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EC / List no.: 207-903-0
CAS no.: 500-38-9
Mol. formula: C18H22O4
Nordihydroguaiaretic acid, informally abbreviated NDGA in research articles, is a classic lignan, a phenylpropane dimer linked by a bond between positions C8 and C8′, as opposed to a neolignan.
Nordihydroguaiaretic acid is a natural compound found in the creosote bush (Larrea tridentata).
Medical properties
As a lignan, it is a member of one of the major classes of phytoestrogens.
While it is commonly asserted that the biological properties of lignans per sé are void, and that only the enterolignans enterodiol and enterolactone, produced from lignans by intestinal bacteria have interesting biological properties, nordihydroguaiaretic acid has antioxidant and anti-inflammatory properties in vitro or in animal models.
Nordihydroguaiaretic acid is a redox-type inhibitor of 5-lipoxygenase.
A 1986 study involved feeding female mosquitos NDGA to test the effect on their average life span.
While the usual mosquito life span was 29 days, the NDGA-fed mosquitos lived an average of 45 days—an increase of 50 percent.
The creosote plant has been used in herbal medicine, but its use is controversial.
Nordihydroguaiaretic acid was widely used during the 1950s as a food preservative and to preserve natural fibers, but was later banned after reports of toxicity during the early 1960s.
Recently, it has been used as a nutritional supplement, however, renal toxicity and hepatotoxicity are reported for chronic use of creosote bush and NDGA.
Description
Nordihydroguaiaretic acid is a kind of antioxidant compound presented in the creosoten bush.
Nordihydroguaiaretic acid is a potent in vitro scavenger of many kind of oxidants such as peroxynitrite, singlet oxygen, hydroxyl radical, superoxide anion and hypochlorous acid.
Studies have shown that it has various physiological effects.
Nordihydroguaiaretic acid can also protect hippocampal neurons against amyloid β-peptide toxicity, and attenuates free radical and calcium accumulation.
Nordihydroguaiaretic acid (NDGA) is a grayish-white crystalline compound that was widely used as an antioxidant in animal fats in the 1950s and 1960s.
Nordihydroguaiaretic acid possesses phenolic properties similar to gallates, including their advantages and disadvantages.
Besides the isolation of natural material (resinous exudate of creosote bush), NDGA has also been chemically synthesized.
As the result of unfavorable toxicological findings, NDGA is prohibited from use in the US.
More specifically, NDGA is a potent lipoxygenase inhibitor which interferes with arachidonic acid metabolism.
The compound also inhibits formyltetrahydrofolate synthetase, carbox- ylesterase,and,to a lesser extent, cyclooxygenase.
Chemical Properties
light yellow crystalline solid
Uses:
Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure.
Inhibitor of broad bean lipoxygenase.
The oxidation product from Resveratrol (R150000) showed a high inhibitory activity, w hereas Resveratrol itself had no activity and its oxidation efficiency was low.
Nordihydroguaiaretic acid is used in the treatment of multiple diseases, including cardiovascular diseases, neurological disorders and cancers.
Nordihydroguaiaretic acid is also used as an antioxidant.
Nordihydroguaiaretic acid (NDGA) is an antioxidant that has poor solubility and shows evidence of discoloration in the presence of metal salts.
Nordihydroguaiaretic acid is used to a limited extent to retard rancidity.
Definition
A tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups.
Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor.
General Description
Nordihydroguaiaretic acid (NDGA) is used as an antioxidant and potent scavenger of reactive oxygen species (ROS).
Nordihydroguaiaretic acid is a tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups.
Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor.
Nordihydroguaiaretic acid has a role as an antioxidant, a plant metabolite, a ferroptosis inhibitor and a geroprotector.
Nordihydroguaiaretic acid is a member of catechols, a tetrol and a lignan.
Nordihydroguaiaretic acid is a natural product found in Arabidopsis thaliana, Larrea tridentata, and Magnolia sinica with data available.
A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism.
The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent.
Nordihydroguaiaretic acid also serves as an antioxidant in fats and oils.
Nordihydroguaiaretic acid (NDGA) is used as an antioxidant and potent scavenger of reactive oxygen species (ROS).
Application
Nordihydroguaiaretic acid can be used:
In the synthesis of nordihydroguaiaretic acid derivatives with potent HIV inhibition activity.
As a starting material in the synthesis of tetra-O-methylnordihydroguaiaretic acid.
Chemical Role(s):
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s):
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ferroptosis inhibitor
Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
Application(s):
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
Product name
Nordihydroguaiaretic acid, Naturally occurring antioxidant
Description
Naturally occurring potent antioxidant
Biological description
Naturally occurring potent antioxidant.
Various pharmacological effects in vitro and in vivo.
Anticancer, antimicrobial, anti-inflammatory and immunosuppressive activities.
Purity: > 97%
CAS Number: 500-38-9
Storage instructions
Store at Room Temperature.
Nordihydroguaiaretic acid is important to note that this product is reported to be light sensitive.
Store In the Dark. The product can be stored for up to 12 months.
Nordihydroguaiaretic acid (NDGA), 2,3-dimethyl-l,4-bis (3,4-dihydroxyphenyl) butane is a plant lignan derived from the leaves and twigs of shrub creosote bush, Larrea tridentata (Sesse and Moc. ex DC) Coville, family Zygophyllaceae.
Creosote bush dominates areas of the desert southwest in the USA and Northern Mexico, as well as some areas of Argentina.
Nordihydroguaiaretic acid is also known as chaparral and greasewood in the USA and gobernadora (governess) and hediondilla (little smelly one) in Mexico.
This shrub has a long history of traditional medicinal use for a variety of health problems by the Native Americans and Mexicans.
Chaparral tea has been used in the folk medicine for the treatment of more than 50 ailments including infertility, tuberculosis, arthritis, diabetes, kidney and gallbladder stones, pain and inflammation .
The concentration of NDGA in L. tridentata leaves is in the range of 5–10 of dry weight .
NDGA is a recognized inhibitor of lipoxygenase (LOX) and has antioxidant and free radical scavenging properties. Protective effect of NDGA has been observed against hepatic and renal toxicities induced by ferric-nitrilotriacetate (Fe-NTA).
Nordihydroguaiaretic acid also showed protective effect against ozone-induced tyrosine nitration in lungs, potassium dichromate-induced oxidative stress and nephrotoxicity and streptozotocin-induced diabetic nephropathy.
Besides its antioxidant activity, NDGA has several other properties, which are of potential use for humans such as it acts as an enzyme inhibitor, antimicrobial agent, potential vaso- and brancho-dilating agent and antimutagenic agent.
Nordihydroguaiaretic acid (NDGA) is a phenolic antioxidant found in the leaves and twigs of the evergreen desert shrub, Larrea tridentata (Sesse and Moc. ex DC) Coville (creosote bush).
Nordihydroguaiaretic acid is a recognized inhibitor of lipoxygenase (LOX) and has antioxidant and free radical scavenging properties. Nordihydroguaiaretic acid (NDGA) is a cytotoxic insulin-like growth factor-I receptor (IGF-1R)/HER2 inhibitor and induces apoptosis.
Nordihydroguaiaretic acid (NDGA) inhibits p300 and activates autophagy.
Nordihydroguaiaretic acid (NDGA) protects cells from ferroptosis.
Nordihydroguaiaretic acid (NDGA) is a phenolic antioxidant found in the leaves and twigs of the evergreen desert shrub, Larrea tridentata (Sesse and Moc. ex DC) Coville (creosote bush).
Nordihydroguaiaretic acid is a recognized inhibitor of lipoxygenase (LOX) and has antioxidant and free radical scavenging properties.
Nordihydroguaiaretic acid is a natural phenolic compound isolated from the creosote bush Larrea divaricata, which has anti-tumor activities both in vitro and in vivo.
Its analogs are in clinical development for use in refractory solid tumors.
In Vitro
The natural dicatechol Nordihydroguaiaretic acid (NDGA) is a selective 5LOX inhibitor from the creosote plant (Larrea tridentata: Zygophyllaceae).
The 5LOX-inhibiting natural dicatechol Nordihydroguaiaretic acid is a very effective, non-toxic antagonist of TNFα-stimulated microglial activation.
Nordihydroguaiaretic acid is approximately six times more potent than Minocycline in vitro, with an IC50 value of 8±3 μM and no toxicity at 100 μM.
Significant NO2- suppression is observed at 800 nM Nordihydroguaiaretic acid. Similar efficacy is observed for natural and synthetic Nordihydroguaiaretic acid, as well as for the acetyl ester of Nordihydroguaiaretic acid. Nordihydroguaiaretic acid also suppresses TNFα-stimulated PGE2 production by EOC-20 cells with an IC50 of 841 nM.
To test the proliferation effect of prostaglandin E1 and Nordihydroguaiaretic acid (NDGA) on cancer cell lines, HepG2 cell lines are treated with various doses of the two compounds and the positive compounds 8-anilino-1-naphtalene sulfonate (ANS), respectively, for 24 h and cell viability is examined by the MTT assay.
ANS displays a dose-dependent inhibition (0, 10, 30, 50, 80, 100, 120, and 150 μM) with the estimated IC50 being 25.888 μM. T
he tested IC50 of prostaglandin E1 is 41.223 μM and Nordihydroguaiaretic acid is 45.646 μM, respectively, at different concentrations of 0, 30, 60, 80, 100, 120, and 140 μM.
In Vivo
Compared with the control ob/ob chow diet group, there is a significant reduction of body weight starting from 9 wk treatment in the high-dose Nordihydroguaiaretic acid (NDGA) diet group, and from 12 wk in the low-dose group.
Nordihydroguaiaretic acid treatment results in higher body (rectal) temperatures of ob/ob mice, especially with the high dose of Nordihydroguaiaretic acid
IUPAC NAMES:
4,4'-(2,3-dimethylbutane-1,4-diyl)dibenzene-1,2-diol
4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
4,4'-(2,3-dimethyltetramethylene)dipyrocatechol
4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-dio
SYNONYMS:
4,4’-(2,3-dimethyltetramethylene)di-pyrocatecho
beta,gamma-Dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butane
Butane, 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-
dihydro-dinorguaiareticaci
Dihydronorguaiaretic acid
dihydro-norguaiareticaci
dihydronorguaiareticacid
Dinorguaiaretic acid, dihydro-
1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane, 4,4μ-(2,3-Dimethyltetramethylene)dipyrocatechol, Masoprocol, NDGA
4,4'-(2,3-Dimethyl-1,4-butylene)dipyrocatechol
4,4'-(2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
Nordihydroguaiaretic acid,95%
[-CH(CH3)CH2C6H3-1,2-(OH)2]2
Nordihydroguaiaretic acid,1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane, 4,4′-(2,3-Dimethyltetramethylene)dipyrocatechol, Masoprocol, NDGA
Nordihydroguaiaretic acid, tech. 90%
To a dihydro-nordihydroguaiaretic acid
Nordihydroguaiaretic acid, 95% 500MG
Nordihydro Guaiaretic Acid (Mixture of diastereoMers)
NSC 4291
β,γ-DiMethyl-α,δ-bis(3,4-dihydroxyphenyl)butane
NDGA 4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
Nordihydroguaiaretic acid >=97.0% (HPLC)
NDGA (Nordihydroguaiaretic acid)
2,6-Di-tert-butyl-4-methylphenol Solution, 1000ppm
NDGA - CAS 500-38-9 - Calbiochem
1,4-Bis(3,4-Dihydroxyphenyl)-2,3-Dimethylbutanenordihydroguaiaretic Acid
Nordihydroguaiaretic acid - pure diastereomer
Nordihydroguairaretic acid
nordihydroguairareticacid
Norguaiaretic acid, dihydro-
Pyrocatechol, 4,4'- (2,3-diemthyltetramethylene) di-
ACTINEX
1,4-BIS(3,4-DIHYDROXYPHENYL)-2,3-DIMETHYLBUTANE
1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-butan
2,3-Bis(3,4-dihydroxyphenylmethyl)butane
4,4'-(2,3-Dimethyl-1,4-Butanediyl)bis(pyrocatechol)
NORDIHYDROGUAIARETIC ACID
NORDIHYDROGUAIRETIC ACID
NDGA
NDGA, LARREA DIVARICATA
TIMTEC-BB SBB005930
NORDIHYDROGUAIARETIC ACID TAN CRYSTALS INHIBITOR OF LIPOXYGENASES
4,4'-(2,3-DIMETHYLTETRAMETHYLENE)DIPYROCATECHOL (NORDIHYDROGUAIARETIC ACID)
Nordihydroguaiareticacid,97%
LABOTEST-BB LT00233087
4,4'-(2,3-DIMETHYL-1,4-BUTANEDIYL)BIS-1,2-BENZENEDIOL
4,4'-(2,3-DIMETHYLTETRAMETHYLENE)DIPYROCATECHOL
Nordihydroguaiaretic Acid >
Nordihydroguaiaretic Acid Standard
Nordihydroguaiaretic acid USP/EP/BP
