Organic alkali Fluorouracil Chemical property Uses Production methods
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Uracil

Organic alkali Fluorouracil Chemical property Uses Production methods
Product Name
Uracil
CAS No.
66-22-8
Chemical Name
Uracil
Synonyms
PYRIMIDINE-2,4(1H,3H)-DIONE;PYRIMIDINE-2,4-DIOL;Ura;2,4-DIHYDROXYPYRIMIDINE;2,4(1H,3H)-PYRIMIDINEDIONE;Uracyl;Uracll;Cellocidin;2,6-Dihydroxypyrimidine;1H-Pyrimidine-2,4-dione
CBNumber
CB8376824
Molecular Formula
C4H4N2O2
Formula Weight
112.09
MOL File
66-22-8.mol
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Uracil Property

Melting point:
>300 °C (lit.)
Boiling point:
209.98°C (rough estimate)
Density 
1.4421 (rough estimate)
refractive index 
1.4610 (estimate)
storage temp. 
2-8°C
solubility 
Aqueous Acid (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly)
form 
Crystalline Powder
pka
9.45(at 25℃)
color 
White to slightly yellow
Water Solubility 
SOLUBLE IN HOT WATER
Merck 
14,9850
BRN 
606623
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
ISAKRJDGNUQOIC-UHFFFAOYSA-N
LogP
-1.037 (est)
CAS DataBase Reference
66-22-8(CAS DataBase Reference)
NIST Chemistry Reference
Uracil(66-22-8)
EPA Substance Registry System
Uracil (66-22-8)
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Safety

Hazard Codes 
Xi
Safety Statements 
22-24/25
WGK Germany 
2
RTECS 
YQ8650000
TSCA 
Yes
HS Code 
29335990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1581
Product name
Uracil
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
100mg
Price
$105
Updated
2024/03/01
Sigma-Aldrich
Product number
1705753
Product name
Uracil
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
15mg
Price
$447
Updated
2024/03/01
TCI Chemical
Product number
U0013
Product name
Uracil
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$26
Updated
2024/03/01
TCI Chemical
Product number
U0013
Product name
Uracil
Purity
>98.0%(HPLC)(T)
Packaging
100g
Price
$60
Updated
2024/03/01
Alfa Aesar
Product number
A15570
Product name
Uracil, 99+%
Packaging
50g
Price
$48.5
Updated
2024/03/01
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Uracil Chemical Properties,Usage,Production

Organic alkali

Uracil is an organic alkali, and is one of the four major bases in RNA. It is a major component of the pyrimidine composition in ribonucleic acid (RNA) as well as in various kinds of uridines. It can connect with ribose to generate UMP whose triphosphate compound being UTP. UTP is the precursor form of uracil in RNA biosynthesis. UTP also acts as a coenzyme to be involved in the biosynthesis of certain sugars. Uracil can block the degradation effect of tegafur, and thus increasing the concentration of fluorouracil which enhance the anti-cancer effects. Fluorouracil has similar clinical indications as uracil. It is mainly used for treating digestive cancer, breast cancer and thyroid cancer. Combination with mitomycin has a good efficacy on treating advanced gastric cancer. Laboratory synthesizes uracil through the cyclization reaction between ethyl malonyl and urea for pharmaceutical and biochemical research.
Uracil has tautomerism effect:

Keto (2,4-2 CPCC) enol (2,4-2-hydroxy pyrimidine) in mainly exist in the form of ketone inside biological cells.
Nature uracil is presented mainly in marine organisms, particulate matter and sea lysate. It is treated as life indicator in the field of organic geochemistry.
Pyrimidine refers to the hexaheterocyclic compound with two nitrogen atoms in 1,3-position of the benzene ring, and it, together with pyridazine and pyrazine, are isomers of each other. Pyrimidine has a unique UV spectrum due to the presence of conjugated double bonds in its structure. Pyrimidine has a lower basicity and a weaker lectrophilic substitution reaction than pyridine. But it is more prone to have nucleophilic substitution. Derivatives of pyrimidine are widely distributed in nature, including vitamin B1, uracil, thymine, and cytosine which all containing a pyrimidine structure.

Fluorouracil

Fluorouracil, briefly referred as FU, is currently one of the most commonly used anti-cancer drug. It is white crystals with pKa = 8.1, m.p.282~283 °C. It is slightly soluble in water (12mg/ml at 25 °C) and ethanol, but insoluble in chloroform and ether. It is easily soluble in diluted acid and alkali. It is hydrolyzed in the presence of strong base but is stable in normal saline. Due to the introduction of a strong electrically fluorine atoms, the acidity of Fu is 30 times higher than its parent, uracil. The injection of Fu usually is an aqueous solution with pH 9.0 adjusted by sodium hydroxide. It is sensitive to light and easy to crystallize when stored at low temperatures or prolonged room temperature.
According to the stronger ability of tumor tissue of rats in utilizing pyrimidine than normal tissue n, in 1957, Duschinsky and Heidelbergere designed and replace the 5-hydrogen in uracil to fluorine with similar size and generated Fu, as an anti-metabolite of uracil to achieve selective anticancer effects. FU has inhibitory effects on many kinds of animal transplanted tumors such as mouse leukemia L1210, L615, and adenocarcinoma 755. Tumor cells has no cross-resistance to it and other commonly used anti-cancer drugs such as cytarabine, methotrexate, mercaptopurine, cyclophosphamide, and carmustine.
FU is converted into 5-fluoro-deoxy-uridine monophosphate (FDUMP) and 5-fluorouracil nucleoside triphosphate (FUTP) in tissues. FDUMP inhibits the thymidylate synthase (TS) via forming compound with TS and 5,10-methenyltetrahydrofolate, thus resulting in a lack of intracellular thymine nucleotide and further inhibition of DNA synthesis, finally leading to cell death. On the other hand, FUTP is incorporated into RNA as the substrate of RNA polymerase substrate and affect the normal synthesis and function of RNA. In tissue culture, supplement of thymidine (TdR) can reverse the FU cytotoxicity, so that it has been realized for many years that the impact on DNA is the primary growth-inhibitory mechanism of FU. However, it was found that TdR didn’t completely reverse the cytotoxicity of FU, and the combination of FU and TdR significantly improved the FU’s incorporation into RNA and its anti-cancer effect. After culturing together of L1210 leukemia cells with 6-H3-5FU for 22 hours, it was found the existence of 80 fmol of FDUMP-TS-5,10CH2-H4 folic acid complexes in 106 cell while 400 fmol of FU bound to RNA. This emphasizes the importance of FU’s incorporation into RNA FU for its anti-tumor effect. FU is a cell cycle-specific drug which playing the significant role at S-phase.
Reference: China Medical Encyclopedia Editing Committee; editor: Liang Huang; Chinese Medical Encyclopedia.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Chemical property

White or light yellow crystalline needle. Melting point 338 °C; easily soluble in water, soluble in diluted ammonia, slightly soluble in cool water, insoluble in alcohol and ether.

Uses

For biochemical research, drugs synthesis; being used as pharmaceutical intermediates, also used in organic synthesis

Production methods

It is produced through the reaction of malate, sulfuric acid and urea.

Description

Uracil is a pyrimidine base and a fundamental component of RNA where it binds to adenine via hydrogen bonds. It is converted into the nucleoside uridine through the addition of a ribose moiety, then to the nucleotide uridine monophosphate by the addition of a phosphate group.

Chemical Properties

Crystalline needles. Soluble in hot water, ammonium hydroxide, and other alkalies; insoluble in alcohol and ether.

Uses

In biochemical research.

Uses

Uracil (Lamivudine EP Impurity F) is a nitrogenous base on RNA nucleosides.

Uses

antineoplastic

Definition

ChEBI: A common and naturally occurring pyrimidine nucleobase in which the pyrimidine ring is substituted with two oxo groups at positions 2 and 4. Found in RNA, it base pairs with adenine and replaces thymine during DNA transcription.

Definition

A nitrogenous base that is found in RNA, replacing the thymine of DNA. It has a pyrimidine ring structure.

Definition

uracil: A pyrimidine derivative andone of the major component bases ofnucleotides and the nucleic acidRNA.

General Description

Certified pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Uracil is one of the nucleotide bases of RNA. It is the precursor of DNA′s thymine. It acts like a carrier of genetic data and is hooked up with a ribose and three phosphates to form a ribonucleoside triphosphate once a human body produces nucleotides.

Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Uracil crystallises from water (m 339-341o) and m 338o after sublimation in high vacuum. Its solubility in H2O at 20o is 1g/300mL. [Beilstein 24 H 312, 24 I 312, 24 II 169, 24 III/IV 1193.]

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Uracil Suppliers

Wuxi Fuze Pharmaceutical Co., Ltd.
Tel
0510-83594580 18012359489
Email
sales@further-pharm.com
Country
China
ProdList
9
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58
Shanghai Longsheng chemical Co.,Ltd.
Tel
021-58099652-8005 13585536065
Fax
021-58099609
Email
bin.wu@shlschem.com
Country
China
ProdList
9816
Advantage
59
ELION INTERNATIONAL(HONGKONG) CO., LTD
Tel
177-6725-7858 15967138206
Fax
0571-85022751
Email
sales@hzbrown.com
Country
China
ProdList
73
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62
Shanghai Xianggeng Technology Development Co. Ltd.
Tel
021-021-56152668 18116302010
Fax
18116300787
Email
sharing@sharingtechcn.com
Country
China
ProdList
500
Advantage
58
Wuxi Jingyao Bio-Technology Co., Ltd.
Tel
0510-88770633 13961738808
Email
jingyaobiotech@126.com
Country
China
ProdList
301
Advantage
55
Changzhou Zhongji Chemical Co.,Ltd
Tel
0519-85156279-811,812
Fax
0519-85156279-816
Email
sales@czzjchem.com
Country
China
ProdList
20
Advantage
58
Yangzhou juhechang Technology Co., Ltd
Tel
0514-0514-83662002 13073488988
Fax
0514-83662002
Email
13073488988@163.com
Country
China
ProdList
37
Advantage
58
Shandong Chenyi Environmental Protection Technology Co., Ltd
Tel
0531-83179999 13395316108
Email
zhongqingyao8@outlook.com
Country
China
ProdList
134
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
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View Lastest Price from Uracil manufacturers

Jinan Finer Chemical Co., Ltd
Product
Uracil 66-22-8
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
500mt
Release date
2022-01-25
hebei hongtan Biotechnology Co., Ltd
Product
Uracil 66-22-8
Price
US $30.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
2000kg
Release date
2024-03-22
airuikechemical co., ltd.
Product
uracil 66-22-8
Price
US $0.00-0.00/Kg
Min. Order
1Kg
Purity
99.9%
Supply Ability
200tons
Release date
2024-04-09

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