12. Absinthin

Nomenclature

CAS number: 1362-42-1
(3S,3aS,6S,6aR,6bS,7S,7aR,8S,10aS,11S,13aS,13bR,13cR,14bS)-3,3a,4,5,6,6a,6b,7,7a,8,9,10,10a,13a,13c,14b-Hexadecahydro-6,8-dihydroxy-3,6,8,11,14,15-hexamethyl-2H-7,13b-ethenopentaleno[1″,2″:6,7;5″,4″:6′,7′]dicyclohepta[1,2-b:1′,2′-b′]difuran-2,12(11H)-dione; absinthiin; absynthin.
C30H40O6; mol wt 496.64.
C 72.55%, H 8.12%, O 19.33%.

Description and references

Chief bitter principle of wormwood, Artemisia absinthium L., Compositae. Isoln by chromatography: V. Herout et al., Collect. Czech. Chem. Commun. 21, 1485 (1956); see also Chem. Ind. (London) 1955, 569. Structural studies: L. Novotny et al., ibid. 1958, 465; Collect. Czech. Chem. Commun. 25, 1492 (1960); K. Vokác et al., Tetrahedron Lett. 9, 3855 (1968) DOI. Structure: J. Beauhaire et al., ibid. 21, 3191 (1980) DOI. Total synthesis: W. Zhang et al., J. Am. Chem. Soc. 127, 18 (2005) DOI PubMed.

Chemical structure

Properties

Colorless crystals from benzene, mp 165-166° (dec). [α]D20 +107.0° (c = 1.9 in CHCl3); [α]D20 +103.5° (c = 1.0 in CHCl3).