CAS No.58-61-7,Adenosine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	58-61-7
Name:	Adenosine
Article Data:	329

Formula:	C₁₀H₁₃N₅O₄
Molecular Weight:	267.244
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;
EINECS:	200-389-9
Density:	2.08 g/cm³
Melting Point:	234-236 °C(lit.)
Boiling Point:	676.3 °C at 760 mmHg
Flash Point:	362.8 °C
Solubility:	Soluble in water, ammonium hydroxide and dimethyl sulfoxide. Insoluble in ethanol.
Appearance:	white crystalline powder
Risk Codes:	36/37/38
Safety:	24/25
PSA:	139.54000
LogP:	-1.39880

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

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 50℃;	100%

: 7387-57-7
triacetyladenosine

: 58-61-7
adenosine

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 51600-11-4
5'-O-(p-methoxyphenyldiphenylmethyl)adenosine

: 58-61-7
adenosine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With ammonium peroxydisulfate; phosphate buffer at 80℃; for 2h;	95%

: 57018-82-3, 81352-25-2
5'-O-dimethoxytrityladenosine

: 58-61-7
adenosine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Raw Materials

56-65-5

634-01-5

146-92-9

Downstream Products

61-19-8

Total:327 Page 1 of 9 1 2 3 4 5 6 …9 Next>>

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Consensus Reports

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

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 O^2',O^3',O^5'-triacetyl-adenosine. This reaction will need reagent methanol and NH₃.

Uses of Adenosine: it can be used to produce O^2'-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.

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