethyl]-;D-octopine dizwitterion;N2-(1-carboxyethyl)-, (R)-L-arginine;CHEBI:57520;Arginine, N2-(1-carboxyethyl)-, L-arginine;(2S)-5-{[amino(iminio)methyl]amino}-2-{[(1R)-1-carboxylatoethyl]ammonio}pentanoate;(2S)-5-{[amino(iminiumyl)methyl]amino}-2-{[(1R)-1-carboxylatoethyl]azaniumyl}pentanoate

Chemical Property of D-Octopine

Chemical Property:

• Vapor Pressure: 1.73E-12mmHg at 25°C
• Melting Point: 283-284 °C(lit.)
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 526.4°Cat760mmHg
• PKA: 2.14±0.10(Predicted)
• Flash Point: 272.1°C
• PSA: 148.53000
• Density: 1.45g/cm³
• LogP: 0.34740
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly), Water (Slightly, Heated, Sonicated)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 246.13280507
• Heavy Atom Count: 17
• Complexity: 290

Purity/Quality:

99%min ^*data from raw suppliers

D-(+)-Octopine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)[O-])[NH2+]C(CCC[NH+]=C(N)N)C(=O)[O-]
• Isomeric SMILES: C[C@H](C(=O)[O-])[NH2+][C@@H](CCC[NH+]=C(N)N)C(=O)[O-]
• Uses: A nitrogenous compound from octopus muscles. D-(+)-Octopine is used for producing seasoning and food additive. A nitrogenous compound from octopus muscles. It is used for producing seasoning and food additive.

Technology Process of D-Octopine

There total 9 articles about D-Octopine 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: 61.0%

2-methylisothiourea sulphate (14527-26-5,867-44-7,147895-43-0) + (R),(S)-octopinic acid → N2-(D-1-carboxyethyl)-L-arginine (34522-32-2,23449-95-8,33034-23-0,499-45-6)

Guidance literature:

With sodium hydroxide; at 35 ℃; for 144h;

DOI:10.1246/bcsj.55.261

Reference yield:

(S)-2-bromopropanoic acid (32644-15-8,10327-08-9) + L-arginine (74-79-3,25212-18-4) → N2-(D-1-carboxyethyl)-L-arginine (34522-32-2,23449-95-8,33034-23-0,499-45-6)

Guidance literature:

With barium dihydroxide; at 37 ℃;

Reference yield:

(S)-2-bromopropanoic acid (32644-15-8,10327-08-9) + L-arginine (74-79-3,25212-18-4) + 1-methyl-4-nitrosobenzene (623-11-0) → N2-(D-1-carboxyethyl)-L-arginine (34522-32-2,23449-95-8,33034-23-0,499-45-6)

Guidance literature:

at 39 ℃; Geschwindigkeit der Reaktion;

DOI:10.1021/ja01560a039

upstream raw materials:

(S)-2-bromopropanoic acid

L-arginine

1-methyl-4-nitrosobenzene

2-Bromopropionic acid

Downstream raw materials:

N^α-(D-1-carboxy-ethyl)-L-ornithine

urea

carbon dioxide

ammonia

Refernces

• 1、 Biellmann,Branlant,Wallen. "Stereochemistry of octopine and of its isomers and their enzymatic properties". . p. 89 - 93. Retrieved 2007/10/05.