Lupeol

Lupeol Basic information
Description References
Product Name:Lupeol
Synonyms:MONOGYNOL;(3-beta)-lup-20(29)-en-3-o;(3-beta)-lup-20(29)-en-3-ol;1H-Cyclopenta[a]chrysene, lup-20(29)-en-3-ol deriv.;Clerodol;Fagarsterol;lup-20(29)-en-3-beta-ol;Lup-20(29)-en-3beta-ol
CAS:545-47-1
MF:C30H50O
MW:426.73
EINECS:208-889-9
Product Categories:chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Tri-Terpenoids;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
Mol File:545-47-1.mol
Lupeol Structure
Lupeol Chemical Properties
Melting point 215°
alpha D20 +27.2° (c = 4.8 in chloroform)
Boiling point 482.1°C (rough estimate)
density 0.9457
refractive index 1.4910 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
form neat
pka15.19±0.70(Predicted)
color White to Off-White
InChIKeyMQYXUWHLBZFQQO-QGTGJCAVSA-N
LogP10.460 (est)
CAS DataBase Reference545-47-1(CAS DataBase Reference)
NIST Chemistry ReferenceLupeol(545-47-1)
Safety Information
Safety Statements 24/25
WGK Germany 2
RTECS OK5763000
HS Code 29061990
Hazardous Substances Data545-47-1(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
Lupeol Usage And Synthesis
DescriptionLupeol 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.
Referenceshttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2764818/
https://en.wikipedia.org/wiki/Lupeol
Chemical PropertiesWhite powder
UsesLupeol 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.
Usesantineoplastic
UsesAbundant 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.
DefinitionChEBI: A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in m ny edible fruits and vegetables.
General DescriptionLupeol is a novel anti-cancer and anti-inflammatory dietary triterpene. They help in stabilizing phospholipid bilayers in plant cell membranes. In general, this group contains 28-29 carbons along with carbon-carbon double bonds, usually one in the sterol nucleus and at times a second in the alkyl side chain.
targetCaspase | PARP | GSK-3 | Akt | PI3K | Wnt/β-catenin | c-Myc | IL Receptor | Bcl-2/Bax | NF-kB | ROS | TNF-α | STAT
Lupeol Preparation Products And Raw materials
Preparation Productspsi-taraxasterol-->alpha-Amyrin-->5α-Lupan-3β-ol
Zearalenone 3BETA-ACETOXYBETULINIC ACID LUPEOL PALMITALE α-L-Arabinofuranosyl-(1→4)-O β-D-glucurouopyranosyl-(1→3)- 3β-hudroxy-lup-20(29)-ene Betulin LUPEOL(SH) LUP-20(29)-EN-3,28-DIOL, 28-ACETATE, (3B) LUP-20(29)-EN-3,28-DIOL, 3B-ACETATE 3-O-(3',3'-DIMETHYLSUCCINYL) BETULINIC ACID Lupeol LUPEOL HEMISUCCINATE LUPEOL ACETATE (REAGENT / STANDARD GRADE),LUPEOL ACETATE(RG),LUPEOL ACETATE Betulinic acid lupeol synthase BETULIN DIACETATE 3-epi-Lupeol BETULINIC ACID METHYL ESTER LUPEOL(RG)

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