Serratenediol

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Serratenediol
Names
IUPAC name
(3S,6R,8S,11R,12S,15S,16R,19S,21R)-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.03,12.06,11.016,21]tricos-1(23)-ene-8,19-diol
Other names
Pinusenediol[1]
Identifiers
3D model (JSmol)
  • InChI=1S/C30H50O2/c1-26(2)21-10-8-19-18-28(5)15-12-22-27(3,4)25(32)14-17-30(22,7)23(28)11-9-20(19)29(21,6)16-13-24(26)31/h8,20-25,31-32H,9-18H2,1-7H3/t20-,21-,22-,23-,24-,25-,28-,29+,30-/m0/s1 ☒N
    Key: FMUNNDDBCLRMSL-PIGMOXAFSA-N
  • C[C@@]12CC[C@@H]3[C@@]([C@H]1CC[C@H]4C(=CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C2)(CC[C@@H](C3(C)C)O)C
Properties
C30H50O2
Molar mass 442.728 g·mol−1
Appearance Powder[2]
poorly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Serratenediol is a naturally occurring pentacyclic triterpenoid.[3] The compound has drawn interest for its distinctive carbon framework and potential biological activities. Serratenediol is characterized by a rare seven‑membered C-ring, a defining feature of the serratene class of triterpenoids[4], which differentiates it from the more common lupane, oleanane, or ursane types.[5] The compound is also called pinusenediol.[6]

The compound is found primarily in plants of the Lycopodiaceae family, especially in the genus Lycopodium (now often segregated into genera like Huperzia and Phlegmariurus).[7][8][9]

Synthesis

The synthesis of serratenediol is accomplished in several steps by using polyene cyclization.[10]

Physical properties

Uses

References

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