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| CAS No.: | 73-03-0 |
|---|---|
| Name: | Cordycepin |
| Molecular Structure: | |
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|
|
| Formula: | C10H13N5O3 |
| Molecular Weight: | 251.245 |
| Synonyms: | Cordycepin(6CI,7CI);3'-Deoxyadenosine;9-(3-Deoxy-b-D-ribofuranosyl)adenine;9-Cordyceposidoadenine;9H-Purin-6-amine, 9-(3-deoxy-b-D-erythro-pentofuranosyl)-;Cordycepine;b-D-erythro-Pentofuranoside,adenine-9 3-deoxy-; |
| EINECS: | 200-791-4 |
| Density: | 1.91 g/cm3 |
| Melting Point: | 225-229 °C |
| Boiling Point: | 627.2 °C at 760 mmHg |
| Flash Point: | 333.1 °C |
| Appearance: | crystalline solid |
| Hazard Symbols: |
 Xn, T
|
| Risk Codes: | 40-36/37/38-25-20/21/22 |
| Safety: | 22-36-45-26 |
| Transport Information: | UN 2811 |
| PSA: | 119.31000 |
| LogP: | -0.36960 |
cordycepin
| Conditions | Yield |
|---|---|
| With ammonia In methanol; ethanol at -20℃; for 48h; | 100% |
| Conditions | Yield |
|---|---|
| With lithium triethylborohydride In tetrahydrofuran; dimethyl sulfoxide 1.) 4 deg C, 1 h, 2.) 19-22 deg C, overnight; | 98% |
| With lithium triethylborohydride In dimethyl sulfoxide | 53% |
| With lithium triethylborohydride; acetic acid 1.) Me2SO, THF, 1 h ice-water cooling, then -> room temperature, 2.) H2O; Yield given. Multistep reaction; |
9-((2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine
cordycepin
| Conditions | Yield |
|---|---|
| With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; | 98% |
cordycepin
| Conditions | Yield |
|---|---|
| With palladium on activated charcoal; hydrogen In methanol at 25℃; under 37503.8 Torr; for 8h; | 95% |
| Conditions | Yield |
|---|---|
| With sodium methylate In methanol for 1h; Heating; | 94% |
((2S,4R,5R)-4-acetoxy-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl acetate
cordycepin
| Conditions | Yield |
|---|---|
| With ammonia In methanol for 3h; Ambient temperature; | 93% |
| With potassium carbonate In methanol; water at 20℃; for 3h; | 93% |
| With methanol; ammonia at 0 - 60℃; for 16h; | 90% |
| Stage #1: ((2S,4R,5R)-4-acetoxy-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl acetate With sodium hydroxide In methanol at 25℃; for 1h; Stage #2: With ammonium chloride In methanol for 0.5h; Reagent/catalyst; | 87% |
6-N-5'-O-Bis-<4-methoxytriphenylmethyl>-3'-deoxyadenosine
cordycepin
| Conditions | Yield |
|---|---|
| With acetic acid at 20℃; for 12h; | 92% |
(2R,3R,5S)-2-(6-amino-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)tetrahydrofuran-3-ol
cordycepin
| Conditions | Yield |
|---|---|
| With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 0.5h; | 91% |
9-(3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)adenine
cordycepin
| Conditions | Yield |
|---|---|
| With acetic acid In methanol; dichloromethane at 20℃; for 4h; pH=Ca. 4; | 90% |
9-<5-O-(monomethoxytrityl)-3-deoxy-β-D-erythro-pentofuranosyl>adenine
cordycepin
| Conditions | Yield |
|---|---|
| With acetic acid at 20℃; for 2h; | 85% |
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Molecular Structure of Cordycepin (CAS NO.73-03-0):
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IUPAC Name: (2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
Empirical Formula: C10H13N5O3
Molecular Weight: 251.2419
H bond acceptors: 8
H bond donors: 4
Freely Rotating Bonds: 4
Polar Surface Area: 74.53Å2
Index of Refraction: 1.863
Molar Refractivity: 59.1 cm3
Molar Volume: 130.8 cm3
Surface Tension: 93.6 dyne/cm
Density: 1.91 g/cm3
Flash Point: 333.1 °C
Enthalpy of Vaporization: 97.57 kJ/mol
Boiling Point: 627.2 °C at 760 mmHg
Vapour Pressure: 1.36E-16 mmHg at 25°C
EINECS: 200-791-4
Melting Point: 225-229 °C
Storage temp: -20 °C
Merck: 13,2555
Product Categories: Miscellaneous Natural Products; Bases & Related Reagents; Intermediates & Fine Chemicals; Nucleotides; PharmaceuticalsIn
ChI
InChI=1/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1
Smiles
n1(c2c(c(ncn2)N)nc1)[C@@H]1O[C@H](CO)C[C@H]1O
| 1. | oms-nml:lng 100 µmol/L | CARYAB Caryologia. 28 (1975),301. | ||
| 2. | dnd-hmn:fbr 500 µmol/L | ENMUDM Environmental Mutagenesis. 7 (1985),267. | ||
| 3. | dni-hmn:hla 20 mg/L | JANTAJ Journal of Antibiotics. 35 (1982),119. |
EPA Genetic Toxicology Program.
Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Safety information of Cordycepin (CAS NO.73-03-0):
Hazard Codes: .gif){kind=small}
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T
Risk Statements:
40 Limited evidence of a carcinogenic effect
36/37/38: Irritating to eyes, respiratory system and skin
25 Toxic if swallowed
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:
22: Do not breathe dust
36: Wear suitable protective clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR: UN 2811
WGK Germany: 3
RTECS: AU7358610
F: 10-21
HS Code: 29349990
Cordycepin , with CAS number of 73-03-0, can be called 9H-Purin-6-amine, 9-(3-deoxy-.beta.-D-erythro-pentofuranosyl)- ; 9H-Purine, 6-amino-9-(3-deoxy-.beta.-D-ribofuranosyl)- ; Cordycepin ; 2'-Hydroxy-3'-deoxyadenosine erythro ; 3'-Deoxyadenosine . It is a crystalline solid. Cordycepin (CAS NO.73-03-0) is the first reported in nucleoside antibiotic.
