7914. Pseudoconhydrine

Nomenclature

CAS number: 140-55-6
(3S-trans)-6-Propyl-3-piperidinol; 5-hydroxy-2-propylpiperidine; 5-hydroxyconiine.
C8H17NO; mol wt 143.23.
C 67.08%, H 11.96%, N 9.78%, O 11.17%.

Description and references

In Conium maculatum L., Umbelliferae (hemlock). Extraction procedure: Ladenburg et al., Ber. 24, 1671 (1891); Braun, Ber. 38, 3108 (1905); L"offler, Ber. 42, 116 (1909). Structure: E. Sp"ath et al., Ber. 66, 591 (1933). Stereochemistry: R. K. Hill, J. Am. Chem. Soc. 80, 1611 (1958); K. Tadano et al., J. Carbohydr. Chem. 4, 129 (1985).

Chemical structure

Properties

Hygroscopic needles from abs ether, mp 106° (monohydrate, scales, mp 60° from moist ether). bp 236°. [α]D20 +11° (c = 10 in alc). pK (18°): 3.70. Soluble in water and most organic solvents.

Derivative

Hydrochloride.
C8H17NO.HCl; mol wt 179.69.
C 53.47%, H 10.10%, N 7.79%, O 8.90%, Cl 19.73%.

Properties

Crystals from alcohol, mp 213°. Freely sol in water, sparingly sol in alcohol, acetone.