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| CAS No.: | 66575-29-9 |
|---|---|
| Name: | FORSKOLIN |
| Article Data: | 9 |
| Molecular Structure: | |
|
|
|
| Formula: | C22H34O7 |
| Molecular Weight: | 410.508 |
| Synonyms: | 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,[3R-(3a,4ab,5b,6b,6aa,10a,10ab,10ba)]-;(-)-Forskolin;Coleonol;ForsLean;HL 362;NSC 357088;NSC 375489; |
| EINECS: | 266-410-9 |
| Density: | 1.23 g/cm3 |
| Melting Point: | 282-232 °C |
| Boiling Point: | 519.9 °C at 760 mmHg |
| Flash Point: | 171.8 °C |
| Solubility: | Soluble in ethanol, dimethylsulfoxide and chloroform. Insolule in water. |
| Appearance: | Colorless crystalline solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 21 |
| Safety: | 22-36/37 |
| PSA: | 113.29000 |
| LogP: | 1.51990 |
- 81281-59-67-Benzylideneaminotheophylline
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 68439-39-4Poly(oxy-1,2-ethanediyl), alpha-(2-ethylhexyl)-omega-hydroxy-,
- 852475-26-4MC1568
- 958254-66-51H-Imidazo[4,5-b]pyridine-2-carboxaldehyde, 1-methyl-, hydrochloride
- 99170-93-1N-Methyl-2-oxazolamine
- 717878-06-31-(4-fluorophenyl)-4-nitro-1H-imidazole
- 914458-26-7[5-(2-fluorophenyl)-1-pentyl-1H-pyrrol-3-yl]-1-naphthalenyl-Methanone
- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
| Conditions | Yield |
|---|---|
| In pyridine at 0℃; for 18h; | 100% |
| With pyridine at 0 - 20℃; for 18h; | 100% |
| With pyridine at 0℃; for 20h; | 83% |
- 220423-84-7
(13R)-Spiroforskolin
- 66575-29-9
forskolin
| Conditions | Yield |
|---|---|
| In methanol for 96h; |
- 64657-20-1
7-deacetyl forskolin
- 75-36-5
acetyl chloride
A
- 64657-21-2
(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-6-(acetyloxy)-3-ethenyldodecahydro-5,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran-1-one
B
- 66575-29-9
forskolin
| Conditions | Yield |
|---|---|
| With diisopropylamine In toluene for 3h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
| With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 3h; Ambient temperature; Yield given. Yields of byproduct given; |
- 898546-13-9
(1S,6S,12S,16S,2R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.0.2,607,12]heptadecan-11-one
- 66575-29-9
forskolin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 2: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 3: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 4: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 5: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 6: 100 percent / pyridine / 18 h / 0 °C View Scheme |
- 93108-68-0
(2S,7S,13S,14S,6R,9R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,607,12]heptadec-11-one
- 66575-29-9
forskolin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 2: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 3: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 4: 100 percent / pyridine / 18 h / 0 °C View Scheme |
- 898546-12-8
(1S,6S,12S,16S,2R,11R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11-ol
- 66575-29-9
forskolin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C 2: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 3: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 4: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 5: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 6: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 7: 100 percent / pyridine / 18 h / 0 °C View Scheme |
- 115155-11-8
(1S,6S,11S,12S,2R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11-ol
- 66575-29-9
forskolin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 2: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 3: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 4: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 5: 100 percent / pyridine / 18 h / 0 °C View Scheme |
- 115155-09-4
(1S,6S,11S,12S,2R,16R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.02,607,12]heptadec-13-en-11-ol
- 66575-29-9
forskolin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 2: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 3: 100 percent / pyridine / 18 h / 0 °C View Scheme |
- 898546-14-0
(6S,11S,16S,1R,2R,12R,13R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11,13-diol
- 66575-29-9
forskolin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 2: 100 percent / pyridine / 18 h / 0 °C View Scheme |
- 157201-96-2
(1S,7S,9S,3R,5R,8R,14R)-14-acetyloxy-8,9-dihydroxy-1,5,7,11,11-pentamethyl-6-oxa-5-vinyltricyclo[8.4.0.02,7]tetradec-3-yl acetate
- 66575-29-9
forskolin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 11 steps 1: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C 2: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C 3: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C 4: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C 5: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C 6: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 7: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 8: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 9: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 10: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 11: 100 percent / pyridine / 18 h / 0 °C View Scheme |
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Chemistry
IUPAC Name: (3-Ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-5-yl) acetate
Systematic of 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)- (CAS NO.66575-29-9 ): 3R,4aR,5S,6S,6aS,10S,10aR,10bS)-Dodecahydro-5,6,10,10b-tetrahydroxy-3,4a,7,7,10a-pentamethyl-3-vinyl-1H-naphtho(2,1-b)pyran-1-one 5-acetate ; 1H-Naphtho(2,1-b)pyran-1-one, 5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-, (3R-(3alpha,4abeta,5beta,6beta,6aalpha,10alpha,10abeta,10balpha))- ; 7-beta-Acetoxy-8,13-epoxy-1-alpha,6-beta,9-alpha-trihydroxylabd-14-en-11-one ; Boforsin ; Colforsinum [Latin] ; EINECS 266-410-9 ; Forskolin ; HL 362 ; L 75 1362B ; M 410 ; NSC 357088 ; NSC 375489 ; UNII-1F7A44V6OU
CAS NO: 66575-29-9
Classification Code: Adjuvants, Immunologic ; Anti-Asthmatic Agents ; Antiglaucoma agent ; Autonomic Agents ; Bronchodilator Agents ; Cardiotonic Agents ; Cardiovascular Agents ; Drug / Therapeutic Agent ; Immunologic Factors ; Natural Product ; Peripheral Nervous System Agents ; Protective Agents ; Respiratory System Agents ; Vasodilator Agents
Molecular Formula of 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)- (CAS NO.66575-29-9 ): C22H34O7
Molecular Weight: 410.5012
Molecular Structure:
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Melting Point: 282-232 °C
H bond acceptors: 7
H bond donors: 3
Freely Rotating Bonds: 6
Polar Surface Area: 80.29 Å2
Index of Refraction: 1.551
Molar Refractivity: 105.82 cm3
Molar Volume: 331.3 cm3
Surface Tension: 51.4 dyne/cm
Density of 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)- (CAS NO.66575-29-9 ): 1.23 g/cm3
Flash Point: 171.8 °C
Enthalpy of Vaporization: 91.23 kJ/mol
Boiling Point: 519.9 °C at 760 mmHg
Vapour Pressure: 5.56E-13 mmHg at 25°C
Uses
1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)- (CAS NO.66575-29-9 ) is used as possessing vasodilating and cardiostimulatory properties.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 68mg/kg (68mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Journal of Ethnopharmacology. Vol. 3, Pg. 1, 1981. |
| mouse | LD50 | oral | 3100mg/kg (3100mg/kg) | Medicinal Research Reviews. Vol. 3, Pg. 201, 1983. | |
| rat | LD50 | intraperitoneal | 92mg/kg (92mg/kg) | Journal of Medicinal Chemistry. Vol. 31, Pg. 1872, 1988. | |
| rat | LD50 | oral | 2550mg/kg (2550mg/kg) | Medicinal Research Reviews. Vol. 3, Pg. 201, 1983. |
Safety Profile
Hazard Codes: 
Xn
Risk Statements: 21
R21: Harmful in contact with skin.
Safety Statements: 22-36/37
S22: Do not breathe dust.
S36/37: Wear suitable protective clothing and gloves.
WGK Germany :3
RTECS: QL6150000
F: 10-21