Cycloartenol

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Cycloartenol
Ball-and-stick model of cycloartenol
Names
IUPAC name
9,19-Cyclo-9β-lanost-24-en-3β-ol
Systematic IUPAC name
(1R,3aS,3bS,5aR,7S,9aR,10aS,12aR)-3a,6,6,12a-Tetramethyl-1-[(2R)-6-methylhept-5-en-2-yl]tetradecahydro-2H,10H-cyclopenta[a]cyclopropa[e]phenanthren-7-ol
Other names
9β,19-cyclo-24-lanosten-3β-ol,
(3β)-9,19-Cyclolanost-24-en-3-ol
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
UNII
  • InChI=1S/C30H50O/c1-20(2)9-8-10-21(3)22-13-16-28(7)24-12-11-23-26(4,5)15-14-25(31)30(23)19-29(24,30)18-17-27(22,28)6/h14,20-24,31H,8-13,15-19H2,1-7H3/t21-,22-,23+,24+,27-,28+,29+,30-/m1/s1 checkY
    Key: UYPYBUZTJLFCHS-DGUMGERNSA-N checkY
  • InChI=1/C30H50O/c1-20(2)9-8-10-21(3)22-13-16-28(7)24-12-11-23-26(4,5)15-14-25(31)30(23)19-29(24,30)18-17-27(22,28)6/h14,20-24,31H,8-13,15-19H2,1-7H3/t21-,22-,23+,24+,27-,28+,29+,30-/m1/s1
    Key: UYPYBUZTJLFCHS-DGUMGERNBH
  • CC(CCC=C(C)C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)O)C)C
  • CC(C)CCC[C@@H](C)[C@H]5CC[C@]1(C)[C@]5(C)CC[C@]24C[C@]34C(/O)=C\C[C@@](C)(C)[C@@H]3CC[C@@H]12
Properties
C30H50O
Molar mass 426.72 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cycloartenol is an important

triterpenoid often found in plants. It belongs to the sterol class of steroids. It is the starting point for the synthesis of almost all plant steroids,[1] making them chemically distinct from the steroids of fungi and animals, which are, instead, produced from lanosterol
.

Synthesis

The

stanols and sterols, referred to as phytostanols and phytosterols in photosynthetic
organisms and plants. The identities and distribution of phytostanols and phytosterols is characteristic of a plant species.

References

  1. PMID 12689617
    .
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