Oleanolic Acid
Title: Oleanolic Acid
CAS Registry Number: 508-02-1
CAS Name: (3b)-3-Hydroxyolean-12-en-28-oic acid
Additional Names: oleanol; caryophyllin
Molecular Formula: C30H48O3
Molecular Weight: 456.70
Percent Composition: C 78.90%, H 10.59%, O 10.51%
Literature References: Occurs in the free state in leaves of Olea europaea, Oleaceae, in leaves of Viscum album L., Loranthaceae, in buds of Syzygium aromaticum (L.) Merr. & Perry, Myrtaceae (cloves), in Swertia japonica (Maxim.) Makino, and in Centaurium umbellatum Gilib. (Erythraea centaurium (L.) Pers.), Gentianaceae; as acetate in birch bark, as glycoside in many saponins. Isoln procedures (from cloves): Winterstein, Stein, Z. Physiol. Chem. 202, 222 (1931); Ruzicka, Hofmann, Helv. Chim. Acta 19, 114 (1936); Picard et al., J. Chem. Soc. 1939, 1047. Structure: Ruzicka et al., Helv. Chim. Acta 29, 210 (1946). Review: J. Simonsen, W. C. T. Ross, The Terpenes vol. 5 (University Press, Cambridge, 1957) pp 221-285. Cf. a- and b-amyrin.
Properties: Fine, solvated needles from alc. After drying, mp 310°. [a]D20 +83.3° (c = 0.6 in chloroform). pK 2.52. Insol in water. Sol in 65 parts ether, 106 parts 95% alcohol, 35 parts boiling 95% alcohol, 118 parts chloroform, 180 parts acetone, 235 parts methanol.
Melting point: mp 310°
pKa: pK 2.52
Optical Rotation: [a]D20 +83.3° (c = 0.6 in chloroform)
 
Derivative Type: Acetate
Molecular Formula: C32H50O4
Molecular Weight: 498.74
Percent Composition: C 77.06%, H 10.10%, O 12.83%
Properties: Needles from methanol, mp 268°. [a]D17 +74.5° (c = 0.6 in CHCl3).
Melting point: mp 268°
Optical Rotation: [a]D17 +74.5° (c = 0.6 in CHCl3)
 
Derivative Type: Methyl ester
Molecular Formula: C31H50O3
Molecular Weight: 470.73
Percent Composition: C 79.10%, H 10.71%, O 10.20%
Properties: mp 201°. [a]D20 +75° (c = 0.6 in CHCl3).
Melting point: mp 201°
Optical Rotation: [a]D20 +75° (c = 0.6 in CHCl3)
 
Derivative Type: Acetate of methyl ester
Molecular Formula: C33H52O4
Molecular Weight: 512.76
Percent Composition: C 77.30%, H 10.22%, O 12.48%
Properties: Needles from alcohol, mp 223°. [a]D20 +70° (c = 0.6 in CHCl3).
Melting point: mp 223°
Optical Rotation: [a]D20 +70° (c = 0.6 in CHCl3)

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