Solasodine supplier | CasNO.126-17-0

Name
Solasodine
EINECS 204-774-2
CAS No. 126-17-0
Article Data61
CAS DataBase
Density 1.12 g/cm³
Solubility
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
Appearance
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
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)-;
PSA 41.49000
LogP 5.61570

Synthetic route

: 1415-78-7, 6159-99-5
solasodine-3β-acetate

: 126-17-0
solasodine

Conditions

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

: C43H61NO2Si

: 126-17-0
solasodine

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: C30H47NO5S

: 126-17-0
solasodine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
Reaktion ueber mehrere Stufen;

: 20311-51-7
solamargine

: 126-17-0
solasodine

Conditions

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

: 19121-58-5, 20318-30-3
solasonine

: 126-17-0
solasodine

Conditions

Conditions	Yield
With hydrogenchloride
With sulfuric acid
With hydrogen bromide
(acid hydrolysis);

: 19121-58-5, 20318-30-3
solasonine

A: 126-17-0
solasodine

B: 3669-17-8
(25R)-22αN-spirosola-3,5-diene

Conditions

Conditions	Yield
With hydrogenchloride

: 107387-55-3
N-((25R)-3β,22-dihydroxy-(22ξH)-furost-5-en-26-yl)-phthalimide

: 126-17-0
solasodine

Conditions

Conditions	Yield
(i) N2H4, MeOH, CH2Cl2, (ii) aq. HCl; Multistep reaction;

: 7604-97-9
N-((25R)-3β-hydroxy-furosta-5,20(22)-dien-26-yl)-phthalimide

: 126-17-0
solasodine

Conditions

Conditions	Yield
(i) (hydrazinolysis), (ii) aq. HCl, MeOH; Multistep reaction;

: 54302-48-6
O4-(22R,25R)-spirosol-3-en-3β-yl-β-L-6-deoxy-mannopyranosyl β-D-glucopyranoside

: 126-17-0
solasodine

Conditions

Conditions	Yield
With hydrogenchloride In methanol Heating;

: 30040-85-8
(25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16β-diol diacetate

: 126-17-0
solasodine

Conditions

Conditions	Yield
With potassium hydroxide In methanol Heating;

: 129938-54-1
(22S,25R)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one

A: 129938-55-2
25-Isoetioline

B: 126-17-0
solasodine

Conditions

Conditions	Yield
Yield given. Multistep reaction. Further byproducts given;

: solanavione-3-acetate

: 126-17-0
solasodine

Conditions

Conditions	Yield
With hydrazine dihydrochloride Product distribution; Wolff-Kishner reduction;

: solamargine

: 126-17-0
solasodine

Conditions

Conditions	Yield
With trifluoroacetic acid

di-O-acetyl-pseudosolasodine-B: di-O-acetyl-pseudosolasodine-B

: 126-17-0
solasodine

Conditions

Conditions	Yield
With potassium hydroxide

: 36506-65-7
pseudosolasodine diacetate

methanol. KOH-solution: methanol. KOH-solution

: 126-17-0
solasodine

pseudodiosgenin: pseudodiosgenin

: 126-17-0
solasodine

Conditions

Conditions	Yield
Reaktion ueber mehrere Stufen;

: 36456-16-3
(22S,25R)-22,26-Epiminocholest-5-ene-3β,16α-diol

: 126-17-0
solasodine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / N-chlorosuccinimide / CHCl3 / 0.5 h / Ambient temperature 2: NaOEt / ethanol / 2 h View Scheme

: 129938-53-0
(22S,25R)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16β-diol

: 126-17-0
solasodine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 60 percent / CrO3, NaOAc*3H2O, AcOH / H2O / 20 h / Ambient temperature 2: Na, i-PrOH / toluene / 2 h 3: 96 percent / N-chlorosuccinimide / CHCl3 / 0.5 h / Ambient temperature 4: NaOEt / ethanol / 2 h View Scheme
Multi-step reaction with 2 steps 1: 60 percent / CrO3, NaOAc*3H2O, AcOH / H2O / 20 h / Ambient temperature View Scheme

: 129938-54-1
(22S,25R)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one

: 126-17-0
solasodine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Na, i-PrOH / toluene / 2 h 2: 96 percent / N-chlorosuccinimide / CHCl3 / 0.5 h / Ambient temperature 3: NaOEt / ethanol / 2 h View Scheme

: 114696-99-0
(25R)-26-iodo-3β-hydroxy-cholest-5-ene-16,22-dione

: 126-17-0
solasodine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide 2: Reaktion ueber mehrere Stufen View Scheme

: 115388-90-4
(25R)-3β-hydroxy-26-(toluene-4-sulfonyloxy)-cholest-5-ene-16,22-dione

: 126-17-0
solasodine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: butanone; NaI 2: dimethylformamide 3: Reaktion ueber mehrere Stufen View Scheme

: 468-99-5
kryptogenin

: 126-17-0
solasodine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: butanone; NaI 3: dimethylformamide 4: Reaktion ueber mehrere Stufen View Scheme

: 19121-58-5, 20318-30-3
solasonine

: 126-17-0
solasodine

Conditions

Conditions	Yield
With hydrogenchloride; water In isopropyl alcohol at 20℃; Product distribution / selectivity; Heating / reflux;

: 108-24-7
acetic anhydride

: 126-17-0
solasodine

: 30040-85-8
(25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16β-diol diacetate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid at 24.84℃; for 0.00555556h;	100%

: 18α-glycyrrhizic acid

: 126-17-0
solasodine

: C42H62O16*C27H43NO2

Conditions

Conditions	Yield
In methanol Reflux;	99%

: 98-59-9
p-toluenesulfonyl chloride

: 126-17-0
solasodine

: 79659-49-7
(25R)-N-(toluene-4-sulfonyl)-3β-(toluene-4-sulfonyloxy)-22αN-spirosol-5-ene

Conditions

Conditions	Yield
With pyridine at 20℃;	95%

: 126-17-0
solasodine

: 68422-03-7
(22R,25R)-22,26-epiminocholest-5-ene-3β,16β-diol

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol; dichloromethane at 0 - 20℃; for 1h;	87%

: 913966-90-2
2-bromo-3,4,4-trichloro-3-butenoyl chloride

: 126-17-0
solasodine

: solasodinyl 2-bromo-3,4,4-trichlorobut-3-enoate

Conditions

Conditions	Yield
With pyridine In benzene at 20 - 23℃;	84%

: C61H64Cl3NO24

: 126-17-0
solasodine

: C86H105NO25

Conditions

Conditions	Yield
Stage #1: solasodine at -20℃; for 0.333333h; Molecular sieve; Sealed tube; Inert atmosphere; Stage #2: C61H64Cl3NO24 With hydrogen tetrakis(pentafluorophenyl)borate for 0.5h; Molecular sieve; Inert atmosphere; Sealed tube;	82%

: 2094-72-6
1-Adamantanecarbonyl chloride

: 126-17-0
solasodine

: (25R)-solasod-5-en-3β-yl 1-adamantanecarboxylate

Conditions

Conditions	Yield
With pyridine In benzene for 8h; Heating;	78%

: 126-17-0
solasodine

: 17094-86-9
(25R)-22αN-spirosol-4-en-3-one

Conditions

Conditions	Yield
With cyclohexanone; aluminum tri-tert-butoxide In toluene for 11h; Heating;	68%
With aluminum tri-tert-butoxide; acetone
With copper
Multi-step reaction with 2 steps 1: 95 percent / anhyd. pyridine / 20 °C 2: 29 percent / anhyd. sodium acetate / dimethylsulfoxide / 4 h / 80 - 90 °C View Scheme

: 64-19-7
acetic acid

: 126-17-0
solasodine

: 979-02-2
16-dehydropregnenolone acetate

Conditions

Conditions	Yield
Stage #1: solasodine With pyridine; ammonium chloride at 125 - 135℃; for 8 - 9h; Stage #2: acetic acid With chromium(VI) oxide In water; 1,2-dichloro-ethane at 0 - 20℃; for 1h; Product distribution / selectivity;	65%

: 1307870-93-4
C25H34O7S

: 126-17-0
solasodine

: 1307870-88-7
C49H69NO9

Conditions

Conditions	Yield
With N-iodo-succinimide; silver trifluoromethanesulfonate at -50℃; for 2h;	65%

: 126-17-0
solasodine

: 1370010-28-8
C27H42N2O3

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; sodium nitrite In acetic acid at 20℃; for 1h;	56.2%

: 108-24-7
acetic anhydride

: 126-17-0
solasodine

: N,O-diacetyl-22-episolasodine

Conditions

Conditions	Yield
With pyridine at 20℃;	55%

: 572-09-8, 3068-32-4, 4026-32-8, 6919-96-6, 13242-53-0, 14227-54-4, 14795-18-7, 19186-59-5, 19285-38-2, 21698-13-5, 29907-26-4, 53369-42-9, 60619-58-1, 61303-35-3, 67337-79-5, 69127-37-3, 70749-15-4, 72002-90-5, 75247-30-2, 75880-74-9, 78418-57-2, 102339-89-9, 102339-90-2, 103530-40-1, 114028-03-4, 114718-45-5, 138514-70-2, 138514-71-3
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

: 126-17-0
solasodine

: 14144-02-6, 14197-67-2
solasodine tetra-O-acetyl-3β-D-glucopyranoside

Conditions

Conditions	Yield
Stage #1: solasodine With silver(I) acetate In benzene Koenigs-Knorr Glycosidation; Reflux; Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide In benzene for 14h; Koenigs-Knorr Glycosidation; Reflux;	51.83%

: 126-17-0
solasodine

: 33282-87-0
3β,16β-dihydroxypregna-5-ene-20-carboxylic acid 22,16-lactone

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; sodium nitrite In chloroform; acetic acid at 20℃; for 2h;	48.2%

: 108-24-7
acetic anhydride

: 126-17-0
solasodine

: 979-02-2
16-dehydropregnenolone acetate

Conditions

Conditions	Yield
Stage #1: acetic anhydride; solasodine With pyridine for 1.5h; Heating / reflux; Stage #2: With acetic acid for 0.25h; Heating / reflux; Stage #3: With sodium sulphite; sodium dichromate Product distribution / selectivity; more than 3 stages;	48%
Stage #1: acetic anhydride; solasodine With pyridine; toluene-4-sulfonic acid at 160℃; for 6h; Heating / reflux; Stage #2: With acetic acid In water at 20 - 160℃; for 4h; Heating / reflux; Stage #3: With chromium(VI) oxide; sodium sulphite; acetic anhydride Product distribution / selectivity; more than 3 stages;	44.6%
Stage #1: acetic anhydride; solasodine With pyridine for 1h; Heating / reflux; Stage #2: With pyridine hydrochloride In pyridine for 2h; Heating / reflux; Stage #3: With sodium sulphite; sodium dichromate Product distribution / selectivity; more than 3 stages;	20%
Stage #1: acetic anhydride; solasodine; toluene-4-sulfonic acid In acetic acid at 20℃; for 7h; Heating / reflux; Stage #2: With sodium dichromate In acetic acid at 15 - 40℃; for 1h; Stage #3: With sodium sulphite In acetic acid for 2h; Product distribution / selectivity; Heating / reflux;	15%
Behandeln des Reaktionsprodukts mit CrO3 in wss. Essigsaeure und Erhitzen des danach erhaltenen Reaktionsprodukts mit Essigsaeure;

: 126-17-0
solasodine

A: 17094-86-9
(25R)-22αN-spirosol-4-en-3-one

B: solasod-5-en-3β-ol salt with 6-methylsalicylic acid

Conditions

Conditions	Yield
fungus penicillium patulum;	A 18% B 0.5%
fungus penicillium patulum;	A 18% B 0.5%

: 108-24-7
acetic anhydride

: 126-17-0
solasodine

: 4860-15-5
(25R)-3β,N-diacetoxysolasod-5-ene

Conditions

Conditions	Yield
With pyridine for 0.5h; Heating;	12.5%

: 126-17-0
solasodine

: 142182-57-8
N-Hydroxysolasodine

Conditions

Conditions	Yield
With selenium(IV) oxide; dihydrogen peroxide In methanol for 264h;	11%

: 126-17-0
solasodine

A: 103369-64-8
3β-hydroxysolasod-5-en-7-one

B: 107297-22-3
solasod-5-ene-3β,7β-diol

C: solasod-5-ene-3β,7α-diol

Conditions

Conditions	Yield
fungus Cunninghamella elegans;	A 0.04% B 8% C 5.8%
fungus Cunninghamella elegans;	A 0.04% B 8% C 5.8%

...Expand

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

Product Name

Solasodine

Synthetic route

Solasodine Specification

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