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9,10-Dihydro-4,5-dihydroxy-9,10-dioxoanthracen-2-carbonsure
RHUBARB EXTRACT · CASSIC ACID · 4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid · 4,5-DIHYDROXYANTHRAQUINONE-2-CARBOXYLIC ACID · Rheinic acid · Rhein synthetic · 1,8-DIHYDROXYANTHRAQUINONE-3-CARBOXYLIC ACID · RHEIN
Identifikatoren & physikalische Daten
| CAS No. | 478-43-3 |
|---|---|
| Summenformel | C15H8O6 |
| Durchschnittliche Molmasse | 284,22 g/mol |
| Monoisotopische Masse | 284,03208798 g/mol |
| SMILES | O=C(O)c1cc(O)c2c(c1)C(=O)c1cccc(O)c1C2=O |
| InChIKey | FCDLCPWAQCPTKC-UHFFFAOYSA-N |
| PubChem CID | 10168 |
| ChEMBL | CHEMBL418068 |
| ChEBI | CHEBI:8825 |
| EC No. | 207-521-4 |
| DTXSID | DTXSID4026000 |
| Lokaler Name | 9,10-Dihydro-4,5-dihydroxy-9,10-dioxoanthracen-2-carbonsure |
Chemische & physikalische Eigenschaften
| XLogP | 2,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 112 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 487 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Metabolite of Senna |
| Lipide | Polyketides [PK] -> Aromatic polyketides [PK13] -> Anthracenes and phenanthrenes [PK1304] |
| Pestizide | Biocide |
| LogP (Verteilungskoeffizient) | 3.68 |
| Löslichkeit | less than 1 mg/mL at 63 °F (NTP, 1992)DMSO (Slightly), Methanol (Slightly)<0.1 g/100 mL at 17 ºC |
| Siedepunkt | Sublimes (NTP, 1992)346.72°C (rough estimate) |
| Schmelzpunkt | 610 °F (NTP, 1992)>300321 °C≥300 °C (lit.) |
| Physical Description | Rhein appears as yellow needles (from methanol) or yellow-brown powder. (NTP, 1992)Solid |
| Dichte | 1.3269 (rough estimate) |
| Brechungsindex | 1.4413 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 3.17±0.20(Predicted) |
| Farbe | Yellow to Dark Orange |
| Merck | 14,8176 |
| BRN | 2222155 |
| Stabilität | Hygroscopic |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIMICROBIAL |
| InChI | 1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21) |
| InChIKey | FCDLCPWAQCPTKC-UHFFFAOYSA-N |
| SMILES | OC(=O)c1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1 |
| LogP (Verteilungskoeffizient) | 4.290 (est) |
| CAS Datenbank | 478-43-3(CAS DataBase Reference) |
| EPA chemische Informationen | 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo- (478-43-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 78 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 22-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26074 |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: This chemical is an irritant. |
| Reaktive Gruppe | Acids, Carboxylic |
| Reactivity Profile | RHEIN forms a red potassium salt and a pink sodium salt. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Wassergefährdungsklasse (WGK) | 2 |
| Zollcode | 29189900 |
| RTECS-Nr. | CA9516000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
Rhein is used to inhibit growth factor beta-1 induced plasminogen activator inhibitor-1 in endothelial cells. It acts as an antibacterial agent against Staphylococcus aureus. It is also used as a laxative. Further, it is employed as a pharmaceutical intermediate.