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Tigogenin

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Name

Tigogenin

EINECS 201-041-9
CAS No. 77-60-1 Density 1.11 g/cm3
PSA 38.69000 LogP 5.79380
Solubility N/A Melting Point 202-204 °C
Formula C27H44O3 Boiling Point 516.6 °C at 760 mmHg
Molecular Weight 416.645 Flash Point 266.2 °C
Transport Information N/A Appearance White, micro-cryst. powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 77-60-1 (Tigogenin) Hazard Symbols N/A
Synonyms

5a-Spirostan-3b-ol (7CI);5a-Spirostan-3b-ol, (25R)- (8CI);(25R)-5a-Spirostan-3b-ol;

Article Data 71

Tigogenin Synthetic route

512-04-9

diosgenin

77-60-1

tigogenin

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol; dichloromethane99%
With hydrogen; acetic acid; palladium on activated charcoal In ethanol; dichloromethane at 20℃; under 760 Torr; for 12h;93%
With 5% Pd/C; hydrogen In ethyl acetate at 20℃; under 3750.38 Torr;
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; for 3h;
915-35-5

hecogenin acetate

77-60-1

tigogenin

Conditions
ConditionsYield
Stage #1: hecogenin acetate With hydrazine hydrate In 2-ethoxy-ethanol at 136℃; Inert atmosphere;
Stage #2: With potassium hydroxide In 2-ethoxy-ethanol at 136℃; for 3h; Inert atmosphere;
98%
61046-18-2

(25R)-5α-Spirostan-2β,3α-diol

77-60-1

tigogenin

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; acetic acid under 1500.15 Torr; for 24h;98%
690275-05-9

C39H72N2O3Si2

77-60-1

tigogenin

Conditions
ConditionsYield
With potassium tert-butylate; tert-butyl alcohol In dimethyl sulfoxide at 100℃; for 24h;95%

26-O-β-D-glucopyransoyl-(25R)-5β-furostane-3β,22ξ,26-triol 3-O-[α-L-rhamnopyranosyl (1->)]-β-D-glucopyranside

77-60-1

tigogenin

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 3h; Heating;57.9%
Conditions
ConditionsYield
With hydrogenchloride for 2.5h; Product distribution; Heating;A 51.5%
B n/a
C n/a
D n/a
470-07-5

tigogenone

A

77-60-1

tigogenin

B

6788-40-5

(25R)-5α-Spirostan-3α-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 3h; Ambient temperature;A 17%
B 8%
64-17-5

ethanol

108990-28-9

(25R)-22-ethoxy-5α,22αH-furostan-3β,26-diol

64-19-7

acetic acid

77-60-1

tigogenin

64-17-5

ethanol

118633-83-3

(25R)-5α-furost-22ξ-ene-3β,26-diol

64-19-7

acetic acid

77-60-1

tigogenin

118633-83-3

(25R)-5α-furost-22ξ-ene-3β,26-diol

77-60-1

tigogenin

Conditions
ConditionsYield
at 150℃;

Tigogenin Specification

The CAS registry number of Tigogenin is 77-60-1. The systematic name is (3β,5α,25R)-spirostan-3-ol. Its EINECS registry number is 201-041-9. In addition, the molecular formula is C27H44O3 and the molecular weight is 416.64. It belongs to the class of Miscellaneous Natural Products.

Physical properties about this chemical are: (1)ACD/LogP: 6.21; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.21; (4)ACD/LogD (pH 7.4): 6.21; (5)ACD/BCF (pH 5.5): 30645.03; (6)ACD/BCF (pH 7.4): 30645.03; (7)ACD/KOC (pH 5.5): 56613.64; (8)ACD/KOC (pH 7.4): 56613.64; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 27.69 Å2; (13)Index of Refraction: 1.552; (14)Molar Refractivity: 119.65 cm3; (15)Molar Volume: 374.3 cm3; (16)Polarizability: 47.43 ×10-24cm3; (17)Surface Tension: 43.8 dyne/cm; (18)Density: 1.11 g/cm3; (19)Flash Point: 266.2 °C; (20)Enthalpy of Vaporization: 90.78 kJ/mol; (21)Boiling Point: 516.6 °C at 760 mmHg; (22)Vapour Pressure: 7.83E-13 mmHg at 25°C.

Uses of Tigogenin: it can be used as raw materials of dehydro-methyl testosterone and rehabilitation dragons. And it can be used to get (20S)-5a-pregnanetriol-(3b.16b.20). This reaction is a kind of Baeyer-Villiger oxidation reaction. And it will need reagents MCPBA, BF3*Et2O and NaOH and solvents CH2Cl2 and methanol. The reaction time is 2 hours at reaction temperature of 10 °C. The yield is about 85%.

Tigogenin can be used to get (20S)-5a-pregnanetriol-(3b.16b.20)

You can still convert the following datas into molecular structure:
(1)SMILES: O1[C@@H]4[C@H]([C@@H]([C@]12OC[C@@H](CC2)C)C)[C@@]5(C)CC[C@@H]3[C@@]6(C)CC[C@H](O)C[C@@H]6CC[C@H]3[C@@H]5C4
(2)InChI: InChI=1/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
(3)InChIKey: GMBQZIIUCVWOCD-MFRNJXNGBQ

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LDLo intraperitoneal 10mg/kg (10mg/kg)   "Toxins of Animal and Plant Origin, Proceedings International Symposium, 2nd, 1970," de Vries A., and E. Kochva, eds., 3 vols., New York, Gordon and Breach Science Pub., 1971-73Vol. 2, Pg. 597, 1972.

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