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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 63.3
実験および物理化学的性質
Cosmetics
Cosmetic ingredients (Phloroglucinol) -> CIR (Cosmetic Ingredient Review)
Hair dyeing
LogP
0.16
0.16
Physical Description
White solid; Discolored by light; [Merck Index] White or cream colored powder; [MSDSonline] Crystallizes in anhydrous or dihydrate form; Sweet tasting crystals; [Ullmann]
Solid
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
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- ジエチルエーテル、エタノール、ピリジンに可溶。
- 外見
- 結晶性粉末
- 酸解離定数(Pka)
- 1 · pK1:8.45(0);pK2:8.88(-1) (25°C)
- 色
- ホワイトからライトベージュ
- 水溶解度
- 11.17 g/L · 11.17g/L(室温)
- Merck
- 14 · 14,7328
- BRN
- 1341907 · 1341907
- 化粧品成分の機能
- ヘアカラーリング
- 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
- 0.55 at · 0.55 at 25℃
- CAS データベース
- 108 · 108-73-6(CAS DataBase Reference)
- NISTの化学物質情報
- 1 · 1,3,5-Benzenetriol(108-73-6)
- EPAの化学物質情報
- 1 · 1,3,5-Benzenetriol (108-73-6)
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
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
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
毒性情報
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)
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
- risk_code
- 11-36/37/38-34-43
- 化審法
- (3)-554
- hazard_code
- F,Xi
- safety_code
- 7-16-24/25-45-36/37/39-26-36/37-37/39
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
MeSH Pharmacological Classification
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
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]
応用分野
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
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
関連ノート
読み込み中…