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66575-29-9

Basic Information
CAS No.: 66575-29-9
Name: 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)-
Article Data: 9
Cas Database
Molecular Structure:
Molecular Structure of 66575-29-9 (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)-)
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: HarmfulXn
Risk Codes: 21
Safety: 22-36/37
Transport Information: N/A
PSA: 113.29000
LogP: 1.51990
Synthetic route
108-24-7

acetic anhydride

64657-20-1

7-deacetyl forskolin

66575-29-9

forskolin

Conditions
ConditionsYield
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
ConditionsYield
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

C

1-acetyl-7-deacetylforskolin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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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    FORSKOLIN

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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:

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: HarmfulXn
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