Limonin

Base Information

• Chemical Name: Limonin
• CAS No.: 1180-71-8
• Deprecated CAS: 1392-24-1
• Molecular Formula: C₂₆H₃₀O₈
• Molecular Weight: 470.519
• Hs Code.: 29321900
• European Community (EC) Number: 808-129-1
• UNII: L0F260866S
• DSSTox Substance ID: DTXSID8045985
• Nikkaji Number: J9.856F
• Wikipedia: Limonin
• Wikidata: Q2398745
• Metabolomics Workbench ID: 50426
• ChEMBL ID: CHEMBL517449
• Mol file: 1180-71-8.mol

Synonyms:7,16-dioxo-7,16-dideoxylimondiol;limonin;obaculactone

Chemical Property of Limonin

Chemical Property:

• Appearance/Colour: White to slightly off white powder
• Vapor Pressure: 9.96E-18mmHg at 25°C
• Melting Point: 298 °C
• Refractive Index: 1.602
• Boiling Point: 668.4 °C at 760 mmHg
• Flash Point: 358 °C
• PSA: 104.57000
• Density: 1.39 g/cm³
• LogP: 3.13740
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Sparingly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 470.19406791
• Heavy Atom Count: 34
• Complexity: 1010

Purity/Quality:

98%, ^*data from raw suppliers

Limone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C
• Isomeric SMILES: C[C@@]12CC[C@H]3[C@]([C@@]14[C@H](O4)C(=O)O[C@H]2C5=COC=C5)(C(=O)C[C@@H]6[C@@]37COC(=O)C[C@@H]7OC6(C)C)C
• description: Limonin is a triterpenoid enriched in citrus fruits, which has antivirus and antitumor ability. Limonin is a phytonutrient found in most citrus fruits. Natural sources of limonin include oranges, grapefruits, lemons, and limes. Within the fruit it is attached to a sugar and the combined molecule is called limonin glucoside.Limonin is what remains after our bodies cleave a glucose, or sugar molecule, from limonin's parent compound, limonin glucoside. Limonin glucoside is present in citrus and citrus juices in about the same amount as vitamin C. The good news is limonin has shown to have exceptional health benefits in humans and other animals. It seems to be able to help reduce the development and growth of cancers. It also has the effect of lowering cholesterol in the blood stream. In 2000, Manners, Hasegawa, and their Canadian co-authors reported that limonin may be among the citrus-juice compounds that lower cholesterol. In lab tests, they found that human liver cells produced less apo B—a compound associated with higher cholesterol levels—when exposed to limonin.
• Uses: It has antiproliferative and anti-apoptotic activity against several tumor cell lines and can inhibit the rat colon cancer induced by azoxymethane. By inhibiting the activity of HIV-1 protease, it inhibits the replication of HIV-1 virus in monocytes, macrophages and monocytes. antiproliferative, antiviral, antiinflammatory, antinociceptive Limonin is a limonoid extracted from various citrus plants. Bioactivity of Limonin have been revolved around its anti-HIV properties. Limonin has been used:to treat human peripheral blood mononuclear cells (PBMCs) to test its effect on human immunodeficiency virus (HIV) replicationto test its effects as an anti-osteoporosis agent in osteoblastogenesis activity in MC3T3-E1 cells and ovariectomized (OVX) rat modelas a reference standard in high-performance liquid chromatography (HPLC) system

Technology Process of Limonin

There total 2 articles about Limonin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

obacunone (751-03-1) → Limonin (1180-71-8,42867-83-4)

Guidance literature:

obacunone; With chromium(VI) oxide; acetic anhydride; at 60 ℃; for 3h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 1h; Further stages;

Reference yield:

→ Limonin (1180-71-8,42867-83-4)

Guidance literature:

DOI:10.1021/jo01345a045

Reference yield: 85.0%

4-methoxy-benzylamine (2393-23-9) + Limonin (1180-71-8,42867-83-4) → 2-((1S,3aS,4aR,4bR,9aR,11aS)-1-(furan-3-yl)-9a-(hydroxymethyl)-4b,7,7,11a-tetramethyl-3,5-dioxotetradecahydroisobenzofuro[5,4-f]oxireno[2,3-d]isochromen-9-yl)-N-(4-methoxybenzyl)acetamide

Guidance literature:

With montmorillonite K-10; In ethanol; at 80 ℃; for 0.5h; Solvent; Temperature; Sealed tube; Microwave irradiation;

DOI:10.5935/0103-5053.20150266

upstream raw materials:

obacunone

Downstream raw materials:

7α-limonol

desoxylimonin

(17S)-1α,4;6β,19;14,15β;21,23-tetraepoxy-17-hydroxy-4,4,8-trimethyl-7-oxo-3,4;16,17-diseco-24-nor-5α,13α,14β-chola-20,22-diene-3,16-dioic acid-16-lactone

shihulimonin A

Refernces

• 1、 -. "Electric heating mosquito killing liquid and its preparation method (by machine translation)". Paragraph 0028. . Retrieved 2017/09/02.