Rhodotorulic acid

Base Information

• Chemical Name: Rhodotorulic acid
• CAS No.: 18928-00-2
• Molecular Formula: C14H24 N4 O6
• Molecular Weight: 344.368
• European Community (EC) Number: 242-681-9
• UNII: 61F3VBQ4G5
• DSSTox Substance ID: DTXSID20940439
• Nikkaji Number: J15.543H
• Wikipedia: Rhodotorulic_acid
• Wikidata: Q7321233
• Metabolomics Workbench ID: 113254
• ChEMBL ID: CHEMBL114350
• Mol file: 18928-00-2.mol

Synonyms:chromic rhodotorulic acid;cyclo-di(alpha-N-acetyl-alpha-hydroxy-L-ornithine);rhodotorulic acid;rhodotorulic acid, Fe(3+) salt, (1S-cis)-isomer

Chemical Property of Rhodotorulic acid

Chemical Property:

• Vapor Pressure: 3.78mmHg at 25°C
• Boiling Point: °Cat760mmHg
• PKA: 9.09±0.50(Predicted)
• Flash Point: °C
• PSA: 139.28000
• Density: 1.277g/cm³
• LogP: -0.33700
• Storage Temp.: 2-8°C
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 344.16958450
• Heavy Atom Count: 24
• Complexity: 454

Purity/Quality:

98%,99%, ^*data from raw suppliers

RHODOTORULIC ACID 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Other Biomolecules
• Canonical SMILES: CC(=O)N(CCCC1C(=O)NC(C(=O)N1)CCCN(C(=O)C)O)O
• Isomeric SMILES: CC(=O)N(CCC[C@H]1C(=O)N[C@H](C(=O)N1)CCCN(C(=O)C)O)O

Technology Process of Rhodotorulic acid

There total 34 articles about Rhodotorulic acid 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: 80.0%

N,N’-{[(2S,5S)-3,6-dioxopiperazine-2,5-diyl]bis(propane-3,1-diyl)}bis[N-(benzyloxy)acetamide] (38532-33-1) → N,N’-{[(2S,5S)-3,6-dioxopiperazine-2,5-diyl]bis(propane-3,1-diyl)}bis(N-hydroxyacetamide) (18928-00-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.3987/COM-14-S(K)67

Reference yield: 79.0%

N-hydroxy-N-(3-((2S,5S)-5-(3-(hydroxyamino)propyl)-3,6-dioxopiperazin-2-yl)propyl)acetamide + acetyl chloride (75-36-5) → N,N’-{[(2S,5S)-3,6-dioxopiperazine-2,5-diyl]bis(propane-3,1-diyl)}bis(N-hydroxyacetamide) (18928-00-2)

Guidance literature:

N-hydroxy-N-(3-((2S,5S)-5-(3-(hydroxyamino)propyl)-3,6-dioxopiperazin-2-yl)propyl)acetamide; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

acetyl chloride; With sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 1h;

DOI:10.1248/cpb.c15-00200

Reference yield:

→ rhodotorulic acid (18928-00-2,39108-08-2)

Guidance literature:

10, methanol. NH3;

DOI:10.1002/hlca.19740570703

upstream raw materials:

N,N’-{[(2S,5S)-3,6-dioxopiperazine-2,5-diyl]bis(propane-3,1-diyl)}bis[N-(benzyloxy)acetamide]

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

(S)-5-(Acetyl-benzyloxy-amino)-2-amino-pentanoic acid methyl ester

(S)-5-Benzyloxyamino-2-tert-butoxycarbonylamino-pentanoic acid tert-butyl ester

Refernces

• 1、 Nakao, Michiyasu,Fukayama, Shintaro,Kitaike, Syuji,Sano, Shigeki. "Synthesis of rhodotorulic acid and its 1,4-dimethylated derivative". . p. 1309 - 1316. Retrieved 2015/03/04.