Conhydrine
Chemical compound From Wikipedia, the free encyclopedia
Conhydrine is a poisonous alkaloid found in poison hemlock (Conium maculatum) in small quantities.
-alpha-Conhydrine.png) | |
| Names | |
|---|---|
| Preferred IUPAC name
(1R)-1-[(2S)-Piperidin-2-yl]propan-1-ol | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.007.090 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H17NO | |
| Molar mass | 143.230 g·mol−1 |
| Melting point | 121 °C (250 °F; 394 K) |
| Boiling point | 226 °C (439 °F; 499 K) |
| moderate | |
| Solubility in ethanol | good |
| Solubility in chloroform | good |
| Solubility in diethylether | moderate |
Chiral rotation ([α]D) |
+10° (natural) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isolation and properties
Summarize
Perspective
This oxygenated alkaloid was isolated by Wertheim from C. maculatum.[1] It crystallises in colourless leaflets, has a coniine-like odour, can be sublimed, and is strongly basic. It crystallises readily from ether. The salts are crystalline; the aurichloride small rhombs or prisms, mp. 133 °C; the benzoyl derivative mp. 132 °C.
Constitution
On oxidation with chromic acid, conhydrine yields L-piperidyl-2-carboxylic acid.[2] It is converted into L-coniine either by reduction of the iodo-derivative (iodoconiine), C8H16IN, formed by the action of hydriodic acid and phosphorus at 180 °C[3][4][5] or by hydrogenation of the mixture of coniceines produced, when it is dehydrated by phosphorus pentoxide in toluene.[6]
These and other observations indicate that the oxygen atom must occur as a hydroxyl group, in the n-propyl side chain in either the α- or β-position, since the γ-position would involve the production of piperidyl-2-propionic acid on oxidation. 2-β-Hydroxypropyl-piperidine suggested by Willstätter[2] seemed to be excluded, since neither of the two forms of this product prepared by Löffler and Tschunke[7] resembled conhydrine, and these authors suggested the α-position as probably representing the alkaloid. Support for this view was provided by Hess and coworkers[8][9][10] ,[11][12] who showed that DL--N-methylconhydrone is N-methyl-2-piperidyl ethyl ketone, that DL-conhydrine (mp. 69–70 °C), produced by a somewhat indirect method, is identical with the product, mp. 69.5–71.5 °C, prepared by Engler and Bauer[13][14] by the reduction with sodium in ethyl alcohol of 2-pyridyl ethyl ketone, and that conhydrine on dehydrogenation over platinum or palladium asbestos gives rise to a mixture of tetrahydropyridyl 2-ethyl ketone and 2-α-hydroxypropyl-pyridine. Späth and Adler[6] have shown that conhydrine can be degraded in two stages by exhaustive methylation to trimethylamine, and a mixture of two products, an oil, C8H14O, bp. 157–159 °C@744 mmHg, and a crystalline substance, C8H16O2, mp. 75–76 °C. The oil, when heated with water at 170 °C is converted, by addition of a molecule of water, into the crystalline substance. The latter contains two active hydrogen atoms (Zerewitinoff estimation), and on exposure to hydrogen over Pd/C absorbs enough to saturate one double bond producing a new substance, mp. 94–96 °C. On oxidation with permanganate in dilute sulfuric acid, propionaldehyde and succinic acid are produced, whilst the saturated substance, mp. 94–96 °C, is oxidised to n-valeric acid. These results indicate that the substance of mp. 75–76 °C is εζ-dihydroxy-Δα-n-octene, that the oil, C8H14O, is the corresponding oxide, and that the representation of conhydrine as 2-α-hydroxypropyl-pyridine accounts for their production.
References
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