Taraxerol

Taraxerol
Names
IUPAC name
13-Methyl-27-nor-13α-olean-14-en-3β-ol
Systematic IUPAC name
(3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-4,4,6a,8a,11,11,12b,14b-Octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-ol
Other names
  • Alnulin
  • Skimmiol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C30H50O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-24,31H,10-19H2,1-8H3/t20-,22+,23+,24-,27-,28-,29-,30+/m0/s1
    Key: GGGUGZHBAOMSFJ-GADYQYKKSA-N
  • InChI=1/C30H50O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-24,31H,10-19H2,1-8H3/t20-,22+,23+,24-,27-,28-,29-,30+/m0/s1
    Key: GGGUGZHBAOMSFJ-GADYQYKKBI
  • C[C@]12CCC(C[C@H]1C3(CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4(C3=CC2)C)(C)C)O)C)C)(C)C
Properties
C30H50O
Molar mass 426.729 g·mol−1
Appearance Colorless solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Taraxerol is a naturally-occurring pentacyclic triterpenoid. It exists in various higher plants, including Taraxacum officinale (Asteraceae), Alnus glutinosa (Betulaceae), Litsea dealbata (Lauraceae), Skimmia spp. (Rutaceae), Dorstenia spp. (Moraceae), Maytenus spp. (Celastraceae), and Alchornea latifolia (Euphobiaceae).[1] Taraxerol was named "alnulin" when it was first isolated in 1923 from the bark of the grey alder (Alnus incana L.) by Zellner and Röglsperger. It also had the name "skimmiol" when Takeda and Yosiki isolated it from Skimmia (Rutaceae).[2] A large number of medicinal plants are known to have this compound in their leaves, roots or seed oil. [3]

  1. ^ Versteegh, Gerard J.M; Schefuß, Enno; Dupont, Lydie; Marret, Fabienne; Sinninghe Damsté, Jaap S; Jansen, J.H.Fred (February 2004). "Taraxerol and Rhizophora pollen as proxies for tracking past mangrove ecosystems". Geochimica et Cosmochimica Acta. 68 (3): 411–422. Bibcode:2004GeCoA..68..411V. doi:10.1016/S0016-7037(03)00456-3.
  2. ^ Beaton, J. M.; Spring, F. S.; Stevenson, Robert; Stewart, J. L. (1955). "Triterpenoids. Part XXXVII. The constitution of taraxerol". Journal of the Chemical Society (Resumed): 2131. doi:10.1039/jr9550002131. ISSN 0368-1769.
  3. ^ Sharma, Kiran; Zafar, Rasheeduz (2015). "Occurrence of taraxerol and taraxasterol in medicinal plants". Pharmacognosy Reviews. 9 (17): 19–23. doi:10.4103/0973-7847.156317. ISSN 0973-7847. PMC 4441157. PMID 26009688.