12-08221. Quillaic Acid [Archived]
Nomenclature
CAS number: 631-01-6
(3β,4α,16α)-3,16-Dihydroxy-23-oxoolean-12-en-28-oic acid; quillaja sapogenin. C30H46O5; mol wt 486.68.
C 74.04%, H 9.53%, O 16.44%.
Description and references
Prepn from quillaja saponin: Windaus et al., Z. Physiol. Chem. 160, 301 (1926); Elliott, Kon, J. Chem. Soc. 1939, 1130. Structure: Windaus, loc. cit.; Ruzicka, van Veen, Z. Physiol. Chem. 184, 69 (1929); Ruzicka et al., Collect. Czech. Chem. Commun. 15, 893 (1950).
Properties
Crystals from ethyl acetate, mp 292-293°; also reported as 258-265° (dec): Kubota et al., Tetrahedron Lett. 1969, 771. [α]D20 +56.1° (c = 2.9 in pyridine). Soluble in alcohol, ether, acetone, ethyl acetate, glacial acetic acid.Derivative
Diacetate.C34H50O7; mol wt 570.76.
C 71.55%, H 8.83%, O 19.62%.
Properties
Needles from glacial acetic acid, mp 180-187°.Derivative
Methyl ester.C31H48O5; mol wt 500.71.
C 74.36%, H 9.66%, O 15.98%.
Properties
Needles from dil methanol, mp 223-225°; also reported as 200-205° (dec), Kubota et al., loc. cit. [α]D20 +40.5° (c = 4 in pyridine).Status
This monograph has been retired and is no longer subject to revision or update.