Welcome to LookChem.com Sign In|Join Free
  • or
Home > Products >  > 

Adenosine

Related Products

Hot Products

Name

Adenosine

EINECS 200-389-9
CAS No. 58-61-7 Density 2.08 g/cm3
PSA 139.54000 LogP -1.39880
Solubility Soluble in water, ammonium hydroxide and dimethyl sulfoxide. Insoluble in ethanol. Melting Point 234-236 °C(lit.)
Formula C10H13N5O4 Boiling Point 676.3 °C at 760 mmHg
Molecular Weight 267.244 Flash Point 362.8 °C
Transport Information N/A Appearance white crystalline powder
Safety 24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 58-61-7 (Adenosine) Hazard Symbols N/A
Synonyms

Adenosine(AR);Adenocor;9-beta-D-Ribofuranosyl-9H-purin-6-amine;(3R,4R,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;9H-Purin-6-amine, 9beta-D-ribofuranosyl-;Sandesin;Usaf cb-10;Myocol;.beta.-Adenosine;Adenosin [German];Boniton;Adenoside;9-β-D-Ribofuranosyladenine;.beta.-D-Ribofuranoside, adenine-9;.beta.-D-Adenosine;Adenocard;46969-16-8;beta-Adenosine;Adrekar;SR 96225;adenine-D-ribose;Adenosine [USAN:BAN];9.beta.-D-Ribofuranosyladenine;6-Amino-9.beta.-D-ribofuranosyl-9H-purine;adenine-9;Riboadenosine;D-Adenosine;Nucleocardyl;beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1-deoxy-;46946-45-6;Adenine nucleoside;(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;6-Amino-9-.beta.-ribofuranosyl-9H-purine;4-Aminopyrazolo[3,4-d]pyrimidine ribonucleoside;9-beta-D-Ribofuranosyladenine;Adenosine (8CI,9CI);Adenine riboside;

Article Data 329

Adenosine Synthetic route

35638-82-5

(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol

58-61-7

adenosine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 50℃;100%
7387-57-7

triacetyladenosine

58-61-7

adenosine

Conditions
ConditionsYield
With lipase A from Aspergillus niger In aq. phosphate buffer; acetonitrile at 25℃; for 0.5h; pH=7; Enzymatic reaction;99%
With ammonia at 25℃;83%
With methanol; ammonia
69304-45-6

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine

58-61-7

adenosine

Conditions
ConditionsYield
With ammonium fluoride In methanol at 60℃; for 3h;99%
With ammonium fluoride In methanol at 60℃; for 3h; other silyl ethers;99%
88121-73-7

N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

74-89-5

methylamine

A

2-(4-nitrophenyl)ethyl N-methylcarbamate

B

58-61-7

adenosine

Conditions
ConditionsYield
In 1,4-dioxane for 1.5h; Product distribution; Mechanism; Ambient temperature;A 93%
B 99%
51600-11-4

5'-O-(p-methoxyphenyldiphenylmethyl)adenosine

58-61-7

adenosine

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 0.1h; detritylation;98%
With hydrogenchloride In water; acetonitrile at 60℃; for 0.25h; pH=Ca. 1; Inert atmosphere;63 mg
1867-73-8

N6-methyladenosine

58-61-7

adenosine

Conditions
ConditionsYield
With benzophenone; Selectfluor In water; acetonitrile for 5h; Reagent/catalyst; Inert atmosphere; UV-irradiation;97%
With Selectfluor; riboflavin In water; acetonitrile at 37℃; under 760.051 Torr; for 2h; Reagent/catalyst; Inert atmosphere; Irradiation;86%
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Mechanism; Kinetics; Reagent/catalyst; Irradiation; chemoselective reaction;79%
With dihydrogen peroxide; ammonium bicarbonate at 37℃; for 24h;
18048-85-6

5'-O-(triphenylmethyl)adenosine

58-61-7

adenosine

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; silica gel In dichloromethane at 25℃; for 1.5h; detritylation;95%
With cerium(IV) triflate; water In acetonitrile at 25℃; for 1.5h;88%
With chlorine In chloroform at 4℃; for 0.5h;85%
With sulfuric acid; water; silica gel In acetonitrile at 25℃; for 0.283333h;82%
With trifluoroacetic acid In water; acetonitrile at 0 - 20℃; for 12h;36 mg
23666-24-2

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-methoxybenzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

58-61-7

adenosine

Conditions
ConditionsYield
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h;95%
57018-82-3, 81352-25-2

5'-O-dimethoxytrityladenosine

58-61-7

adenosine

Conditions
ConditionsYield
With K 10 clay In methanol; water for 20h; Ambient temperature;95%
With cerium(IV) triflate; water In acetonitrile at 25℃; for 0.75h;95%
With 1,1,1,3',3',3'-hexafluoro-propanol for 1h; Ambient temperature;87 % Turnov.
Multi-step reaction with 6 steps
1: Et3N; DMAP / CH2Cl2
2: dichloroacetic acid; pyrrole / CH2Cl2
3: 87 percent / 2,4,6-triisopropylbenzenesulfonyl chloride; 3-nitro-1,2,4-1H-triazole; pyridine / 1 h / 20 °C
4: Me3SiCl / acetonitrile / 6 h / 60 °C
5: 0.060 g / aq. NH3 / acetonitrile / 0.08 h / 20 °C
6: CD3CO2D; D2O / 23 °C
View Scheme
2946-39-6

8-bromoadenosine

58-61-7

adenosine

Conditions
ConditionsYield
With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol In water at 100℃; for 4h;94%
With potassium fluoride; N,O-bis-(trimethylsilyl)-acetamide; perhydrodibenzo-18-crown-6 In acetonitrile for 96h; Heating;36%
With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol; 1,1'-azobis(1-cyanocyclohexanenitrile); triethylamine In water at 100℃; for 1h;94 % Turnov.
Multi-step reaction with 2 steps
1.1: H2SO4; NaNO2; KBr / 3 h / -15 - 20 °C
1.2: H2O / 65 °C
1.3: 0.14 g / aq. NaOH / dimethylsulfoxide / 5 h
2.1: UV-irradiation
View Scheme
Multi-step reaction with 3 steps
1: pyridine / 0.5 h
2: sodium naphthalenide / tetrahydrofuran / -60 °C
3: aq. NH3 / methanol / 0.5 h
View Scheme

Adenosine Consensus Reports

  Adenosine (CAS NO.58-61-7) is reported in EPA TSCA Inventory.

Adenosine Specification

The Adenosine, with the CAS registry number 58-61-7, is also known as 9H-Purin-6-amine, 9beta-D-ribofuranosyl-. It belongs to the product categories of Pharmaceutical Intermediates; Fine Chemical & Intermediates; Purine; API intermediates; Nucleosides and their analogs; Biochemistry; Nucleosides, Nucleotides & Related Reagents; Nucleic acids. Its EINECS registry number is 200-389-9. This chemical's molecular formula is C10H13N5O4 and molecular weight is 267.24. Its IUPAC name is called (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol. This chemical's classification codes are Analgesics; Anti-arrhythmia agents; Cardiac depressant [anti-arrhythmic]; Cardiovascular agents; Central Nervous System Agents; Drug / Therapeutic Agent; Human Data; Mutation data; Peripheral Nervous System Agents; Sensory System Agents; Vasodilator agents. When you are using this chemical, please be cautious about it. You must avoid contacting it with skin and eyes. 

Physical properties of Adenosine: (1)# of Rule of 5 Violations: 1; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 8.94; (5)ACD/KOC (pH 7.4): 9.254; (6)#H bond acceptors: 9; (7)#H bond donors: 5; (8)#Freely Rotating Bonds: 5; (9)Index of Refraction: 1.907; (10)Molar Refractivity: 59.959 cm3; (11)Molar Volume: 128.164 cm3; (12)Surface Tension: 107.624 dyne/cm; (13)Density: 2.085 g/cm3; (14)Flash Point: 362.796 °C; (15)Enthalpy of Vaporization: 104.298 kJ/mol; (16)Boiling Point: 676.271 °C at 760 mmHg; (17)Vapour Pressure: 0 mmHg at 25°C.

Preparation: Adenosine can be prepared by O2',O3',O5'-triacetyl-adenosine. This reaction will need reagent methanol and NH3.



Uses of Adenosine: it can be used to produce O2'-methyl-adenosine. This reaction will need reagent aqueous 1,2-dimethoxy-ethane.



Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a β-N9-glycosidic bond. Adenosine is an endogenous purine nucleoside that modulates many physiological processes. Adenosine plays an important role in biochemical processes, such as energy transfer—as adenosine triphosphate (ATP) and adenosine diphosphate (ADP)—as well as in signal transduction as cyclic adenosine monophosphate, cAMP.

You can still convert the following datas into molecular structure:
(1)SMILES:c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N;
(2)Std. InChI:InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1;
(3)Std. InChIKey:OIRDTQYFTABQOQ-KQYNXXCUSA-N;

The toxicity data is of Adenosine as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 50ug/kg/1M-I (0.05mg/kg) LUNGS, THORAX, OR RESPIRATION: BRONCHIOLAR CONSTRICTION Human & Experimental Toxicology. Vol. 13, Pg. 263, 1994.
man TDLo intravenous 143ug/kg/I (0.143mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: HEADACHE
Medical Journal of Australia.
man TDLo intravenous 171ug/kg (0.171mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

CARDIAC: PULSE RATE
American Journal of Emergency Medicine. Vol. 11, Pg. 192, 1993.
man TDLo intravenous 257ug/kg (0.257mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
American Journal of Emergency Medicine. Vol. 11, Pg. 249, 1993.
man TDLo intravenous 257ug/kg/1D-I (0.257mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: CHANGE IN RATE
Annals of Internal Medicine. Vol. 122, Pg. 351, 1995.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral > 20gm/kg (20000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 45, 1980.
women TDLo intravenous 240ug/kg (0.24mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) American Journal of Emergency Medicine. Vol. 14, Pg. 300, 1996.
women TDLo intravenous 360ug/kg/1H-I (0.36mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: CHANGE IN RATE
American Journal of Emergency Medicine. Vol. 10, Pg. 326, 1992.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 58-61-7