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Showing Compound 3,3',4,4'-Tetrahydroxylignan (FDB011903)

Record Information
Version1.0
Creation date2010-04-08 22:09:53 UTC
Update date2019-11-26 03:05:42 UTC
Primary IDFDB011903
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,3',4,4'-Tetrahydroxylignan
Description3,3',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.
CAS Number500-38-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutaneChEBI
2,3-Bis(3,4-dihydroxyphenylmethyl)butaneChEBI
4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)ChEBI
4,4'-(2,3-Dimethyltetramethylene)dipyrocatecholChEBI
beta,gamma-Dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butaneChEBI
NDGAChEBI
Norhydroguaiaretic acidChEBI
NSC 4291ChEBI
b,g-Dimethyl-a,delta-bis(3,4-dihydroxyphenyl)butaneGenerator
Β,γ-dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butaneGenerator
NorhydroguaiaretateGenerator
b,g-Dimethyl-a,δ-bis(3,4-dihydroxyphenyl)butaneGenerator
(R*,s*)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatecholMeSH
1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethyl-butaneHMDB
2,3-Bis(3,4-dihydroxybenzyl)butanedb_source
4, 4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)HMDB
4,4'- (2,3-Diemthyltetramethylene)-dipyrocatecholHMDB
4,4'-(2, 3-Dimethyltetramethylene)dipyrocatecholHMDB
4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1, 2-benzenediolHMDB
Bisdemethyldihyroguaiaretic aciddb_source
dihydro-Dinorguaiaretic acidHMDB
dihydro-Norguaiaretic acidHMDB
Dihydronorguaiaretic acidHMDB
Nordihydroguaiaretic aciddb_source
Nordihydroguairaretic acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.44ALOGPS
logP4.76ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity86.62 m³·mol⁻¹ChemAxon
Polarizability32.84 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H22O4
IUPAC name4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol
InChI IdentifierInChI=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
InChI KeyHCZKYJDFEPMADG-UHFFFAOYSA-N
Isomeric SMILESCC(CC1=CC(O)=C(O)C=C1)C(C)CC1=CC=C(O)C(O)=C1
Average Molecular Weight302.3649
Monoisotopic Molecular Weight302.151809192
Classification
Description Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassNot Available
Direct ParentDibenzylbutane lignans
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 71.50%; H 7.33%; O 21.17%DFC
Melting Point185.5 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID599529
ChEMBL IDNot Available
KEGG Compound IDC10719
Pubchem Compound ID688035
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12270
CRC / DFC (Dictionary of Food Compounds) IDHBR28-Y:HBR28-Y
EAFUS ID2721
Dr. Duke IDNORDIHYDROGUAIARETIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
12-lipoxygenase inhibitor23924 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 inhibitor23924 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
allelopathicDUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
analgesic35480 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 aggregantDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti conjunctivitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti galactagogueDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti metaboliteDUKE
anti mutagenicDUKE
antioxidant22586 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 septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti thyroidDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 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 antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
carcinogenic50903 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 inhibitor35544 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
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
herbistatDUKE
larvicideDUKE
lipoxygenase inhibitor35856 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 inhibitor23924 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 inhibitor50423 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
pesticide25944 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 inhibitor23924 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
phytotoxicDUKE
respiroinhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).