5754. Marrubiin
Nomenclature
CAS number: 465-92-9
[2aS-(2aα,5aβ,6α,7α,8aα,8bα)]-6-[2-(3-Furanyl)ethyl]decahydro-6-hydroxy-2a,5a,7-trimethyl-2H-naphtho[1,8-bc]furan-2-one; 15,16-epoxy-6β,9-dihydroxy-8βH-labda-13(16),14-dien-19-oic
acid γ-lactone; 5-[2-(3-furyl)ethyl]decahydro-5,8-dihydroxy-1,4a,6-trimethyl-1-naphthoic
acid γ-lactone. C20H28O4; mol wt 332.43.
C 72.26%, H 8.49%, O 19.25%.
Description and references
Diterpene lactone principle isolated from white horehound, Marrubium vulgare (Tourn.) L., Labiatae: Harms, Arch. Pharm. 83, 144 (1842); Ludwig, Kromayer, ibid. 158, 257 (1861); Nicholas, J. Pharm. Sci. 53, 895 (1964). Alternate view that marrubiin is an artefact generated from premarrubiin during the isoln: Henderson, McCrindle, J. Chem. Soc. C 1969, 2014. Structure and stereochemistry: Cocker et al., J. Chem. Soc. 1953, 2540; Chem. Ind. (London) 1954, 1561; 1955, 1484; Fulke, McCrindle, ibid. 1965, 647. Total stereochemistry: Wheeler et al., Tetrahedron 23, 3909 (1967); Appleton et al., J. Chem. Soc. C 1967, 1943. Synthesis: Mangoni et al., Tetrahedron 28, 611 (1972).
