Skip to Content
Merck
CN

L9647

Limonin

from citrus seeds, >90% (HPLC)

Synonym(s):

Citrolimonin, Dictamnolactone, Evodin, Limonoic acid 3,19:16,17 dilactone, Obaculactone

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C26H30O8
CAS Number:
1180-71-8
Molecular Weight:
470.51
NACRES:
NA.25
PubChem Substance ID:
24896458
UNSPSC Code:
12352205
MDL number:
MFCD00075922

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Limonin, from citrus seeds, >90% (HPLC)

InChI

1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1

SMILES string

CC1(C)O[C@H]2CC(=O)OC[C@]23[C@H]4CC[C@@]5(C)[C@@H](OC(=O)[C@H]6O[C@@]56[C@]4(C)C(=O)C[C@@H]13)c7ccoc7

InChI key

KBDSLGBFQAGHBE-MSGMIQHVSA-N

biological source

citrus seeds

assay

>90% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

Quality Level

200

Looking for similar products? Visit Product Comparison Guide

Related Categories

Application

Limonin has been used:
  • to treat human peripheral blood mononuclear cells (PBMCs) to test its effect on human immunodeficiency virus (HIV) replication
  • to test its effects as an anti-osteoporosis agent in osteoblastogenesis activity in MC3T3-E1 cells and ovariectomized (OVX) rat model
  • as a reference standard in high-performance liquid chromatography (HPLC) system

Biochem/physiol Actions

Limonin exerts its anti-inflammatory activity by downregulating signal transducer and activator of transcription 3/ microRNA-214 (STAT3/miR-214) signaling pathway in Ulcerative colitis (UC) condition. It is an anti-carcinogenic agent, involved in the down-regulation Wingless-related integration site (Wnt) signaling pathway component in in vitro studies.
Limonin is a triterpenoid aglycone that is a bitter principle of citrus fruits. It has anti-proliferative, proapoptotic activity on several cancer cell lines and inhibits azoxymethane-induced colon cancer in rats. It also inhibits HIV-1 replication in culturedf monocytes, macrophages, and mononuclear cells, perhaps by inhibition of HIV-1 protease activity.

General description

Limonin also known as citrolimonin and evodin, is a secondary plant metabolite present in citrus seeds at high concentrations. It is a derivative of limonoids.
Limonin may be used in assays to quantify limonin in citrus products. It may also be used in other assays as a control, standard, or competitor or in studies on the physiology, metabolism, and biosynthesis of limonin.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000482205
0000482205
0000420488
0000420488
0000389395

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Yong-Long Han et al.
Toxicology in vitro : an international journal published in association with BIBRA, 25(8), 1828-1833 (2011-10-18)
Among the various possible causes for drug interactions, pharmacokinetic factors such as inhibition of drug-metabolizing enzymes and transporters, especially cytochrome P450 (CYP) isoenzymes and P-glycoprotein (P-gp), are regarded as the most frequent and clinically important. Limonin is a widely used
Lilibeth Dagulo et al.
Journal of food science, 75(2), C199-C207 (2010-05-25)
The effects due to Candidatus Liberibacter infection, commonly called citrus greening or Huanglongbing (HLB), on volatile and nonvolatile components of orange juices, OJ, were examined using GC-MS and high-performance liquid chromatography (HPLC). HLB symptomatic, asymptomatic, and control "Hamlin" and "Valencia"
Juanjuan Zhao et al.
Analytical and bioanalytical chemistry, 401(1), 289-296 (2011-05-17)
A liquid chromatographic-mass spectrometric (LC-MS) method has been developed and validated for simultaneous determination of dehydroevodiamine and limonin from Evodia rutaecarpa in rat plasma. After addition of the internal standard, domperidone, plasma samples were extracted by liquid-liquid extraction with ethyl
Fangyuan Gong et al.
Biochemical pharmacology, 80(2), 218-225 (2010-04-07)
Allograft rejection is a predominantly Th1 immune response. In this study, we showed that obaculactone, a natural compound derived from citrus fruit, prolonged skin graft survival in mice when treated after but not before transplantation. Furthermore, obaculactone inhibited alloantigen-specific production
Mahmoud Zaki El-Readi et al.
European journal of pharmacology, 626(2-3), 139-145 (2009-09-29)
P-glycoprotein (P-gp), a membrane transporter encoded by the MDR1 gene in human cells, mediates drug efflux from cells and plays a major role in causing multidrug resistance; which is one of the most accepted mechanisms for failure of chemotherapy in
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service