What molecule am I?
(–)-α-Santonin, often referred to simply as santonin, is compound isolated from the flowers of the Artemisia genus of plants found in Russia and central Asia. It was used as anthelmintic, a drug that kills parasitic worms or removes them from the body. But it has severe side effects (see the hazards information box) and has been replaced by much safer ascaricides.
But santonin lives on in organic synthesis. In a recent report, Phil B. Alper and colleagues at the Genomics Institute of the Novartis Research Foundation (San Diego) describe novel photoinduced rearrangements of 2,5-dienones, including santonin.
The authors found that the rearrangements can be “rerouted” in the presence of amines to give previously unknown structures. When they irradiated tricyclic santonin in the presence of methylamine in a continuous-flow reactor, they obtained unusual [4.4.0] and [5.3.0] fused-ring molecules as major products. Elucidation of the precise mechanisms of the phototransformations is under way.
(–)-α-Santonin hazard information
|GHS classification: acute toxicity, oral, category 4|
|H302—Harmful if swallowed|
|GHS classification: acute toxicity, dermal and inhalation, category 2|
|H310/H330—Fatal in contact with skin or if inhaled|
|GHS classification: skin irritation, category 2|
|H315—Causes skin irritation|
|GHS classification: eye irritation, category 2A|
|H319—Causes serious eye irritation|
|GHS classification: specific target organ toxicity—single exposure, category 3, respiratory system|
|H335—May cause respiratory irritation|
(–)-α-Santonin fast facts
|CAS Reg. No.||481-06-1|
|Molar mass||264.30 g/mol|
|Appearance||Colorless to yellow crystals|
|Melting point||175 ºC|
|Water solubility||≈750 mg/L|
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