1.0 2010-04-08 22:06:20 UTC 2019-11-26 03:00:09 UTC FDB004670 Latoxanthin Latoxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Latoxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Latoxanthin can be found in a number of food items such as red bell pepper, yellow bell pepper, orange bell pepper, and pepper (c. annuum), which makes latoxanthin a potential biomarker for the consumption of these food products. (3S,3'S,5R,5'R,6R,6'S)-5,6-Epoxy-5,5',6,6'-tetrahydro-3,3',5',6'-tetrahydroxy-beta,beta-carotene Latoxanthin C40H58O5 618.8855 618.428424966 (1R,2R,4S)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol (1R,2R,4S)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol 7235-40-7 O[C@@H]1C[C@@]2(C)O[C@@]2(\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@@]2(O)C(C)(C)C[C@H](O)C[C@@]2(C)O)C(C)(C)C1 InChI=1S/C40H58O5/c1-29(17-13-19-31(3)21-23-39(44)35(5,6)25-33(41)27-37(39,9)43)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)45-40/h11-24,33-34,41-44H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39+,40-/m0/s1 IHFACKVTKFGBBA-UVAHLJQVSA-N belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Xanthophylls Organic compounds Lipids and lipid-like molecules Prenol lipids Tetraterpenoids Aliphatic heteropolycyclic compounds Cyclitols and derivatives Cyclohexanols Dialkyl ethers Epoxides Hydrocarbon derivatives Oxacyclic compounds Oxepanes Polyols Tertiary alcohols Alcohol Aliphatic heteropolycyclic compound Cyclic alcohol Cyclitol or derivatives Cyclohexanol Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxepane Oxirane Polyol Secondary alcohol Tertiary alcohol Xanthophyll logp 7.06 ALOGPS logs -5.73 ALOGPS solubility 1.15e-03 g/l ALOGPS logp 6.1 ChemAxon pka_strongest_acidic 12.9 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac (1R,2R,4S)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol ChemAxon average_mass 618.8855 ChemAxon mono_mass 618.428424966 ChemAxon smiles O[C@@H]1C[C@@]2(C)O[C@@]2(\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@@]2(O)C(C)(C)C[C@H](O)C[C@@]2(C)O)C(C)(C)C1 ChemAxon formula C40H58O5 ChemAxon inchi InChI=1S/C40H58O5/c1-29(17-13-19-31(3)21-23-39(44)35(5,6)25-33(41)27-37(39,9)43)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)45-40/h11-24,33-34,41-44H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39+,40-/m0/s1 ChemAxon inchikey IHFACKVTKFGBBA-UVAHLJQVSA-N ChemAxon polar_surface_area 93.45 ChemAxon refractivity 195.84 ChemAxon polarizability 75.89 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 68928 Specdb::MsMs 68929 Specdb::MsMs 68930 Specdb::MsMs 127077 Specdb::MsMs 127078 Specdb::MsMs 127079 Specdb::MsMs 3600827 Specdb::MsMs 3600828 Specdb::MsMs 3600829 Specdb::MsMs 3601877 Specdb::MsMs 3601878 Specdb::MsMs 3601879 Green bell pepper Type 1 specific Capsicum annuum 4072 Orange bell pepper Type 1 specific Capsicum annuum 4072 Pepper Type 1 specific Capsicum annuum 4072 Pepper (C. frutescens) Type 1 specific Capsicum annuum var. annuum 40321 Red bell pepper Type 1 specific Capsicum annuum 4072 Yellow bell pepper Type 1 specific Capsicum annuum 4072