Orotidine

Base Information

• Chemical Name: Orotidine
• CAS No.: 314-50-1
• Molecular Formula: C10H12 N2 O8
• Molecular Weight: 288.214
• Hs Code.: 29349990
• UNII: B350MC02GZ
• DSSTox Substance ID: DTXSID90953435
• Nikkaji Number: J10.652F
• Wikipedia: Orotidine
• Wikidata: Q10859719
• Metabolomics Workbench ID: 37427
• Mol file: 314-50-1.mol

Synonyms:3-ribofuranosylorotic acid;6-carboxyuridine;orotidine;orotidine, ammonium salt

Chemical Property of Orotidine

Chemical Property:

• Melting Point: 200ºC
• Boiling Point: °Cat760mmHg
• PKA: 2.62±0.20(Predicted)
• Flash Point: °C
• PSA: 162.08000
• Density: 1.847 g/cm³
• LogP: -3.15370
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 288.05936535
• Heavy Atom Count: 20
• Complexity: 490

Purity/Quality:

99%, ^*data from raw suppliers

Orotidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(N(C(=O)NC1=O)C2C(C(C(O2)CO)O)O)C(=O)O
• Isomeric SMILES: C1=C(N(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)O
• Uses: Orotidine is a metabolite of Orotic Acid (O691500); a compound used in the preparation of therapeutic agents for chronic obstructive pulmonary disease (COPD) treatment.

Technology Process of Orotidine

There total 11 articles about Orotidine 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: 100.0%

6-methoxycarbonyl uridine (55878-70-1) → (1-β-D-erythrofuranosyl)orotic acid (314-50-1)

Guidance literature:

6-methoxycarbonyl uridine; With water; sodium hydroxide; In acetonitrile; at 0 - 20 ℃;

In acetonitrile; pH=3; Acidic conditions;

DOI:10.1039/c5cc00111k

Reference yield:

orotic acid (65-86-1,58915-47-2,6784-70-9) → (1-β-D-erythrofuranosyl)orotic acid (314-50-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 16 h / 20 °C

1.2: 20 °C

2.1: bis-(trimethylsilyl)acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 49 h / 20 - 50 °C

3.1: indium(III) triflate / water; acetonitrile / 0.5 h / 120 °C / Microwave irradiation

3.2: 20 °C

4.1: sodium hydroxide; water / acetonitrile / 0 - 20 °C

4.2: IR-120 / pH 3 / Acidic conditions

With indium(III) triflate; trimethylsilyl trifluoromethanesulfonate; water; bis-(trimethylsilyl)acetamide; 1,1'-carbonyldiimidazole; sodium hydroxide; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c5cc00111k

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → (1-β-D-erythrofuranosyl)orotic acid (314-50-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,1'-carbonyldiimidazole; pyridine hydrochloride / N,N-dimethyl-formamide / 20 °C

2.1: bis-(trimethylsilyl)acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 21 h / 20 - 50 °C

3.1: indium(III) triflate / water; acetonitrile / 0.5 h / 120 °C / Microwave irradiation

3.2: 20 °C

4.1: sodium hydroxide; water / acetonitrile / 0 - 20 °C

4.2: IR-120 / pH 3 / Acidic conditions

With indium(III) triflate; trimethylsilyl trifluoromethanesulfonate; water; pyridine hydrochloride; bis-(trimethylsilyl)acetamide; 1,1'-carbonyldiimidazole; sodium hydroxide; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c5cc00111k

upstream raw materials:

orotic acid

2,3-O-isopropylidene-D-ribofuranose

2',3'-O-isopropylideneorotidine methyl ester

6-methoxycarbonyl uridine

Downstream raw materials:

uridine

ribavirin

Refernces

• 1、 Holy. "Preparation of orotidine, 2' deoxyorotidine, and related compounds". . p. 738 - 752. Retrieved 2007/10/09.