Lupeol

Base Information

• Chemical Name: Lupeol
• CAS No.: 545-47-1
• Molecular Formula: C30H50O
• Molecular Weight: 426.726
• Hs Code.: 29061990
• European Community (EC) Number: 208-889-9
• NSC Number: 90487
• UNII: O268W13H3O
• DSSTox Substance ID: DTXSID901025006
• Nikkaji Number: J6.423H
• Wikipedia: Lupeol
• Wikidata: Q409366
• Pharos Ligand ID: 18SW8Y6AQVVK
• Metabolomics Workbench ID: 28737
• ChEMBL ID: CHEMBL289191
• Mol file: 545-47-1.mol

Synonyms:lup-20(29)-en-3-ol;lup-20(29)-en-3beta-ol;lup-20(29)-ene-3alpha-ol;lupeol;lupeol, (3alpha)-isomer;lupeol, (3beta,18beta,19beta)-isomer

Chemical Property of Lupeol

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.41E-11mmHg at 25°C
• Melting Point: 215-216oC
• Refractive Index: 1.515
• Boiling Point: 488.1 °C at 760 mmHg
• PKA: 15.19±0.70(Predicted)
• Flash Point: 216.9 °C
• PSA: 20.23000
• Density: 0.978 g/cm³
• LogP: 8.02480
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 9.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 426.386166214
• Heavy Atom Count: 31
• Complexity: 766

Purity/Quality:

99.5% ^*data from raw suppliers

Lupeol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C
• Recent ClinicalTrials: Clinical Study for Topical Lupeol in Acne
• Description: Lupeol is a kind of novel anti-inflammatory and anti-cancer dietary triterpene that can be found in white cabbage, green pepper, strawberry, olive, mangoes and grapes. In recent years, much progress has been made on the application of this molecule for clinical treatment of various kind of disorders. On the one hand, it has been extensively studied that it is capable of inhibiting inflammation under both in vitro and in animal models. Studies have shown that Lupeol is a multi-target agent during its anti-inflammation effect, targeting on many key molecular pathways involving nuclear factor kappa B (NFκB), cFLIP, Fas, Kras, phosphatidylinositol-3-kinase (PI3K)/Akt and Wnt/β-catenin. On the other hand, Lupeol has strong anti-tumor effect during treatment of various cancer types such as prostate, skin, pancreatic and breast cancer. The anti-tumor effect might be related to its potential to modulate important signaling pathways such as nuclear factor kappa B (NFκB) and the phosphatidylinositol 3-kinase [PI3K] /Akt (protein kinase B pathway), which are crucial during tumorigenesis.
• Uses: antineoplastic Abundant plant triterpene. Occurs in the skin of lupin seeds, in circle, in the latex of fig trees and of rubber plants. It was detected in cocoons of Bombyx mori. Lupeol was used as reference standard in method development and validation of lupeol from Vernonia Cinerea using HPLC method. It has been used as a standard for the identification and quantification of triterpenoids in blueberry cuticular wax by GC.

Technology Process of Lupeol

There total 37 articles about Lupeol 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: 90.0%

lupeol acetate (1617-68-1,6610-54-4,55870-40-1,74345-30-5,101627-42-3) → lupenol (545-47-1)

Guidance literature:

With potassium hydroxide; In methanol; for 0.0166667h; microwave irradiation;

Reference yield: 90.0%

tert-butyl((1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-9-yloxy)dimethylsilane (1190597-45-5) → lupenol (545-47-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ja906335u

Reference yield: 68.0%

3-O-acetylbetulinal (27570-21-4) → lupenol (545-47-1)

Guidance literature:

3-O-acetylbetulinal; With hydrazine hydrate; In diethylene glycol dimethyl ether; at 80 ℃; for 3h;

With potassium hydroxide; In diethylene glycol dimethyl ether; for 5h; Reagent/catalyst; Temperature; Reflux;

upstream raw materials:

lupenone

aluminum isopropoxide

isopropyl alcohol

benzene

Downstream raw materials:

lupeol acetate

lupan-3-one

3-Oxolupane

Lupane

Refernces

• 1、 Wahyuono, Subagus,Hoffmann, Joseph J.,Jolad, Shivanand D.,Dentali, Steven J.. "TRITERPENOIDS OF AMSONIA GRANDIFLORA". . p. 1213. Retrieved 1987.
• 2、 Garifullina,Myasoedova, Yu. V.,Ishmuratova. "Synthesis of Lupeol from Betulin". . p. 765 - 767. Retrieved 2019/08/07.
• 3、 -. "And reclaims to clean rough synthesis method". Paragraph 0036-0041; 0053-0055. . Retrieved 2017/08/25.