Соласодин

Description

Solasodine is a steroidal alkaloid-sapogenin of the spirosolan series, an aglycone of nightshade glycoalkaloids: solasonine and solamargine. Found in plants of the Solanum genus, including the potato Solanum tuberosum and eggplant Solanum melongena; industrial raw materials are species with increased accumulation of glycoalkaloids. The main practical value of solasodin is as a raw material for the semisynthesis of steroid hormones and medicinal substances based on them.

Identification

• CAS No.: 126-17-0
• Chemical formula: C27H43NO2
• English name: Solasodine
• EU number: 204-774-2
• NSC Number: 179187/178260
• Synonyms: solasod-5-en-3β-ol, (3β,22α,25R)-spirosol-5-en-3-ol, purapuridine, solancarpidine, (−)-solasodine
• Class: steroids, steroidal alkaloids of the spirosolan series

Basic Attributes

• Molecular Weight: 413.64
• Exact weight: 413.64
• PSA Specifications: 41.49000
• XLogP3: 5.78
• Appearance: White to Beige
• Crystal color and shape: hexagonal plates made of methanol or obtained by sublimation in a high vacuum
• Density: 1.0159 (estimated)
• Melting point: 200–202 °C
• Boiling point: 532.75°C (approximate estimate)
• Flash point: 279.1 ± 30.1 °C
• Refractive index: 1.6400 (estimate)
• Solubility: DMSO - 0.5 mg/ml, the solution is transparent when heated; does not dissolve in water
• Vapor pressure: 8.21 × 10⁻¹⁴ mm Hg. Art. at 25 °C
• Specific rotation: D25 −98° (c = 0.14 in methanol); D −113° (in chloroform)
• Dissociation constant: pKb 6.3
• Experimental properties: alkaline reaction to litmus paper in an alcoholic environment
• Storage conditions: 2–8 °C

What do these numbers mean for work?

The pKb value of 6.3, together with the alkaline reaction in an alcoholic medium, confirms the basic nature of the molecule: solasodine forms salts with acids, and this is the basis for the scheme of its isolation from plant materials - extraction with acid, precipitation with alkali, recrystallization. XLogP3 5.78 at PSA 41.49 explains the low solubility even in DMSO (0.5 mg/ml) and the need for heating. The shape of the crystals—hexagonal plates upon recrystallization from methanol—serves as an additional sign of batch identity. Density, boiling point, and refractive index are marked as estimates.

Scope of application

• starting material for the semisynthesis of steroid hormones: on its basis, contraceptives, corticosteroids and other steroid drugs are obtained
• parent compound for the synthesis of derivatives with a glucocorticoid-like profile and selective cytotoxicity to squamous cell carcinoma cells
• analytical standard for the determination of glycoalkaloids and their aglycones in nightshade raw materials and food products
• object of research: neuroprotective, antifungal, hypotensive, antitumor, antiatherosclerotic, antiandrogenic and anti-inflammatory effects are described

Storage and handling

The recommended temperature range is 2–8 °C, the container is tightly closed, away from light and moisture. Separated from acids, otherwise the substance goes into the salt form. Steroidal alkaloids of nightshades are toxic when taken orally: wear gloves, avoid dust, keep records of samples.