Parkeol

Parkeol is a relatively uncommon sterol secondary metabolite found mostly in plants, particularly noted in Butyrospermum parkii (now called Vitellaria paradoxa, or the shea tree).^[1] It can be synthesized as a minor product by several oxidosqualene cyclase enzymes, and is the sole product of the enzyme parkeol synthase.^[2]

Quick facts Names, Identifiers ...

Parkeol

Names
IUPAC name Lanosta-9(11),24-dien-3β-ol
Systematic IUPAC name (1R,3aS,3bS,5aR,7S,9aS,11aR)-3a,6,6,9a,11a-Pentamethyl-1-[(2R)-6-methylhept-5-en-2-yl]-2,3,3a,3b,4,5,5a,6,7,8,9,9a,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
CAS Number	514-45-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:63460
ChemSpider	23255009
PubChem CID	12313974
CompTox Dashboard (EPA)	DTXSID20487430
InChI InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,15,21-22,24-26,31H,9,11-14,16-19H2,1-8H3/t21-,22-,24-,25+,26+,28-,29-,30+/m1/s1 Key: MLVSYGCURCOSKP-FXCPCPCLSA-N
SMILES [H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@@]4([H])C(C)(C)[C@@H](O)CC[C@]4(C)C3=CC[C@]12C)[C@H](C)CCC=C(C)C
Properties
Chemical formula	C30H50O
Molar mass	426.729 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Parkeol is the dominant sterol found in the planctomycete Gemmata obscuriglobus, a rare example of a sterol-synthesizing prokaryote. The only other sterol identified in this organism is lanosterol, a key component of the sterol biosynthetic pathway in animals and fungi; this relatively limited sterol repertoire may resemble the early evolution of sterol synthesis, which is ubiquitous in eukaryotes.^[3]