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 

Solid

pka

15.19±0.70(Predicted)

color 

White to Off-White

optical activity

+26.420 (c 3.51, CHCl3)

InChIKey

MQYXUWHLBZFQQO-QGTGJCAVSA-N

LogP

10.460 (est)

CAS DataBase Reference

545-47-1(CAS DataBase Reference)

NIST Chemistry Reference

Lupeol(545-47-1)

Safety Information

Safety Statements 

24/25

WGK Germany 

2

RTECS 

OK5763000

HS Code 

29061990

Hazardous Substances Data

545-47-1(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

Lupeol Usage And Synthesis

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.

References

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2764818/
https://en.wikipedia.org/wiki/Lupeol

Chemical Properties

White powder

Uses

antineoplastic

Uses

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.

Uses

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.

Definition

ChEBI: 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 Description

Lupeol 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.

target

Caspase | PARP | GSK-3 | Akt | PI3K | Wnt/β-catenin | c-Myc | IL Receptor | Bcl-2/Bax | NF-kB | ROS | TNF-α | STAT

Lupeol(545-47-1)Related Product Information

• (-)-LUPININE
• Zearalenone
• SodiuM new houttuyfonate
• Quillaic acid
• PROTOPANAXDIOL
• illudin S
• LUPEOL ACETATE (REAGENT / STANDARD GRADE),LUPEOL ACETATE(RG),LUPEOL ACETATE
• Betulin
• Betulinic acid
• BETULIN DIACETATE
• BETULINIC ACID METHYL ESTER
• lupeol synthase
• 3-epi-Lupeol
• LUPEOL3-PALMITATE
• lupeol caffeate
• 3BETA-ACETOXYBETULINIC ACID
• LUPEOL PALMITALE
• Lupeol