| Identification | More | [Name]
Nordihydroguaiaretic acid | [CAS]
500-38-9 | [Synonyms]
1,4-BIS(3,4-DIHYDROXYPHENYL)-2,3-DIMETHYLBUTANE
4,4'-(2,3-DIMETHYL-1,4-BUTANEDIYL)BIS-1,2-BENZENEDIOL
4,4'-(2,3-DIMETHYLTETRAMETHYLENE)DIPYROCATECHOL
ACTINEX
LABOTEST-BB LT00233087
NDGA
NDGA, LARREA DIVARICATA
NORDIHYDROGUAIARETIC ACID
NORDIHYDROGUAIRETIC ACID
TIMTEC-BB SBB005930
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)
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 | [EINECS(EC#)]
207-903-0 | [Molecular Formula]
C18H22O4 | [MDL Number]
MFCD00002206 | [Molecular Weight]
302.36 | [MOL File]
500-38-9.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow crystalline solid | [Melting point ]
184-186 °C (lit.) | [Boiling point ]
363.4°C (rough estimate) | [density ]
1.0772 (rough estimate) | [refractive index ]
1.4230 (estimate) | [storage temp. ]
Freezer (-20°C) | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
9.56±0.10(Predicted) | [color ]
White to off-white | [Stability:]
Stable. Incompatible with oxidizing agents. | [Water Solubility ]
slightly soluble | [Merck ]
14,6693 | [BRN ]
2056825 | [LogP]
4.640 (est) | [Uses]
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. | [CAS DataBase Reference]
500-38-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-(500-38-9) | [EPA Substance Registry System]
500-38-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S37/39:Wear suitable gloves and eye/face protection .
S24/25:Avoid contact with skin and eyes .
S22:Do not breathe dust . | [WGK Germany ]
3
| [RTECS ]
UX1750000
| [HS Code ]
29072990 | [Safety Profile]
Moderately toxic by
intraperitoneal route. An antioxidant food
additive. When heated to decomposition it
emits acrid smoke and irritating fumes. |
| Hazard Information | Back Directory | [Description]
Nordihydroguaiaretic acid (NDGA, 500-38-9) 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. | [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. | [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. | [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 antioxidant and potent scavenger of reactive oxygen species (ROS). | [Hazard]
Use in foods prohibited by FDA. | [Biochem/physiol Actions]
Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure. | [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. |
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