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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:
Molecular Weight:
426.72
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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)
Mohammad Saleem
Cancer letters, 285(2), 109-115 (2009-05-26)
In the Western world, an average of 250 mg per day of triterpenes (member of phytosterol family), largely derived from vegetable oils, cereals, fruits and vegetables is consumed by humans. During the last decade, there has been an unprecedented escalation
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.

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