Limonin

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Limonin
File:Limonin.svg
Ball-and-stick model of limonin
Names
Preferred IUPAC name
(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
Other names
  • Limonoate D-ring-lactone
  • Limonoic acid di-δ-lactone
  • 7,16-Dioxo-7,16-dideoxylimondiol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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 checkY
    Key: KBDSLGBFQAGHBE-MSGMIQHVSA-N checkY
  • 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
    Key: KBDSLGBFQAGHBE-MSGMIQHVBF
  • 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
Properties
C26H30O8
Molar mass 470.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Not to be confused with 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

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Limonin is enriched in citrus fruits and is often found at higher concentrations in seeds, for example orange and lemon seeds.[1]

Presence in citrus products

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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.[2]

Research

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Limonin is under basic research to assess its possible biological properties.[1]

References

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