Chamazulene

Title: Chamazulene
CAS Registry Number: 529-05-5
CAS Name: 7-Ethyl-1,4-dimethylazulene
Additional Names: 1,4-dimethyl-7-ethylazulene; dimethulene
Molecular Formula: C14H16
Molecular Weight: 184.28
Percent Composition: C 91.25%, H 8.75%
Literature 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).
Properties: Blue oil. bp12 161°; bp11 145°. d420 0.9883. uv max: 370 nm (log e 3.7). LD50 i.m. in white mice: 3 g/kg (Boldina, Nazarenko).
Boiling point: bp12 161°; bp11 145°
Absorption maximum: uv max: 370 nm (log e 3.7)
Density: d420 0.9883
Toxicity data: LD50 i.m. in white mice: 3 g/kg (Boldina, Nazarenko)
Derivative Type: Trinitrobenzene derivative
Molecular Formula: C20H19N3O6
Molecular Weight: 397.38
Percent Composition: C 60.45%, H 4.82%, N 10.57%, O 24.16%
Properties: Dark violet needles from abs ethanol, mp 131.5-132.5°.
Melting point: mp 131.5-132.5°
Chanoclavine Chaperonins Chartreusin Charybdotoxin Chaulmoogra Oil

Chamazulene
Chamazulene.svg
Identifiers
CAS number 529-05-5 YesY
PubChem 10719
ChemSpider 10268
Jmol-3D images Image 1
Properties
Molecular formula C14H16
Molar mass 184.28 g mol−1
Appearance Blue oil[1]
Density 0.9883 (at 20 °C)[1]
Boiling point 161 °C (at 12 mmHg)[1]
Hazards
LD50 3 g/kg (i.m., mouse)[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Chamazulene is an aromatic chemical compound with the molecular formula C14H16 found in a variety of plants including in chamomile (Matricaria chamomilla), wormwood (Artemisia absinthium), and yarrow (Achillea millefolium).[1] It is a blue-violet derivative of azulene which is biosynthesized from the sesquiterpene matricin.[2]

Chamazulene has anti-inflammatory properties in vivo.[2]