Limonin

Modify Date: 2024-01-01 22:11:31

Limonin Structure
Limonin structure
Common Name Limonin
CAS Number 1180-71-8 Molecular Weight 470.512
Density 1.4±0.1 g/cm3 Boiling Point 668.4±55.0 °C at 760 mmHg
Molecular Formula C26H30O8 Melting Point 298ºC
MSDS Chinese USA Flash Point 358.0±31.5 °C

 Use of Limonin


Limonin is a triterpenoid enriched in citrus fruits, which has antivirus and antitumor ability.IC50 Value: Target: HIV; anticancerLimonin is a triterpenoid aglycone that is a bitter principle of citrus fruits. Limonin is chemically induced carcinogenesis inhibitor and HIV-1 replication inhibitor. Limonin has anti-proliferative, proapoptotic activity on several cancer cell lines and inhibits azoxymethane-induced colon cancer in rats. Limonin also inhibits HIV-1 replication in culturedf monocytes, macrophages, and mononuclear cells, perhaps by inhibition of HIV-1 protease activity.

 Names

Name limonin
Synonym More Synonyms

 Limonin Biological Activity

Description Limonin is a triterpenoid enriched in citrus fruits, which has antivirus and antitumor ability.IC50 Value: Target: HIV; anticancerLimonin is a triterpenoid aglycone that is a bitter principle of citrus fruits. Limonin is chemically induced carcinogenesis inhibitor and HIV-1 replication inhibitor. Limonin has anti-proliferative, proapoptotic activity on several cancer cell lines and inhibits azoxymethane-induced colon cancer in rats. Limonin also inhibits HIV-1 replication in culturedf monocytes, macrophages, and mononuclear cells, perhaps by inhibition of HIV-1 protease activity.
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References

[1]. Han YL, Yu HL, Li D, et al. Inhibitory effects of limonin on six human cytochrome P450 enzymes and P-glycoprotein in vitro. Toxicol In Vitro. 2011 Dec;25(8):1828-33.

[2]. Kotamballi N. Chidambara Murthy, Jayaprakasha, Vinod Kumar, et al. Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis. J. Agric. Food Chem., 2011, 59 (6):2314-2323.

[3]. Mahmoud Zaki El-Readi, Dalia Hamdana, Nawal Farrag, et al. Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines. European Journal of Pharmacology. 2010,626 (2-3): 139-145.

[4]. Battinelli L, Mengoni F, Lichtner M, et al. Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells. Planta Med. 2003 Oct;69(10):910-3.

[5]. Tanaka T, Kohno H, Tsukio Y, et al. Citrus limonoids obacunone and limonin inhibit azoxymethane-induced colon carcinogenesis in rats. Biofactors. 2000;13(1-4):213-8.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 668.4±55.0 °C at 760 mmHg
Melting Point 298ºC
Molecular Formula C26H30O8
Molecular Weight 470.512
Flash Point 358.0±31.5 °C
Exact Mass 470.194061
PSA 104.57000
LogP 1.66
Vapour Pressure 0.0±2.0 mmHg at 25°C
Index of Refraction 1.602

 Safety Information

Hazard Codes Xn: Harmful;
Risk Phrases R20/21/22
Safety Phrases S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS RR1122000

 Articles31

More Articles
Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques.

J. Food Sci. 77(9) , C921-6, (2012)

Grapefruits (Citrus paradisi Macfad) contain several phytochemicals known to have health maintaining properties. Due to the consumer's interest in obtaining high levels of these phytochemicals, it is ...

Ethylene degreening modulates health promoting phytochemicals in Rio Red grapefruit.

Food Chem. 188 , 77-83, (2015)

In the current study, we examined the effects of postharvest degreening and storage on phytochemicals in Rio Red grapefruit. Grapefruits were degreened with 3.5 μl/l of ethylene at 21 °C and 80% relat...

Quinine Bitterness and Grapefruit Liking Associate with Allelic Variants in TAS2R31.

Chem. Senses 40 , 437-43, (2015)

Multiple psychophysical gene-association studies suggest a single nucleotide polymorphism (SNP) within the bitter receptor gene TAS2R19 on chromosome 12 may be functional. Previously, the Arg299Cys SN...

 Synonyms

Limonoic acid di-δ-lactone
8-(3-Furyl)decahydro-2,2,4a,8a-tetramethyl-11H,13H-oxireno[d]pyrano[4',3':3,3a]isobenzofuro[5,4-f][2]benzopyran-4,6,13(2H,5aH)-trione
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione
Limonoic acid 3,19:16,17 dilactone
1H,3H-Oxireno[c]pyrano[4'',3'':2',3']furo[3',4':5,6]naphtho[1,2-d]pyran-3,8,10(6H,9aH)-trione, 12-(3-furanyl)decahydro-6,6,8a,12a-tetramethyl-, (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-
LiMone
DICTAMNOLACTONE
CITROLIMONIN
Limonin
Evodine
Limonoic Acid Di-d-lactone
LIMONINE
(4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione
EVODIN
OBACULACTONE
(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(3-Furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione
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