Lactucin
Structural Formula Vector Image
Title: Lactucin
CAS Registry Number: 1891-29-8
CAS Name: [3aR-(3aa,4b,9aa,9bb)]-3,3a,4,5,9a,9b-Hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methyleneazuleno[4,5-b]furan-2,7-dione
Molecular Formula: C15H16O5
Molecular Weight: 276.28
Percent Composition: C 65.21%, H 5.84%, O 28.96%
Literature References: From various Lactuca spp and Cichorium intybus L., Compositae. Isoln: Schenck, Graf, Arch. Pharm. 274, 537 (1936); 275, 36 (1937); Schenck et al., ibid. 294, 17 (1961). Purification: Späth et al., Monatsh. Chem. 82, 114 (1951). Structure: Dolejs et al., Collect. Czech. Chem. Commun. 23, 2195 (1958); Barton, Narayanan, J. Chem. Soc. 1958, 963; Michl, Högenauer, Monatsh. Chem. 89, 317 (1958). Revised stereochemistry: Bachelor, Itô, Can. J. Chem. 51, 3626 (1973).
Properties: Crystals from methanol, sinters at 218°, mp 228-233°. [a]D +49° (c = 0.90 in methanol), +77.9° (c = 3.44 in pyridine). uv max: 257 nm (e 14,000). Soluble in water, ethanol, methanol, ethyl acetate, dioxane anisol.
Melting point: mp 228-233°
Optical Rotation: [a]D +49° (c = 0.90 in methanol), +77.9° (c = 3.44 in pyridine)
Absorption maximum: uv max: 257 nm (e 14,000)
 
Derivative Type: p-Hydroxyphenylacetate hydrate
Additional Names: Intybin; lactucopicrin
Molecular Formula: C23H22O7
Molecular Weight: 410.42
Percent Composition: C 67.31%, H 5.40%, O 27.29%
Literature References: Identity with intybin: Schmitt, Bot. Arch. 40, 516 (1940), C.A. 36, 5616 (1942). Structure: Michl, Högenauer, Monatsh. Chem. 91, 500 (1960).
Properties: Crystals from water, dec 148-151°. [a]D17.5 +67.3° (pyridine).
Optical Rotation: [a]D17.5 +67.3° (pyridine)

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