Phloroglucin
Benzene-1,3,5-triol · 1,3,5-TRIHYDROXYBENZENE · 1,3,5-BENZENETRIOL · PHLOROGLUCIN · Floroglucinol · 3,5-DIHYDROXYPHENOL · Dilospan S · Anhydrous Phloroglucinol
Identifikatoren & physikalische Daten
| CAS No. | 108-73-6 |
|---|---|
| Summenformel | C6H6O3 |
| Durchschnittliche Molmasse | 126,11 g/mol |
| Monoisotopische Masse | 126,03169405 g/mol |
| SMILES | Oc1cc(O)cc(O)c1 |
| InChIKey | QCDYQQDYXPDABM-UHFFFAOYSA-N |
| PubChem CID | 359 |
| ChEMBL | CHEMBL473159 |
| ChEBI | CHEBI:16204 |
| EC No. | 203-611-2 |
| DTXSID | DTXSID9048354 |
| Lokaler Name | Phloroglucin |
Chemische & physikalische Eigenschaften
| XLogP | 0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 60,7 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 63,3 |
| Stoffklassen | Other Classes -> Phenols |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Kosmetika | Cosmetic ingredients (Phloroglucinol) -> CIR (Cosmetic Ingredient Review)Hair dyeing |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | 0.16 |
| Löslichkeit | 10.6 mg/mL at 20 °CSoluble in diethyl ether, ethanol and pyridine.11.17g/L(room temperature) |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 218.5 °C215-220 °C |
| Dampfdruck | 0.00016 [mmHg]0.001Pa at 25℃ |
| Physical Description | White solidDiscolored by light[Merck Index] White or cream colored powder[MSDSonline] Crystallizes in anhydrous or dihydrate formSweet tasting crystals[Ullmann] |
| Collision Cross Section | 121.6 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID3046586] |
| Siedepunkt | 194.21°C (rough estimate) |
| Dichte | 0.801 g/mL at 20 °C |
| Brechungsindex | n20/D 1.365 |
| Flammpunkt | 14 °C |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | pK1:8.45(0)pK2:8.88(-1) (25°C) |
| Farbe | White to light beige |
| Merck | 14,7328 |
| BRN | 1341907 |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR DYEING |
| InChI | 1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H |
| InChIKey | QCDYQQDYXPDABM-UHFFFAOYSA-N |
| SMILES | Oc1cc(O)cc(O)c1 |
| LogP (Verteilungskoeffizient) | 0.55 at 25℃ |
| CAS Datenbank | 108-73-6(CAS DataBase Reference) |
| NIST chemische Informationen | 1,3,5-Benzenetriol(108-73-6) |
| EPA chemische Informationen | 1,3,5-Benzenetriol (108-73-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.9% (2 of 108) of reports.WarningH315 (81.5%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 108 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1,3,5-BenzenetriolStatus: Active Update: 25-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23677Phloroglucinol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1,3,5-Benzenetriol: Environment tier I assessment |
| Gefahrenübersicht | A skin and eye irritant[eChemPortal: ERMA] An irritant[MSDSonline] Oral LD50 (mouse) = 4550 mg/kg[Ullmann] |
| Hazard Classes and Categories | Skin Irrit. 2 (81.5%) |
| Toxizitätsübersicht | On the basis of the available data, the CIR Panel cannot conclude that Phloroglucinol is safe for use in cosmetic products until the appropriate safety data have been obtained and evaluated.Ingredients for which the data are insufficient and their use in cosmetics is not supported |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)PhloroglucinolDILI PositiveDOI:10.1016/j.drudis.2019.09.022 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1170 3/PG 2 |
| Zollcode | 29072900 |
| RTECS-Nr. | SY1050000 |
| R-Sätze (R) | 11-36/37/38-34-43 |
| Toxizität | LD50 in mice, rats (g/kg): 4.7, 4.0 i.g. (Cahen) |
| Gefahrensymbole | F,Xi |
| Sicherheitshinweise (S) | 7-16-24/25-45-36/37/39-26-36/37-37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
Phloroglucinol is a naturally occurring phenol that exhibits diverse biological activities. Phloroglucinol protects V79-4 Chinese hamster lung fibroblast cells from oxidative stress and inhibits lipid peroxidation by scavenging reactive oxygen species (ROS). It induces apoptosis in HT-29 human colon cancer cells and inhibits metastasis of BT549 and MDA-MB-231 human breast cancer cells. Phloroglucinol protects primary neurons from β-amyloid-induced dendritic spine loss in vitro and shortens the latency to find the platform in a Morris water maze test in an Alzheimer’s disease (AD) mouse model. Phloroglucinol has been used to stain histological plant sections and in the synthesis of numerous natural products. Phloroglucinol slows the frequency and decreases the amplitude of contraction in isolated rabbit and rat intestine at a concentration of 100 and 1 μM, respectively. Formulations containing phloroglucinol have been used as antispasmodics.
Verwenden
Phloroglucinol is mainly used as a coupling agent in printing. It is an active component of Tollen's reagent and Gunzburg reagent used to test pentoses and hydrochloric acid in gastric juice respectively. In analytical chemistry, it is used to study condensed tannins by means of depolymerization. It is also involved in the synthesis of 2,4,6-triamino-1,3,5- trinitrobenzene, trinitrophloroglucinol and pharmaceuticals like flopropione.