MW: 516.55
CAS: 82-08-6
TNP NUMBER: TNP00157
MDL NUMBER: MFCD00017361
IUPAC: 3-{[8-((2E)-3-phenylprop-2-enoyl)-5,7-dihydroxy-2,2-dimethyl(2H-chromen-6-yl)] methyl}-1-acetyl-2,4,6-trihydroxy-5-methylbenzene
Smiles: c1(c(Cc2c(c(c(c(c2O)C(=O)C)O)C)O)c(c2c(OC(C=C2)(C)C)c1C(=O)/C=C\c1ccccc1)O)O
Principal phenolic component of kamala, q.v., an anthelmintic dye obtained from Mallotus philippinensis (Lam.) Muell. Arg, Euphorbiaceae.
REFERENCE: Gschwendt, M., et al. Biochem. Biophys. Res. Commun. 199, 93, (1994) abstract Haoyu Zeng, et al., , Mallotoxin Is a Novel Human Ether-a-go-go-Related Gene (hERG) Potassium Channel Activator J. Pharmacol. Exp. Ther. 319, 957-962, (2006) abstract Zakharov, S.I., et al., Activation of the BK (SLO1) Potassium Channel by Mallotoxin J. Biol. Chem. 35, 30882-30887, (2005) Gschwendt, M., et al. FEBS Lett. 338, 85, (1994
SOURCE: Principal phenolic component of kamala, q.v., an anthelmintic dye obtained from Mallotus philippinensis (Lam.) Muell. Arg, Euphorbiaceae.
ACCEPTORS: 8
DONORS: 5
ROTATION BONDS: 10
N+O: 8
Chiral Centers: 0
LogP: 5.31
LogS: -5.67
LIPINSKI: 3
Monograph Number: 0008352
Title: Rottlerin
CAS Registry Number: 82-08-6
CAS Name: (E)-1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
Additional Names: 5,7-dihydroxy-2,2-dimethyl-6-(2,4,6-trihydroxy-3-methyl-5-acetylbenzyl)-8-cinnamoyl-1,2-chromene; mallotoxin
Molecular Formula: C30H28O8
Molecular Weight: 516.54.
Percent Composition: C 69.76%, H 5.46%, O 24.78%
Literature 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.
Melting point: mp 212 (McGookin); mp 206-207 (Dutt)
Derivative Type: 5,7-Dimethyl ether
Molecular Formula: C32H32O8
Molecular Weight: 544.59.
Percent Composition: 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 Type: Pentamethyl ether
Molecular Formula: C35H38O8
Molecular Weight: 586.67.
Percent Composition: 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.
Melting point: mp 144
Derivative Type: Pentaacetate
Molecular Formula: C40H38O13
Molecular Weight: 726.72.
Percent Composition: C 66.11%, H 5.27%, O 28.62%
Properties: Leaflets from benzene + alcohol or acetone + alcohol, prisms from ethyl acetate, mp 212.
Melting point: mp 212
Derivative Type: Tetrahydrorottlerin
Molecular Formula: C30H32O8
Molecular Weight: 520.57.
Percent Composition: C 69.22%, H 6.20%, O 24.59%
Properties: Yellow prisms from alcohol, mp 214.
Melting point: mp 214
Synonyms: MALLOTOXIN;3'-[(8-CINNAMOYL-5,7-DIHYDROXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-YL)METHYL]-2',4',6'-TRIHYDROXY-5'-METHYLACETOPHENONE;4
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