Nomenclature
CAS number: 82-08-6
(
E)-1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2
H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one; 5,7-dihydroxy-2,2-dimethyl-6-(2,4,6-trihydroxy-3-methyl-5-acetylbenzyl)-8-cinnamoyl-1,2-chromene; mallotoxin.
C
30H
28O
8; mol wt 516.54.
C 69.76%, H 5.46%, O 24.78%.
Description and references
Principal phenolic component of kamala, q.v., an anthelmintic dye
obtained from Mallotus philippinensis (Lam.) Muell. Arg.
(also known as Rottlera tinctoria Roxb.), Euphorbiaceae. Isoln: H. Telle, Arch. Pharm. 244, 446 (1906); S. Dutt, J.
Chem. Soc. 127, 2044 (1925); A. McGookin et al., ibid. 1937, 748. Structure: Brockmann, Maier, Ann. 535, 149 (1938); A. McGookin et al., J. Chem. Soc. 1939, 1579. Synthesis
of tetrahydrorottlerin: Backhouse et al., ibid. 1948, 113. Review of isoln
and chemistry: M. Lounasmaa et al., Planta Med. 28, 16 (1975). Activity as protein
kinase inhibitor: M. Gschwendt et al., Biochem. Biophys. Res. Commun. 199, 93 (1994). HPTLC determn in serum and pharmacokinetics: V. D.
Mody et al., J. Pharm. Technol. 10, 71 (1994).
Properties
Light reddish-brown plates or needles with golden
lustre from ethyl acetate, mp 212° (McGookin). Also reported as brownish-yellow plates
from toluene, mp 206-207° (Dutt). Sol in ether, chloroform, benzene, ethyl acetate;
sparingly sol in cold alc, acetic acid. Practically insol in water.Derivative
5,7-Dimethyl ether.
C
32H
32O
8; mol wt 544.59.
C 70.57%, H 5.92%, O 23.50%.
Properties
Yellow crystals from ethyl acetate + acetone or
chloroform + methanol, dec 245-246°. Sol in chloroform, pyridine,
hot glacial acetic acid; slightly sol in cold methanol, ethyl acetate,
acetone, benzene, ether.Derivative
Pentamethyl ether.
C
35H
38O
8; mol wt 586.67.
C 71.65%, H 6.53%, O 21.82%.
Properties
Crystals from petr ether, methanol or 90% alcohol, mp 144°. Very sol in
acetone, glacial acetic acid, benzene, ethyl acetate.Derivative
Pentaacetate.
C
40H
38O
13; mol wt 726.72.
C 66.11%, H 5.27%, O 28.62%.
Properties
Leaflets from benzene + alcohol or acetone + alcohol,
prisms from ethyl acetate, mp 212°.Derivative
Tetrahydrorottlerin.
C
30H
32O
8; mol wt 520.57.
C 69.22%, H 6.20%, O 24.59%.
Properties
Yellow prisms from alcohol, mp 214°.