Adenosine 5'-monophosphate
- Iupac Name：[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
- CAS No.: 61-19-8
- Molecular Weight：347.221221
- Modify Date.: 2023-02-14 11:40
- Introduction: White crystalline powder. Melting point: 196-200°C (decomposition). Specific optical rotation:-47.5° (20°C, 2% in sodium hydroxide (2%)). Soluble in water, slightly soluble in alcohol, insoluble in ether. colorless to white crystalline powder
View more+
1. Names and Identifiers
- 1.1 Name
- Adenosine 5'-monophosphate
- 1.2 Synonyms
)-monophosphate disodium salt (mixed isomers) [(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanyl]methyl dihydrogen phosphate 3-Hydroxy Tibolone-d5 |(mixture of 3αadenosine5’-phosphate 4-PREGNEN-18-OL, 3, 20-DIONE (20αOLS) 18, 20-HEMIKETAL 5'-Adenylic acid 5'-AMP 9-(5-O-Phosphono-α-D-lyxofuranosyl)-9H-purin-6-amine 9H-Purin-6-amine, 9-(5-O-phosphono-α-D-lyxofuranosyl)- Adenosine -5'- Monophosphate（AMP-H） adenosine 5″-monophosphate Adenosine 5'-phosphoric acid adenosine,mono(dihydrogenphosphate)(ester) adenosine-5″-monophosphate Adenosine-5'-monophosphate ADENOSINE-5'-MONOPHOSPHORIC ACID Adenosine-5'-phosphoric Acid Ado-5'-P MFCD00005750 phosphate d'adénosine phosphate d'adenosine t-Adenylic Acid
- View all
- 1.3 CAS No.
- 61-19-8
- 1.4 CID
- 6083
- 1.5 EINECS(EC#)
- 200-500-0
- 1.6 Molecular Formula
- C10H14N5O7P (isomer)
- 1.7 Inchi
- InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
- 1.8 InChIkey
- UDMBCSSLTHHNCD-KQYNXXCUSA-N
- 1.9 Canonical Smiles
- C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)N
- 1.10 Isomers Smiles
- C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
2. Properties
- 2.1 Density
- 2.32
- 2.1 Melting point
- 178-185℃
- 2.1 Boiling point
- 798.518°C at 760 mmHg
- 2.1 Refractive index
- 1.905
- 2.1 Flash Point
- 436.728°C
- 2.1 Precise Quality
- 347.06300
- 2.1 PSA
- 195.88000
- 2.1 logP
- -1.28180
- 2.1 Solubility
- H2O: with addition of mild alkalisoluble
- 2.2 Appearance
- white crystalline powder
- 2.3 Storage
- Keep Cold.
- 2.4 Chemical Properties
- White crystalline powder. Melting point: 196-200°C (decomposition). Specific optical rotation:-47.5° (20°C, 2% in sodium hydroxide (2%)). Soluble in water, slightly soluble in alcohol, insoluble in ether.
- 2.5 Color/Form
- Powder
- 2.6 pKa
- 3.8, 6.2(at 25℃)
- 2.7 Water Solubility
- H2O: with addition of mild alkalisoluble
- 2.8 Spectral Properties
- SPECIFIC OPTICAL ROTATION: -26 DEG @ 20 DEG C/D (C= 2, 10% HCL); & -47.5 DEG @ 20 DEG C/D (C= 2, 2% NAOH)
MAX ABSORPTION (WATER, PH= 1.1): 255 NM (LOG E= 4.16); SPECIFIC OPTICAL ROTATION: -41.78 DEG @ 50 DEG C/D (WATER)
IR: 14657 (Sadtler Research Laboratories Prism Collection)
UV: 8-173 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
- 2.9 Stability
- FREE ACID & ITS SALTS ARE STABLE FOR LONG PERIODS IN DRY STATE; NEUTRAL SOLN ARE ALSO STABLE
- 2.10 StorageTemp
- Keep in dark place,Inert atmosphere,Room temperature
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A purine ribonucleoside 5'-monophosphate having adenine as the nucleobase.
- 3.2 Usage
- antiasthmatic
4. Safety and Handling
- 4.1 Risk Statements
- S24/25
- 4.1 Safety Statements
- S24/25
- 4.1 RIDADR
- OTH
- 4.1 Safety Profile
- Slightly toxic byintraperitoneal route. Experimentalreproductive effects. Human mutation datareported. When heated to decomposition itemits toxic fumes of PO, and NOx. Adenosine 5'-monophosphate Preparation Products And Raw materials Preparation Products
- 4.2 WGK Germany
- 3
- 4.2 RTECS
- AU7480500
- 4.2 Report
-
AMP is reported in EPA TSCA Inventory.
- 4.3 Safety
-
Slightly toxic by intraperitoneal route. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of POx and NOx.
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: AU7480500
- 4.4 Specification
-
?AMP (CAS NO.61-19-8), its Synonyms are Adenosine 5'-phosphate ; Adenosine monophosphate ; Adenosine phosphate ; 5'-AMP ; 5'-Adenylic acid ; A5MP ; Adenosine 5'-(dihydrogen phosphate) ; Adenosine 5'-monophosphate ; Adenosine 5'-monophosphoric acid ; Ergadenylic acid ; Fosfato de adenosina ; Monophosphadenine ; Muscle adenylic acid ; Muskeladenosin-phosphorsaeure ; Muskeladenylsaeure ; My-B-Den ; Myoston . It is colorless to white crystalline powder.
- 4.5 Toxicity
-
| 1. |
??? |
oms-hmn:oth 100 μmol/L
|
??? |
JIDEAE ?? Journal of Investigative Dermatology. 65 (1975),52. |
| 2. |
??? |
oms-mus:oth 50 μmol/L
|
??? |
JIDEAE ?? Journal of Investigative Dermatology. 66 (1976),313. |
| 3. |
??? |
ipr-mus LD50:4?g/kg
|
??? |
PCJOAU ?? Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. 20 (1986),160. |
- View all
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
61-19-8Total: 97 Synthesis Route
9. Other Information
- 9.0 Merck
- 14,158
- 9.1 Chemical Properties
- White crystalline powder. Melting point: 196-200°C (decomposition). Specific optical rotation:-47.5° (20°C, 2% in sodium hydroxide (2%)). Soluble in water, slightly soluble in alcohol, insoluble in ether.
- 9.2 Applications
- Clinically it is used to treat disseminated sclerosis, porphyria, itching, liver disease, varicose ulcer complication. Eye drops with denosine monophosphate as the main component can be used to treat eye fatigue, central amphiblestitis, ocular pannus, herpes and other corneal surface diseases. Intramuscular injection shows local erythema, generalized essential telangiectasia, red face, dizziness, breathing difficulty and palpitation.
As nutrition enhancer; as intermediate to produce nucleotide drugs; as food additive; as biological products; as dietary supplement and biochemical reagent. It is used to produce adenosine triphosphate (ATP), cyclic adenylate (cAMP) and other biochemical drugs. It is a type of nucleotide products and to produce antiviral drugs, synthetic energy drugs and cardiovascular and cerebrovascular drugs, such as adenosine, ATP, 3 '-5'-cyclic adenosine monophosphate.
- 9.3 Preparation
- Candida utilis fungi is treated with hot water to obtain nucleic acids, which is hydrolyzed by enzymes and separated to obtain the final product.
Take mycelia as the raw material:
Subtraction and sedimentation of mycelia are carried out with 3 times amount of water. Industry base is added to reach a base concentration of 0.25% (g/100mL). After stirring for 1 hours, 20% sulfuric acid is added until the PH value is 7. The solution is filtrated and the pH value of filtrate is adjusted with 20% sulfuric acid to 2.5. Centrifugation is then applied to obtain nucleic acid mud.
mycelia [sodium hydroxide]→[1h] extract solution [20% sulfuric acid] → [pH=7, filtration] filtrate [20% sulfuric acid] →[pH=2.5, centrifugation] nucleic acid mud
1% nucleic acid solution is made by subsequent dissolution, enzymolysis, absorption and elution. 10% ammonia water is then used to adjust the pH value to 6-6.2. Then the mixture is heated at 90°C for 20 min and cooled. After centrifugation, the supernatant is heated up to 65-70°C and added with 1/3 phosphodiesterase solution. After 2 hours, the temperature is raised to 90°C. 10min later, it is cooled to room temperature. 20% sulfuric acid is added to adjust the pH value to 2.5-3. After filtration, the filtrate is adjusted with ammonia solution until the pH=7.2-7.5. 0.3% (3 g/L) diatomite is then added to assist the filtration. The corresponding supernatant is filtered with an anion exchange resin column (717-type) and eluted with 0.05 mol/L sulfuric acid. Afterwards, absorption, elution and crystallization are carried out. The detailed procedures of these three steps are:
The eluate is first absorbed with a cation exchange column (732-type) and eluted with distilled water (pH=1.5). The collection of eluate starts when the eluate turned red with bromine water. The eluate is then concentrated to 80-90 mg/mL under reduced pressure, added with diatomite and stirred for 30 min before filtration. The filtrate is adjusted with 6 mol/L hydrochloric acid till pH=2.5. To realize full crystallization, the filtrate is cooled during stirring. After followed filtration, it is washed with dry ethanol for 3 times. Vacuum drying at 60°C is applied to obtain the final AMP products.
Nucleic acid mud [ammonia gas] →[pH=6-6.2, 90°C, 20min] supernatant [phosphodiesterase] →[65-70°C,2h,] hydrolysis solution [717 resin] →absorbent [sulfuric acid] →elution solution [732 resin] →AMP, CMP, GMP absorbent mixtures. - View all
- 9.4 Usage restriction
- GB 2760-2001：infant formula milk powder 0.2~0.58 g/kg (based on the total amount of nucleotide)
- 9.5 Category
- Toxic substance
- 9.6 Toxicity Grading
- Middle toxicity
- 9.7 Acute Toxicity
- Peritoneal-mouse LD50: 4000 mg/kg
- 9.8 Flammability Hazardous Characteristics
- Flammable; generation of toxic nitrogen oxides and phosphorous oxide smoke when heated.
- 9.9 Storage and Transport
- Stored in well ventilated area, low temperature, and dry.
- 9.10 Extinguishing Agent
- Dry powder, foam, sand, carbon dioxide.
- 9.11 Chemical Properties
- colorless to white crystalline powder
- 9.12 Uses
- antiasthmatic
- 9.13 Uses
- vasodilator, neuromodulator
- 9.14 Uses
- Adenosine 5'-Monophosphate is a natural occurring nucleotide and a useful ligand determinant that facilitate the binding of APS reductase inhibitors and activates adenosine receptor agonists.
- 9.15 Uses
- A useful ligand determinant that facilitates the binding of APS reductase inhibitors.
- 9.16 Uses
- Adenosine 5'-monophosphate is a nucleotide (building blocks of nucleic acid) added to skin care products to bind water and moisture.
- 9.17 Definition
- ChEBI: A purine ribonucleoside 5'-monophosphate having adenine as the nucleobase.
- 9.18 Brand name
- Adenyl (Wyeth-Ayerst); My-BDen (Bayer.
- 9.19 Safety Profile
- Slightly toxic by intraperitoneal route. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of PO, and NOx.
- 9.20 Usage
- a useful ligand determinant that facilitate the binding of APS reductase inhibitors and activates adenosine receptor agonists. 5?-AMP is an activator of a class of protein kinases known as AMP-activated protein kinase, an activator of phosphorylase b in the polymerization reaction for the synthesis of branched polysaccharides, a reagent in the synthesis of adenosine-5?-phosphoimidazolide, an inhibitor of endogenous NMN adenylyltransferase (NMNAT) activity that converts NMN to NAD+.
10. Computational chemical data
- Molecular Weight: 347.221221g/mol
- Molecular Formula: C10H14N5O7P
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 347.06308480
- Monoisotopic Mass: 347.06308480
- Complexity: 481
- Rotatable Bond Count: 4
- Hydrogen Bond Donor Count: 5
- Hydrogen Bond Acceptor Count: 11
- Topological Polar Surface Area: 186
- Heavy Atom Count: 23
- Defined Atom Stereocenter Count: 4
- 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: AAADccBzuAIAAAAAAAAAAAAAAAAAAWJAAAAsAAAAAAAAAFgB+AAAHgAQCCAACBzhlwYF8L9MFxCgQQZhZICAgC0REKABUCAoVBCDWAJAyEAeRAgPAALTACDwMAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
5'-Adenosine 5'-monophosphate (AMP) is a compound composed of adenine, ribose, and a phosphate group. It is one of the four main nucleotides that make up ribonucleic acid (RNA) in animal cells and ser..
-
In the early 20th century, scientists confirmed that extracellular small molecule information substances are synthesized and released by various cells such as gland cells, and are transported through ..
-
2'-5'-Oligoadenylate synthetase 2 (OAS2) is a monoclonal immunoglobulin that specifically binds to 2'-5'-oligoadenylate synthetase 2, an enzyme that synthesizes 2',5'-phosphodiester bonds in oligoaden..
12. Recommended Suppliers
-
- Products:specialize in research and producing Nucleotide products.
- Tel:86-571-89939007
- Email:kaipengbio@gmail.com
-
- Products:specialize in research and producing Nucleotide products.
- Tel:86-571-89939007
- Email:kaipengbio@gmail.com
-
- Products:Pharma &Food Intermediates
Water Treatment Chemicals
Industrial Specialties
Fine Chemicals
- Tel:86-27-85835203
- Email:steven@cspharmchem.com
-
- Products:chemicals, pharmaceutical intermediates,
- Tel:00-86-13315469778
- Email:sales03@cn-js.cn
-
- Products:Top quality and high purity with safe transportation and low price
- Tel:+86187-59294010-18759294010
- Email:Beata@xmwonderfulbio.com
-
- Products:Our company specializes in the research and development of fine chemicals, food additives and pharmaceutical raw materials
- Tel:86-13126149-050
- Email:linda@hbsaisier.cn
13. Realated Product Infomation
skype
9YRS
