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18422-05-4

18422-05-4 Structure

18422-05-4 Structure
IdentificationMore
[Name]

Adenosine 5'-monophosphate monohydrate
[CAS]

18422-05-4
[Synonyms]

5'-ADENYLIC ACID
5-ADENYLIC ACID
5'-AMP H2O
5'-AMP MONOHYDRATE
A-5'-P
ADENOSINE 5'-MONOPHOSPHATE
ADENOSINE 5'-MONOPHOSPHATE MONOHYDRATE
ADENOSINE 5'-MONOPHOSPHORIC ACID MONOHYDRATE
ADENYLIC ACID MONOHYDRATE
AMP
ADENOSINE 5'-MONOPHOSPHATE FREE ACID97+% FROM YEAS
5'-AMP=Adenylicacid
ADENOSINE-5'-MONOPHOSPHATE 1-HYDRATE
5-Adenylic acid, monohydrate
Adenosine-5''-monophosphoric acid (and/or unspecified salts)
5'-AMP
Adenosine-5'-monophosphoric acid monohydrate >96%
AMP monohydrate
5μ-AMP, Adenylic acid from muscle, AMP
5μ-Adenylic acid, 5μ-AMP, A-5μ-P, AMP
[EINECS(EC#)]

200-500-0
[Molecular Formula]

C10H16N5O8P
[MDL Number]

MFCD00149360
[Molecular Weight]

365.24
[MOL File]

18422-05-4.mol
Chemical PropertiesBack Directory
[Appearance]

White crystalline powder
[Melting point ]

183-188 °C (dec.)(lit.)
[alpha ]

-48 º (c=2% in 2% NaOH)
[FEMA ]

4224 | ADENOSINE MONOPHOSPHATE; MONOSODIUM, OR DISODIUM ADENYLATE
[storage temp. ]

2-8°C
[solubility ]

H2O: with addition of mild alkalisoluble
[form ]

Solid
[pka]

~6.5
[color ]

White to Off-White
[biological source]

yeast
[Water Solubility ]

1 M NH4OH: soluble 50mg/mL, clear, colorless
H2O: soluble (with addition of mild alkali)
[Merck ]

14,158
[BRN ]

5205540
[InChIKey]

ZOEFQKVADUBYKV-MCDZGGTQSA-N
[SMILES]

O[C@H]1[C@@H](O)[C@H](N(C=N2)C3=C2C(N)=NC=N3)O[C@@H]1COP(O)(O)=O.O
[CAS DataBase Reference]

18422-05-4(CAS DataBase Reference)
Questions And AnswerBack Directory
[Pharmacodynamics]

Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP is used as a dietary supplement to boost immune activity, and is also used as a substitute sweetener to aid in the maintenance of a low-calorie diet.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[RTECS ]

AU7480500
[F ]

8-10-21
[TSCA ]

Yes
[HS Code ]

2934999090
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

Adenosine 5'-monophosphate monohydrate is an adenosine A1 receptor agonist. Adenosine 5'-monophosphate monohydrate has significant antiviral activity against HSV-1 and HSV-2. It plays an important role in various biochemical pathways such as energy metabolism, gene expression and signal transduction.
[Chemical Properties]

White crystalline powder
[Uses]

Adenosine 5′-monophosphate (5′AMP) is suitable for use as
  • a reagent in the synthesis of adenosine-5′-phosphoimidazolide
  • an activator of phosphorylase b in the polymerization reaction for the synthesis of branched polysaccharides
  • an inhibitor of endogenous NMN adenylyltransferase (NMNAT) activity that converts NMN to NAD+
[Uses]

Nutrient;Ca++ channel block
[Definition]

ChEBI: Adenosine 5'-monophosphate monohydrate is a purine ribonucleoside monophosphate.
[Biochem/physiol Actions]

Adenosine 5′-monophosphate (5′-AMP) has many uses in nature. 5′-AMP is an activator of a class of protein kinases known as AMP-activated protein kinase (AMPK). AMP inhibits dephosphorylation of AMPK and promotes phosphorylation of AMPK by upstream kinases.
[Purification Methods]

The acid has been recrystallised from H2O (fine needles) and is freely soluble in boiling H2O. It crystallises also from H2O on addition of acetone. Alternatively purify it by chromatography on Dowex 1 (in formate form), eluting with 0.25M formic acid. It is then adsorbed onto charcoal (which had been boiled for 15minutes with M HCl, washed free of chloride and dried at 100o) and recovered by stirring three times with isoamyl alcohol/H2O (1:9 v/v). The aqueous layer from the combined extracts is evaporated to dryness under reduced pressure, and the product is crystallised twice from hot H2O. [Morrison & Doherty Biochem J 79 433 1961]. It has max 259nm ( 15,400) in H2O at pH 7.0. [Alberty et al. J Biol Chem 193 425 1951, Martell & Schwarzenbach Helv Chim Acta 39 653 1956]. The acridinium salt has m 208o [Baddiley & Todd J Chem Soc 648 1947, Pettit Synthetic Nucleotides, van Nostrand-Reinhold, NY, Vol 1 252 1972, NMR: Sarma et al. J Am Chem Soc 96 7337 1974, Norton et al. J Am Chem Soc 98 1007 1976, IR of diNa salt: Miles Biochem Biophys Acta 27 324 1958]. [Beilstein 26 III/IV 3615.]
Spectrum DetailBack Directory
[Spectrum Detail]

Adenosine 5'-monophosphate monohydrate(18422-05-4)1HNMR
Adenosine 5'-monophosphate monohydrate(18422-05-4)IR
Adenosine 5'-monophosphate monohydrate(18422-05-4)Raman
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

18422-05-4(sigmaaldrich)
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