Matricarin
Title: Matricarin
CAS Registry Number: 5989-43-5
CAS Name: (3S,3aR,4S,9aS,9bR)-4-(Acetyloxy)-3,3a,4,5,9a,9b-hexahydro-3,6,9-trimethylazuleno[4,5-b]furan-2,7-dione
Molecular Formula: C17H20O5
Molecular Weight: 304.34
Percent Composition: C 67.09%, H 6.62%, O 26.29%
Literature References: Isoln from Matricaria chamomilla L. and Artemisia tilesii Ledeb, Compositae: Z. Cekan et al., Collect. Czech. Chem. Commun. 24, 1554 (1959). Structure: W. Herz, K. Ueda, J. Am. Chem. Soc. 83, 1139 (1961). Molecular conformation: M. Martinez V. et al., J. Nat. Prod. 51, 221 (1988).
Properties: Plates from benzene + petr ether and acetone + petr ether, mp 190-191°. [a]D23 +23.5° (c = 0.65 in chloroform). uv max: 255 nm (e 15,100).
Melting point: mp 190-191°
Optical Rotation: [a]D23 +23.5° (c = 0.65 in chloroform)
Absorption maximum: uv max: 255 nm (e 15,100)
 
Derivative Type: Desacetoxymatricarin
CAS Registry Number: 17946-87-1
Molecular Formula: C15H18O3
Molecular Weight: 246.30
Percent Composition: C 73.15%, H 7.37%, O 19.49%
Literature References: Isoln from Artemisia spp.: M. Holub, V. Herout, Collect. Czech. Chem. Commun. 27, 2980 (1962); H. H. A. Linde, M. S. Ragab, Helv. Chim. Acta 50, 1961 (1967). Synthesis and stereochemistry: E. H. White et al., Tetrahedron 25, 2099 (1969).
Properties: Crystals from ether, mp 205-205.5°, also reported as mp 202-203° (Holub). [a]D24 +52.5° (c = 1 in chloroform).
Melting point: mp 205-205.5°; mp 202-203° (Holub)
Optical Rotation: [a]D24 +52.5° (c = 1 in chloroform)
 
Derivative Type: Desacetylmatricarin monohydrate
Molecular Formula: C15H18O4.H2O
Molecular Weight: 280.32
Percent Composition: C 64.27%, H 7.19%, O 28.54%
Properties: Crystals from benzene + acetone, mp 123-125°, resolidifies and mp 143-146°.
Melting point: mp 123-125°; mp 143-146°
 
Derivative Type: Tetrahydromatricarin
Molecular Formula: C17H24O5
Molecular Weight: 308.37
Percent Composition: C 66.21%, H 7.84%, O 25.94%
Properties: Needles from benzene + petr ether, mp 175-178°. [a]D22 +32.3° (c = 1.92 in chloroform).
Melting point: mp 175-178°
Optical Rotation: [a]D22 +32.3° (c = 1.92 in chloroform)

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