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Steroid


DATA No : SST0136 INFORMANT : Hideaki Nishino

NAME : Olean-12-en-3b-ol / 3b-Hydroxyolean-12-ene

COMMON NAME: b-Amyrin / b-Amyrenol
SYMBOL:
FORMULA: C30H50O MOL.WT (average) : 426.717


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BIOLOGICAL ACTIVITY
Total synthesis of biogenetic form. (Ref. 0606) Conversion from d-amyrene to b-amyrin. (Ref. 0605)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:197-197.5degC (petr. ether or alc.) (Ref. 0605)

BOILING POINT:bp0.8 260degC (Ref. 0605)

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]19/D=+99.8deg (c=1.3 in benzene) (Ref. 0605)

DENSITY:

SOLUBILITY:Less solubility than a-form. Sol in 37 parts of 98% alcohol. (Ref. 0605)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Plants. Along with a-amyrin, found in extracted fluid of Baranophora elongata Blume, Balanophoraceae, Erythroxylum coca Lam, var novogranatense Morris, var spruceanum Burck, Erythroxylaceae, Ficus variegata Blume, Moraceae. (Ref. 0600/0601/0602/0603/0604)
CHEMICAL SYNTHESIS
Biogenetic pathway from squalene. (Ref. 0607/0608)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0600]
AUTHOR:Vesterberg,M.K.Alb
TITLE:L'alcool paltreubylique-a, une forme inactive de l'amyrine-b.
JOURNAL:Bull. Soc. Chim.
VOL:37 PAGE : 742 -744 (1925)
[TOP]

[0601]
AUTHOR:Horrmann,P.
TITLE:Beiträge zur Kenntnis der Harze. 2. Über die Reindarstellung und einige Versuche zur Aufklärung der Konstitution des a- und b- Amyrins von Johannes Firzlaff.
JOURNAL:Arch. Pharm.
VOL:268 PAGE : 64 -76 (1930)
[TOP]

[0602]
AUTHOR:Ruzicka,L.,and Marxer,A.
TITLE:Zur Kenntnis der Triterpene. (44. Mitteilung). Umwandlung der Glycyrrhetinsäure in b-Amyrin.
JOURNAL:Helv. Chim. Acta
VOL:22 PAGE : 195 -201 (1939)
[TOP]

[0603]
AUTHOR:Jeger,O.,and Ruzicka,L.
TITLE:Zur Kenntnis der Triterpene. (94. Mitteilung). Überführung des b-Amyrins in ein neues Dien-dion-Derivat.
JOURNAL:Helv. Chim. Acta
VOL:28 PAGE : 209 -212 (1945)
[TOP]

[0604]
AUTHOR:Prelog,V.,Norymberski,J.,and Jeger,O.
TITLE:Zur Kenntnis der Triterpene. (103. Mitteilung). Ein neuer Weg zur Überführung der Carboxyl-Gruppe in die Methyl-Gruppe.
JOURNAL:Helv. Chim. Acta
VOL:29 PAGE : 360 -363 (1946)
[TOP]

[0605]
AUTHOR:Barton,D.H.R.,Lier,E.F.,and McGhie,J.F.
TITLE:The synthesis of b-amyrin.
JOURNAL:J. Chem. Soc. (C)
VOL:1968 PAGE : 1031 -1040 (1968)
[TOP]

[0606]
AUTHOR:van Tamelen,E.E.,Seiler,M.P.,and Wierenga,W.
TITLE:Biogenetic-type total synthesis. d-Amyrin, b-amyrin, and germanicol.
JOURNAL:J. Am. Chem. Soc.
VOL:94 PAGE : 8229 -8231 (1972)
[TOP]

[0607]
AUTHOR:Suga,T.,Shishibori,T.,and Kimoto,S.
TITLE:Biosynthesis of triterpenoids. The stereochemistry of the squalene formation and its cyclization to b-amyrin.
JOURNAL:Chem. Lett.
VOL:1972 PAGE : 129 -130 (1972)
[TOP]

[0608]
AUTHOR:Suga,T.,Shishibori,T.,and Kimoto,S.
TITLE:Triterpenoid biosynthesis. The stereospecificity in the enzymatic cyclization of squalene to b-amyrin.
JOURNAL:Chem. Lett.
VOL:1972 PAGE : 313 -314 (1972)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.