80-78-4

Basic information

• Product Name: SOLANIDINE
• Synonyms: SOLATUBINE;SOLANIDINE;SOLANIDINE HCL;(3-beta)-solanid-5-en-3-o;22R,25S-Solanidanine;3-beta-Solanid-5-en-3-ol;solanid-5-en-3-beta-ol;Solanid-5-en-3beta-ol
• CAS NO: 80-78-4
• Molecular Formula: C27H43NO
• Molecular Weight: 397.64
• EINECS: 201-309-5
• Product Categories: Alkaloids
• Mol File: 80-78-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 212-214°C
• Boiling Point: 503.1°C at 760 mmHg
• Flash Point: 223.5°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 3.13E-12mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: SOLANIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: SOLANIDINE(80-78-4)
• EPA Substance Registry System: SOLANIDINE(80-78-4)

Safety Data

• Hazard Codes: T+,Xn
• Statements: 23/24/25-53-22
• Safety Statements: 2-13-45-36/37/39-22
• RIDADR: 1544
• WGK Germany: 3
• RTECS: WF0500000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 80-78-4(Hazardous Substances Data)

Usage

Uses

Soladine has been shown to display mutagenic properties in the liver, and is stored in the body for prolonged periods of time.

Purification Methods

Solanidine crystallises from CHCl3/MeOH, aqueous EtOH or aqueous MeOH as needles. TLC on Al2O3 plates using CH2Cl2/MeOH (98:2) gives a spot at RF 0.47. The hydrochloride crystallises from aqueous EtOH with m 345o(dec). The acetate crystallises from EtOH with m 208o. [Schreiber & Roensch Tetrahedron 21 6451965, Kessar et al. Tetrahedron 27 2153 1971, Reichestein & Reich Ann Rev Biochem 15 155 1946, Beilstein 21 III/IV 1398, 27 III/IV 2000.]

InChI:InChI=1/C27H43NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,29H,5,7-15H2,1-4H3

Synthetic route

C43H61NOSi → solanidine (80-78-4)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 2h;	99%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 2h;	99%

3β-Hydroxy-7'-oxo-3'α,6'α-dimethyl-1'αH,3aαH-indolizidino<1',2';16,17>androst-5-en (19330-95-1) → solanidine (80-78-4)

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 0 - 20℃; for 3.5h; Inert atmosphere;	73%
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 0 - 20℃; for 3.5h; Inert atmosphere;	73%

C30H47NO5S (78720-01-1) → solanidine (80-78-4) + camtschatcanidine (78719-99-0) + camtschatcanidine monomesylate (78720-00-0)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating;	A 63.8% B 20% C 15.7%

3β-hydroxy-18,28-cyclo-solanid-5-enium; iodide → 18,28-cyclo-16,28-seco-solanid-5-en-3β-ol (468-24-6) + solanidine (80-78-4)

Conditions	Yield
With ethanol; sodium

3β-benzoyloxy-solanid-5-en-12-one semicarbazone → solanidine (80-78-4)

Conditions	Yield
With ethanol; sodium ethanolate at 200 - 210℃;

solanidine 3-O-α-L-rhamnopyranosyl-(1<*>2)-O-<β-D-glucopyranosyl-(1<*>4)>-β-D-glucopyranoside (81942-09-8) → solanidine (80-78-4)

Conditions	Yield
With hesperidinase In acetic acid at 37℃; for 24h;
Multi-step reaction with 2 steps 1: 38 mg / 1 N H2SO4 / 2 h / Heating 2: hesperidinase / aq. acetic acid / 24 h / 37 °C View Scheme

solanidine 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside (472-51-5) → solanidine (80-78-4)

Conditions	Yield
With hesperidinase In acetic acid at 37℃; for 24h;

solanidine 3-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside → solanidine (80-78-4)

Conditions	Yield
With hesperidinase In acetic acid at 37℃; for 24h;

α-chaconine (20562-03-2) → solanidine 3-O-β-D-glucopyranoside (511-36-4) + L-rhamnose (73-34-7) + solanidine (80-78-4)

Conditions	Yield
With water In 1,4-dioxane at 120℃; for 70h;	A 25 mg B 20 mg C 9 mg

α-chaconine (20562-03-2) → solanidine 3-O-β-D-glucopyranoside (511-36-4) + solanidine (80-78-4) + solanidine 3-O-α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranoside (469-14-7) + solanidine 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside (472-51-5)

Conditions	Yield
at 300℃;	A 27 mg B 15 mg C 19 mg D 31 mg

α-chaconine (20562-03-2) → L-rhamnose (6014-42-2) + solanidine (80-78-4) + β2-chaconine

Conditions	Yield
With Gibberella pilicaris; MacIlvain buffer at 30℃; Product distribution; various strains of G. pulicaris;

α-chaconine → solanidine (80-78-4)

Conditions	Yield
With hydrogenchloride; methanol; water

α-solanine → solanidine (80-78-4)

Conditions	Yield
With hydrogenchloride; ethanol; water

solacaulin → solanidine (80-78-4)

Conditions	Yield
With hydrogenchloride; water

α-solanine → solanida-3,5-diene (26516-51-8) + solanidine (80-78-4)

Conditions	Yield
With hydrogenchloride
With hydrogenchloride; water

3β-hydroxy-18,28-cyclo-solanid-5-enium- → 18,28-cyclo-16,28-seco-solanid-5-en-3β-ol (468-24-6) + solanidine (80-78-4)

Conditions	Yield
With ethanol; sodium

3β-hydroxy-18,28-cyclo-solanid-5-enium- → solanidine (80-78-4) + pseudosolanidyne

Conditions	Yield
With ethanol; sodium

3β-hydroxy-18,28-cyclo-solanid-5-enium; iodide → solanidine (80-78-4) + pseudosolanidyne

Conditions	Yield
With ethanol; sodium

ethanol (64-17-5) + 3β-hydroxy-18,28-cyclo-solanid-5-enium; iodide + sodium → solanidine (80-78-4) + pseudosolanidyne

camtschatcanidine monomesylate (78720-00-0) → solanidine (80-78-4)

Conditions	Yield
Multi-step reaction with 2 steps 2: 63.8 percent / LiAlH4 / diethyl ether / 1 h / Heating View Scheme

C28H43NO3 → solanidine (80-78-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 2 h / 20 °C / Inert atmosphere; Reflux 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 3.5 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 2 h / 20 °C / Inert atmosphere 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 3.5 h / 0 - 20 °C / Inert atmosphere View Scheme

C43H59N3O3Si → solanidine (80-78-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -70 °C 2.1: dmap; pyridine / dichloromethane / 9 h / 0 - 20 °C 3.1: acetonitrile / 7 h / Reflux 3.2: 10 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C View Scheme

C43H63N3O3Si → solanidine (80-78-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap; pyridine / dichloromethane / 9 h / 0 - 20 °C 2.1: acetonitrile / 7 h / Reflux 2.2: 10 h / 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C View Scheme

(22R,25R)-3β-acetoxy-5-en-furostan-26-oic acid → solanidine (80-78-4)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: tetra-(n-butyl)ammonium iodide; boron trifluoride diethyl etherate; acetic anhydride / dichloromethane / 7 h 2.1: sodium azide / N,N-dimethyl-formamide / 65 °C 3.1: potassium carbonate / methanol / 45 °C 4.1: 1H-imidazole / dichloromethane / 1 h / 0 - 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -70 °C 6.1: dmap; pyridine / dichloromethane / 9 h / 0 - 20 °C 7.1: acetonitrile / 7 h / Reflux 7.2: 10 h / 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C View Scheme

C45H67N3O7S2Si → solanidine (80-78-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetonitrile / 7 h / Reflux 1.2: 10 h / 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C View Scheme

C29H43IO4 → solanidine (80-78-4)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: sodium azide / N,N-dimethyl-formamide / 65 °C 2.1: potassium carbonate / methanol / 45 °C 3.1: 1H-imidazole / dichloromethane / 1 h / 0 - 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -70 °C 5.1: dmap; pyridine / dichloromethane / 9 h / 0 - 20 °C 6.1: acetonitrile / 7 h / Reflux 6.2: 10 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C View Scheme

C29H43N3O4 → solanidine (80-78-4)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium carbonate / methanol / 45 °C 2.1: 1H-imidazole / dichloromethane / 1 h / 0 - 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -70 °C 4.1: dmap; pyridine / dichloromethane / 9 h / 0 - 20 °C 5.1: acetonitrile / 7 h / Reflux 5.2: 10 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C View Scheme

C27H41N3O3 → solanidine (80-78-4)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 1H-imidazole / dichloromethane / 1 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -70 °C 3.1: dmap; pyridine / dichloromethane / 9 h / 0 - 20 °C 4.1: acetonitrile / 7 h / Reflux 4.2: 10 h / 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C View Scheme

C43H64O4Si → solanidine (80-78-4)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: dmap; triethylamine / dichloromethane / 20 °C 2.1: sodium azide / N,N-dimethyl-formamide / 6 h / 60 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C 3.2: 0.5 h / 0 - 20 °C 4.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 2.5 h / 0 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 50 °C View Scheme

acetic anhydride (108-24-7) + solanidine (80-78-4) → 3β-acetoxy-5-solanidene (4216-84-6)

Conditions	Yield
With pyridine Ambient temperature;	90%

solanidine (80-78-4) + acetic acid (64-19-7) → 3β-Acetoxy-5α-chlorosolanidene (153472-18-5)

Conditions	Yield
With hydrogenchloride In chloroform at 4℃; for 72h;	88%

solanidine (80-78-4) + Trichloroacetyl chloride (76-02-8) → 3β-trichloroacetoxy-5-solanidene (187959-85-9)

Conditions	Yield
With pyridine for 1.5h;	84%

solanidine (80-78-4) → solanidine N-oxide

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -10℃; for 168000h; Oxidation;	80%

solanidine (80-78-4) → 3β-hydroxy-5α-chlorosolanidane (187959-86-0)

Conditions	Yield
With hydrogenchloride In ethanol; chloroform at 4℃; for 96h;	73%

solanidine (80-78-4) + toluenesulfonic acid 3-azidopropyl ester (153207-76-2) → 3-O-(3-azidopropyl)solanidine

Conditions	Yield
Stage #1: solanidine With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: toluenesulfonic acid 3-azidopropyl ester In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;	71%

solanidine (80-78-4) → solanidine N-oxide + 5,6α-epoxy-5α,22αH,25βH-solanidan-3β-ol N-oxide

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 1h; Ambient temperature;	A 56% B 39%

solanidine (80-78-4) + p-toluenesulfonyl chloride (98-59-9) → 3β(p-toluenesulfonyloxy)-22αH,25βH-solanid-5-en-3-ol (160381-26-0) + 3α,5-cyclo-5α,22αH,25βH-solanidan-6β-ol (160381-27-1)

Conditions	Yield
With pyridine 1.) 0 deg C, 1 h, 2.) room temp., 24 h;	A 37% B 35%

formic acid (64-18-6) + solanidine (80-78-4) → 3β-formyloxy-solanid-5-ene

Conditions	Yield
With water

solanid-5-en-3β-ol; hydrochloride (5189-62-8) + solanidine (80-78-4) → solanida-3,5-diene (26516-51-8)

Conditions	Yield
at 360℃;

solanidine (80-78-4) + benzoyl chloride (98-88-4) → 3β-benzoyloxy-solanid-5-ene (124226-61-5)

Conditions	Yield
With pyridine; chloroform

solanidine (80-78-4) + p-toluenesulfonyl chloride (98-59-9) → 3β(p-toluenesulfonyloxy)-22αH,25βH-solanid-5-en-3-ol (160381-26-0)

Conditions	Yield
With pyridine at -10℃;

aluminum isopropoxide (555-31-7) + solanidine (80-78-4) + acetone (67-64-1) + benzene (71-43-2) → Δ4-Solaniden-3-one (4847-18-1)

aluminum tri-tert-butoxide (556-91-2) + solanidine (80-78-4) + acetone (67-64-1) + benzene (71-43-2) → Δ4-Solaniden-3-one (4847-18-1)

solanidine (80-78-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → solanidine 3-O-β-D-glucopyranoside (511-36-4)

solanidine (80-78-4) + methyl iodide (74-88-4) → 3-hydroxy-28ξ-methyl-solanid-5-enium; iodide (5189-63-9)

Conditions	Yield
Im Druckgefaess auf dem Dampfbad;
With xylene at 130 - 140℃;

solanidine (80-78-4) + n-hexadecanoyl chloride (112-67-4) → 3β-palmitoyloxy-solanid-5-ene

Conditions	Yield
at 150℃;

solanidine (80-78-4) → demissidine (474-08-8)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

solanidine (80-78-4) → Leptinidin, Δ5-Solanidendiol-(3β,23β), 23β-Hydroxysolanidin (24884-17-1)

Conditions	Yield
With n-octyl glucopyranoside; NADPH In water at 25℃; for 2h; Mechanism; 14C labeled study on hydroxylation by microsomal fractions from solanum chacoense;;

solanidine (80-78-4) → C27H45NO3 (119766-93-7)

Conditions	Yield
With Peroxyformic acid; dihydrogen peroxide 1.) 75 deg C, 5 min; 2.) 35 deg C, 30 min; Yield given. Multistep reaction;

Upstream product

• 81942-09-8 solanidine 3-O-α-L-rhamnopyranosyl-(1<*>2)-O-<β-D-glucopyranosyl-(1<*>4)>-β-D-glucopyranoside 
• 472-51-5 solanidine 3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside 
• 78720-01-1 C₃₀H₄₇NO₅S 
• 20562-03-2 α-chaconine 
• 64-17-5 ethanol 
• 78720-00-0 camtschatcanidine monomesylate 
• 19330-95-1 3β-Hydroxy-7'-oxo-3'α,6'α-dimethyl-1'αH,3aαH-indolizidino<1',2';16,17>androst-5-en 

Downstream Products

• 160381-26-0 3β(p-toluenesulfonyloxy)-22αH,25βH-solanid-5-en-3-ol 
• 474-08-8 demissidine 
• 160381-27-1 3α,5-cyclo-5α,22αH,25βH-solanidan-6β-ol 
• 511-37-5 solanidine β-D-galactopyranoside 

Relevant articles and documents

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Asymmetric synthesis of (-)-solanidine and (-)-tomatidenol

A concise asymmetric synthesis of two naturally occurring seco-type cholestane alkaloids (-)-solanidine and (-)-tomatidenol from (-)-diosgenin with a linear reaction sequence of 12 steps and 13 steps, respectively, is reported. The synthetic strategy includes the highly controlled establishment of highly functionalized octahydroindolizine ((-)-solanidine) and 1-oxa-6-azaspiro[4.5]decane ((-)-tomatidenol) cores with five stereocenters, respectively, from (-)-diosgenin, featuring two stereoselective cascade transformations including a modified cascade ring-switching process of furostan-26-acid to open the E-ring of (-)-diosgenin and a cascade azide reduction/intramolecular reductive amination to close the E- and F-rings of (-)-solanidine and (-)-tomatidenol. This work should enable further explorations of chemical and biological spaces based on solanidine, tomatidenol and related natural products.

Metabolism of the potato saponins α-chaconine and α-solanine by Gibberella pilicaris

Potato tubers accumulate varying amounts of several saponins preferentially in the peel. These compounds are toxic to living cells containing sterols in their plasma membrane and are therefore thought to be preformed chemical defence compounds. Two strains of the potato pathogen Gibberella pulicaris (Fusarium sambucinum), R-6380 and R-7843, were analysed for their ability to metabolize the most predominant saponins found in tubers, α-chaconine and α-solanine. The first compound is degraded by both strains via removal of α-1,2-L-rhamnose leading to β2-chaconine. This product is converted to the aglycone, solanidine, which is further metabolized to unknown products. The release of α-1,2-L-rhamnose is also the first step in the break down of α-solanine by strain R-6380, followed by the removal of the β-1,3-bound glucose molecule leading to γ-solanine, which is not metabolized any further. Strain R-7843 is not able to metabolize α- solanine. Crude protein extracts of the culture fluid of both strains contained enzymes able to convert α-chaconine to β2-chaconine, but with no α-solanine metabolic activity. This result indicates that G. pulicaris excretes enzymes specific for different saponins.