4,4'-(2,3-Dimethyltetramethylen)dibrenzcatechin
NDGA · ACTINEX · NORDIHYDROGUAIRETIC ACID · NSC 4291 · TIMTEC-BB SBB005930 · LABOTEST-BB LT00233087 · NDGA, LARREA DIVARICATA · nordihydroguaiareticaci
Identifikatoren & physikalische Daten
| CAS No. | 500-38-9 |
|---|---|
| Summenformel | C18H22O4 |
| Durchschnittliche Molmasse | 302,4 g/mol |
| Monoisotopische Masse | 302,15180918 g/mol |
| SMILES | CC(Cc1ccc(O)c(O)c1)C(C)Cc1ccc(O)c(O)c1 |
| InChIKey | HCZKYJDFEPMADG-UHFFFAOYSA-N |
| PubChem CID | 4534 |
| ChEMBL | CHEMBL52 |
| ChEBI | CHEBI:7625 |
| EC No. | 207-903-0 |
| DTXSID | DTXSID5022437 |
| Lokaler Name | 4,4'-(2,3-Dimethyltetramethylen)dibrenzcatechin |
Chemische & physikalische Eigenschaften
| XLogP | 4,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 80,9 |
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 303 |
| Stoffklassen | Biological Agents -> Plant Toxins |
| Kosmetika | Antioxidant |
| Lebensmittelzusatzstoffe | ANTIOXIDANT -> FDA Substance added to food |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Food Contact Substances | FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Physical Description | Solid[Merck Index] White odorless powder[Alfa Aesar MSDS] |
| Collision Cross Section | 167.5 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID5022437] |
| Schmelzpunkt | 184-186 °C (lit.) |
| Siedepunkt | 363.4°C (rough estimate) |
| Dichte | 1.0772 (rough estimate) |
| Brechungsindex | 1.4230 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly)slightly soluble |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 9.56±0.10(Predicted) |
| Farbe | White to off-white |
| Biologische Quelle | Larrea divaricata (creosote bush) |
| Merck | 14,6693 |
| BRN | 2056825 |
| Stabilität | Stable. Incompatible with oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIOXIDANT |
| InChI | 1S/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 |
| InChIKey | HCZKYJDFEPMADG-UHFFFAOYSA-N |
| SMILES | CC(Cc1ccc(O)c(O)c1)C(C)Cc2ccc(O)c(O)c2 |
| LogP (Verteilungskoeffizient) | 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 & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 188 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis- |
| Gefahrenübersicht | This CAS# refers to the unspecified stereoisomer formThe meso- form is CAS# 27686-84-6[Merck Index] A skin and strong eye irritantHarmful by ingestion[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29072990 |
| RTECS-Nr. | UX1750000 |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36/37-37/39-24/25-22 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
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.
Herstellung & Synthese
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.