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

Description

Parkeol, also known as a tetracyclic triterpenoid, is a compound that features a lanostane skeleton with a 3beta-hydroxylated structure and double bonds at the 9(11)and 24-positions. This unique molecular configuration endows Parkeol with various potential applications across different industries.

Uses

Used in Pharmaceutical Industry:
Parkeol is used as a therapeutic agent for its potential medicinal properties. The expression is: Parkeol is used as a pharmaceutical compound for its unique molecular structure that may contribute to the development of new drugs and treatments.
Used in Chemical Research:
In the field of chemical research, Parkeol is used as a subject of study for its distinctive tetracyclic triterpenoid structure. The expression is: Parkeol is used as a research subject for understanding its chemical properties and potential applications in various scientific domains.
Used in Cosmetics Industry:
Parkeol may also find applications in the cosmetics industry, where its unique properties could be harnessed for the development of skincare products. The expression is: Parkeol is used as an ingredient in the cosmetics industry for its potential benefits in skincare formulations.

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.

Steric bulk at cycloartenol synthase position 481 influences cyclization and deprotonation.

Cycloartenol synthase converts oxidosqualene to the pentacyclic sterol precursor cycloartenol. An Arabidopsis thaliana cycloartenol synthase Ile481Val mutant was previously shown to produce lanosterol and parkeol in addition to its native product cycloartenol. Experiments are described here to construct Phe, Leu, Ala, and Gly mutants at position 481 and to determine their cyclization product profiles. The Phe mutant was inactive, and the Leu mutant produced cycloartenol and parkeol. The Ala and Gly mutants formed lanosterol, cycloartenol, parkeol, achilleol A, and camelliol C. Monocycles comprise most of the Gly mutant product, showing that an alternate cyclization route can be made the major pathway by a single nonpolar mutation.