Quillaic Acid
Title: Quillaic Acid
CAS Registry Number: 631-01-6
CAS Name: (3b,4a,16a)-3,16-Dihydroxy-23-oxoolean-12-en-28-oic acid
Additional Names: quillaja sapogenin
Molecular Formula: C30H46O5
Molecular Weight: 486.68
Percent Composition: C 74.04%, H 9.53%, O 16.44%
Literature 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. [a]D20 +56.1° (c = 2.9 in pyridine). Soluble in alcohol, ether, acetone, ethyl acetate, glacial acetic acid.
Melting point: mp 292-293°; also reported as 258-265° (dec)
Optical Rotation: [a]D20 +56.1° (c = 2.9 in pyridine)
Derivative Type: Diacetate
Molecular Formula: C34H50O7
Molecular Weight: 570.76
Percent Composition: C 71.55%, H 8.83%, O 19.62%
Properties: Needles from glacial acetic acid, mp 180-187°.
Melting point: mp 180-187°
Derivative Type: Methyl ester
Molecular Formula: C31H48O5
Molecular Weight: 500.71
Percent Composition: 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. [a]D20 +40.5° (c = 4 in pyridine).
Melting point: mp 223-225°; also reported as 200-205° (dec)
Optical Rotation: [a]D20 +40.5° (c = 4 in pyridine)
Status: This monograph has been retired and is no longer subject to revision or update.

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