Cycloartenol
{{Chembox
| verifiedrevid = 443547574
| ImageFile=Cycloartenol.svg
| ImageSize=240px
| ImageFile1 = Cycloartenol molecule ball.png
| ImageSize1 = 260
| ImageAlt1 = Ball-and-stick model of cycloartenol
| IUPACName=9,19-Cyclo-9β-lanost-24-en-3β-ol
| SystematicName=(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
| OtherNames=9β,19-cyclo-24-lanosten-3β-ol,
(3β)-9,19-Cyclolanost-24-en-3-ol
|Section1={{Chembox Identifiers
| InChI1 = 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
| InChIKey1 = UYPYBUZTJLFCHS-DGUMGERNBH
| SMILES1 = 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
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=469-38-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YU32VE82N3
| ChEBI = 17030
| PubChem=92110
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=16788581
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UYPYBUZTJLFCHS-DGUMGERNSA-N
| SMILES=CC(CCC=C(C)C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)O)C)C
}}
|Section2={{Chembox Properties
| Formula=C30H50O
| MolarMass=426.72 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
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,{{cite journal|last1=Schaller|first1=Hubert|title=The role of sterols in plant growth and development|journal=Progress in Lipid Research|date=May 2003|volume=42|issue=3|pages=163–175|doi=10.1016/S0163-7827(02)00047-4| pmid=12689617 }} 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.{{cite journal |doi=10.1021/cr200021m |title=Biosynthesis of Cholesterol and Other Sterols |date=2011 |last1=Nes |first1=W. David |journal=Chemical Reviews |volume=111 |issue=10 |pages=6423–6451 |pmid=21902244 |pmc=3191736 }} 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.