ChemicalBook > Product Catalog >Biochemical Engineering >Saccharides >Monosaccharide >AICAR

AICAR

AICAR Suppliers list
Company Name: HONG KONG IPURE BIOLOGY CO.,LIMITED
Tel: 86 18062405514
Email: ada@ipurechemical.com
Products Intro: Product Name:AICAR Acadesine
CAS:2627-69-2
Purity:98% Package:1BOU/Drum;1USD
Company Name: Shanghai Biolang Biotechnology Co., Ltd.
Tel:
Email: Jason@biolang.cn
Products Intro: Product Name:AICAR
CAS:2627-69-2
Purity:99.99% Package:1Kg/Bag;99.99USD
Company Name: Henan DaKen Chemical CO.,LTD.
Tel: +86-371-66670886
Email: info@dakenchem.com
Products Intro: Product Name:AICAR
CAS:2627-69-2
Purity:99% Package:100g,500g,1KG,10KG,100KG
Company Name: Henan Tianfu Chemical Co.,Ltd.
Tel: 0371-55170693
Email: info@tianfuchem.com
Products Intro: CAS:2627-69-2
Purity:99% Package:500G;1KG;5KG;25KG
Company Name: Hangzhou FandaChem Co.,Ltd.
Tel: 008615858145714
Email: fandachem@gmail.com
Products Intro: Product Name:AICAR fandachem
CAS:2627-69-2
Purity:As coa Package:As request Remarks:2627-69-2

Lastest Price from AICAR manufacturers

  • AICAR
  • US $0.00 / KG
  • 2021-10-22
  • CAS:2627-69-2
  • Min. Order: 100g
  • Purity: 98%+
  • Supply Ability: 100kg
  • AICAR
  • US $0.00 / KG
  • 2021-10-22
  • CAS:
  • Min. Order: 100g
  • Purity: 98%+
  • Supply Ability: 100kg
AICAR Basic information
adenosine regulating agents
Product Name:AICAR
Synonyms:5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside,98%;5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosideAICAR;5-Aminomidazole-4-carboxamide-1-β-D-ribofuranoside;ACADESINE;AICAR;AICA-RIBOSIDE;AMPK;1-Deoxy-1-[(4-carbamoyl-5-amino-1H-imidazole)-1-yl]-β-D-ribofuranose
CAS:2627-69-2
MF:C9H14N4O5
MW:258.23
EINECS:220-097-5
Product Categories:ARASINE;Cardiovascular APIs;PI3K/Akt/mTOR;Akt;mTOR;PI3K;Bases & Related Reagents;Carbohydrates & Derivatives;Nucleotides;Protein Kinase
Mol File:2627-69-2.mol
AICAR Structure
AICAR Chemical Properties
Melting point 214-215 °C
Boiling point 726.3±60.0 °C(Predicted)
density 2.06±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility H2O: >10 mg/mL
form powder
pka13.27±0.70(Predicted)
color tan
Water Solubility Soluble in DMSO at 2mg/ml. Soluble in water or ethanol at less than 1mg/ml
λmax265nm(NaOH)(lit.)
Merck 14,16
InChIKeyRTRQQBHATOEIAF-UUOKFMHZSA-N
CAS DataBase Reference2627-69-2(CAS DataBase Reference)
EPA Substance Registry System1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl- (2627-69-2)
Safety Information
Hazard Codes Xi,T
Risk Statements 36/37/38-61
Safety Statements 26-36-45-53
WGK Germany 3
TSCA Yes
HS Code 29349990
MSDS Information
ProviderLanguage
SigmaAldrich English
AICAR Usage And Synthesis
adenosine regulating agentsAcadesine is the prototype of a new class of compounds termed adenosine regulating agents. Acadesine is a purine nucleosid analogue that enters the myocyte and is immediately phosphorylated to ZMP (AICA ribotide), which is further metabolised to Inosine mono-phosphate (an intermediate in the synthesis ofadenosine triphosphate (ATP) and guanosine triphos-phate).
Claims that acadesine may serve as a substrate for ATP synthesis and result in repletion of myocardial ATP were supported by some studies and refuted by others. Because acadesine may be a precursor in the synthesis of myocardial ATP it was proposed as a possible agent of myocardial protection during ischaemia, particularly because myocardial ATP depletion has been linked to cell death.
Chemical PropertiesSolid
OriginatorAICA,BIOMOL
Usesglucose uptake stimulant; AMPK activator
UsesAICAR is a nucleoside analogue that is able to enter nucleoside pools and is able to significantly increase levels of adenosine during periods of ATP breakdown. Adenosine-regulating agents (ARAs) hav e been recognized for therapeutic potential in myocardial ischemia. Cardioprotective.
DefinitionChEBI: A 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects.
Manufacturing ProcessAdenosine 3', 5'-cyclic phosphate N'-oxide (76.0 g, 0.200 mole) as the dihydrate was dissolved in a solution of 400 ml DMSO and 31.0 g (0.204 mole) 1,5-diazabicyclo[5.4.0]undec-5-ene. The solution was cooled to 15°C and 40 ml methyl iodide was added with stirring at room temperature. After 30 min, the mixture had gelled; 1.5 L ethanol was added and the solid was thoroughly homogenized by vigorous stirring. The solid was filtered, and the resulting paste was resuspended in 2 L ethanol and homogenized. The product was again filtered, washed with ethanol and ether, and dried, giving 80.4 g of 1-methoxyadenosine 3',5'-cyclic phosphate suitable for further transformation (recrystallization from aqueous methanol with ether).
A solution of 30.0 g 1-methoxyadenosine 3',5'-cyclic phosphate (81.5 mmole), 20.0 g NaHCO3 (238 mmole), and 300 ml H2O was refluxed 45 mm. The pH of the solution was adjusted to 2.5 with Dowex 50x8 (H)+ while warm, and a water pump vacuum was applied to mixture to remove CO2. The pH was readjusted to 9-10 with NaOH, and the resin was removed by filtration. The solution was passed onto a column containing 400 ml Dowex 1x2 (formate, 100-200 mesh), and the column was washed well with water. The column was eluted with a gradient of 4 L water in the mixing chamber and 4 L 4 N formic acid in the reservoir. The first major product, coming after about 2 L eluate, was 5-amino-N-methoxy-1-β-D-ribofuranosylimidazole-4-carboxamidine 3',5'- cyclic phosphate, giving 5.4 g (19%) after evaporation of the solvent and trituration of the residue with ethanol (recrystallization from water). A solution of 5.0 g (14.3 mmoles) 5-amino-N-methoxy-1-β-Dribofuranosylimidazole- 4-carboxamidine 3',5'-cyclic phosphate in 200 ml H2 preheated to 60°C and containing approximately 5.0 g moist sponge nickel catalyst, was shaken with 2-3 atm. H2 at 60°C for 2 h. The filtered solution was evaporated to dryness to give 3.75 g of 5-amino-1-β-Dribofuranosylimidazole- 4-carboxamidine 3',5'-cyclic phosphate (82%), (recrystallization from water).
A mixture of 4.0 g (12.5 mmole) 5-amino-1-β-D-ribofuranosylimidazole-4- carboxamidine 3',5'-cyclic phosphate and 100 ml conc. NH4OH was heated in a bomb at 100°C for 16 h, then cooled and evaporated in vacuum. The residue was taken up in 100 ml H2O and applied to a 2.5x20 cm column of Dowex 1x2 (formate form, 100-200 mesh). After washing well with H2O the column was eluted with a gradient of 1 L H2O in the mixing chamber and 1 L 3 N formic acid in the reservoir. Fractions containing the product, appearing near the end of the elution, were evaporated. Trituration of the residue with EtOH gave 2.90 g (68%) of 5-amino-1-β-D-ribofuranosylimidazole-4- carboxamide 3',5'-cyclic phosphate.
The 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide may be produced by hydrolysis of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide 3',5'- cyclic phosphate with NaOH.
Therapeutic FunctionCardiotonic, Platelet aggregation inhibitor
Biological ActivityCell-permeable, allosteric activator of AMP-activated protein kinase (AMPK). Augments proliferation, differentiation and mineralization of osteoblastic MC3T3-EI cells and attenuates psychosine-induced expression of proinflammatory cytokines and iNOS in astrocytes.
AICAR Preparation Products And Raw materials
Raw materialsIodomethane-->Cyclic AMP-->Sodium hydroxide-->Hydrogen-->Sodium bicarbonate-->Nickel-->Formic acid-->Ammonium hydroxide
Tag:AICAR(2627-69-2) Related Product Information
AICAR (phosphate) Inosine Impurity 1 L-Inosine 2-CHLOROINOSINE Inosine GUANOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT 2-AMINO-8-BROMO-9-((2R,3R,4S,5R)-3,4-DIHYDROXY-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-1,9-DIHYDRO-PURIN-6-ONE XANTHOSINE 2',3',5'-TRI-O-ACETYLINOSINE TIMTEC-BB SBB006472 8-AMINOGUANOSINE IDP INOSINE-5'-TRIPHOSPHORIC ACID, DISODIUM 8-BROMOXANTHOSINE CYTIDYLYL-(3'->5')-GUANOSINE 3'-GMP DISODIUM SALT INOSINE-3',5'-CYCLIC PHOSPHATE 8-BR-CGMP