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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.236.039 Edit this at Wikidata
UNII
  • 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).
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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.

Sources

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

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

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

References

  1. ^ a b "Limonin". PubChem, US National Library of Medicine. 17 December 2022. Retrieved 21 December 2022.
  2. ^ 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.

External links