1.0 2010-04-08 22:06:30 UTC 2025-11-18 22:58:07 UTC FDB005049 Linonin Linonin, also known as 7,16-dioxo-7,16-dideoxylimondiol or evodin, is a member of the class of compounds known as limonoids. Limonoids 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. Linonin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Linonin can be found in lemon, which makes linonin a potential biomarker for the consumption of this food product. C26H30O8 470.518 470.194067926 (1R,2R,7S,10R,13R,14R,16S,19R,20S)-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)O[C@H]2CC(=O)OC[C@@]22[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)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/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1 KBDSLGBFQAGHBE-MSGMIQHVSA-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 Limonoids epoxide furans hexacyclic triterpenoid lactone limonoid organic heterohexacyclic compound logp 3.47 ALOGPS logs -3.77 ALOGPS solubility 7.99e-02 g/l ALOGPS logp 2.46 ChemAxon pka_strongest_acidic 17.61 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (1R,2R,7S,10R,13R,14R,16S,19R,20S)-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 470.518 ChemAxon mono_mass 470.194067926 ChemAxon smiles CC1(C)O[C@H]2CC(=O)OC[C@@]22[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)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/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1 ChemAxon inchikey KBDSLGBFQAGHBE-MSGMIQHVSA-N ChemAxon polar_surface_area 104.57 ChemAxon refractivity 114.72 ChemAxon polarizability 47.81 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 63771 Specdb::MsMs 63772 Specdb::MsMs 63773 Specdb::MsMs 120774 Specdb::MsMs 120775 Specdb::MsMs 120776 Specdb::MsMs 3601301 Specdb::MsMs 3601302 Specdb::MsMs 3601303 Specdb::MsMs 3601304 Specdb::MsMs 3601305 Specdb::MsMs 3601306 Grapefruit Type 1 specific Citrus X paradisi 37656 Lemon Type 1 specific Citrus limon 2708 Sour orange Type 1 Citrus × aurantium Sweet orange Type 1 specific Citrus sinensis 2711