フロログルシノール (無水)

Phloroglucinol

HCID 359CAS 108-73-6

基本情報

標準SMILES
Oc1cc(O)cc(O)c1
InChIKey
QCDYQQDYXPDABM-UHFFFAOYSA-N
分子式
C6H6O3
平均分子量
126.11 g/mol
単同位体質量
126.03169405

概要

Phloroglucinol is a benzenetriol with hydroxy groups at position 1, 3 and 5. It has a role as an algal metabolite. It is a phenolic donor and a benzenetriol.

名称と識別子

優先名称
Phloroglucinol
IUPAC
benzene-1,3,5-triol
現地名
フロログルシノール (無水)
英語名
Phloroglucinol
分子式
C6H6O3
分子量
126.11

名称と別名

phloroglucinol108-73-6Benzene-1,3,5-triol1,3,5-benzenetriol1,3,5-trihydroxybenzenePhloroglucinPhloroglucineSpasfon-LyocDilospan Ssym-Trihydroxybenzenes-TrihydroxybenzeneBenzene, trihydroxy
名称をさらに表示
フロログルシノール (無水)ディロスパンSジロスパンSフロログルシノールスパスホン-リオックsym-トリヒドロキシベンゼンキナルギナフロシノン3,5-ジヒドロキシフェノール1,3,5-トリヒドロキシベンゼンネロジレクサンフロログルシントリオギールベンゼン-s-トリオールシンテロールベンゼン-1,3,5-トリオールドロパックス1,3,5-ベンゼントリオールフロログルシノール(無水)3,5-DIHYDROXYPHENOLAnhydrous PhloroglucinolNero
FloroglucinFloroglucinolDHD7FFG6YSBenezene-1,3,5-triolNSC-1572DTXSID9048354CHEBI:16204RefChem:6129

データベース識別子

CAS
108-73-6
PubChem CID
359
DTXSID
DTXSID9048354
ChEMBL
CHEMBL473159
ChEBI
CHEBI:16204
UNII
DHD7FFG6YS
EC Number
203-611-2
Nikkaji
J2.866E

物性

構造計算による物性

XLogP
0.2
極性表面積
60.7 Ų
水素結合供与体数
3
水素結合受容体数
3
回転可能結合数
0
重原子数
9

実験および物理化学的性質

Chemical ClassesOther Classes -> Phenols
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics · 2 件

Cosmetic ingredients (Phloroglucinol) -> CIR (Cosmetic Ingredient Review)

Hair dyeing

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 2 件

0.16

0.16

Solubility10.6 mg/mL at 20 °C

物理化学的性質

融点
215 · 215-220 °C
沸点
194.21 °C · 194.21°C (rough estimate)
比重(密度)
0.801 g/mL · 0.801 g/mL at 20 °C
蒸気圧
0.001 Pa · 0.001Pa at 25℃
屈折率
20 · n20/D 1.365
闪点
14 °C · 14 °C

化学的性質

化学的特性white to light yellow crystal

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 1.9% (2 of 108) of reports.

Warning

H315 (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.

危険有害性情報

Regulatory Information · 3 件

Chemical: 1,3,5-Benzenetriol

Status: Active Update: 25-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23677

Phloroglucinol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1,3,5-Benzenetriol: Environment tier I assessment
Hazards SummaryA skin and eye irritant; [eChemPortal: ERMA] An irritant; [MSDSonline] Oral LD50 (mouse) = 4550 mg/kg; [Ullmann]
Hazard Classes and CategoriesSkin Irrit. 2 (81.5%)

毒性情報

Toxicity Summary · 2 件

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 · 4 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Phloroglucinol

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

安全データ

wgk
2
tsca
TSCA listed
rtecs
SY1050000
ridadr
UN 1170 3/PG 2
毒性
LD50 in mice, rats (g/kg): 4.7, 4.0 i.g. (Cahen)
hs_code
29072900

化学と産業

薬理情報

ATC Code · 2 件

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Metabolism/MetabolitesPhloroglucinol is a known human metabolite of Epicatechin and 2-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one.
MeSH Pharmacological Classification · 1 件

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

用途と製造

Uses · 3 件

CIR ingredient: Phloroglucinol

Used to decalcify bones, to make pharmaceuticals and dyes, to preserve cut flowers, and to dye and print textiles; [Hawley] Used in diazo-type printing, cosmetics (antioxidant), hair colorants, chemical reagents, cloud seeding, tree and shrub rooting, and pharmaceuticals (antispasmodic); [Merck Index] Isolated from bark of fruit trees in 1855; [Ullmann]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

Use ClassificationCosmetics -> Hair dyeing
General Manufacturing Information1,3,5-Benzenetriol: ACTIVE
応用分野 · 7 件

解説1,3,5-benzenetriol.C6H6O3(126.12).各種の植物成分中に配糖体として存在し,フロレチンの分解によって得られた.合成的には,1,3,5-トリニトロベンゼンを還元してトリアミノベンゼンとし,塩酸塩を水と煮沸して加水分解すると得られる.融点216~219 ℃.pKa1 7.97,pKa2 9.23(20 ℃).エタノール,エーテル,熱水など可溶.塩化鉄(Ⅲ)により紫色を呈し,フェーリング液を還元する.空気中で着色しやすく,とくにアルカリ水溶液はすみやかに酸素を吸収する.フロログルシノールはケト形としての反応性を示し,たとえば,ヒドロキシルアミンによってトリオキシムを生じる.分析試薬に用いられ,リグニンとの呈色反応を示し,ペントースなどの検出,定量(トレンス反応)にも使われ,フロログルシノール反応とよばれる.糖の検出,定量の試薬などに使われる.医薬品,色素原料,油脂,潤滑油などの酸化防止剤に使われる.LD50 1550 mg/kg(ラット,皮下).森北出版「化学辞典(第2版)

用途医薬中間体,写真感光剤,染料用カップリング剤。

用途有機合成原料。

説明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.

使用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.

一般的な説明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.

使用用途多官能性であるフロログルシノールは、有機合成の中間体として有用です。主に医薬品や爆薬の合成原料などに使用されます。 例えば、フロプロピオンの合成原料に利用されます。ジアゾ染料と結合して速やかに黒色になるため、印刷のカップリング剤としても使用可能です。リグニンと呈色反応を示し、分析試薬に用いられます。ペントースなどの検出や定量 (トレンス反応) にも有用で、フロログルシノール反応と呼ばれています。

調製方法

純化方法Crystallise the triol from water, and store it in the dark under nitrogen. [Beilstein 6 IV 7361.]

サプライヤー50 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
张家港博迈化学有限公司15601563028
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

補足説明

定義ChEBI: Phloroglucinol is a benzenetriol with hydroxy groups at position 1, 3 and 5. It has a role as an algal metabolite.

関連反応

99 件

関連ノート

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