Phloroglucinol
Benzene-1,3,5-triol · 1,3,5-TRIHYDROXYBENZENE · 1,3,5-BENZENETRIOL · PHLOROGLUCIN · Floroglucinol · 3,5-DIHYDROXYPHENOL · Dilospan S · Anhydrous Phloroglucinol
Identifiers & Physical Properties
| CAS No. | 108-73-6 |
|---|---|
| Molecular formula | C6H6O3 |
| Average molar mass | 126.11 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | 0.2 |
|---|---|
| Topological polar surface area | 60.7 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 0 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 63.3 |
| Chemical classes | Other Classes -> Phenols |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Cosmetics | Cosmetic ingredients (Phloroglucinol) -> CIR (Cosmetic Ingredient Review)Hair dyeing |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (partition coefficient) | 0.16 |
| Solubility | 10.6 mg/mL at 20 °CSoluble in diethyl ether, ethanol and pyridine.11.17g/L(room temperature) |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Melting point | 218.5 °C215-220 °C |
| Vapor pressure | 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] |
| Boiling point | 194.21°C (rough estimate) |
| Density | 0.801 g/mL at 20 °C |
| Bulk density | 560kg/m3 |
| Refractive index | n20/D 1.365 |
| Flash point | 14 °C |
| Storage conditions | Store below +30°C. |
| Physical state | Crystalline Powder |
| pKa (acidity coefficient) | pK1:8.45(0)pK2:8.88(-1) (25°C) |
| Color | White to light beige |
| Sensitivity | Light Sensitive & Hygroscopic |
| Merck | 14,7328 |
| BRN | 1341907 |
| Cosmetics Ingredients Functions | 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 (partition coefficient) | 0.55 at 25℃ |
| CAS DataBase Reference | 108-73-6(CAS DataBase Reference) |
| EWG's Food Scores | 3-6 |
| FDA UNII | DHD7FFG6YS |
| ATC code | A03AX12 |
| NIST Chemistry Reference | 1,3,5-Benzenetriol(108-73-6) |
| EPA Substance Registry System | 1,3,5-Benzenetriol (108-73-6) |
| UNSPSC Code | 41116107 |
| NACRES | SE.11 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H303-H315-H319-H335 |
| GHS precautionary statements | P501-P261-P271-P264-P280-P302+P352-P312-P337+P313-P305+P351+P338-P362+P364-P332+P313-P304+P340+P312-P403+P233-P405 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | F,Xi |
| Risk statements (R) | 11-36/37/38-34-43 |
| Safety statements (S) | 7-16-24/25-45-36/37/39-26-36/37-37/39 |
| UN transport number | UN 1170 3/PG 2 |
| Water hazard class (WGK) | 2 |
| RTECS number | SY1050000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29072900 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Toxicity | LD50 in mice, rats (g/kg): 4.7, 4.0 i.g. (Cahen) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | 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. |
|---|---|
| Regulatory information | 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 |
| Other safety information | IMAP assessments - 1,3,5-Benzenetriol: Environment tier I assessment |
| Hazards summary | 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%) |
| Toxicity summary | 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 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
Applications & Uses
Uses
Phloroglucinol can be used in verifications of antimony, arsenic, cerium, chromate, chromium, gold, iron, mercury, nitrites, osmium, palladium, tin, vanadium, vanillin and lignin, and measurement of furfural, pentose, pentosan, methanol, chloral hydrate, turpentine, Lignified cell tissues, free acid in gastric juice (HCl) and decalcified bone specimens. Besides it can also be used as biological reagent dyes.
Description
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.
Uses
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.
Uses
Phloroglucinol (1,3,5-trihydroxybenzene) is the core structure of a large family of substituted phenolics with broad, albeit weak, biological activity. Phloroglucinol is a useful metabolite for HPLC/DAD and bioassay dereplication.diagnostic aid growth hormone releasing factor. Antispasmodic.
General Description
Phloroglucinol is a trihydroxybenzene with antithrombotic, profibrinolytic, antimicrobial, antimalarial, cancer chemopreventive, anti-HIV and anti-leishmanial activities. Phloroglucinol (PG) is a biosynthetic precursor of the 2,4-diacetylphloroglucinol (DAPG) an antibiotic against soil-borne diseases. Phloroglucinol is a useful intermediate because it is polyfunctional.