4,4'-(2,3-Dimethyltetramethylen)dibrenzcatechin

Bezeichnung:4,4'-(2,3-Dimethyltetramethylen)dibrenzcatechin

CAS-Nr500-38-9

Englisch Name:Nordihydroguaiaretic acid

CBNumberCB5755745

SummenformelC18H22O4

Molgewicht302.36

MOL-Datei500-38-9.mol

Synonyma

4,4'-(2,3-Dimethyltetramethylen)dibrenzcatechin

4,4'-(2,3-Dimethyltetramethylen)dibrenzcatechin physikalisch-chemischer Eigenschaften

Schmelzpunkt	184-186 °C (lit.)
Siedepunkt	363.4°C (rough estimate)
Dichte	1.0772 (rough estimate)
Brechungsindex	1.4230 (estimate)
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Powder
pka	9.56±0.10(Predicted)
Farbe	White to off-white
Wasserlöslichkeit	slightly soluble
Merck	14,6693
BRN	2056825
Stabilität	Stable. Incompatible with oxidizing agents.
LogP	4.640 (est)
CAS Datenbank	500-38-9(CAS DataBase Reference)
NIST chemische Informationen	Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-(500-38-9)
EPA chemische Informationen	Nordihydroguaiaretic acid (500-38-9)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	26-36/37-37/39-24/25-22
WGK Germany	3
RTECS-Nr.	UX1750000
HS Code	29072990

Gefahreninformationscode (GHS)

Nordihydroguaiaretic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S22:Staub nicht einatmen.
Beschreibung
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.
Chemische Eigenschaften
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.
Verwenden
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.
synthetische
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.
Application
Nordihydroguaiaretic acid (NDGA, 500-38-9) 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.
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.
Allgemeine Beschreibung
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.
Sicherheitsprofil
Moderately toxic by intraperitoneal route. An antioxidant food additive. When heated to decomposition it emits acrid smoke and irritating fumes.
läuterung methode
Crystallise the acid from dilute acetic acid. [Beilstein 6 IV 7771.]
Einzelnachweise
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 Upstream-Materialien And Downstream Produkte

4,4'-(2,3-Dimethyltetramethylen)dibrenzcatechin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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