Uracil
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Hodoodo CAT#: H106612

CAS#: 66-22-8

Description: Uracil is one of the four nucleobases in the nucleic acid of RNA that are represented by the letters A, G, C and U. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine. Uracil is a demethylated form of thymine. Uracil's use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as allosteric regulator and coenzyme for reactions in the human body and in plants. Uracil can be used to determine microbial contamination of tomatoes.


Chemical Structure

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Uracil
CAS# 66-22-8

Theoretical Analysis

Hodoodo Cat#: H106612
Name: Uracil
CAS#: 66-22-8
Chemical Formula: C4H4N2O2
Exact Mass: 112.03
Molecular Weight: 112.088
Elemental Analysis: C, 42.86; H, 3.60; N, 24.99; O, 28.55

Price and Availability

Size Price Availability Quantity
5kg USD -1
1g USD 65
2g USD 95
5g USD 150
10g USD 190
20g USD 250
50g USD 290
100g USD 350
200g USD 550
500g USD 750
1kg USD 1250
2kg USD 2150
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Synonym: Uracil; 2,4-Dioxopyrimidine; 2,4-Pyrimidinedione; Pirod; Pyrod.

IUPAC/Chemical Name: Pyrimidine-2,4(1H,3H)-dione

InChi Key: ISAKRJDGNUQOIC-UHFFFAOYSA-N

InChi Code: InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)

SMILES Code: O=C1NC(C=CN1)=O

Appearance: White to light yellow crystalline solid

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 112.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Pałasz A, Cież D. In search of uracil derivatives as bioactive agents. Uracils and fused uracils: Synthesis, biological activity and applications. Eur J Med Chem. 2015 Jun 5;97:582-611. doi: 10.1016/j.ejmech.2014.10.008. Epub 2014 Oct 5. Review. PubMed PMID: 25306174.

2: van Staveren MC, Opdam F, Guchelaar HJ, van Kuilenburg AB, Maring JG, Gelderblom H. Influence of metastatic disease on the usefulness of uracil pharmacokinetics as a screening tool for DPD activity in colorectal cancer patients. Cancer Chemother Pharmacol. 2015 Jul;76(1):47-52. doi: 10.1007/s00280-015-2746-3. Epub 2015 May 10. PubMed PMID: 25957957.

3: Sakakibara N, Baba M, Okamoto M, Toyama M, Demizu Y, Misawa T, Kurihara M, Irie K, Kato Y, Maruyama T. Design, synthesis, and anti-HIV-1 activity of 1-aromatic methyl-substituted 3-(3,5-dimethylbenzyl)uracil and N-3,5-dimethylbenzyl-substituted urea derivatives. Antivir Chem Chemother. 2015 Feb;24(1):3-18. doi: 10.1177/2040206614566584. PubMed PMID: 26149262.

4: Galvão TL, Rocha IM, da Silva MD, da Silva MA. Is uracil aromatic? The enthalpies of hydrogenation in the gaseous and crystalline phases, and in aqueous solution, as tools to obtain an answer. J Phys Chem A. 2013 Jul 18;117(28):5826-36. doi: 10.1021/jp404938u. Epub 2013 Jul 9. PubMed PMID: 23796002.

5: Kossoski F, Bettega MH, Varella MT. Shape resonance spectra of uracil, 5-fluorouracil, and 5-chlorouracil. J Chem Phys. 2014 Jan 14;140(2):024317. doi: 10.1063/1.4861589. PubMed PMID: 24437887.

6: Horváth A, Békési A, Muha V, Erdélyi M, Vértessy BG. Expanding the DNA alphabet in the fruit fly: uracil enrichment in genomic DNA. Fly (Austin). 2013 Jan-Mar;7(1):23-7. doi: 10.4161/fly.23192. Epub 2012 Dec 13. PubMed PMID: 23238493; PubMed Central PMCID: PMC3660747.

7: Sun S, Brown A. Simulation of the resonance Raman spectra for 5-halogenated (F, Cl, and Br) uracils. J Phys Chem A. 2015 Apr 30;119(17):3961-71. doi: 10.1021/acs.jpca.5b01052. Epub 2015 Apr 21. PubMed PMID: 25856119.

8: Liang Y, Pitteloud JP, Wnuk SF. Hydrogermylation of 5-ethynyluracil nucleosides: formation of 5-(2-germylvinyl)uracil and 5-(2-germylacetyl)uracil nucleosides. J Org Chem. 2013 Jun 7;78(11):5761-7. doi: 10.1021/jo400590z. Epub 2013 May 13. PubMed PMID: 23631719; PubMed Central PMCID: PMC3703441.

9: Büchel B, Rhyn P, Schürch S, Bühr C, Amstutz U, Largiadèr CR. LC-MS/MS method for simultaneous analysis of uracil, 5,6-dihydrouracil, 5-fluorouracil and 5-fluoro-5,6-dihydrouracil in human plasma for therapeutic drug monitoring and toxicity prediction in cancer patients. Biomed Chromatogr. 2013 Jan;27(1):7-16. doi: 10.1002/bmc.2741. Epub 2012 Mar 27. PubMed PMID: 22454320.

10: van Staveren MC, van Kuilenburg AB, Guchelaar HJ, Meijer J, Punt CJ, de Jong RS, Gelderblom H, Maring JG. Evaluation of an oral uracil loading test to identify DPD-deficient patients using a limited sampling strategy. Br J Clin Pharmacol. 2016 Mar;81(3):553-61. doi: 10.1111/bcp.12821. Epub 2016 Jan 8. PubMed PMID: 26551538; PubMed Central PMCID: PMC4767209.

11: Koyama T, Funato Y, Yamaguchi Y, Oda M, Ito K. [Results of a Special Drug Use-Results Survey on Compliance to Tegafur/Uracil(UFT)Adjuvant Chemotherapy for Non-Small Cell Lung Cancer]. Gan To Kagaku Ryoho. 2015 Aug;42(8):973-80. Japanese. PubMed PMID: 26321712.

12: Muha V, Horváth A, Békési A, Pukáncsik M, Hodoscsek B, Merényi G, Róna G, Batki J, Kiss I, Jankovics F, Vilmos P, Erdélyi M, Vértessy BG. Uracil-containing DNA in Drosophila: stability, stage-specific accumulation, and developmental involvement. PLoS Genet. 2012;8(6):e1002738. doi: 10.1371/journal.pgen.1002738. Epub 2012 Jun 7. PubMed PMID: 22685418; PubMed Central PMCID: PMC3369950.

13: Ito Y, Masaki Y, Kanamori T, Ohkubo A, Seio K, Sekine M. Synthesis of 5-[3-(2-aminopyrimidin-4-yl)aminopropyn-1-yl]uracil derivative that recognizes Ade-Thy base pairs in double-stranded DNA. Bioorg Med Chem Lett. 2016 Jan 1;26(1):194-6. doi: 10.1016/j.bmcl.2015.11.003. Epub 2015 Nov 2. PubMed PMID: 26602276.

14: Geisman AN, Valuev-Elliston VT, Ozerov AA, Khandazhinskaya AL, Chizhov AO, Kochetkov SN, Pannecouque C, Naesens L, Seley-Radtke KL, Novikov MS. 1,6-Bis[(benzyloxy)methyl]uracil derivatives-Novel antivirals with activity against HIV-1 and influenza H1N1 virus. Bioorg Med Chem. 2016 Jun 1;24(11):2476-85. doi: 10.1016/j.bmc.2016.04.010. Epub 2016 Apr 5. PubMed PMID: 27112451.

15: Seiler VK, Hützler WM, Bolte M. Eight new crystal structures of 5-(hydroxymethyl)uracil, 5-carboxyuracil and 5-carboxy-2-thiouracil: insights into the hydrogen-bonded networks and the predominant conformations of the C5-bound residues. Acta Crystallogr C Struct Chem. 2016 May 1;72(Pt 5):379-88. doi: 10.1107/S2053229616004861. Epub 2016 Apr 6. PubMed PMID: 27146565.

16: Sakakibara N, Hamasaki T, Baba M, Demizu Y, Kurihara M, Irie K, Iwai M, Asada E, Kato Y, Maruyama T. Synthesis and evaluation of novel 3-(3,5-dimethylbenzyl)uracil analogs as potential anti-HIV-1 agents. Bioorg Med Chem. 2013 Sep 15;21(18):5900-6. doi: 10.1016/j.bmc.2013.06.061. Epub 2013 Jul 3. PubMed PMID: 23916148.

17: Francois E, Smith D, Dahan L, Michel C, Perrier H, Mari V, Seitz JF, Follana P, Evesque L, Chamorey E. Uracil-tegafur/leucovorin and mitomycin C salvage therapy in patients with advanced colorectal cancer: a phase II study. J Chemother. 2012 Aug;24(4):207-11. doi: 10.1179/1973947812Y.0000000021. PubMed PMID: 23040684.

18: Miyakoshi H, Miyahara S, Yokogawa T, Chong KT, Taguchi J, Endoh K, Yano W, Wakasa T, Ueno H, Takao Y, Nomura M, Shuto S, Nagasawa H, Fukuoka M. Synthesis and discovery of N-carbonylpyrrolidine- or N-sulfonylpyrrolidine-containing uracil derivatives as potent human deoxyuridine triphosphatase inhibitors. J Med Chem. 2012 Apr 12;55(7):2960-9. doi: 10.1021/jm201627n. Epub 2012 Mar 26. PubMed PMID: 22404301.

19: Matyugina E, Khandazhinskaya A, Chernousova L, Andreevskaya S, Smirnova T, Chizhov A, Karpenko I, Kochetkov S, Alexandrova L. The synthesis and antituberculosis activity of 5'-nor carbocyclic uracil derivatives. Bioorg Med Chem. 2012 Nov 15;20(22):6680-6. doi: 10.1016/j.bmc.2012.09.019. Epub 2012 Sep 19. PubMed PMID: 23062712.

20: Accetta A, Corradini R, Sforza S, Tedeschi T, Brognara E, Borgatti M, Gambari R, Marchelli R. New uracil dimers showing erythroid differentiation inducing activities. J Med Chem. 2009 Jan 8;52(1):87-94. doi: 10.1021/jm800982q. PubMed PMID: 19072686.