500-38-9 Usage
Description
Nordihydroguaiaretic acid (NDGA) is a grayish-white crystalline compound that is a phenolic lignan obtained from Larrea tridentata, a plant used in traditional medicine. It possesses phenolic properties similar to gallates and has been used as a powerful antioxidant and potent scavenger of reactive oxygen species (ROS). NDGA has been utilized in the treatment of various diseases, including cancer, renal, cardiovascular, immunological, and neurological disorders, and even aging.
Uses
Used in Pharmaceutical Applications:
Nordihydroguaiaretic acid is used as a therapeutic agent for the treatment of multiple diseases, such as cardiovascular diseases, neurological disorders, and cancers. It modulates several signaling pathways and exhibits inhibitory effects on tumor growth and progression.
Used in Antioxidant Applications:
Nordihydroguaiaretic acid is used as a potent antioxidant, effective against mildew, and has a synergistic effect when used in combination with citric acid and ascorbic acid. It has been used to a limited extent to retard rancidity in the food industry.
Used in Chemical Synthesis:
NDGA is used as a chemical intermediate in the synthesis of various compounds due to its unique structure and properties.
Used in Research:
Nordihydroguaiaretic acid is used as a research tool in the study of lipoxygenase inhibition and other biological processes, as it is a potent lipoxygenase inhibitor with a polyphenol-bearing o-dihydroxy (catechol) structure.
Note: The provided materials mention that NDGA has been prohibited from use in the US due to unfavorable toxicological findings. This should be considered when discussing its applications.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 500-38-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 0 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 500-38:
(5*5)+(4*0)+(3*0)+(2*3)+(1*8)=39
39 % 10 = 9
So 500-38-9 is a valid CAS Registry Number.
InChI:InChI=1/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/t11-,12-/m1/s1
500-38-9Relevant articles and documents
Novel synthetic method of nordihydroguaiaretic acid (NDGA)
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, (2020/06/16)
Nordihydroguaiaretic acid has wide physiological activity and pharmacological activity. The invention discloses a novel synthetic method of nordihydroguaiaretic acid, wherein the method comprises thefollowing steps: carrying out reductive coupling reaction on veratone serving as a raw material under the action of a catalyst to obtain pinacol; reducing pinacol by trialkylsilane or triarylsilane under the catalysis of protonic acid or Lewis acid to generate 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane; and finally, under the action of haloid acid or Lewis acid, breaking ether bonds, and synthesizing nordihydroguaiaretic acid. The structure of the compound is characterized by 1H-NMR. Raw materials and reagents used in the method are easy to obtain, the reaction route is short, the reaction conditions are mild, the yield is high, the cost is low, and a simple and convenient path is opened up for industrial synthesis of nordihydroguaiaretic acid.
Diarylalkanes as potent inhibitors of binuclear enzymes
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Page/Page column 17, (2008/06/13)
The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.
