2040. Chamazulene

Nomenclature

CAS number: 529-05-5
7-Ethyl-1,4-dimethylazulene; 1,4-dimethyl-7-ethylazulene; dimethulene.
C14H16; mol wt 184.28.
C 91.25%, H 8.75%.

Description and references

Anti-inflammatory principle obtained from chamazulenogenic compds found in chamomile (Matricaria chamomilla L.), wormwood (Artemisia absinthium L.), and yarrow (Achillea millefolium L., Compositae). Isoln: Ruzicka, Rudolph, Helv. Chim. Acta 9, 118 (1926); Ruzicka, Haagen-Smit, ibid. 14, 1104 (1931). Structure: Sorm et al., Collect. Czech. Chem. Commun. 18, 527 (1953); Meisels, Weizmann, J. Am. Chem. Soc. 75, 3865 (1953); Suchy et al., Collect. Czech. Chem. Commun. 21, 477 (1956). Synthesis: Mangoni, Bandiera, Gazz. Chim. Ital. 90, 947 (1960); White, Winter, Tetrahedron Lett. 1963, 137; D. Mukherjee et al., J. Am. Chem. Soc. 101, 251 (1979). Pharmacology: I. G. Boldina, Farmakol. Toksikol. 29, 672 (1966); I. G. Boldina, M. V. Nazarenko, C.A. 67, 42441h (1967).

Chemical structure

Properties

Blue oil. bp12 161°; bp11 145°. d420 0.9883. uv max: 370 nm (log ε 3.7). LD50 i.m. in white mice: 3 g/kg (Boldina, Nazarenko).

Derivative

Trinitrobenzene derivative.
C20H19N3O6; mol wt 397.38.
C 60.45%, H 4.82%, N 10.57%, O 24.16%.

Properties

Dark violet needles from abs ethanol, mp 131.5-132.5°.