1.0 2010-04-08 22:06:30 UTC 2025-11-18 22:58:07 UTC FDB005048 Limonoate a-ring-lactone Limonoate a-ring-lactone 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. Limonoate a-ring-lactone is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Limonoate a-ring-lactone can be found in lemon and sweet orange, which makes limonoate a-ring-lactone a potential biomarker for the consumption of these food products. C26H32O9 488.533 488.20463261 (1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-(furan-3-yl)(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid limonoate A-ring-lactone [H][C@](O)(C1=COC=C1)[C@]1(C)CC[C@]2([H])[C@@]34COC(=O)C[C@]3([H])OC(C)(C)[C@]4([H])CC(=O)[C@@]2(C)[C@]11O[C@]1([H])C(O)=O InChI=1S/C26H32O9/c1-22(2)15-9-16(27)24(4)14(25(15)12-33-18(28)10-17(25)34-22)5-7-23(3,19(29)13-6-8-32-11-13)26(24)20(35-26)21(30)31/h6,8,11,14-15,17,19-20,29H,5,7,9-10,12H2,1-4H3,(H,30,31)/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1 JQTDUZWQZNXSOU-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 Aromatic alcohols Carboxylic acid esters Carboxylic acids Delta valerolactones Dialkyl ethers Dicarboxylic acids and derivatives Furans Heteroaromatic compounds Hydrocarbon derivatives Ketones Organic oxides Oxacyclic compounds Oxanes Oxirane carboxylic acids Secondary alcohols Tetrahydrofurans Alcohol Aromatic alcohol Aromatic heteropolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Delta valerolactone Delta_valerolactone Dialkyl ether Dicarboxylic acid or derivatives Ether Furan Heteroaromatic compound Hydrocarbon derivative Ketone Lactone Limonoid skeleton Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Oxirane Oxirane carboxylic acid Oxirane carboxylic acid or derivatives Secondary alcohol Tetrahydrofuran limonoid logp 2.37 ALOGPS logs -3.54 ALOGPS solubility 1.42e-01 g/l ALOGPS logp 1.79 ChemAxon pka_strongest_acidic 4.07 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-(furan-3-yl)(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid ChemAxon average_mass 488.533 ChemAxon mono_mass 488.20463261 ChemAxon smiles [H][C@](O)(C1=COC=C1)[C@]1(C)CC[C@]2([H])[C@@]34COC(=O)C[C@]3([H])OC(C)(C)[C@]4([H])CC(=O)[C@@]2(C)[C@]11O[C@]1([H])C(O)=O ChemAxon formula C26H32O9 ChemAxon inchi InChI=1S/C26H32O9/c1-22(2)15-9-16(27)24(4)14(25(15)12-33-18(28)10-17(25)34-22)5-7-23(3,19(29)13-6-8-32-11-13)26(24)20(35-26)21(30)31/h6,8,11,14-15,17,19-20,29H,5,7,9-10,12H2,1-4H3,(H,30,31)/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1 ChemAxon inchikey JQTDUZWQZNXSOU-MSGMIQHVSA-N ChemAxon polar_surface_area 135.8 ChemAxon refractivity 118.21 ChemAxon polarizability 49.21 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 7 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 47223 Specdb::MsMs 47224 Specdb::MsMs 47225 Specdb::MsMs 155589 Specdb::MsMs 155590 Specdb::MsMs 155591 Specdb::MsMs 3601295 Specdb::MsMs 3601296 Specdb::MsMs 3601297 Specdb::MsMs 3601298 Specdb::MsMs 3601299 Specdb::MsMs 3601300 Lemon Type 1 specific Citrus limon 2708 Sweet orange Type 1 specific Citrus sinensis 2711