Limonin
{{chembox
| Verifiedfields = changed
| verifiedrevid = 477498078
| ImageFile = Limonin.svg
| ImageSize =
| ImageFile1 = Limonin molecule ball.png
| ImageSize1 = 220
| ImageAlt1 = Ball-and-stick model of limonin
| PIN = (2aR,4aR,4bR,5aS,8S,8aS,10aR,10bR,14aS)-8-(Furan-3-yl)-2,2,4a,8a-tetramethyldecahydro-11H,13H-oxireno[2,3-c]pyrano[4′′,3′′:2′,3′]furo[3′,4′:5,6]naphtho[1,2-d]pyran-4,6,13(2H,5aH)-trione
| OtherNames = {{ubl|Limonoate D-ring-lactone|Limonoic acid di-δ-lactone|7,16-Dioxo-7,16-dideoxylimondiol}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1180-71-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L0F260866S
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16226
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 517449
| PubChem = 179651
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 156367
| SMILES = O=C4[C@@]6(C)[C@@]72O[C@@H]7C(=O)O[C@@H](c1ccoc1)[C@]2(C)CC[C@@H]6[C@]35COC(=O)C[C@@H]5OC([C@@H]3C4)(C)C
| InChI = 1/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
| InChIKey = KBDSLGBFQAGHBE-MSGMIQHVBF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KBDSLGBFQAGHBE-MSGMIQHVSA-N
}}
|Section2={{Chembox Properties
| Formula = C26H30O8
| MolarMass = 470.52 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
{{distinguish|Limonene}}
Limonin is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones.
Sources
Presence in citrus products
Limonin and other limonoid compounds contribute to the bitter taste of some citrus food products. Researchers have proposed removal of limonoids from orange juice and other products (known as "debittering") through the use of polymeric films.{{Cite journal
| last1 = Fayoux | first1 = S. P. C.
| last2 = Hernandez | first2 = R. J.
| last3 = Holland | first3 = R. V.
| doi = 10.1111/j.1750-3841.2007.00283.x
| title = The Debittering of Navel Orange Juice Using Polymeric Films
| journal = Journal of Food Science
| volume = 72
| issue = 4
| pages = E143–E154
| year = 2007
| pmid = 17995766
| pmc =
}}
Research
Limonin is under basic research to assess its possible biological properties.{{cite web |title=Limonin |url=https://pubchem.ncbi.nlm.nih.gov/compound/Limonin |publisher=PubChem, US National Library of Medicine |access-date=21 December 2022 |date=17 December 2022}}
References
{{Reflist}}
External links
- [http://www.ars.usda.gov/is/AR/archive/feb05/citrus0205.htm "Citrus Compound: ready to help your body!"] (Agricultural Research Service, USDA)