1.0 2010-04-08 22:11:26 UTC 2025-11-19 00:49:07 UTC FDB014715 Limonin Isolated from oranges and other citrus fruits (Citrus subspecies). Limonin is a limonoid, and a bitter, white, crystalline substance found in orange and lemon seeds. 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. 7,16-Dioxo-7,16-dideoxylimondiol Citrolimonin Dictamnolactone Evodia fruit Evodia fruit (JP15) Evodia fruit (TN) Evodin Evodine? Limone? Limonoate d-ring-lactone limonoic acid 3,19:16,17-dilactone Limonoic acid, di-delta-lactone Obaculactone C26H30O8 470.5116 470.194067936 19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione limonin 1180-71-8 CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1 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 KBDSLGBFQAGHBE-UHFFFAOYSA-N belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Limonoids Organic compounds Lipids and lipid-like molecules Prenol lipids Triterpenoids Aromatic heteropolycyclic compounds 1,4-dioxepanes 11-oxosteroids Carboxylic acid esters Delta valerolactones Dialkyl ethers Dicarboxylic acids and derivatives Epoxides Furans Heteroaromatic compounds Hydrocarbon derivatives Ketones Naphthalenes Naphthopyrans Organic oxides Oxacyclic compounds Oxanes Pyrans Steroid lactones Tetrahydrofurans 1,4-dioxepane 11-oxosteroid 2-oxosteroid Aromatic heteropolycyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Delta valerolactone Delta_valerolactone Dialkyl ether Dicarboxylic acid or derivatives Dioxepane Ether Furan Heteroaromatic compound Hydrocarbon derivative Ketone Lactone Limonoid skeleton Naphthalene Naphthopyran Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Oxirane Oxosteroid Pyran Steroid Steroid lactone Tetrahydrofuran a small molecule logp 3.47 ALOGPS logs -3.77 ALOGPS solubility 7.99e-02 g/l ALOGPS melting_point Mp 298° logp 2.46 ChemAxon pka_strongest_acidic 17.61 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac 19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione ChemAxon average_mass 470.5116 ChemAxon mono_mass 470.194067936 ChemAxon smiles CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1 ChemAxon formula C26H30O8 ChemAxon 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 ChemAxon inchikey KBDSLGBFQAGHBE-UHFFFAOYSA-N ChemAxon polar_surface_area 104.57 ChemAxon refractivity 114.72 ChemAxon polarizability 47.86 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 11021 Specdb::CMs 150448 Specdb::MsMs 290305 Specdb::MsMs 290306 Specdb::MsMs 290307 Specdb::MsMs 329956 Specdb::MsMs 329957 Specdb::MsMs 329958 Specdb::MsMs 2829886 Specdb::MsMs 2829887 Specdb::MsMs 2829888 Specdb::MsMs 2852533 Specdb::MsMs 2852534 Specdb::MsMs 2852535 HMDB35921 16226 #<Reference:0x000055ce319df580> #<Reference:0x000055ce319df3c8> Citrus Unknown generic Grapefruit Type 1 specific Citrus X paradisi 37656 Lemon Type 1 specific Citrus limon 2708 Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 Sour orange Type 1 Citrus × aurantium Sweet orange Type 1 specific Citrus sinensis 2711 bitter Anti cataleptic 167 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti feedant 275 Anti leukemic 393 A substance that inhibits or prevents the proliferation of neoplasms. Anti-malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.