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Limonin





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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.

Limonin
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

    CAS Number

    3D model (JSmol)

    ChEBI
    ChEMBL
    ChemSpider
    ECHA InfoCard 100.236.039 Edit this at Wikidata

    PubChem CID

    UNII

    CompTox Dashboard (EPA)

    • 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

    Chemical formula

    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).

    ☒N verify (what is checkY☒N ?)

    Infobox references

    Sources

    edit

    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

    edit

    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

    edit

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

    References

    edit
    1. ^ a b "Limonin". PubChem, US National Library of Medicine. 17 December 2022. Retrieved 21 December 2022.
  • ^ Fayoux, S. P. C.; Hernandez, R. J.; Holland, R. V. (2007). "The Debittering of Navel Orange Juice Using Polymeric Films". Journal of Food Science. 72 (4): E143–E154. doi:10.1111/j.1750-3841.2007.00283.x. PMID 17995766.
  • edit

    Retrieved from "https://en.wikipedia.org/w/index.php?title=Limonin&oldid=1128632888"
     



    Last edited on 21 December 2022, at 04:16  





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    This page was last edited on 21 December 2022, at 04:16 (UTC).

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