Orotic acid

Base Information

• Chemical Name: Orotic acid
• CAS No.: 65-86-1
• Deprecated CAS: 6784-70-9,58915-47-2,58915-47-2
• Molecular Formula: C5H4N2O4
• Molecular Weight: 156.098
• Hs Code.: 29335990
• European Community (EC) Number: 500-150-1,200-619-8
• NSC Number: 758903,9791
• UNII: 61H4T033E5
• DSSTox Substance ID: DTXSID0025814
• Nikkaji Number: J2.359K
• Wikipedia: Orotic acid
• Wikidata: Q425536
• NCI Thesaurus Code: C81628
• Metabolomics Workbench ID: 37146
• ChEMBL ID: CHEMBL1235017
• Mol file: 65-86-1.mol

Synonyms:Acid, Orotic;Orotate, Potassium;Orotate, Sodium;Orotate, Zinc;Orotic Acid;Potassium Orotate;Sodium Orotate;Zinc Orotate

Chemical Property of Orotic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 345-346 °C
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 656.9 °C at 760 mmHg
• PKA: pK1:1.8(+1);pK2:9.55(0) (25°C)
• Flash Point: 351.1 °C
• PSA: 103.02000
• Density: 1.642 g/cm³
• LogP: -1.23860
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Slightly soluble
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 156.01710661
• Heavy Atom Count: 11
• Complexity: 268

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39-22-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Polyoxyethylenes
• Canonical SMILES: C1=C(NC(=O)NC1=O)C(=O)O
• Uses: Orotic acid is an intermediate in de novo pyrimidine biosynthesis that may be used to study the specificity and kinetics of orotate phosphoribosyltransferase (OPRT) which catalyzes the reversible phosphoribosyl transfer from 5?-phospho-α-d-ribose 1?-diphosphate (PRPP) to orotic acid (OA), forming pyrophosphate and orotidine 5?-monophosphate (OMP). It is used as a starting material for the potential commercial bioproduction of uridine 5?-monophosphate (UMP) by microbes such as Corynebacterium ammoniagenes (ATCC 6872) or Saccharomyces cerevisiae. It may be used to study the AMPK/SREBP-1 dependent cell signaling pathway and transcription regulation mechanisms that induce hepatic lipogenesis. hepatoprotectant, uricosuric agent An intermediate in de novo pyrimidine biosynthesis.

Technology Process of Orotic acid

There total 33 articles about Orotic 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: 92.0%

6-Methyluracil (626-48-2) → orotic acid (65-86-1,58915-47-2,6784-70-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); oxygen; cobalt(II) acetate; acetic acid; at 80 ℃; for 15h;

Reference yield: 91.9%

2,4-imidazolidinedione (461-72-3) + Glyoxilic acid (298-12-4) → orotic acid (65-86-1,58915-47-2,6784-70-9)

Guidance literature:

With sodium hydroxide; In water; at 115 - 120 ℃; for 2h; Temperature; Large scale;

Reference yield: 85.0%

C5H6N2O4 (15059-25-3) → orotic acid (65-86-1,58915-47-2,6784-70-9)

Guidance literature:

With oxygen; palladium dichloride; In N,N-dimethyl-formamide; at 80 ℃; for 36h; under 760.051 Torr; Reagent/catalyst; Solvent; Pressure; Temperature;

upstream raw materials:

6-Methyluracil

orotoaldehyde

6-oxo-2-thioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbaldehyde

2-thioorotic acid

Downstream raw materials:

methyl orotate

furo<3,4-d>pyrimidine-2,4,7(1H,3H,5H)-trione

ethyl orotate

1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid

Refernces

• 1、 -. "Synthetic method of orotic acid". Paragraph 0062-0071. . Retrieved 2020/08/22.
• 2、 Cao, Liangxian,Weetall, Marla,Trotta, Christopher,Cintron, Katherine,Ma, Jiyuan,Kim, Min Jung,Furia, Bansri,Romfo, Charles,Graci, Jason D.,Li, Wencheng,Du, Joshua,Sheedy, Josephine,Hedrick, Jean,Risher, Nicole,Yeh, Shirley,Qi, Hongyan,Arasu, Tamil,Hwang, Seongwoo,Lennox, William,Kong, Ronald,Petruska, Janet,Moon, Young-Choon,Babiak, John,Davis, Thomas W.,Jacobson, Allan,Almstead, Neil G.,Branstrom, Art,Colacino, Joseph M.,Peltz, Stuart W.. "Targeting of hematologic malignancies with PTC299, a novel potent inhibitor of dihydroorotate dehydrogenase with favorable pharmaceutical properties". . p. 3 - 16. Retrieved 2019/01/26.