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

Record Information

Version

1.0

Creation date

2010-04-08 22:09:53 UTC

Update date

2019-11-26 03:05:42 UTC

Primary ID

FDB011903

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3,3',4,4'-Tetrahydroxylignan

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.

CAS Number

500-38-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(R,s)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatechol	MeSH
1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethyl-butane	HMDB
1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane	ChEBI
2,3-Bis(3,4-dihydroxybenzyl)butane	db_source
2,3-Bis(3,4-dihydroxyphenylmethyl)butane	ChEBI
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(pyrocatechol)	ChEBI
4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1, 2-benzenediol	HMDB

Showing 1 to 10 of 25 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	3.44	ALOGPS
logP	4.76	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.62 m³·mol⁻¹	ChemAxon
Polarizability	32.84 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H22O4

IUPAC name

4-{3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl}benzene-1,2-diol

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

InChI Key

HCZKYJDFEPMADG-UHFFFAOYSA-N

Isomeric SMILES

CC(CC1=CC(O)=C(O)C=C1)C(C)CC1=CC=C(O)C(O)=C1

Average Molecular Weight

302.3649

Monoisotopic Molecular Weight

302.151809192

Classification

Description

Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:7625 )
tetrol (CHEBI:7625 )
lignan (CHEBI:7625 )
a small molecule (CPD-7661 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 71.50%; H 7.33%; O 21.17%	DFC
Melting Point	185.5 oC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

599529

ChEMBL ID

Not Available

KEGG Compound ID

C10719

Pubchem Compound ID

688035

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB12270

CRC / DFC (Dictionary of Food Compounds) ID

HBR28-Y:HBR28-Y

EAFUS ID

2721

Dr. Duke ID

NORDIHYDROGUAIARETIC-ACID

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
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