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Limonin information


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
  • 1180-71-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16226 checkY
ChEMBL
  • ChEMBL517449 ☒N
ChemSpider
  • 156367 checkY
ECHA InfoCard 100.236.039 Edit this at Wikidata
PubChem CID
  • 179651
UNII
  • L0F260866S checkY
CompTox Dashboard (EPA)
  • DTXSID8045985 Edit this at Wikidata
InChI
  • 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
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
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).
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Infobox references

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.

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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...

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Limonoid

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are classed as tetranortriterpenes. Citrus fruits contain the limonoids limonin, nomilin and nomilinic acid, while both neem seeds and leaves contain the...

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Neohesperidin dihydrochalcone

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masking the bitter tastes of other compounds found in citrus, including limonin and naringin. Industrially, it is produced by extracting neohesperidin...

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Limonoid glucosyltransferase

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UDP-glucose + limonin ⇌ {\displaystyle \rightleftharpoons } glucosyl-limonin + UDP Thus, the two substrates of this enzyme are UDP-glucose and limonin, whereas...

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Antifeedant

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Limonoids such as limonin are antifeedants produced by a number of plants of the families cucurbitaceae Rutaceae and Meliaceae....

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Terpenoid

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a diterpenoid. Hinokitiol is a monoterpenoid, a tropolone derivative. Limonin, a common limonoid, is a triterpenoid. Geosmin is a sesquiterpenoid. Terpenoids...

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Citrus limetta

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to six months. It is possible to freeze slices of the fruit, though the limonin content may cause the pulp to taste bitter over time. This can be avoided...

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Citrus depressa

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properties. Similarly, there is a high concentration of anti-tumorous compounds limonin glucoside and nomilin glucoside in the fruits' seed. NBL in C. depressa...

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Clausena anisata

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furanocoumarin-lactone type (indicolactone, anisolactone), the tetranortriterpenoids limonin, zapoterin, clausenolide, carbazole alkaloids furanoclausamine A and B...

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TAS2R38

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T2R38 has been found to interact with other intriguing ligands, including limonin, a compound commonly found in citrus fruits, cyclamate, an artificial sweetener...

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Furanolactone

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A Columbin, a bitter diterpenoid from Calumbae Radix Limonoids such as limonin, nomilin, and nomilinic acid Tinosporide, a diterpenoid originally isolated...

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John Monteath Robertson

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most exciting work." In 1960, Robertson's group reported the structure of limonin, a complex organic molecule whose structure had eluded chemists since its...

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Albert James Bernays

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Giessen, where he graduated PhD. His doctoral thesis was probably a paper on limonin, a bitter principle which he discovered in the pips of oranges and lemons...

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Huang Bai

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acid (+/-)-5,5'-dimethoxylariciresinol methyl beta-orsellinate obacunone limonin and 12alpha-hydroxylimonin nomilin gamma-fagarine canthin-6-one...

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Lactonase

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Deoxylimonate A-ring-lactonase Gluconolactonase L-rhamnono-1,4-lactonase Limonin-D-ring-lactonase Steroid-lactonase Triacetate-lactonase Xylono-1,4-lactonase...

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