Glaucarubin

Title: Glaucarubin
CAS Registry Number: 1448-23-3
CAS Name: [1b,2a,11b,12a,15b(S)]-11,20-Epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-en-16-one
Additional Names: 2-hydroxy-2-methylbutyric acid 4-ester with 1,2,3,3ab,4,6ab,7,7aa,10,11,11a,11ba-dodecahydro-1a,2a,4b,10a,11b-pentahydroxy-3a,8,11ab-trimethyl-5H-1,11cb-(epoxymethano)phenanthro[10,1-bc]pyran-5-one; a-kirondrin
Molecular Formula: C25H36O10
Molecular Weight: 496.55
Percent Composition: C 60.47%, H 7.31%, O 32.22%
Literature References: Antiamebic compound isolated from seeds of Simaruba glauca DC, Simarubaceae: E. A. Ham et al., J. Am. Chem. Soc. 76, 6066 (1954); H. M. Shafer, US 2864745 (1958 to Merck & Co.). Pharmacology: A. C. Cuckler et al., Arch. Int. Pharmacodyn. 114, 307 (1958). Structure: Polonsky et al., Bull. Soc. Chim. Fr. 1964, 1827. Identity of a- and b-kirondrin with glaucarubinone and glaucarubin, resp: Bourguignon, Polonsky, Bull. Soc. Chim. Biol. 46, 1145 (1964). Crystal structure: Kartha et al., Nature 202, 389 (1964). Configuration: Nyburg et al., Chem. Commun. 1965, 203.
Properties: Bitter crystals from methanol, dec 250-255°. [a]D25 +45° (c = 1.7 in pyridine); [a]D25 +69° (c = 0.6 in methanol). Sol in 0.1N NaOH soln. Practically insol in aq sodium bicarbonate solns. Only slightly sol in water (less than 1.8 mg/ml). Prompt acidification of an alkaline soln regenerates glaucarubin, but standing in alkaline soln leads to decompn.
Optical Rotation: [a]D25 +45° (c = 1.7 in pyridine); [a]D25 +69° (c = 0.6 in methanol)
Derivative Type: Tetramethoxyglaucarubin
Molecular Formula: C29H44O10
Molecular Weight: 552.65
Percent Composition: C 63.03%, H 8.02%, O 28.95%
Properties: Crystals from ether, mp 202-205°. [a]D +17.7° (c = 0.705 in pyridine); [a]D +65.5° (c = 0.926 in methanol).
Melting point: mp 202-205°
Optical Rotation: [a]D +17.7° (c = 0.705 in pyridine); [a]D +65.5° (c = 0.926 in methanol)
Derivative Type: Pentaacetate
Molecular Formula: C35H46O15
Molecular Weight: 706.73
Percent Composition: C 59.48%, H 6.56%, O 33.96%
Properties: Crystals from benzene + petr ether, mp 158-160°. [a]D +49° (c = 0.534 in pyridine).
Melting point: mp 158-160°
Optical Rotation: [a]D +49° (c = 0.534 in pyridine)
Status: This monograph has been retired and is no longer subject to revision or update.
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