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
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
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 An agent that blocks the activity of 12-lipoxygenase, an enzyme involved in inflammation and oxidative stress. It has therapeutic applications in reducing inflammation and is used to treat conditions such as cancer, atherosclerosis, and neurodegenerative diseases.DUKE
5-lipoxygenase inhibitor23924 An agent that blocks the activity of 5-lipoxygenase, an enzyme involved in leukotriene production, reducing inflammation and allergic responses. Therapeutically, it's used to treat asthma, allergies, and inflammatory disorders, such as arthritis, by inhibiting the synthesis of pro-inflammatory leukotrienes.DUKE
AllelopathicBiochemicals that inhibit growth, survival, or reproduction in other organisms, with potential therapeutic applications in weed control, antimicrobial, and anticancer treatments, and key medical uses in developing novel pesticides, antibiotics, and chemotherapeutics.DUKE
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti carcinogenic35610 An agent that prevents or inhibits the formation of cancer, reducing tumor growth and proliferation. It plays a biological role in protecting cells from DNA damage and mutation. Therapeutically, it is used to prevent cancer development, with key medical applications in chemotherapy, radiation protection, and cancer prevention programs.DUKE
Anti-conjunctivitic52217 An agent that reduces inflammation and prevents conjunctivitis, commonly used to treat eye infections, allergies, and irritations, promoting healthy vision and relieving symptoms such as redness, itching, and discharge.DUKE
Anti galactagogueAn agent that prevents or decreases milk secretion in nursing mothers, used to suppress lactation in cases of stillbirth, abortion, or breast cancer, and to alleviate engorgement and discomfort in mothers who are not breastfeeding.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti metaboliteA substance that interferes with normal metabolic processes by competing with or replacing a natural metabolite, used therapeutically to treat diseases such as cancer and infections by inhibiting cell growth and proliferation.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-thyroidAn agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti ulcer49201 An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Carcinogenic50903 An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.DUKE
Cyclooxygenase inhibitor35544 An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
HerbistatA topical herbal preparation with antimicrobial and anti-inflammatory properties, used to treat skin ailments such as cuts, bites, and infections, promoting wound healing and reducing the risk of infection.DUKE
LarvicideAn insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.DUKE
Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.DUKE
Lyase inhibitor23924 An agent that blocks the activity of lyase enzymes, which break down biomolecules. It has therapeutic applications in reducing inflammation and oxidative stress, with key medical uses in managing cancer, cardiovascular disease, and neurodegenerative disorders.DUKE
NADPH-oxidase inhibitor50423 An agent that blocks the activity of NADPH-oxidase, reducing oxidative stress and inflammation. Therapeutically, it's used to manage conditions like atherosclerosis, hypertension, and neurodegenerative diseases, by mitigating oxidative damage and improving cardiovascular health.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Phospholipase inhibitor23924 An agent that blocks phospholipase enzymes, reducing inflammation and cell damage. Therapeutically, it's used to treat conditions like pancreatitis and sepsis, and has potential in managing neurodegenerative and cardiovascular diseases by inhibiting phospholipid breakdown and modulating immune responses.DUKE
PhytotoxicAn agent poisonous to plants, inhibiting growth and development. Its biological role involves disrupting plant cell function. Therapeutically, phytotoxic agents are used as herbicides, while medically, they have applications in cancer treatment and as antimicrobial agents, targeting plant-like pathogens.DUKE
Respiroinhibitor35222 An agent that inhibits cellular respiration, reducing energy production. Therapeutically, it is used to manage cancer, infectious diseases, and other conditions by targeting abnormal cell metabolism, with key applications in oncology and antimicrobial therapy.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).