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L5632

Sigma-Aldrich

Lupeol

≥94%

Synonym(s):

β-Viscol, 20(29)-Lupen-3β-ol, 3β-Hydroxy-20(29)-lupene, Clerodol, Fagarasterol, Lupenol, Monogynol B

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About This Item

Empirical Formula (Hill Notation):
C30H50O
CAS Number:
545-47-1
Molecular Weight:
426.72
EC Number:
208-889-9
MDL number:
MFCD00017351
UNSPSC Code:
12352002
PubChem Substance ID:
57654331
NACRES:
NA.22

Quality Level

100

Assay

≥94% (TLC)
≥94%

storage temp.

2-8°C

SMILES string

[H]C12CCC3C4(C)CCC(O)C(C)(C)[C@]4([H])CCC3(C)[C@]1(C)CCC5(C)CC[C@H](C(C)=C)[C@]25[H]

InChI

1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1

InChI key

MQYXUWHLBZFQQO-QGTGJCAVSA-N

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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.

Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fruit characteristics and cuticle triterpenes as related to postharvest quality of highbush blueberries.
Moggia C, et al.
Sci. Hortic., 211, 449-457 (2016)
Shuang Liang et al.
Journal of natural products, 73(4), 532-535 (2010-03-03)
Phytochemical examination of the methanolic extract from the stem bark of Daphne aurantiaca led to the isolation of six new sesquiterpenoids, dauca-3,11-dien-2alpha,15-diol (1), 3-oxoguai-4-ene-11,12-diol (2), 4alpha,5alpha,8alpha,11alphaH-3-oxoguai-1(10)-en-12,8-olide-7alpha-diol (3), 4alpha,5alpha,8alpha,11betaH-3-oxoguai-1(10)-en-12,8-olide-7beta-diol (4), 4alpha,5betaH-guai-9,7(11)-dien-12,8-olide-1alpha,8alpha-diol (5), 4alpha,5alphaH-guai-9,7(11)-dien-12,8-olide-1alpha,8alpha-diol (6), and a new diterpenoid, 12-O-benzoylphorbol 13-nonanoate (7)
Development and validation of High Performance Liquid Chromatographic Method for the Simultaneous Determination of ?-sitosterol and Lupeol in Veronica cinerea Linn.
Shah, Willy, M. B. Kekare, and Vikas Vaidya.
International Journal of Pharma and Bio Sciences, 1 (3), 1-5 (2010)
Jean Fotie et al.
Journal of natural products, 69(1), 62-67 (2006-01-31)
An ethnopharmacological investigation was conducted among the Baka pygmies of Dja biosphere reserve (Cameroon) to collect information on the antimalarial plants used in their daily life. Holarrhena floribunda is one of those plants. Extracts of the stem barks of H.
Anupam Maurya et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 47(1), 152-161 (2012-06-05)
Two triterpenoids ursolic acid (1) and lupeol (2) isolated and characterized from Eucalyptus tereticornis and Gentiana kurroo were subjected to in silico QSAR modeling and docking studies and later the predicted results were confirmed through in vivo experiments. QSAR modeling
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