Diplopterol

Base Information

• Chemical Name: Diplopterol
• CAS No.: 1721-59-1
• Molecular Formula: C30H52 O
• Molecular Weight: 428.742
• DSSTox Substance ID: DTXSID40169206
• Nikkaji Number: J7.814J
• Wikidata: Q27104361
• Metabolomics Workbench ID: 29149
• ChEMBL ID: CHEMBL2448591
• Mol file: 1721-59-1.mol

Synonyms:22-hydroxyhopane;diplopterol;hopan-22-ol

Chemical Property of Diplopterol

Chemical Property:

• Vapor Pressure: 3.15E-11mmHg at 25°C
• Boiling Point: 480°C at 760 mmHg
• Flash Point: 222.4°C
• PSA: 20.23000
• Density: 0.971g/cm³
• LogP: 8.24880
• XLogP3: 9.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 428.401816278
• Heavy Atom Count: 31
• Complexity: 737

Purity/Quality:

99% ^*data from raw suppliers

17BETA(H),21BETA(H)-22-HYDROXYHOPANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3(C2CCC4C3(CCC5C4(CCC5C(C)(C)O)C)C)C)C)C
• Isomeric SMILES: C[C@]12CC[C@@H]([C@@H]1CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCCC5(C)C)C)C)C)C(C)(C)O

Technology Process of Diplopterol

There total 28 articles about Diplopterol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

hydroxyhopanone (1981-81-3) → hopan-22-ol (1721-59-1)

Guidance literature:

hydroxyhopanone; With hydrazine hydrate; In diethylene glycol; at 200 ℃; for 2h;

With potassium hydroxide; at 200 ℃; for 6h;

DOI:10.1002/anie.201911584

Reference yield:

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene (111-02-4) → diploptene (1615-91-4,1812-64-2,33323-60-3,33323-61-4,43206-60-6) + hopan-22-ol (1721-59-1) + 17-epi-dammara-20(21),24-diene

Guidance literature:

With cell-free homogenate of Alicyclobacillus acidocaldarius W₁₆₉F mutant; at 45 ℃; for 16h; Product distribution; cell-free homogenates of other mutants, other temperature; K_m, V_max;

DOI:10.1039/a806948d

Reference yield:

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene (111-02-4) → diploptene (1615-91-4,1812-64-2,33323-60-3,33323-61-4,43206-60-6) + hopan-22-ol (1721-59-1) + 17-epi-dammara-20(21),24-diene + 17(E)-13α(H)-malabarica-14(27),17(E),21-triene

Guidance literature:

With mutant F₆₀₁A of SHC enzyme; In water; at 60 ℃; for 16h; pH=6.0; Further Variations:; Reagents; Temperatures; Product distribution; Kinetics;

DOI:10.1271/bbb.63.2038

upstream raw materials:

(3R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3-(1-Hydroxy-1-methyl-ethyl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydro-cyclopenta[a]chrysene-4,9,13-trione

spergulagenol

hydroxyhopanone

zeorinone

Downstream raw materials:

hop-22⁽²⁹⁾-ene

diploptene

30-Normoretan-22-one

30-Norhopan-22-one

Refernces

• 1、 Mallory et al.. "". . p. 3564. Retrieved 1968.
• 2、 Kaneko, Ikki,Terasawa, Yuri,Hoshino, Tsutomu. "Squalene-Hopene Cyclase: Mechanistic Insights into the Polycyclization Cascades of Squalene Analogs Bearing Ethyl and Hydroxymethyl Groups at the C-2 and C-23 Positions". . p. 11139 - 11157. Retrieved 2018/08/03.
• 3、 Syren, Per-Olof,Hammer, Stephan C.,Claasen, Birgit,Hauer, Bernhard. "Entropy is key to the formation of pentacyclic terpenoids by enzyme-catalyzed polycyclization". supporting information. p. 4845 - 4849. Retrieved 2014/05/20.