514-45-4

Basic information

• Product Name: Parkeol
• Synonyms: (3beta)-Lanosta-9(11),24-dien-3-ol
• CAS NO: 514-45-4
• Molecular Formula: C₃₀H₅₀O
• Molecular Weight: 426.72
• Mol File: 514-45-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 498.3°C at 760 mmHg
• Flash Point: 221°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 5.11E-12mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: Parkeol(CAS DataBase Reference)
• NIST Chemistry Reference: Parkeol(514-45-4)
• EPA Substance Registry System: Parkeol(514-45-4)

Safety Data

• Hazardous Substances Data: 514-45-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A tetracyclic triterpenoid comprised of a lanostane skeleton which is 3beta-hydroxylated and has double bonds at the 9(11)- and 24-positions.

InChI:InChI=1/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

Upstream product

• 14050-42-1 2,3-Oxidosqualene 
• 54910-48-4 squalene 2,3(S)-oxide 
• 469-38-5 cycloartenol 

Downstream Products

• 55570-91-7 (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH.8cH)-Δ⁹⁽¹¹⁾-tetradecahydro-1H-cyclopenta[a]phenanthren 

Relevant articles and documents

Protostadienol synthase from Aspergillus fumigatus: Functional conversion into lanosterol synthase

Oxidosqualene:protostadienol cyclase (OSPC) from the fungus Aspergillus fumigatus, catalyzes the cyclization of (3S)-2,3-oxidosqualene into protosta-17(20)Z,24-dien-3β-ol which is the precursor of the steroidal antibiotic helvolic acid. To shed light on the structure-function relationship between OSPC and oxidosqualene:lanosterol cyclase (OSLC), we constructed an OSPC mutant in which the C-terminal residues 702APPGGMR708 were replaced with 702NKSCAIS708, as in human OSLC. As a result, the mutant no longer produced the protostadienol, but instead efficiently produced a 1:1 mixture of lanosterol and parkeol. This is the first report of the functional conversion of OSPC into OSLC, which resulted in a 14-fold decrease in the Vmax/KM value, whereas the binding affinity for the substrate did not change significantly. Homology modeling suggested that stabilization of the C-20 protosteryl cation by the active-site Phe701 through cation-π interactions is important for the product outcome between protostadienol and lanosterol.

A putative precursor of isomalabaricane triterpenoids from lanosterol synthase mutants

Known lanosterol synthase mutants produce monocyclic or tetracyclic byproducts from oxidosqualene. We describe Erg7 Tyr510 mutants that cause partial substrate misfolding and generate a tricyclic byproduct. This novel triterpene, (13αH)-isomalabarica-14(27),17E,21-trien-3β-ol, is the likely biosynthetic precursor of isomalabaricane triterpenoids in sponges. The results suggest the facile evolution of protective triterpenoids in sessile animals.

Oxidosqualene Cyclase Residues that Promote Formation of Cycloartenol, Lanosterol, and Parkeol

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