| Identification | Back Directory | [Name]
(Z)-2-Methyl-2-butenoic acid [(1S,2R,7aR)-hexahydro-2β-hydroxy-1H-pyrrolizin-1β-yl]methyl ester | [CAS]
27841-97-0 | [Synonyms]
Macrophylline
Macrophylline【Senecio】
(Z)-2-Methyl-2-butenoic acid [(1S,2R,7aR)-hexahydro-2β-hydroxy-1H-pyrrolizin-1β-yl]methyl ester
2-Butenoic acid, 2-methyl-, [(1S,2R,7aR)-hexahydro-2-hydroxy-1H-pyrrolizin-1-yl]methyl ester, (2Z)- | [Molecular Formula]
C13H21NO3 | [MOL File]
27841-97-0.mol | [Molecular Weight]
239.31 |
| Hazard Information | Back Directory | [Description]
A pyrrolizidine alkaloid, macrophylline has been isolated from Senecio amphibolus
and S. macrophylla MB. It forms a low melting solid which has not yet been
obtained in a crystalline form. The base is dextrorotatory having a specific rotation
of [α]20D + 34.52° (c 1.68, EtOH). When hydrolyzed with dilute acids the base
furnishes macronecine and angelic acid. It has been characterized as the crystalline
bitartrate which melts at 162-4°C. | [Uses]
Macrophylline (Compound 4) is isolated from the
natural Rauwolfia[1]. | [Definition]
ChEBI: Macrophylline is a member of pyrrolizines. | [References]
Danilova et al.,J. Gen. Chem. USSR, 23,1417 (1953)
Danilova, Kuzovkov, ibid, 23,1597 (1953)
Danilova, Utkin, Massagetov, ibid, 25, 797 (1955)
Danilova, Utkin, ibid, 30, 345 (1960)
Culvenor, Geissman,J. Org. Chem., 26, 3045 (1961) |
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