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Cycloartenol information


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
CAS Number
  • 469-38-5 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:17030
ChemSpider
  • 16788581 checkY
PubChem CID
  • 92110
UNII
  • YU32VE82N3 checkY
CompTox Dashboard (EPA)
  • DTXSID60894760 Edit this at Wikidata
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 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
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 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.

  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. PMID 12689617.

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cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene...

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fungal steroids are derived. By contrast, plant steroids are produced via cycloartenol. Elaboration of lanosterol under enzyme catalysis leads to the core structure...

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higher terpenes. Triterpenoids commonly purified from hardwoods include cycloartenol, betulin and squalene. Hardwood polyterpenes are rubber, gutta percha...

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they are biosynthesised from either lanosterol (animals and fungi) or cycloartenol (plants) via the cyclization of squalene. Steroids have two principal...

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lambertianic acid, communic acid, mercusic acid and secodehydroabietic acid. Cycloartenol, betulin and squalene are triterpenoids purified from hardwood. Examples...

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4,4,14-trimethyl-9,19-cyclo-5alpha,9beta-cholestane. Its derivative cycloartenol is the starting point for the synthesis of almost all plant steroids...

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flavonoids, alkaloids, tannins, neriifolins (also found in oleander), cycloartenol, lectin, and taraxerol, among others. Some species of this family are...

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sterol-producing OSC enzymes: Cycloartenol synthase (CAS), found in all plants, which produces primarily cycloartenol Lanosterol synthase (LAS), found...

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biosynthesis of withaferin A uses enzymes such as squalene epoxidase (SQE), cycloartenol synthase (CAS), sterol methyl transferase (SMT), obtusifoliol-14 –demethylase...

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