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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

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

Storage Class Code

11 - Combustible Solids

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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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)
Fruit characteristics and cuticle triterpenes as related to postharvest quality of highbush blueberries.
Moggia C, et al.
Sci. Hortic., 211, 449-457 (2016)
Archana Kumari et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(5), 1781-1789 (2012-03-13)
Drug induced hepatotoxicity is a major problem where phytochemicals hold promise for its abrogation. This study was carried out to explore cytoprotective potential of lupeol, a triterpene, against acetaminophen (AAP)-induced toxicity in rat hepatocytes. AAP exposure significantly (p<0.05) reduced cell
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
Marvin J Núñez et al.
Journal of natural products, 68(7), 1018-1021 (2005-07-26)
Five new lupane triterpenes (1-5), in addition to 24 known ones, were isolated from Maytenus cuzcoina and M. chiapensis. Their structures were elucidated on the basis of spectroscopic analysis, including homonuclear and heteronuclear correlation NMR (COSY, ROESY, HSQC, and HMBC)
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