methyl iodide
A
O3',O5'-methoxyphosphoryl-adenosine
B
O3',O5'-hydroxyphosphoryl-1-methyl-6,N6-didehydro-1,6-dihydro-adenosine
C
cAMP
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl acetamide at 80℃; for 0.0833333h; Yields of byproduct given; | A 68.5% B n/a C n/a |
benzyl bromide
A
(4aR,6R,7R,7aS)-6-(1-Benzyl-6-imino-1,6-dihydro-purin-9-yl)-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol
B
(4aR,6R,7R,7aS)-6-(1-Benzyl-6-imino-1,6-dihydro-purin-9-yl)-2-benzyloxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
C
cAMP
D
cAMP benzyl ester
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl acetamide at 80℃; for 0.25h; | A n/a B 0.7% C n/a D 34% |
With sodium carbonate In N,N-dimethyl acetamide at 80℃; for 0.25h; Product distribution; other alkyl halide; var. inorganic carbonates; | A 2 % Chromat. B 5 % Chromat. C 17 % Chromat. D 74 % Chromat. |
C10H12Cl2N5O5P
cAMP
Conditions | Yield |
---|---|
With potassium hydroxide In water; acetonitrile at 0℃; Yield given; |
2-carboxy-1,N6-etheno adenosine 3',5'-cyclic phosphate
cAMP
Conditions | Yield |
---|---|
In dimethyl sulfoxide Heating; role of the 1,N6-etheno bridge in decarboxylation (without that decarboxylation did not take place at all); |
Conditions | Yield |
---|---|
In 1,4-dioxane; water Quantum yield; Rate constant; Mechanism; Irradiation; var. solvents, var. pH; | |
With Tris buffer In water-d2 at 40℃; Quantum yield; Irradiation; |
A
6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran
B
cAMP
Conditions | Yield |
---|---|
With water In 1,4-dioxane Irradiation; |
A
6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran
B
cAMP
Conditions | Yield |
---|---|
With HEPES buffer In methanol; water Quantum yield; photolytic cleavage; UV-irradiation; | |
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
A
6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran
B
cAMP
Conditions | Yield |
---|---|
With HEPES buffer In methanol; water Quantum yield; photolytic cleavage; UV-irradiation; | |
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
cAMP
Conditions | Yield |
---|---|
With pyridine; tributyl-amine; dicyclohexyl-carbodiimide |
cAMP
Conditions | Yield |
---|---|
With barium dihydroxide |
equatorial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate
cAMP
Conditions | Yield |
---|---|
In water Quantum yield; Irradiation; |
axial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate
cAMP
Conditions | Yield |
---|---|
In water Quantum yield; Irradiation; |
[7-(carboxymethoxy)coumarin-4-yl]methyl ester of cAMP
cAMP
Conditions | Yield |
---|---|
In water Quantum yield; Irradiation; |
[7-(carboxymethoxy)coumarin-4-yl]methyl ester of cAMP
cAMP
Conditions | Yield |
---|---|
In water Quantum yield; Irradiation; |
cyclic adenosine-3',5'-monophosphate [6,7-bis(carboxymethoxy)coumarin-4-yl]methyl ester
cAMP
Conditions | Yield |
---|---|
In water Quantum yield; Irradiation; |
cyclic adenosine-3',5'-monophosphate [6,7-bis(carboxymethoxy)coumarin-4-yl]methyl ester
cAMP
Conditions | Yield |
---|---|
In water Quantum yield; Irradiation; |
equatorial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate
A
7-(diethylamino)-4-(hydroxymethyl)-2H-chromen-2-one
B
cAMP
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
axial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate
A
7-(diethylamino)-4-(hydroxymethyl)-2H-chromen-2-one
B
cAMP
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
equatorial-(coumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
A
4-(hydroxymethyl)coumarin
B
cAMP
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
axial-(coumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
A
4-(hydroxymethyl)coumarin
B
cAMP
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
equatorial-(6-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
A
cAMP
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
axial-(6-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
A
cAMP
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
A
cAMP
B
7-(dimethylamino)-4-(hydroxymethyl)-2H-chromen-2-one
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
A
cAMP
B
7-(dimethylamino)-4-(hydroxymethyl)-2H-chromen-2-one
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
A
cAMP
B
6,7-dimethoxy-4-(hydroxymethyl)coumarin
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
axial-(6,7-dimethoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
A
cAMP
B
6,7-dimethoxy-4-(hydroxymethyl)coumarin
Conditions | Yield |
---|---|
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
Diadenosine triphosphate
A
cAMP
B
5'-adenosine monophosphate
C
adenosine 5'-diphosphate
Conditions | Yield |
---|---|
With sodium hydroxide at 90℃; Kinetics; Product distribution; Further Variations:; pH-values; |
cAMP
Conditions | Yield |
---|---|
With calcium chloride In ethanol; water at 20℃; for 0.166667h; | 96.98% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 7h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; | 96.09% |
cAMP
adenosine 3',5'-(cyclic)phosphate monosodium salt
Conditions | Yield |
---|---|
With sodium hydroxide In water at 40℃; for 0.666667h; pH=6.6 - 6.7; Temperature; | 96% |
cAMP
Conditions | Yield |
---|---|
With calcium carbonate In water at 60℃; for 0.833333h; pH=6.7 - 6.8; Reagent/catalyst; Temperature; | 93.8% |
Conditions | Yield |
---|---|
With phosphate buffer at 25℃; for 5h; AMP deaminase from Aspergillus sp.; | 93% |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane Ambient temperature; | 80% |
cAMP
Br-cAMP
Conditions | Yield |
---|---|
With bromine; sodium acetate In water at 20℃; for 24h; | 76% |
With bromine; sodium acetate In water at 20℃; for 25h; | 76% |
With bromine; sodium acetate In water at 20℃; for 24h; |
cAMP
Conditions | Yield |
---|---|
Stage #1: cAMP With tributyl-amine In methanol; ethanol for 1h; Reflux; Stage #2: (E)-di-tert-butyl 2-(3-(7-(diethylamino)-4-(((methylsulfonyl)oxy)methyl)-2-oxo-2H-chromen-3-yl)acrylamido)succinate In acetonitrile for 2.5h; Reflux; | 65% |
cAMP
Conditions | Yield |
---|---|
In methanol at 20℃; for 25.5h; | 57% |
Conditions | Yield |
---|---|
With silver(l) oxide In dimethyl sulfoxide; acetonitrile at 65℃; for 18h; | 52% |
4-(bromomethyl)-7-methoxycoumarin
cAMP
Conditions | Yield |
---|---|
With silver(l) oxide In dimethyl sulfoxide; acetonitrile at 60℃; for 45h; | 44% |
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide at 30℃; for 18h; | 38% |
Conditions | Yield |
---|---|
With silver(l) oxide In dimethyl sulfoxide; acetonitrile at 60℃; for 45h; | A 31% B 27% |
Conditions | Yield |
---|---|
With silver(l) oxide In dimethyl sulfoxide; acetonitrile at 60℃; for 45h; | 14% |
Conditions | Yield |
---|---|
at 98℃; zeitlicher Verlauf.Hydrolysis; | |
at 100℃; zeitlicher Verlauf.Hydrolysis; |
cAMP
phosphoric acid inosine-3',5'-diyl ester
Conditions | Yield |
---|---|
With potassium nitrite; water wss.Loesung vom pH 3; |
Conditions | Yield |
---|---|
With cerium(III) chloride; water at 30℃; Rate constant; Mechanism; pH 8.0; velocity const. - var. pH's dependence; | |
With buffer pH 7; tris(3-aminopropyl)amine cobalt(III) hydroxo aqua at 25℃; relative rates of hydrolysis to the monoesters 3'-AMP and 5'-AMP; var. cobalt(III)-complexes; | |
With hydrogenchloride at 90.1℃; Rate constant; |
Conditions | Yield |
---|---|
With tributyl-amine In acetic acid at 50℃; for 0.5h; |
Conditions | Yield |
---|---|
With sodium hydroxide; silver nitrate 1.) water; 2.) DMF, rt, 3 days; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With barium(II) iodide; sodium perchlorate; triethylamine 1.) pyridine, heating 3-4 min, then Rt, 6 d; 2.) water, methanol, ether; 3.) methanol, acetone; Multistep reaction; |
Conditions | Yield |
---|---|
With tributyl-amine In acetic acid at 50℃; for 0.5h; |
(E/Z)-crotyl bromide
cAMP
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; 1,5-Diazabicyclo[5.4.0]undec-5-ene In N,N-dimethyl-formamide at 60℃; for 5h; | 146 g |
Conditions | Yield |
---|---|
With tributyl-amine In acetic acid at 50℃; for 0.5h; |
Conditions | Yield |
---|---|
With tributyl-amine In acetic acid at 50℃; for 0.5h; |
Conditions | Yield |
---|---|
With tributyl-amine In acetic acid at 50℃; for 0.5h; |
Conditions | Yield |
---|---|
With tributyl-amine In acetic acid at 50℃; for 0.5h; |
Conditions | Yield |
---|---|
With tributyl-amine In chloroform; acetic acid at 50℃; for 0.5h; |
Molecule structure of Cyclic AMP (CAS NO.60-92-4):
IUPAC Name: (1S,6R,8R,9R)-8-(6-Aminopurin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3λ5-phosphabicyclo[4.3.0]nonan-9-ol
Molecular Formula: C10H12N5O6P
Molecular Weight: 329.24 g/mol
EINECS: 200-492-9
Density: 2.47 g/cm3
Melting Point: 260 °C
Boiling Point: 701.5 °C at 760 mmHg
Flash Point: 378 °C
Water Solubility: 50 mg/mL
Index of Refraction: 2.011
Molar Refractivity: 67.04 cm3
Molar Volume: 133 cm3
Surface Tension: 153.8 dyne/cm
XLogP3-AA: -2.6
H-Bond Donor: 3
H-Bond Acceptor: 10
Rotatable Bond Count: 1
Tautomer Count: 3
Exact Mass: 329.05252
MonoIsotopic Mass: 329.05252
Topological Polar Surface Area: 155
Heavy Atom Count: 22
Canonical SMILES: C1C2C(C(C(O2)N3C=NC4=C3N=CN=C4N)O)OP(=O)(O1)O
Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=CN=C4N)O)OP(=O)(O1)O
InChI: InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChIKey: IVOMOUWHDPKRLL-KQYNXXCUSA-N
Product Categories: Pharmaceutical Intermediates; Nucleotides and Nucleic Acids; Nucleic acids
Cyclic AMP (CAS NO.60-92-4) is used for intracellular signal transduction, such as transferring the effects of hormones like adrenaline and glucagon, which cannot pass through the cell membrane. Cyclic AMP also regulates the passage of Ca2+ through ion channels.
Cyclic AMP is synthesised from ATP by adenylyl cyclase located on the inner side of the plasma membrane.
1. | oms-hmn:oth 100 µmol/L | JIDEAE Journal of Investigative Dermatology. 65 (1975),52. | ||
2. | oms-mus:fbr 1 mmol/L | IJCNAW International Journal of Cancer. 13 (1974),404. | ||
3. | dns-ham:oth 130 mmol/L | CNREA8 Cancer Research. 42 (1982),3669. |
Reported in EPA TSCA Inventory.
Hazard Codes: C, Xi
Risk Statements: 34-36/37/38
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-45-36/37/39-26-36
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
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: AU7357600
F: 10-21
Human mutation data reported. When heated to decomposition it emits toxic fumes of POx and NOx.
Cyclic AMP (CAS NO.60-92-4) is also named as 3',5'-AMP ; 4-26-00-03618 (Beilstein Handbook Reference) ; Adenosine 3',5'-cyclic monophosphate ; Adenosine 3',5'-cyclophosphate ; Adenosine 3',5'-monophosphate ; Adenosine 3',5'-phosphate ; Adenosine cyclic 3',5'-phosphate ; Adenosine cyclic monophosphate ; cAMP ; cyclic 3',5'-AMP ; cyclic 3',5'-Adenylic acid ; cyclic Adenosine 3',5'-monophosphate ; cyclic Adenosine 3',5'-phosphate . Cyclic AMP (CAS NO.60-92-4) is white crystalline powder. It is slightly soluble in water, almost insoluble in ethanol or ether.
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