Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:53 UTC |
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Update date | 2019-11-26 03:05:42 UTC |
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Primary ID | FDB011903 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3,3',4,4'-Tetrahydroxylignan |
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Description | 3,3',4,4'-Tetrahydroxylignan, also known as NDGA or norhydroguaiaretic acid, belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. 3,3',4,4'-Tetrahydroxylignan is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,3',4,4'-Tetrahydroxylignan has been detected, but not quantified in, flaxseeds. This could make 3,3',4,4'-tetrahydroxylignan a potential biomarker for the consumption of these foods. |
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CAS Number | 500-38-9 |
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Structure | |
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Synonyms | Synonym | Source |
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1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane | ChEBI | 2,3-Bis(3,4-dihydroxyphenylmethyl)butane | ChEBI | 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol) | ChEBI | 4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol | ChEBI | beta,gamma-Dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butane | ChEBI | NDGA | ChEBI | Norhydroguaiaretic acid | ChEBI | NSC 4291 | ChEBI | b,g-Dimethyl-a,delta-bis(3,4-dihydroxyphenyl)butane | Generator | Β,γ-dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butane | Generator | Norhydroguaiaretate | Generator | b,g-Dimethyl-a,δ-bis(3,4-dihydroxyphenyl)butane | Generator | (R*,s*)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatechol | MeSH | 1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethyl-butane | HMDB | 2,3-Bis(3,4-dihydroxybenzyl)butane | db_source | 4, 4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol) | HMDB | 4,4'- (2,3-Diemthyltetramethylene)-dipyrocatechol | HMDB | 4,4'-(2, 3-Dimethyltetramethylene)dipyrocatechol | HMDB | 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1, 2-benzenediol | HMDB | Bisdemethyldihyroguaiaretic acid | db_source | dihydro-Dinorguaiaretic acid | HMDB | dihydro-Norguaiaretic acid | HMDB | Dihydronorguaiaretic acid | HMDB | Nordihydroguaiaretic acid | db_source | Nordihydroguairaretic acid | HMDB |
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Predicted Properties | |
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Chemical Formula | C18H22O4 |
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IUPAC name | 4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol |
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InChI Identifier | 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 |
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InChI Key | HCZKYJDFEPMADG-UHFFFAOYSA-N |
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Isomeric SMILES | CC(CC1=CC(O)=C(O)C=C1)C(C)CC1=CC=C(O)C(O)=C1 |
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Average Molecular Weight | 302.3649 |
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Monoisotopic Molecular Weight | 302.151809192 |
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Classification |
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Description | Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Dibenzylbutane lignans |
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Sub Class | Not Available |
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Direct Parent | Dibenzylbutane lignans |
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Alternative Parents | |
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Substituents | - Dibenzylbutane lignan skeleton
- Phenylpropane
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 71.50%; H 7.33%; O 21.17% | DFC |
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Melting Point | 185.5 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | Not Available |
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External Links |
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ChemSpider ID | 599529 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C10719 |
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Pubchem Compound ID | 688035 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB12270 |
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CRC / DFC (Dictionary of Food Compounds) ID | HBR28-Y:HBR28-Y |
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EAFUS ID | 2721 |
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Dr. Duke ID | NORDIHYDROGUAIARETIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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12-lipoxygenase inhibitor | 23924 | 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. | DUKE | 5-lipoxygenase inhibitor | 23924 | 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. | DUKE | allelopathic | | | DUKE | allergenic | 50904 | A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. | DUKE | analgesic | 35480 | 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. | DUKE | anti aggregant | | | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti carcinogenic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti conjunctivitic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti galactagogue | | | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti metabolite | | | DUKE | anti mutagenic | | | DUKE | antioxidant | 22586 | 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. | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti thyroid | | | DUKE | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | DUKE | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | carcinogenic | 50903 | 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. | DUKE | cyclooxygenase inhibitor | 35544 | 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. | DUKE | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | herbistat | | | DUKE | larvicide | | | DUKE | lipoxygenase inhibitor | 35856 | 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. | DUKE | lyase inhibitor | 23924 | 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. | DUKE | NADPH-oxidase inhibitor | 50423 | 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. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | phospholipase inhibitor | 23924 | 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. | DUKE | phytotoxic | | | DUKE | respiroinhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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