beta-Amyrin

Title: b-Amyrin
CAS Registry Number: 559-70-6
CAS Name: (3b)-Olean-12-en-3-ol
Additional Names: b-amyrenol
Molecular Formula: C30H50O
Molecular Weight: 426.72
Percent Composition: C 84.44%, H 11.81%, O 3.75%
Literature References: Occurs together with a-amyrin. Isoln and structural studies: see a-amyrin. See also Vesterberg, Bull. Soc. Chim. 37, 742 (1925); Horrmann, Firzlaff, Arch. Pharm. 268, 64 (1930); Ruzicka, Marxer, Helv. Chim. Acta 22, 195 (1939); Jeger, Ruzicka, ibid. 28, 209 (1945); Prelog et al., ibid. 29, 360 (1946). Conversion of d-amyrene to b-amyrin: Barton et al., J. Chem. Soc. C 1968, 1031. Biogenetic-type total synthesis: van Tamelen et al., J. Am. Chem. Soc. 94, 8229 (1972). Biosynthesis from squalene: Suga et al., Chem. Lett. 1972, 129, 313.
Properties: Needles from petr ether or alc, mp 197-197.5°. bp0.8 260°. [a]D19 +99.8° (c = 1.3 in benzene). Somewhat less soluble than the a-form. Soluble in 37 parts of 98% alc.
Melting point: mp 197-197.5°
Boiling point: bp0.8 260°
Optical Rotation: [a]D19 +99.8° (c = 1.3 in benzene)
Derivative Type: Acetate
Molecular Formula: C32H52O2
Molecular Weight: 468.75
Percent Composition: C 81.99%, H 11.18%, O 6.83%
Properties: Prisms from petr ether, mp 241°. [a]D17 +79° (c = 0.9 in benzene).
Melting point: mp 241°
Optical Rotation: [a]D17 +79° (c = 0.9 in benzene)
Derivative Type: Palmitate
Additional Names: Balanophorin
Molecular Formula: C46H80O2
Molecular Weight: 665.13
Percent Composition: C 83.07%, H 12.12%, O 4.81%
Properties: mp 77°. [a]D15 +54.5° (c = 1.1 in benzene). Occurs in Balanophora elongata Blume, Balanophoraceae, in Erythroxylum coca Lam. var novogranatense Morris, and var spruceanum Burck, Erythroxylaceae, in latex from Ficus variegata Blume, Moraceae.
Melting point: mp 77°
Optical Rotation: [a]D15 +54.5° (c = 1.1 in benzene)
Derivative Type: Di-b-amyrin ether
Molecular Formula: C60H98O
Molecular Weight: 835.42
Percent Composition: C 86.26%, H 11.82%, O 1.92%
Properties: mp 135-136°: Rollett, Monatsh. Chem. 47, 437 (1926).
Melting point: mp 135-136°: Rollett, Monatsh. Chem. 47, 437 (1926)
beta-Benzalbutyramide beta-Boswellic Acid beta-Bromoisovaleric Acid beta-Bromopropionic Acid beta-Carboxyaspartic Acid