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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 443546056 |
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| verifiedrevid = 443547574 |
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|ImageFile=Cycloartenol.png |
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| ImageFile=Cycloartenol.svg |
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|ImageSize=200px |
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| ImageSize=240px |
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| ImageFile1 = Cycloartenol molecule ball.png |
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|IUPACName= |
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| ImageSize1 = 260 |
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|OtherNames=9beta,19-cyclo-24-lanosten-3beta-ol,<br>(3beta)-9,19-Cyclolanost-24-en-3-ol |
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| ImageAlt1 = Ball-and-stick model of cycloartenol |
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|Section1= {{Chembox Identifiers |
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| IUPACName=9,19-Cyclo-9β-lanost-24-en-3β-ol |
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| 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 |
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| SystematicName=(1''R'',3a''S'',3b''S'',5a''R'',7''S'',9a''R'',10a''S'',12a''R'')-3a,6,6,12a-Tetramethyl-1-tetradecahydro-2''H'',10''H''-cyclopentacyclopropaphenanthren-7-ol |
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| OtherNames=9β,19-cyclo-24-lanosten-3β-ol,<br>(3β)-9,19-Cyclolanost-24-en-3-ol |
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|Section1={{Chembox Identifiers |
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| 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 |
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| InChIKey1 = UYPYBUZTJLFCHS-DGUMGERNBH |
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| InChIKey1 = UYPYBUZTJLFCHS-DGUMGERNBH |
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| SMILES1 = CC(C)CCC(C)5CC1(C)5(C)CC24C34C(/O)=C\C(C)(C)3CC12 |
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| SMILES1 = CC(C)CCC(C)5CC1(C)5(C)CC24C34C(/O)=C\C(C)(C)3CC12 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=469-38-5 |
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| CASNo=469-38-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=92110 |
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| UNII = YU32VE82N3 |
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| ChEBI = 17030 |
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| PubChem=92110 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=16788581 |
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| ChemSpiderID=16788581 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES=CC(CCC=C(C)C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)O)C)C |
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| SMILES=CC(CCC=C(C)C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)O)C)C |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>30</sub>H<sub>50</sub>O |
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| Formula=C<sub>30</sub>H<sub>50</sub>O |
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| MolarMass=426.72 g/mol |
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| MolarMass=426.72 g/mol |
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| Appearance= |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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}} |
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'''Cycloartenol''' is an important ] often found in plants. It belongs to the ] class of steroids. It is the starting point for the synthesis of almost all plant ]s,<ref>{{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 }}</ref> making them chemically distinct from the steroids of fungi and animals, which are, instead, produced from ]. |
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'''Cycloartenol''' is an important type of stanol found in plants. The ] of cycloartenol starts from the ] ]. It is the first precursor in the biosynthesis of other stanols and ]s, referred to as phytostanols and ]s in ] organisms and plants. The identities and distribution of phytostanols and phytosterols is characteristic of a plant species. |
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==Synthesis== |
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One notable product of cycloartenol biosynthesis is the ] ]. |
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The ] of cycloartenol starts from the ] ].<ref>{{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 |pmc=3191736 }}</ref> It is the first precursor in the biosynthesis of other ]s and ]s, referred to as phytostanols and ]s in ] organisms and plants. The identities and distribution of phytostanols and phytosterols is characteristic of a plant species. |
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== References == |
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{{Reflist}} |
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{{Alcohol-stub}} |
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{{Alcohol-stub}} |
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] |
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