프로로글루신올
프로로글루신올 · 플로로글루시놀 · 플로로글루신올 · 1,3,5-트라이하이드록시벤젠 · Benzene-1,3,5-triol · 1,3,5-TRIHYDROXYBENZENE · 1,3,5-BENZENETRIOL · PHLOROGLUCIN
식별자 및 물리적 특성
| CAS No. | 108-73-6 |
|---|---|
| 분자식 | C6H6O3 |
| 평균 분자량 | 126.11 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 프로로글루신올 |
화학 및 물리적 성질
| XLogP | 0.2 |
|---|---|
| 극성 표면적 | 60.7 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 9 |
| 형식 전하 | 0 |
| 복잡도 | 63.3 |
| 물질 분류 | Other Classes -> Phenols |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| 화장품 | Cosmetic ingredients (Phloroglucinol) -> CIR (Cosmetic Ingredient Review)Hair dyeing |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP(분배 계수) | 0.16 |
| 용해도 | 10.6 mg/mL at 20 °C디에틸 에테르, 에탄올 및 피리딘에 용해됩니다. |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 녹는점 | 218.5 °C215-220 °C |
| 증기압 | 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] |
| 끓는 점 | 194.21°C (rough estimate) |
| 밀도 | 0.801 g/mL at 20 °C |
| 굴절률 | n20/D 1.365 |
| 인화점 | 14 °C |
| 저장 조건 | Store below +30°C. |
| 물리적 상태 | 결정성 분말 |
| pKa(산도 계수) | pK1:8.45(0)pK2:8.88(-1) (25°C) |
| 색상 | 흰색~밝은 베이지 |
| 용해도 | 11.17g/L(상온) |
| Merck | 14,7328 |
| BRN | 1341907 |
| 화장품 원료 기능 | 머리 염색 |
| 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(분배 계수) | 0.55 at 25℃ |
| NIST | 1,3,5-Benzenetriol(108-73-6) |
| EPA | 1,3,5-Benzenetriol (108-73-6) |
화학적 성질
white to light yellow crystal
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | 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 |
| 기타 안전 정보 | IMAP assessments - 1,3,5-Benzenetriol: Environment tier I assessment |
| 유해성 요약 | 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%) |
| 독성 요약 | 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 |
| 수질 위해 등급(WGK) | 2 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | SY1050000 |
| 운송 번호(UN) | UN 1170 3/PG 2 |
| 독성 | LD50 in mice, rats (g/kg): 4.7, 4.0 i.g. (Cahen) |
| 관세 코드 | 29072900 |
| 위험 문구(R) | 11-36/37/38-34-43 |
| 위험 표시 | F,Xi |
| 안전 문구(S) | 7-16-24/25-45-36/37/39-26-36/37-37/39 |
| 기존화학 물질 | KE-02671 |
| 위험 등급 | Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
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.
용도
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.
일반 설명
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.