1.0 2010-04-08 22:09:53 UTC 2025-11-18 23:32:00 UTC FDB011903 3,3',4,4'-Tetrahydroxylignan Antioxidant. Formerly approved as a food additive; now banned by FDA (USA) Masoprocol is a novel antineoplastic agent. It is not known exactly how masoprocol works. Laboratory experiments have shown that masoprocol prevents cells similar to the ones found in actinic keratoses from multiplying. Masoprocol was withdrawn from the U.S. market in June 1996. 1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethyl-butane 1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane 2,3-Bis(3,4-dihydroxybenzyl)butane 2,3-Bis(3,4-dihydroxyphenylmethyl)butane 4, 4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol) 4,4'- (2,3-Diemthyltetramethylene)-dipyrocatechol 4,4'-(2, 3-Dimethyltetramethylene)dipyrocatechol 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1, 2-benzenediol 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol) 4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol Bisdemethyldihyroguaiaretic acid dihydro-Dinorguaiaretic acid dihydro-Norguaiaretic acid Dihydronorguaiaretic acid NDGA Nordihydroguaiaretic acid Nordihydroguairaretic acid Norhydroguaiaretic acid C18H22O4 302.3649 302.151809192 4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol nordihydroguaiaretic acid 500-38-9 CC(CC1=CC(O)=C(O)C=C1)C(C)CC1=CC=C(O)C(O)=C1 InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3 HCZKYJDFEPMADG-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. Dibenzylbutane lignans Organic compounds Lignans, neolignans and related compounds Dibenzylbutane lignans Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Catechols Hydrocarbon derivatives Organooxygen compounds Phenylpropanes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Catechol Dibenzylbutane lignan skeleton Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Phenylpropane a small molecule catechols lignan tetrol Solid logp 3.44 ALOGPS logs -4.35 ALOGPS solubility 1.36e-02 g/l ALOGPS melting_point 185.5 oC logp 4.76 ChemAxon pka_strongest_acidic 9.21 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac 4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol ChemAxon average_mass 302.3649 ChemAxon mono_mass 302.151809192 ChemAxon smiles CC(CC1=CC(O)=C(O)C=C1)C(C)CC1=CC=C(O)C(O)=C1 ChemAxon formula C18H22O4 ChemAxon inchi InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3 ChemAxon inchikey HCZKYJDFEPMADG-UHFFFAOYSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 86.62 ChemAxon polarizability 32.84 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB12270 Flaxseed Type 1 specific Linum usitatissimum 4006 12-lipoxygenase inhibitor 5 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. 5-lipoxygenase inhibitor 10 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Allelopathic 42 Allergenic 43 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. Analgesic 56 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti carcinogenic 161 A substance that inhibits or prevents the proliferation of neoplasms. Anti galactagogue 287 Anti metabolite 432 Anti septic 603 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti ulcer 676 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. Anti-aggregant 94 Anti-conjunctivitic 202 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-mutagenic 451 Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Anti-thyroid 654 Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Calcium antagonist 748 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. Carcinogenic 762 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. Cyclooxygenase inhibitor 849 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Fungicide 940 A substance used to destroy fungal pests. Herbistat 987 Larvicide 1063 Lipoxygenase inhibitor 1077 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. Lyase inhibitor 1082 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. NADPH-oxidase inhibitor 1137 An EC 1.6.3.* (oxidoreductase acting on NADH or NADPH with oxygen as acceptor) inhibitor that interferes with the action of NAD(P)H oxidase (H2O2-forming), EC 1.6.3.1. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Phospholipase inhibitor 1217 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Phytotoxic 1226 Respiroinhibitor 1291 A substance that diminishes the rate of a chemical reaction.