Rottlerin

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°
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Rottlerin
Rottlerin.svg
Systematic (IUPAC) name
(E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
Clinical data
Legal status  ?
Identifiers
ATC code  ?
PubChem CID 5281847
ChemSpider 4445144
ChEBI CHEBI:8899
Chemical data
Formula C30H28O8 
Mol. mass 516.53852 g/mol

Rottlerin is a potent large conductance potassium channel (BKCa++) opener.[1] BKCa++ is found in the inner mitochondrial membrane of cardiomyocytes.[2] Opening these channels is beneficial for post-ischemic changes in vasodilation.[3] Other BKCa++ channel openers are reported to limit the mitochondrial calcium overload due to ischemia.[4][5] Rottlerin is also capable of reducing oxygen radical formation.[6]