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Solasodine

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Name

Solasodine

EINECS 204-774-2
CAS No. 126-17-0 Density 1.12 g/cm3
PSA 41.49000 LogP 5.61570
Solubility N/A Melting Point 284°C (dec.)(lit.)
Formula C27H43NO2 Boiling Point 537.9 °C at 760 mmHg
Molecular Weight 413.644 Flash Point 279.1 °C
Transport Information N/A Appearance N/A
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 126-17-0 (Solasodine) Hazard Symbols N/A
Synonyms

Solasod-5-en-3b-ol (7CI,8CI);(3β,22α,25R)-Spirosol-5-en-3-ol;(-)-Solasodine;NSC 178260;NSC 179187;Purapuridine;Solancarpidine;Solasodin;Spirosol-5-en-3-ol, (3β,22α,25R)-;

Article Data 61

Solasodine Synthetic route

1415-78-7, 6159-99-5

solasodine-3β-acetate

126-17-0

solasodine

Conditions
ConditionsYield
With water; sodium hydroxide In methanol; dichloromethane at 20℃; for 3h;93%

C43H61NO2Si

126-17-0

solasodine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 70℃; Inert atmosphere;88%
With hydrogenchloride; water In ethanol for 2h; Reflux;
1000612-48-5

C27H41N3O2

126-17-0

solasodine

Conditions
ConditionsYield
Stage #1: C27H41N3O2 With chloro-trimethyl-silane; sodium iodide In acetonitrile at 20℃; for 2h;
Stage #2: With sodium thiosulfate In water; acetonitrile
Stage #3: With sodium hydroxide In water; acetonitrile pH=9; diastereoselective reaction;
72%
Multi-step reaction with 2 steps
1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 20 °C
2: sodium thiosulfate; sodium hydroxide / water; acetonitrile
View Scheme
6785-55-3

(22S,25R)-22,26-epiminocholest-5-ene-3β,16β-diol

A

17094-86-9

(25R)-22αN-spirosol-4-en-3-one

B

126-17-0

solasodine

Conditions
ConditionsYield
With manganese(IV) oxideA 12%
B 68%
With manganese(IV) oxide In chloroform at 20℃; for 24h;A 12%
B 68%

C30H47NO5S

126-17-0

solasodine

Conditions
ConditionsYield
Stage #1: C30H47NO5S With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: With oxygen In tetrahydrofuran; hexane at 20℃; for 3h;
44%
514-32-9

C27H43NO2

126-17-0

solasodine

Conditions
ConditionsYield
With chloro-trimethyl-silane In dichloromethane for 12h; Inert atmosphere;43%
Stage #1: C27H43NO2 With sodium thiosulfate; sodium hydroxide In water; acetonitrile
Stage #2: In water; acetonitrile

N,O-diacetyl-22-episolasodine

126-17-0

solasodine

Conditions
ConditionsYield
With sodium; butan-1-ol for 24h; Reflux;40%
129850-55-1

(22S,25R)-N-Chloro-22,26-epiminocholest-5-ene-3β,16α-diol

A

129938-55-2

25-Isoetioline

B

126-17-0

solasodine

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 2h;A 27%
B n/a
122387-24-0

(25R)-3β-hydroxy-26-phthalimido-cholest-5-ene-16,22-dione

126-17-0

solasodine

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
20311-51-7

solamargine

126-17-0

solasodine

Conditions
ConditionsYield
With hydrogenchloride; ethanol
With hydrogenchloride
(acid hydrolysis);

Solasodine Specification

The Solasodine, with the CAS registry number 126-17-0, is also known as Spirosol-5-en-3-ol, (3β,22α,25R)-. It belongs to the product category of Alkaloids. Its EINECS number is 204-774-2. This chemical's molecular formula is C27H43NO2 and molecular weight is 413.64. What's more, its systematic name is (3β,22α,25R)-spirosol-5-en-3-ol. Its classification codes are: (1)Natural Product; (2)Reproductive Effect. It is a poisonous glycoalkaloid chemical compound that occurs in plants of the solanaceae family. It is commercially used as a precursor for the production of complex steroidal compounds such as contraceptive pills.When you use it ,please avoid contact with skin and eyes and do not breathe dust.

Physical properties of Solasodine are:
 (1)ACD/LogP: 5.78; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.92; (4)ACD/LogD (pH 7.4): 4.44; (5)ACD/BCF (pH 5.5): 20.11; (6)ACD/BCF (pH 7.4): 661.15; (7)ACD/KOC (pH 5.5): 45.91; (8)ACD/KOC (pH 7.4): 1509.67; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 21.7 Å2; (13)Index of Refraction: 1.572; (14)Molar Refractivity: 121.27 cm3; (15)Molar Volume: 368.3 cm3; (16)Polarizability: 48.07×10-24cm3; (17)Surface Tension: 45.5 dyne/cm; (18)Density: 1.12 g/cm3; (19)Flash Point: 279.1 °C; (20)Enthalpy of Vaporization: 93.71 kJ/mol; (21)Boiling Point: 537.9 °C at 760 mmHg; (22)Vapour Pressure: 8.21E-14 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O[C@@H]6C/C5=C/C[C@@H]1[C@H](CC[C@]3([C@H]1C[C@@H]4O[C@@]2(NC[C@H](C)CC2)[C@H]([C@H]34)C)C)[C@@]5(C)CC6;
(2)Std. InChI: InChI=1S/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1;
(3)Std. InChIKey: KWVISVAMQJWJSZ-VKROHFNGSA-N.

The toxicity data of Solasodine is as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 103mg/kg (103mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Farmakologiya i Toksikologiya Vol. 37, Pg. 719, 1974.
hamster LDLo oral 1200mg/kg (1200mg/kg)   Teratology, The International Journal of Abnormal Development. Vol. 17, Pg. 327, 1978.
mouse LD50 intraperitoneal 899mg/kg (899mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Pharmaceutical Chemistry Journal Vol. 11, Pg. 1095, 1977.
mouse LD50 oral 27500ug/kg (27.5mg/kg)   Farmakologiya i Toksikologiya Vol. 24, Pg. 469, 1961.
rat LD50 intraperitoneal 396mg/kg (396mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Pharmaceutical Chemistry Journal Vol. 11, Pg. 1095, 1977.
rat LD50 oral 4978mg/kg (4978mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Pharmaceutical Chemistry Journal Vol. 11, Pg. 1095, 1977

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