Pseudoconhydrine ((3S-trans)-6-Propyl-3-piperidinol)

E. Pseudoconhydrine


Biological Source Its biological source is same as for (Coniine) through ( N-Methylconiine)
Chemical Structure

Pseudoconhydrine
(3S-trans)-6-Propyl-3-piperidinol.
Characteristic Features
(i) It gives hygroscopic needles from absolute ether.
(ii) Its mp stands at 106°C, whereas its monohydrate, scales, gives mp 60°C from moist ether.
(iii) Its physical parameters are: bp 236°C ;[α]D20 +110 (c = 10 in alcohol); pK (18°C): 3.70
(iv) It is soluble in water and
Identification Tests It readily forms the hydrochloride salt (C8H17NO.HCl) as the crystals from ethanol having mp 213ºC.
Biosynthesis of γ-Coniceine and Coniine A fatty acid precursor octanoic acid (capric acid) is employed, which is subsequently transformed into the ketoaldehyde through successive oxidation and reduction steps. The resulting ketoaldehyde acts as a substrate for a transamination reaction, the amino moiety is derived from L-alanine. The ultimate transformation lead to the formation of imine giving the heterocyclic ring present in g-coniceine, and then reduction the coniine as shown below:

Biosynthesis of g-Coniceine and Coniine

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