1.0 2010-04-08 22:12:30 UTC 2025-11-19 01:47:53 UTC FDB016545 Xanthohumol Isolated from Humulus lupulus (hops). Xanthohumol is found in beer and alcoholic beverages. 2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone Xanthohumol C21H22O5 354.3964 354.146723814 (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one xanthohumol 6754-58-1 COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC=C(C)C)C(O)=C1 InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+ ORXQGKIUCDPEAJ-YRNVUSSQSA-N belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. 3-prenylated chalcones Organic compounds Phenylpropanoids and polyketides Linear 1,3-diarylpropanoids Chalcones and dihydrochalcones Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2'-Hydroxychalcones Acryloyl compounds Alkyl aryl ethers Anisoles Aryl ketones Benzoyl derivatives Cinnamylphenols Enones Hydrocarbon derivatives Hydroxycinnamic acids and derivatives Methoxybenzenes Methoxyphenols Organic oxides Phenoxy compounds Resorcinols Styrenes Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2'-hydroxychalcone 3-prenylated chalcone Acryloyl-group Alkyl aryl ether Alpha,beta-unsaturated ketone Anisole Aromatic homomonocyclic compound Aryl ketone Benzenoid Benzoyl Cinnamylphenol Enone Ether Hydrocarbon derivative Hydroxycinnamic acid or derivatives Ketone Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Resorcinol Styrene Vinylogous acid Chalcones and dihydrochalcones Chalcones and dihydrochalcones aromatic ether chalcones chalcones polyphenol logp 3.91 ALOGPS logs -4.80 ALOGPS solubility 5.56e-03 g/l ALOGPS melting_point Mp 172° logp 5.2 ChemAxon pka_strongest_acidic 7.65 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one ChemAxon average_mass 354.3964 ChemAxon mono_mass 354.146723814 ChemAxon smiles COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C(CC=C(C)C)C(O)=C1 ChemAxon formula C21H22O5 ChemAxon inchi InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+ ChemAxon inchikey ORXQGKIUCDPEAJ-YRNVUSSQSA-N ChemAxon polar_surface_area 86.99 ChemAxon refractivity 103.53 ChemAxon polarizability 38.55 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 9835 Specdb::CMs 45412 Specdb::CMs 131858 Specdb::CMs 139592 Specdb::MsMs 86673 Specdb::MsMs 86674 Specdb::MsMs 86675 Specdb::MsMs 149025 Specdb::MsMs 149026 Specdb::MsMs 149027 Specdb::MsMs 285877 Specdb::MsMs 285878 Specdb::MsMs 373690 Specdb::MsMs 373691 Specdb::MsMs 437078 Specdb::MsMs 437079 Specdb::MsMs 437080 Specdb::MsMs 440225 Specdb::MsMs 440503 Specdb::MsMs 445377 Specdb::MsMs 445378 Specdb::MsMs 445379 Specdb::MsMs 445397 Specdb::MsMs 445398 Specdb::MsMs 445399 Specdb::MsMs 447435 Specdb::MsMs 447436 Specdb::MsMs 447437 Specdb::MsMs 447438 HMDB37479 #<Reference:0x000055ce3249eb38> #<Reference:0x000055ce3249e980> Alcoholic beverages Unknown generic Beer Type 2 specific 0.014054 0.0345 0.0003 mg/100 g bitter