Cycloartenol

Cycloartenol

Names
Other names 9beta,19-cyclo-24-lanosten-3beta-ol, (3beta)-9,19-Cyclolanost-24-en-3-ol
Identifiers
CAS Number	469-38-5
3D model (Jmol)	Interactive image Interactive image
ChemSpider	16788581
PubChem	92110
InChI 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 Key: UYPYBUZTJLFCHS-DGUMGERNSA-N 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
SMILES 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
Chemical formula	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).
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Infobox references

Cycloartenol is an important triterpenoid of the sterol class which is found in plants. 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 biosynthesis of cycloartenol starts from the triterpenoid squalene. It is the first precursor in the biosynthesis of other 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. Schaller, Hubert (May 2003). "The role of sterols in plant growth and development". Progress in Lipid Research. 42 (3): 163–175. doi:10.1016/S0163-7827(02)00047-4.