Stable. Incompatible with strong oxidizing agents.- 2.9 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: An aminopyrimidine that is pyrimidin-2-one having the amino group located at position 4.
- 3.2 Description
-
Cytosine (CAS 71-30-7) is a pyrimidine base that is one of the four nucleobases found in DNA and RNA. It is a colorless crystalline solid with a molecular formula of C4H5N3O. Cytosine is soluble in water, with a solubility of approximately 2.5 g/L at 25°C. It has a melting point of 320-325°C and a boiling point of 320-325°C. Cytosine is a weak base and can form hydrogen bonds with other nucleobases.
Applicable Fields Pharmaceutical Industry: Cytosine is used in the pharmaceutical industry for various purposes. It is a key component in the synthesis of nucleoside analogs, which are used as antiviral and anticancer drugs. Cytosine analogs can inhibit the replication of viral DNA or RNA, or interfere with the synthesis of DNA in cancer cells.
Mechanism of Action The mechanism of action of cytosine analogs involves their incorporation into the growing DNA chain during replication. Once incorporated, they can disrupt the normal base pairing and cause chain termination, leading to the inhibition of viral replication or cancer cell growth.
Storage Conditions Store in a cool, dry place.
- 3.3 Purification Methods
- Cytosine crystallises from H2O as the monohydrate which loses water on heating above 100o. Its solubility in H2O is 0.77%. UV: max 267nm ( 6,100) in H2O pH 8.8 and 275nm ( 10,400) in 0.1N HCl. [Hilbert & Johnson J Am Chem Soc 52 1152 1930, Hilbert et al. J Am Chem Soc 57 552 1935, Beistein 25 III/IV 3654.] Cytosine Preparation Products And Raw materials Preparation Products
- 3.4 Usage
- Widely distributed in nature; constituent of nucleic acids
4. Safety and Handling
- 4.1 Safety
-
Hazard Codes:?Xi,?Xn
Risk Statements: 36/37/38-20/21/22?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.?
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 1
RTECS: UW7350150
Hazard Note: Irritant
- 4.2 Specification
-
?Cytosine (CAS NO.71-30-7) is also named as 4-Amino-2(1H)-pyrimidinone ; 4-Amino-2-hydroxypyrimidine ; AI3-52281 ; Cyt ; Cytosinimine ; NSC 27787?; 2(1H)-Pyrimidinone, 4-amino- .?Cytosine (CAS NO.71-30-7) is white solid.
- 4.3 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| mouse |
LD50 |
intraperitoneal |
> 2222mg/kg (2222mg/kg) |
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) |
Journal of Pharmacology and Experimental Therapeutics. Vol. 207, Pg. 504, 1978.
? |
5. MSDS
2.Hazard identification 2.1 Classification of the substance or mixture Skin irritation, Category 2 Eye irritation, Category 2 Specific target organ toxicity \u2013 single exposure, Category 3 2.2 GHS label elements, including precautionary statements | Pictogram(s) |  | | Signal word | Warning | | Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation | | Precautionary statement(s) | | | Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. | | Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. | | Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. | | Disposal | P501 Dispose of contents/container to ... | 2.3 Other hazards which do not result in classification none
6. NMR Spectrum
SOLID (1 mg / 650 mg KBr DISC)
SOLID (1.2 mg / 380 mg KBr DISC) PURITY - ANALYTICAL
Mass spectrum (electron ionization)
7. Synthesis Route
71-30-7Total: 45 Synthesis Route
8. Precursor and Product
9. Computed Properties
- Molecular Weight：111.102g/mol
- Molecular Formula：C4H5N3O
- Compound Is Canonicalized：True
- XLogP3-AA：111.043261792
- Monoisotopic Mass：111.043261792
- Complexity：170
- Rotatable Bond Count：0
- Hydrogen Bond Donor Count：2
- Hydrogen Bond Acceptor Count：2
- Topological Polar Surface Area：67.5
- Heavy Atom Count：：8
- Defined Atom Stereocenter Count：0
- Undefined Atom Stereocenter Count：0
- Defined Bond Stereocenter Count：0
- Undefined Bond Stereocenter Count：0
- Isotope Atom Count：0
- Covalently-Bonded Unit Count：1
- CACTVS Substructure Key Fingerprint：AAADcYBjIAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAHgAQAAAACADBAAQBAALAAACoADBjVAAAAAAAAgAAAAAQABCAAAAAAAAAAAAAAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10.Other Information
- Usage
- Cytosine is a nucleoside used for proteomics research. It is also used as an enzyme substrate or precursor of effector molecules such as cytosine sugars.
- Merck
- 14,2795
- BRN
- 2637
- Description
- Cytosine is pyrimidine; along with adenine and guanine they account for the fi ve nucleic acid bases. Pyrimidines are heterocyclic single-ringed compounds based on the structure of pyrimidine. Cytosinelike adenine and guanine, form nucleosides and nucleotides in RNA and DNA. When the bases combine with ribose, a ribonucleoside forms; and when it attaches to deoxyribose, a deoxyribosenucleoside is formed. Names of the nucleoside are summarized in Table 29.1.these in turn combine with phosphoryl groups, in a process called phosphorylation, to form their respective nucleotides that form nucleic acids.the nucleotides can be tri, di, and mono phosphate nucleotides similar to the way in which adenine forms ATP, ADP, and AMP.
- Chemical Properties
- White Solid
- History
- Cytosine is first isolated by hydrolysis of calf thymus tissue by Albrecht Kossel (1853–1927) and A. Neumann during 1893–1894. Thymine’s structure was published in 1900 and confi rmed over the next several years when it was synthesized by several investigators. In 1903, cytosine was synthesized by Henry Lord Wheeler (1867–1914) and Treat B. Johnson, confirming its structure. Uracil was first isolated in 1900 from yeast nucleic acid found in bovine thymus and herring sperm.the methylation of uracil produces thymine; thymine is also called 5-methyluracil because methylation takes place at the fi fth carbon in uracil to produce thymine.
- Uses
-
Cytosine has been used:
- for the preparation of nucleobase solutions
- as a standard for high-performance liquid chromatography (HPLC)
- for the estimation of global methylation rate
- for nucleoside 5′-triphosphate (NTP) synthesis
- purification
-
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12. Related Questions
13. Realated Product Infomation
1. Names and Identifiers
2. Properties
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