Shopping on line can be easy, simple and save you lots of money. It can also take a lot of your time, frustrate you, and result in unwanted purchases. Now the same can be said for regular high street shopping, but with the vast opportunity presented by the Internet it will pay you to spend a few minutes reading this and understanding how to better optimize your Uracil shopping experience:
1. Compare - without doubt the biggest advantage that the Uracil offers shoppers today is the ability to compare thousands of Uracil at a time. This is a great thing, but not necessarily all the time! Too much can be daunting at times so take advantage of the great comparison sites and where possible let them do the hard work for you.
2. Research - if it has been said it will be on the internet. Ignorance is no longer a justifiable reason for buying the wrong thing. Take the time to research in detail everything that you could possible want to know about
3. Testimonials - don't know anybody that has bought a Uracil? Wrong! If the Uracil is good the internet will let you know. Use the Internet as a friend and get testimonials before you buy.
4. Questions - Got a question about Uracil then search the Forums, FAQ's, Blogs etc. Don't be afraid to ask .....
5. Reputation - Never heard of the company selling Uracil? Don't worry, no reason why you should know every company in the world, but you know someone that does! Use the internet to find out what people are saying about Uracil and build up a picture of their reputation for sales, returns, customer service, delivery etc.
6. Returns - still worried that even after all of the above your Uracil wont be what you want? Check out the returns policy. There is so much competition now that someone, somewhere is bound to offer the terms that you are comfortable with.
7. Feedback - happy with your Uracil then let people know, after all you are depending on others people input in your buying decision, so why not give a little back.
8. Security - check for the yellow padlock on the Uracil site before you buy, and the s after http:/ /i.e. https:// = a secure site
9. Contact - got a question about Uracil, or want to leave a comment then check out the sites contact page. Reputable companies have them and respond.
10. Payment - ready to pay for your Uracil, then use your credit card or PayPal! Be aware of companies that don't accept them, there may be genuine reasons but given the huge amount of choice you have when buying online there is no reason at all not to buy via credit card or PayPal.
{{Chembox new| Name = Uracil| ImageFile = Uracil_chemical_structure.png| IUPACName = Pyrimidine-2,4(1
H,3
H)-dione| OtherNames = Uracil, 2-oxy-4-oxy pyrimidine,2,4(1H,3H)-pyrimidinedione,2,4-dihydroxypryimidine,
2,4-pyrimidinediol| Section1 = {{Chembox Identifiers| SMILES = O=C1NC=CC(=O)N1| CASNo = 66-22-8| RTECS = YQ8650000 -->
| Section2 = {{Chembox Properties| Formula = C4H4N2O2| MolarMass = 112.08676 g/mol| Appearance = Solid| Density =| Solubility = Soluble| MeltingPt = 335 °C| BoilingPt = N/A -->
| Section7 = {{Chembox Hazards| MainHazards = carcinogen & teratogen with chronic exposure| NFPA-H = 1| NFPA-F = 1| NFPA-R =| FlashPt = non flammable -->
| Section8 = {{Chembox Related| OtherCpds = Thymine -->
-->
Uracil is a pyrimidine which is common and naturally occurring.Garrett, Reginald H.; Grisham, Charles M. Principals of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. Uracil was originally discovered in 1900. It was isolated by
hydrolysis of
yeast nuclein that was found in bovine
thymus and spleen,
herring sperm, and
wheat germ.Brown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994. Uracil is a planar, unsaturated compound that has the ability to absorb lightHorton, Robert H.;
et al.Principles of Biochemistry. 3rd ed. Upper Saddle River, NJ: Prentice Hall, 2002.
Properties
Found in RNA, it
base pairs with adenine and is replaced by thymine in DNA. Methylation of uracil produces
thymine.www.madsci.org It turns into thymine to protect the DNA and to improve the efficiency of DNA replication. Uracil can base pair with any of the bases depending on how the molecule arranges itself on the
helix, but readily pairs with
adenine because the methyl group is repelled into a fixed position.www.madsci.org As stated, uracil pairs with adenosine through
hydrogen bonding. Uracil is the
hydrogen bond acceptor and can form two hydrogen bonds. Uracil can also bind with a ribose sugar to form a ribonucleoside, uridine. When a
phosphate attaches to uridine, uridine 5'-monophosphate is produced.Horton, Robert H.;
et al.Principles of Biochemistry. 3rd ed. Upper Saddle River, NJ: Prentice Hall, 2002.
Uracil, U, undergoes amide-iminol tautomeric shifts because of its resonance structures resulting from the N and O substitutents. Also because any nuclear instability the molecule may have from the lack of formal
aromaticity is compensated by the cyclic-amidic stability.Brown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994. The keto tautomer is referred to the lactam structure, while the enol tautomer is referred to as the
lactim structure. These tautomeric forms are predominant at
pH=7. The lactam structure is the most common form of uracil.
Uracil also recycles itself to form nucleotides by undergoing a series of phosphoribosyltransferase reactions.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. Degradation of uracil produces substrates,
aspartate,
carbon dioxide, and ammonia.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997.
C4H4N2O2 → H3NCH2CH2COO- + NH4 + CO2
Oxidative degradation of uracil produces urea and maleic acid in the presence of
hydrogen peroxide and
Fe2+ or in the presence of diatomic oxygen and Fe2+.
Uracil is a weak acid, the first site of
ionization of uracil is not known.Zorbach, W.W. Synthetic Procedures in Nucleic Acid Chemistry: Physical and Physicochemical Aids in Determination of Structure. Vol 2. New York: Wiley-Interscience, 1973. The negative charge is placed on the oxygen anion and produces a pka of less than or equal to 12. The basic pKa = -3.4, while the acidic pKa = 9.389. In the gas phase, uracil has 4 sites that are more acidic than water.Lee, J.K.; Kurinovich, Ma.
J Am Soc Mass Spectrom.13'(8), 2005, 985-95.
Synthesis
There are many laboratory
synthesis of uracil available. The first reaction is the simplest of the syntheses, by adding water to cytosine to produce uracil and
ammonia.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. The most common way to synthesize uracil is by the condensation of maleic acid with urea in fuming sulfuric acidBrown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994. as seen below also. Uracil can also be synthesized by a double decomposition of
thiouracil in aqueous
chloroacetic acid.Brown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994.
C4H5N3O + H2O → C4H4N2O2 + NH3
C4H4O4 + CH4N2O → C4H4N2O2 + 2 H2O + CO
Photodehydrogenation of 5,6-diuracil, which is synthesized by beta-alanine reacting with
urea, produces uracil.Chittenden, G.J.F.; Schwartz, Alan W.
Nature.263,'(5575), 350-1.
Reactions
Uracil readily undergoes regular reactions including oxidation,
nitration, and alkylation. While in the presence of
phenol/
Sodium hypochlorite, uracil can be visualized in the blue region of
UV light.Brown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994. Uracil also has the capability to react with elemental halogens because of the presence of more than one strongly electron donating group.Brown, D.J. Heterocyclic COmpounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994.
Uracil readily undergoes addition to
ribose sugars and
phosphates to partake in synthesis and further reactions in the body. Uracil becomes
Uridine-monophosphate, uridine-diphosphate,
uridine-triphosphate, and
Uridine diphosphate glucose. Each one of these molecules in synthesized in the body and has specific functions.
When uracil reactes with anhydrous hydrazine a first order kinetic reaction occurs and the ring of uracil opens up.Kochetkov, N.K. and Budovskii, E.I. Organic Chemistry of Nucleic Acids Part B. New York: Plenum Press, 1972. If the pH of the reaction increases to >10.5 the uracil anion forms making the reaction go much slower, the same slowing of the reaction occurs if the pH decreases because of the protonation of the hydrazine.Kochetkov, N.K. and Budovskii, E.I. Organic Chemistry of Nucleic Acids Part B. New York: Plenum Press, 1972. The reactivity of uracil is unchanged even if the temperature changes.Kochetkov, N.K. and Budovskii, E.I. Organic Chemistry of Nucleic Acids Part B. New York: Plenum Press, 1972.
Uses
Uracil can be used for drug delivery and as a pharmaceutical. When elemental fluorine is reacted with uracil,
5-fluorouracil is produced. 5-Fluorouracil is an anticancer drug (antimetabolite) used to masquerade as uracil during the nucleic acid replication process.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. The drug molecule also fools the enzymes that help in this process to incorporate this compound in the replication and not uracil, this causes the biological polymer (cancer) not to continue synthesizing.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997.
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.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. Uracil serves as
allosteric regulator and coenzyme for reactions in the human body and in plants.Brown, E.G. Ring Nitrogen and Key Biomolecules: The Biochemistry of N-Heterocycles. Boston: Lluwer Academic Publishers, 1998. UMP controls the activity of carbamoyl phosphate synthetase and aspartate transcarbamoylase in plants, while UDP and UTP requlate CPSase II activity in
animals. UDP-glucose regulates the conversion of glucose to galactose in the liver and other tissues in the process of carbohydrate metabolism.Brown, E.G. Ring Nitrogen and Key Biomolecules: The Biochemistry of N-Heterocycles. Boston: Lluwer Academic Publishers, 1998. Uracil is also involved in the biosynthesis of
polysaccharides and the transportation of sugars containing aldehydes.Brown, E.G. Ring Nitrogen and Key Biomolecules: The Biochemistry of N-Heterocycles. Boston: Lluwer Academic Publishers, 1998.
It can also increase the risk for cancer in cases where the body is extremely deficient in folate.Mashiyama, S.T;
et al.Anal Biochem. '330'(1),2004, 58-69. The deficiency in folate leads to increased ratio of deoxyuracilmonophosphates (dUMP)/deoxythyminemonophosphates (dTMP) and uracil misincorporation into DNA and eventually low production of DNA.Mashiyama, S.T;
et al.Anal Biochem. '330'(1),2004, 58-69.
Uracil can be used to determine microbial contamination of
tomatoes. Only after
lactic acid bacteria have contaminated the fruit, uracil appears.Hildalgo, A;
et al.J Agric Food Chem.'53'(2),2005, 349-55. Uracil's derivatives, that contain a
diazine ring, are used in pesticides.Pozharskii, A.F.;
et al.Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry and Biochemistry and the Role of Heterocycles in Science, Technology, Medicine, and Agriculture. New York: John Wiley and Sons, 1997. More often used as
antiphotosynthesis herbicides and destroy weeds in
cotton, sugar beet,
turnips, soybean,
peas,
sunflower crops,
vineyards, berry plantations, and
orchards.Pozharskii, A.F.;
et al.Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry and Biochemistry and the Role of Heterocycles in Science, Technology, Medicine, and Agriculture. New York: John Wiley and Sons, 1997.
References
{{Chembox new| Name = Uracil| ImageFile = Uracil_chemical_structure.png| IUPACName = Pyrimidine-2,4(1
H,3
H)-dione| OtherNames = Uracil, 2-oxy-4-oxy pyrimidine,2,4(1H,3H)-pyrimidinedione,2,4-dihydroxypryimidine,
2,4-pyrimidinediol| Section1 = {{Chembox Identifiers| SMILES = O=C1NC=CC(=O)N1| CASNo = 66-22-8| RTECS = YQ8650000 -->
| Section2 = {{Chembox Properties| Formula = C4H4N2O2| MolarMass = 112.08676 g/mol| Appearance = Solid| Density =| Solubility = Soluble| MeltingPt = 335 °C| BoilingPt = N/A -->
| Section7 = {{Chembox Hazards| MainHazards = carcinogen & teratogen with chronic exposure| NFPA-H = 1| NFPA-F = 1| NFPA-R =| FlashPt = non flammable -->
| Section8 = {{Chembox Related| OtherCpds = Thymine -->
-->
Uracil is a pyrimidine which is common and naturally occurring.Garrett, Reginald H.; Grisham, Charles M. Principals of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. Uracil was originally discovered in 1900. It was isolated by hydrolysis of yeast
nuclein that was found in
bovine thymus and
spleen, herring
sperm, and wheat
germ.Brown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994. Uracil is a planar, unsaturated compound that has the ability to absorb lightHorton, Robert H.;
et al.Principles of Biochemistry. 3rd ed. Upper Saddle River, NJ: Prentice Hall, 2002.
Properties
Found in
RNA, it base pairs with adenine and is replaced by
thymine in
DNA. Methylation of uracil produces thymine.www.madsci.org It turns into thymine to protect the DNA and to improve the efficiency of
DNA replication. Uracil can base pair with any of the bases depending on how the molecule arranges itself on the helix, but readily pairs with adenine because the methyl group is repelled into a fixed position.www.madsci.org As stated, uracil pairs with adenosine through
hydrogen bonding. Uracil is the hydrogen bond acceptor and can form two hydrogen bonds. Uracil can also bind with a ribose sugar to form a ribonucleoside,
uridine. When a phosphate attaches to uridine, uridine 5'-monophosphate is produced.Horton, Robert H.;
et al.Principles of Biochemistry. 3rd ed. Upper Saddle River, NJ: Prentice Hall, 2002.
Uracil, U, undergoes amide-iminol tautomeric shifts because of its resonance structures resulting from the N and O substitutents. Also because any nuclear instability the molecule may have from the lack of formal
aromaticity is compensated by the cyclic-amidic stability.Brown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994. The keto tautomer is referred to the lactam structure, while the enol tautomer is referred to as the
lactim structure. These tautomeric forms are predominant at
pH=7. The lactam structure is the most common form of uracil.
Uracil also recycles itself to form nucleotides by undergoing a series of
phosphoribosyltransferase reactions.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. Degradation of uracil produces substrates, aspartate,
carbon dioxide, and ammonia.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997.
C4H4N2O2 → H3NCH2CH2COO- + NH4 + CO2
Oxidative degradation of uracil produces urea and maleic acid in the presence of hydrogen peroxide and
Fe2+ or in the presence of diatomic oxygen and Fe2+.
Uracil is a weak acid, the first site of ionization of uracil is not known.Zorbach, W.W. Synthetic Procedures in Nucleic Acid Chemistry: Physical and Physicochemical Aids in Determination of Structure. Vol 2. New York: Wiley-Interscience, 1973. The negative charge is placed on the oxygen anion and produces a pka of less than or equal to 12. The basic pKa = -3.4, while the acidic pKa = 9.389. In the gas phase, uracil has 4 sites that are more acidic than water.Lee, J.K.; Kurinovich, Ma.
J Am Soc Mass Spectrom.13'(8), 2005, 985-95.
Synthesis
There are many laboratory synthesis of uracil available. The first reaction is the simplest of the syntheses, by adding water to cytosine to produce uracil and
ammonia.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. The most common way to synthesize uracil is by the
condensation of maleic acid with urea in
fuming sulfuric acidBrown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994. as seen below also. Uracil can also be synthesized by a double decomposition of thiouracil in aqueous
chloroacetic acid.Brown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994.
C4H5N3O + H2O → C4H4N2O2 + NH3
C4H4O4 + CH4N2O → C4H4N2O2 + 2 H2O + CO
Photodehydrogenation of 5,6-diuracil, which is synthesized by beta-alanine reacting with urea, produces uracil.Chittenden, G.J.F.; Schwartz, Alan W.
Nature.263,'(5575), 350-1.
Reactions
Uracil readily undergoes regular reactions including
oxidation,
nitration, and
alkylation. While in the presence of phenol/
Sodium hypochlorite, uracil can be visualized in the blue region of
UV light.Brown, D.J. Heterocyclic Compounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994. Uracil also has the capability to react with elemental halogens because of the presence of more than one strongly electron donating group.Brown, D.J. Heterocyclic COmpounds: Thy Pyrimidines. Vol 52. New York: Interscience, 1994.
Uracil readily undergoes addition to ribose
sugars and phosphates to partake in synthesis and further reactions in the body. Uracil becomes Uridine-monophosphate,
uridine-diphosphate,
uridine-triphosphate, and Uridine diphosphate glucose. Each one of these molecules in synthesized in the body and has specific functions.
When uracil reactes with anhydrous hydrazine a first order kinetic reaction occurs and the ring of uracil opens up.Kochetkov, N.K. and Budovskii, E.I. Organic Chemistry of Nucleic Acids Part B. New York: Plenum Press, 1972. If the pH of the reaction increases to >10.5 the uracil anion forms making the reaction go much slower, the same slowing of the reaction occurs if the pH decreases because of the protonation of the hydrazine.Kochetkov, N.K. and Budovskii, E.I. Organic Chemistry of Nucleic Acids Part B. New York: Plenum Press, 1972. The reactivity of uracil is unchanged even if the temperature changes.Kochetkov, N.K. and Budovskii, E.I. Organic Chemistry of Nucleic Acids Part B. New York: Plenum Press, 1972.
Uses
Uracil can be used for drug delivery and as a pharmaceutical. When elemental fluorine is reacted with uracil,
5-fluorouracil is produced. 5-Fluorouracil is an anticancer drug (antimetabolite) used to
masquerade as uracil during the nucleic acid replication process.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. The drug molecule also fools the enzymes that help in this process to incorporate this compound in the replication and not uracil, this causes the biological polymer (cancer) not to continue synthesizing.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997.
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.Garrett, Reginald H.; Grisham, Charles M. Principles of Biochemistry with a Human Focus. United States: Brooks/Cole Thomson Learning, 1997. Uracil serves as allosteric regulator and coenzyme for reactions in the human body and in plants.Brown, E.G. Ring Nitrogen and Key Biomolecules: The Biochemistry of N-Heterocycles. Boston: Lluwer Academic Publishers, 1998. UMP controls the activity of carbamoyl phosphate synthetase and aspartate transcarbamoylase in plants, while UDP and UTP requlate
CPSase II activity in animals. UDP-glucose regulates the conversion of glucose to
galactose in the
liver and other tissues in the process of
carbohydrate metabolism.Brown, E.G. Ring Nitrogen and Key Biomolecules: The Biochemistry of N-Heterocycles. Boston: Lluwer Academic Publishers, 1998. Uracil is also involved in the biosynthesis of polysaccharides and the transportation of sugars containing aldehydes.Brown, E.G. Ring Nitrogen and Key Biomolecules: The Biochemistry of N-Heterocycles. Boston: Lluwer Academic Publishers, 1998.
It can also increase the risk for cancer in cases where the body is extremely deficient in
folate.Mashiyama, S.T;
et al.Anal Biochem. '330'(1),2004, 58-69. The deficiency in folate leads to increased ratio of deoxyuracilmonophosphates (dUMP)/
deoxythyminemonophosphates (dTMP) and uracil misincorporation into DNA and eventually low production of DNA.Mashiyama, S.T;
et al.Anal Biochem. '330'(1),2004, 58-69.
Uracil can be used to determine microbial contamination of
tomatoes. Only after
lactic acid bacteria have contaminated the fruit, uracil appears.Hildalgo, A;
et al.J Agric Food Chem.'53'(2),2005, 349-55. Uracil's derivatives, that contain a
diazine ring, are used in pesticides.Pozharskii, A.F.;
et al.Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry and Biochemistry and the Role of Heterocycles in Science, Technology, Medicine, and Agriculture. New York: John Wiley and Sons, 1997. More often used as
antiphotosynthesis herbicides and destroy weeds in cotton, sugar beet, turnips, soybean,
peas,
sunflower crops,
vineyards,
berry plantations, and
orchards.Pozharskii, A.F.;
et al.Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry and Biochemistry and the Role of Heterocycles in Science, Technology, Medicine, and Agriculture. New York: John Wiley and Sons, 1997.
References
Uracil - Wikipedia, the free encyclopedia
Uracil is a pyrimidine which is common and naturally occurring. [1] Uracil was originally discovered in 1900. It was isolated by hydrolysis of yeast nuclein that was found in ...
Definition: uracil from Online Medical Dictionary
The Online Medical Dictionary is a searchable dictionary of definitions from medicine, science and technology.
Definition: uracil-DNA glycosidase from Online Medical Dictionary
The Online Medical Dictionary is a searchable dictionary of definitions from medicine, science and technology.
Colorectal cancer - capecitabine and tegafur uracil
The summary for the published technology appraisal on using capecitabine and tegafur uracil in the treatment of colorectal cancer. It links to the published guidance and key ...
TA61 Colorectal cancer - capecitabine and tegafur uracil: Guidance
This is the full guidance on the use of capecitabine and tegafur uracil for matastatic colorectal cancer
Tegafur-uracil (Uftoral®) : Cancerbackup
Tefafure-uracil (Uftoral®) is a chemotherapy drug that is given as a treatment for some types of cancer, especially bowel cancer. This section describes how it is given and some ...
uracil - Hutchinson encyclopedia article about uracil
21st letter of the English alphabet, and the 20th in the ancient Roman, in which it was identical with v. U has many different sounds, as in the pronunciation of the English words ...
uracil - definition of uracil by the Free Online Dictionary, Thesaurus ...
n. Abbr. U. A pyrimidine base, C 4 H 4 N 2 O 2, that is an essential constituent of RNA. [
genome.gov | Talking Glossary: "uracil"
Easy-to-use, talking glossary of genetic terms, produced by the National Human Genome Research Institute.
uracil - definition of uracil in the Medical dictionary - by the Free ...
uracil /ura·cil/ (ur´ah-sil) a pyrimidine base, in animal cells usually occurring condensed with ribose to form the ribonucleoside uridine; the corresponding deoxyribonucleoside ...
