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Uracil-6-carboxylic acid

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Identification
Molecular formula
C5H2N2O4
CAS number
617-86-7
IUPAC name
2,4-dioxo-1H-pyrimidine-6-carboxylic acid
State
State

At room temperature, this compound is typically a solid.

Melting point (Celsius)
305.00
Melting point (Kelvin)
578.15
Boiling point (Celsius)
315.00
Boiling point (Kelvin)
588.15
General information
Molecular weight
154.08g/mol
Molar mass
154.0950g/mol
Density
2.1400g/cm3
Appearence

Uracil-6-carboxylic acid appears as a white to off-white crystalline solid. It is typically available in powder form and is known to be sparingly soluble in water but soluble in alkaline solutions, where it can form salts.

Comment on solubility

Solubility of 2,4-Dioxo-1H-pyrimidine-6-carboxylic Acid

The solubility of 2,4-dioxo-1H-pyrimidine-6-carboxylic acid (C5H2N2O4) can be characterized by its interactions with solvents and its molecular structure. Here are some key points regarding its solubility:

  • Polarity: The presence of multiple functional groups, including carbonyls and a carboxylic acid, enhances polarity, which generally increases solubility in polar solvents like water.
  • Hydrogen Bonding: The carboxylic acid group can engage in hydrogen bonding with water molecules, facilitating its dissolution.
  • Solvent Dependence: This compound may exhibit varying solubility in organic solvents such as ethanol or acetone. It is likely more soluble in protic solvents due to the ability to donate protons.
  • Temperature Influence: Like many organic acids, solubility can be influenced by temperature; typically, higher temperatures enhance solubility.
  • pH Sensitivity: At different pH levels, the ionization of the carboxylic acid can significantly affect solubility, with anionic forms being more soluble in basic conditions.

In summary, while 2,4-dioxo-1H-pyrimidine-6-carboxylic acid is expected to have good solubility in polar solvents due to its structural features, specific solubility can vary based on solvent choice, temperature, and pH conditions. These factors make the solubility profile of this compound a complex and intriguing subject of study.

Interesting facts

Exploring 2,4-Dioxo-1H-pyrimidine-6-carboxylic Acid

2,4-Dioxo-1H-pyrimidine-6-carboxylic acid, commonly referred to as a pyrimidine derivative, is a fascinating compound with noteworthy characteristics. This compound belongs to a class of heterocyclic organic compounds that play essential roles in biochemistry and medicinal chemistry. Below are some engaging facts about this intriguing compound:

  • Biological Significance: Pyrimidine derivatives are fundamental components of nucleic acids, like DNA and RNA. The presence of dioxo groups adds additional functionality, possibly influencing interactions with biological targets.
  • Potential Therapeutic Uses: Research has indicated that derivatives of pyrimidine can exhibit antimicrobial and antitumor properties. The compound's structure suggests it may be a candidate for developing new pharmaceuticals.
  • Synthetic Versatility: The synthesis of 2,4-dioxo-1H-pyrimidine-6-carboxylic acid can be approached through various synthetic routes, making it a convenient target for organic chemists looking to explore heterocyclic chemistry.
  • Chemical Reactivity: The carboxylic acid functional group can undergo typical reactions, such as esterification and amide formation, allowing for the derivatization of this compound and the formation of a range of new derivatives.

Furthermore, the compound’s reactions and transformations can reveal unparalleled insights into the chemistry of heterocycles, captivating both students and experienced chemists alike. "Understanding how different structures influence biochemical activity is one of the most challenging yet rewarding aspects of chemical research." This emphasizes the excitement of studying compounds like 2,4-dioxo-1H-pyrimidine-6-carboxylic acid that stand at the intersection of chemistry, biology, and medicine.

Synonyms
Orotic acid
65-86-1
6-Carboxyuracil
Oropur
Orodin
Orotonin
Orotyl
Orotonsan
Vitamin B13
Whey factor
Oroturic
2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Uracil-6-carboxylic acid
Animal galactose factor
6-Uracilcarboxylic acid
Molkensaeure
Orotsaeure
2,6-Dihydroxypyrimidine-4-carboxylic acid
Uracil-6-carbosaeure
orotate
Acide orotique
Acido orotico
4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-
Acidum oroticum
Orotsaeure [German]
2,6-Dihydroxy-4-pyrimidinecarboxylic acid
Acide orotique [French]
Acido orotico [Spanish]
Acidum oroticum [Latin]
Acide orotique [INN-French]
Acido orotico [INN-Spanish]
Acidum oroticum [INN-Latin]
NSC 9791
CCRIS 3929
2,4-dioxo-1H-pyrimidine-6-carboxylic acid
HSDB 6377
6-Carboxy-2,4-dihydroxypyrimidine
Orotic acid (VAN)
1,2,3,6-tetrahydro-2,6-dioxo-4-Pyrimidinecarboxylic acid
AI3-25478
Orotic acid (6-Carboxyuracil)
Orotsaure
1,2,3,6-Tetrahydro-2,6-dioxopyrimidin-4-carbonsaeure
1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acid
NSC-9791
EINECS 200-619-8
MFCD00006027
Orotic acid [INN:BAN:JAN]
uracil-6-carboxylate
Orotic acid anhydrous
Orotic acid (JAN)
DTXSID0025814
UNII-61H4T033E5
CHEBI:16742
NSC9791
OROTIC ACID [MI]
OROTIC ACID [INN]
OROTIC ACID [JAN]
61H4T033E5
OROTIC ACID [HSDB]
OROTIC ACID [MART.]
OROTIC ACID [WHO-DD]
Orotic acid (VAN) (8CI)
2,6-dihydroxy-pyrimidine-4-carboxylic acid
DTXCID005814
1,2,3,4-Tetrahydro-2,6-dioxopyrimidine-4-carboxylic acid
2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid
2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid
Orotic acid, anhydrous
NCGC00091357-01
Oroticacid
Orotic Acid-15N2
Acide orotique (French)
Acido orotico (Spanish)
Acidum oroticum (Latin)
OROTIC ACID (MART.)
15184-25-5
Acide orotique (INN-French)
Acido orotico (INN-Spanish)
Acidum oroticum (INN-Latin)
Orotic acid [INN:JAN]
Acid, Orotic
CAS-65-86-1
NSC627082
4-Pyrimidinecarboxylicacid
orotic-acid
6-Carboxyuracil(Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 822)
6-Carboxyuracil[Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 822]
OG6
Orodin(Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2536)
Orodin[Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2536]
Orotonin(Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2536)
Orotonin[Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2536]
Oroturic(Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2536)
Oroturic[Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2536]
Orotyl(Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2536)
Orotyl[Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2536]
Uracil-6-carboxylic acid(Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 822)
Uracil-6-carboxylic acid[Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 822]
orazamide|orotic acid
Orotic acid (8CI)
OROTIC-ACID-
Orotic acid (Standard)
bmse000283
OROTIC ACID [INCI]
SCHEMBL20865
MLS006011823
GTPL4690
CHEMBL1235017
HY-N0157R
HMS3264K19
HMS3651I20
Pharmakon1600-01504525
BCP09063
HY-N0157
Tox21_111121
Tox21_201104
BBL013050
NSC758903
s2336
STK301771
STK629991
AKOS000119689
AKOS004115502
Tox21_111121_1
CCG-213952
DB02262
FO33319
NSC-758903
SB55525
NCGC00091357-02
NCGC00188943-01
NCGC00188943-03
NCGC00188943-04
NCGC00258656-01
SMR001550463
SY006030
TS-00078
2,6-dihydroxy-pyrimidin-4-carboxylic acid
SBI-0207042.P001
DB-073669
4-Pyrimidinecarboxylic acid, 2,6-dihydroxy-
A8909
NS00003862
O0065
Orotic acid, >=98% (titration), anhydrous
SW219707-1
EN300-16897
C00295
D00055
D70614
AB00373897_03
AB-323/25048164
Q425536
SR-01000872754
SR-01000872754-1
BRD-K32572029-001-04-4
BRD-K32572029-001-05-1
F2191-0093
37C71C07-0D69-452C-8C54-7D01BE02C146
4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo- (9CI)
2,6-dihydroxypyrimidine-4-carboxyli cacid;6-Carboxy-2,4-dihydroxypyrimidine;6-Carboxyuracil
200-619-8
610-580-2
Orotsaure (German)[Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2536]