Nordihydroguaiaretic Acid, commonly abbreviated as NDGA, is a naturally occurring lignan compound containing four phenolic hydroxyl groups. It is associated with antioxidant activity and inhibition of lipoxygenase enzymes and occurs naturally in plants including Larrea tridentata (creosote bush). PubChem identifies Nordihydroguaiaretic Acid as a lignan, catechol-containing compound and antioxidant.
Nordihydroguaiaretic Acid has applications in pharmaceutical research, biochemical research, antioxidant studies and lipoxygenase-related research.
Nordihydroguaiaretic Acid is a specialized pharmaceutical and research-use chemical ingredient used in the development and analytical investigation of antioxidant and enzyme-inhibition systems.
Important quality attributes include identity, assay/purity, related substances, water content, residue on ignition, elemental impurities, melting point and solubility.
CAS Number: 500-38-9
Molecular Formula: C₁₈H₂₂O₄
Molecular Weight: 302.36 g/mol
Chemical Name: 4,4'-(2,3-Dimethyltetramethylene)-dipyrocatechol
IUPAC Name: 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
Synonyms: NDGA, Nordihydroguaiaretic Acid, Dihydronorguaiaretic Acid, Masoprocol
Drug/Class Type: Natural Product / Lignan
Therapeutic Area: Pharmaceutical and Biochemical Research
Molecule Type: Natural Product / Small Molecule
Biological Source: Larrea tridentata / Larrea divaricata
PubChem confirms CAS 500-38-9, formula C₁₈H₂₂O₄ and molecular weight 302.4 g/mol. JECFA reports a formula weight of 302.36.
Nordihydroguaiaretic Acid is recognized particularly for its ability to inhibit lipoxygenase enzymes, which participate in the metabolism of arachidonic acid and formation of lipid mediators.
Its biological activities include:
PubChem describes Nordihydroguaiaretic Acid as a potent lipoxygenase inhibitor and antioxidant.
Nordihydroguaiaretic Acid is relevant to:
NDGA contains multiple phenolic hydroxyl groups that contribute to its antioxidant properties. It has been investigated for its ability to interact with oxidative processes and free-radical pathways.
JECFA identifies Nordihydroguaiaretic Acid as an antioxidant and describes it as a white to greyish-white crystalline solid.
Lipoxygenases are enzymes involved in the oxidation of polyunsaturated fatty acids.
Nordihydroguaiaretic Acid has historically been studied as a lipoxygenase inhibitor, making it useful as a research compound for investigating lipid oxidation, inflammatory signaling and related biochemical pathways.
Nordihydroguaiaretic Acid is generally described as a white to greyish-white crystalline solid or white/off-white crystalline powder.
JECFA reports a melting point of approximately 184°C, while commercial analytical specifications report ranges around 184–189°C.
Nordihydroguaiaretic Acid is insoluble or only slightly soluble in water. It is soluble in organic solvents including ethanol and ether. JECFA specifically describes it as freely soluble in ethanol and ether, and in propylene glycol at elevated temperature.
Nordihydroguaiaretic Acid is naturally associated with the creosote bush, Larrea tridentata, and related Larrea species.
It is also reported as a natural product in several plant species.
A controlled Nordihydroguaiaretic Acid manufacturing process may involve:
Typical Nordihydroguaiaretic Acid quality-control testing may include:
Store Nordihydroguaiaretic Acid in a tightly closed, light-resistant container under controlled conditions, protected from excessive heat, moisture and incompatible oxidizing agents.
Some commercial analytical products recommend refrigerated storage, while storage requirements for a pharmaceutical-grade material should follow its validated stability data and approved specification.
Nordihydroguaiaretic Acid is relevant to research involving:
Nordihydroguaiaretic Acid is a natural lignan and antioxidant compound with CAS 500-38-9, molecular formula C₁₈H₂₂O₄ and molecular weight 302.36 g/mol. It is associated particularly with lipoxygenase inhibition and antioxidant research. JECFA reports an assay range of 95–102%, melting point of approximately 184°C, and describes the material as a white to greyish-white crystalline solid.
| Parameter | Specification |
|---|---|
| Appearance | White crystalline powder or crystals |
| Identification | IR & HPLC compliant |
| Assay (HPLC) | 95.0% – 102.0% |
| Loss on Drying | NMT 2.0% |
| Residue on Ignition | NMT 0.5% |
| Individual Impurity | NMT 0.10% |
| Total Impurities | NMT 0.50% |
| Water Content | NMT 1.0% |
| Melting Point | About 184°C |