Parkeol

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;
UNII	FM88E87P32 ;
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

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 from cycloartenol under Brønsted and Lewis acidic conditions^[2]^[3], as a minor product by several oxidosqualene cyclase enzymes, and is the sole product of the enzyme parkeol synthase.^[4]

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.^[5]

References

↑ Itoh, Toshihiro; Uetsuki, Toshimitsu; Tamura, Toshitake; Matsumoto, Taro (June 1980). "Characterization of triterpene alcohols of seed oils from some species of theaceae, phytolaccaceae and sapotaceae". Lipids. 15 (6): 407–411. doi:10.1007/BF02534064. S2CID 25505422.
↑ Shimizu, Naoto; Itoh, Toshihiro; Saito, Masao; Matsumoto, Taro (February 1984). "Acid-catalyzed isomerization of cycloartane triterpene alcohols. The formation of cucurbitane- and lanostane-type isomers". The Journal of Organic Chemistry. 49 (4): 709–712. doi:10.1021/jo00178a030. ISSN 0022-3263.
↑ Kizakis, Manuel; Treger, Marvin; Dräger, Gerald; König, Carolin; Heretsch, Philipp (2026-03-26). "Navigating the Landscape of Cycloartanyl Cations: Synthesis of Fortunefuroic Acid I, Parkeol, 25,26,27-Trinor-3α-hydroxy-17,13-friedolanosta-8,12-dien-23-one, and Spirochensilide A". Journal of the American Chemical Society. doi:10.1021/jacs.5c22292. ISSN 0002-7863.
↑ Ito, R; Mori, K; Hashimoto, I; Nakano, C; Sato, T; Hoshino, T (20 May 2011). "Triterpene cyclases from Oryza sativa L.: cycloartenol, parkeol and achilleol B synthases". Organic Letters. 13 (10): 2678–81. doi:10.1021/ol200777d. PMID 21526825.
↑ Pearson, A; Budin, M; Brocks, JJ (23 December 2003). "Phylogenetic and biochemical evidence for sterol synthesis in the bacterium Gemmata obscuriglobus". Proceedings of the National Academy of Sciences of the United States of America. 100 (26): 15352–7. Bibcode:2003PNAS..10015352P. doi:10.1073/pnas.2536559100. PMC 307571. PMID 14660793.

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[itoh-1] Itoh, Toshihiro; Uetsuki, Toshimitsu; Tamura, Toshitake; Matsumoto, Taro (June 1980). "Characterization of triterpene alcohols of seed oils from some species of theaceae, phytolaccaceae and sapotaceae". Lipids. 15 (6): 407–411. doi:10.1007/BF02534064. S2CID 25505422.

[2] Shimizu, Naoto; Itoh, Toshihiro; Saito, Masao; Matsumoto, Taro (February 1984). "Acid-catalyzed isomerization of cycloartane triterpene alcohols. The formation of cucurbitane- and lanostane-type isomers". The Journal of Organic Chemistry. 49 (4): 709–712. doi:10.1021/jo00178a030. ISSN 0022-3263.

[3] Kizakis, Manuel; Treger, Marvin; Dräger, Gerald; König, Carolin; Heretsch, Philipp (2026-03-26). "Navigating the Landscape of Cycloartanyl Cations: Synthesis of Fortunefuroic Acid I, Parkeol, 25,26,27-Trinor-3α-hydroxy-17,13-friedolanosta-8,12-dien-23-one, and Spirochensilide A". Journal of the American Chemical Society. doi:10.1021/jacs.5c22292. ISSN 0002-7863.

[ito-4] Ito, R; Mori, K; Hashimoto, I; Nakano, C; Sato, T; Hoshino, T (20 May 2011). "Triterpene cyclases from Oryza sativa L.: cycloartenol, parkeol and achilleol B synthases". Organic Letters. 13 (10): 2678–81. doi:10.1021/ol200777d. PMID 21526825.

[pearson-5] Pearson, A; Budin, M; Brocks, JJ (23 December 2003). "Phylogenetic and biochemical evidence for sterol synthesis in the bacterium Gemmata obscuriglobus". Proceedings of the National Academy of Sciences of the United States of America. 100 (26): 15352–7. Bibcode:2003PNAS..10015352P. doi:10.1073/pnas.2536559100. PMC 307571. PMID 14660793.

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References