CAS 569-77-7 Purpurogallin (HCID 135403797)

基本情報

CAS: 569-77-7
標準SMILES: O=c1c(O)cccc2cc(O)c(O)c(O)c12
InChIKey: WDGFFVCWBZVLCE-UHFFFAOYSA-N
分子式: C11H8O5
平均分子量: 220.18 g/mol

概要

Purpurogallin is a cyclic ketone that is 5H-benzocycloheptene bearing an oxo group at position 5 and hydroxy groups at positions 2, 3, 4 and 6. It has a role as an antioxidant, an antibacterial agent, an EC 1.17.3.2 (xanthine oxidase) inhibitor and a protective agent. It is a tetrol, a member of phenols and a cyclic ketone. It derives from a hydride of a 5H-benzocycloheptene.

名称と識別子

優先名称: Purpurogallin
IUPAC: 2,3,4,6-tetrahydroxybenzo[7]annulen-5-one
現地名: プルプロガリン
英語名: PURPUROGALLIN
分子式: C11H8O5
分子量: 220.18

名称と別名

purpurogallin569-77-72,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-oneCHEBI:86472,3,4,6-Tetrahydroxy-5H-benzocycloheptene-5-oneNSC-35676NSC-6466532,3,4,5-tetrahydroxybenzo[7]annulen-6-one2,3,4,5-tetrahydroxybenzo(7)annulen-6-one2,3,4,6-tetrahydroxybenzo(7)annulen-5-one2,3,4,6-tetrahydroxybenzo[7]annulen-5-one2,3,4,6-tetrahydroxy-5H-benzo(7)annulen-5-one

名称をさらに表示

プルプロガリン2,3,4,6-テトラヒドロキシ-5H-ベンゾシクロヘプテン-5-オン2,3,4,6-テトラヒドロキシ-5H-ベンゾ[7]アニュレン-5-オン2,3,4,6-テトラヒドロキシ-5H-ベンゾ[7]アンヌレン-5-オンC09964MLS0007NSC 35676NSC 646653AIDS138915AIDS-138915AKOS 209-004KBio1_001351KBio2_000828

RefChem:177322DTXCID40127927209-324-92,3,4,6-Tetrahydroxy-5H-benzocyclohepten-5-oneDTXSID40205436L3Z7U4N28PPurpurogallineMLS000738105

物性

構造計算による物性

XLogP: 2.1
極性表面積: 98 Å²
水素結合供与体数: 4
水素結合受容体数: 5
回転可能結合数: 0
重原子数: 16
形式電荷: 0
複雑度: 359

実験および物理化学的性質

SpringerMaterials Properties13C nuclear magnetic resonance spectrum

Collision Cross Section139.48 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 275 °C · 275 °C (dec.)(lit.)
沸点: 321.11 °C · 321.11°C (rough estimate)
比重(密度): 1.3824 · 1.3824 (rough estimate)
屈折率: 1.514 · 1.5140 (estimate)
貯蔵温度: 20 °C · −20°C
溶解性: DMSO（微量）、メタノール（微量）
酸解離定数(Pka): 6.75 · 6.75±0.20(Predicted)
外見: 個体
色: ベリーダークブラウン
Merck: 7946 · 7946
安定性: 空気に敏感
化粧品成分の機能: 保湿剤スキンコンディショニング
LogP: 2.05 · 2.050 (est)

化学的性質

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

安全データ

wgk: 3
rtecs: DE8380000
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36

化学と産業

薬理情報

MeSH Pharmacological Classification · 5 件

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Substances capable of inhibiting, retarding or arresting the process of fermentation, acidification or other deterioration of foods.

Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES.

応用分野 · 2 件

解説2,3,4,6-tetrahydroxy-5H-benzocyclohepten-5-one．C11H8O5(220.18)．カシワ，ナラ，カシなどQuercus属の木にできる虫こぶのなかのタンニンに，配糖体の形で含まれている．合成的には，ピロガロールをヨウ素酸ナトリウムのような酸化剤を作用させると得られる．"暗赤色の針状晶．分解点275 ℃．エタノール，クロロホルムに可溶．過酸化水素酸化するとトロポロンのカルボン酸誘導体となり，ついで脱炭酸すると4-メチルトロポロンが得られる．Ce，Mo，Th，Zrなどの重量分析に用いられる．[CAS 569-77-7]森北出版「化学辞典（第2版）

使用xanthine oxidase inhibitor, antioxidant