1.0 2010-04-08 22:10:05 UTC 2025-11-18 23:35:31 UTC FDB012290 Isoxanthohumol Isolated from hop (Humulus lupulus). Isoxanthohumol is a biomarker for the consumption of beer. Isoxanthohumol is found in beer and alcoholic beverages. 4',7-Dihydroxy-5-methoxy-8-prenylflavanone 5-Methyl-8-prenylnaringenin 7,4'-Dihydroxy-5-methoxy-8-prenylflavanone Isoxanthohumol C21H22O5 354.402 354.146723808 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one isoxanthohumol(sophora) 70872-29-6 COC1=C2C(=O)CC(OC2=C(CC=C(C)C)C(O)=C1)C1=CC=C(O)C=C1 InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3 YKGCBLWILMDSAV-UHFFFAOYSA-N belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. 8-prenylated flavanones Organic compounds Phenylpropanoids and polyketides Flavonoids Flavans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 4'-hydroxyflavonoids 5-O-methylated flavonoids 7-hydroxyflavonoids Alkyl aryl ethers Anisoles Aryl alkyl ketones Benzene and substituted derivatives Chromones Flavanones Hydrocarbon derivatives Organic oxides Oxacyclic compounds 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 4'-hydroxyflavonoid 5-methoxyflavonoid-skeleton 7-hydroxyflavonoid 8-prenylated flavanone Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Chromane Chromone Ether Flavanone Hydrocarbon derivative Hydroxyflavonoid Ketone Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Flavanones logp 3.25 ALOGPS logs -4.40 ALOGPS solubility 1.42e-02 g/l ALOGPS melting_point Mp 204-206° logp 4.06 ChemAxon pka_strongest_acidic 7.66 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one ChemAxon average_mass 354.402 ChemAxon mono_mass 354.146723808 ChemAxon smiles COC1=C2C(=O)CC(OC2=C(CC=C(C)C)C(O)=C1)C1=CC=C(O)C=C1 ChemAxon formula C21H22O5 ChemAxon inchi InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3 ChemAxon inchikey YKGCBLWILMDSAV-UHFFFAOYSA-N ChemAxon polar_surface_area 75.99 ChemAxon refractivity 100.01 ChemAxon polarizability 38.4 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 17525 Specdb::MsMs 11381 Specdb::MsMs 11382 Specdb::MsMs 11383 Specdb::MsMs 18053 Specdb::MsMs 18054 Specdb::MsMs 18055 Specdb::MsMs 285648 Specdb::MsMs 285649 Specdb::MsMs 285650 Specdb::MsMs 285651 Specdb::MsMs 285652 Specdb::MsMs 285653 Specdb::MsMs 373722 Specdb::MsMs 373723 Specdb::MsMs 373724 Specdb::MsMs 373725 Specdb::MsMs 373726 Specdb::MsMs 373727 Specdb::MsMs 373728 Specdb::MsMs 373729 Specdb::MsMs 373730 Specdb::MsMs 440237 Specdb::MsMs 440238 Specdb::MsMs 440239 HMDB34048 #<Reference:0x000055ce320c1740> Alcoholic beverages Unknown generic Beer Type 2 specific 0.09844 0.212000005 0.011 mg/100 g bitter