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| | Nordihydroguaiaretic acid Basic information |
| Product Name: | Nordihydroguaiaretic acid | | 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- | | CAS: | 500-38-9 | | MF: | C18H22O4 | | MW: | 302.36 | | EINECS: | 207-903-0 | | Product Categories: | Aromatics;Inhibitors;Aromatic Phenols;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 500-38-9.mol |  |
| | Nordihydroguaiaretic acid Chemical Properties |
| | Nordihydroguaiaretic acid Usage And Synthesis |
| Description | Nordihydroguaiaretic acid (NDGA) is a grayish-white crystalline compound that was widely used as an antioxidant in animal fats in the 1950s and 1960s. It 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 | Nordihydroguaiaretic acid is a white to light yellow crystalline powder. Melting range 183～185℃. Insoluble in water. Slightly soluble in hot water. Soluble in alcohol, ether, glycerol, propylene glycol. About 0.5% is dissolved in oil. It has good antioxidant effect and is also effective against mildew. It has a synergistic effect when used in combination with citric acid and ascorbic acid. | | Uses | Nordihydroguaiaretic acid is used in the treatment of multiple diseases, including cardiovascular diseases, neurological disorders and cancers. It is also used as an antioxidant. | | Definition | ChEBI: 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. It has a role as an antioxidant, a plant metabolite, a ferroptosis inhibitor and a geroprotector. It is a member of catechols, a tetrol and a lignan. | | Application | Nordihydroguaiaretic acid (NDGA) is an antioxidant that has poor solubility and shows evidence of discoloration in the presence of metal salts. It is used to a limited extent to retard rancidity. NDGA is a broad bean lipoxygenase inhibitor that polyphenol-bearing o-dihydroxy (catechol) structure. The oxidation product from Resveratrol (R150000) showed a high inhibitory activity, w hereas Resveratrol itself had no activity and its oxidation efficiency was low. | | Preparation | Nordihydroguaiaretic acid is obtained by hydrodemethylation of dimethyl ether of guaiacolinic acid, a component of guaiac resin. It is also produced from desert plant, creosote bush (Larrea divaricata Cav. Or Corillea tridentate), which can be widely found in the border zone of southern of USA and northern of Mexico. | | benefits | Nordihydroguaiaretic acid is a kind of antioxidant compound presented in the creosoten bush. It 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. It can also protect hippocampal neurons against amyloid β-peptide toxicity, and attenuates free radical and calcium accumulation. Rat study has shown that it can block the synaptic component of long-term potentiation and the associated increases in release of glutamate and arachidonate. Two most exciting results are that: (1) it has the potential to increase lifespan of animals; (2) it can suppress growth of breast cancer cells through inhibiting the IGF-1 and c-erbB2/HER/NEU receptors. | | General Description | Nordihydroguaiaretic acid (NDGA) is used as an powerful antioxidant and potent scavenger of reactive oxygen species (ROS). NDGA is a phenolic lignan obtained from Larrea tridentata, that has been used in traditional medicine for the treatment of numerous diseases such as cancer, renal, cardiovascular, immunological, and neurological disorders, and even aging. | | Hazard | Use in foods prohibited by FDA. | | Biochem/physiol Actions | Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure. | | Safety Profile | Moderately toxic by
intraperitoneal route. An antioxidant food
additive. When heated to decomposition it
emits acrid smoke and irritating fumes. | | Purification Methods | Crystallise the acid from dilute acetic acid. [Beilstein 6 IV 7771.] | | References | Floriano-Sánchez, E, et al. "Nordihydroguaiaretic acid is a potent in vitro scavenger of peroxynitrite, singlet oxygen, hydroxyl radical, superoxide anion and hypochlorous acid and prevents in vivo ozone-induced tyrosine nitration in lungs." Free Radical Research 40.5(2006):523.
Goodman, Yadong, et al. "Nordihydroguaiaretic acid protects hippocampal neurons against amyloid β-peptide toxicity, and attenuates free radical and calcium accumulation." Brain Research 654.1(1994):171.
Lynch, M. A., M. L. Errington, and T. V. Bliss. "Nordihydroguaiaretic acid blocks the synaptic component of long-term potentiation and the associated increases in release of glutamate and arachidonate: an in vivo study in the dentate gyrus of the rat." Neuroscience 30.3(1989):693-701.
Strong, Randy, et al. "Nordihydroguaiaretic acid and aspirin increase lifespan of genetically heterogeneous male mice." Aging Cell 7.5(2008):641-650.
Youngren, Jack F., et al. "Nordihydroguaiaretic Acid (NDGA) Inhibits the IGF-1 and c-erbB2/HER2/neu Receptors and Suppresses Growth in Breast Cancer Cells." Breast Cancer Research & Treatment 94.1(2005):37-46. |
| | Nordihydroguaiaretic acid Preparation Products And Raw materials |
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