キニザリン

Quinizarin

HCID 6688CAS 81-64-1

基本情報

標準SMILES
O=C1c2ccccc2C(=O)c2c(O)ccc(O)c21
InChIKey
GUEIZVNYDFNHJU-UHFFFAOYSA-N
分子式
C14H8O4
平均分子量
240.21 g/mol
単同位体質量
240.04225874

概要

Quinizarin is a dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups. It has a role as a dye.

名称と識別子

優先名称
Quinizarin
IUPAC
1,4-dihydroxyanthracene-9,10-dione
現地名
キニザリン
英語名
1,4-Dihydroxyanthraquinone
分子式
C14H8O4
分子量
240.21

名称と別名

Quinizarin1,4-Dihydroxyanthraquinone81-64-11,4-dihydroxyanthracene-9,10-dioneQuinizarineChinizarinSolvent Orange 86Smoke Orange R1,4-DihydroxyanthrachinonMacrolex Orange GG1,4-Dihydroxy-9,10-anthraquinone9,10-Anthracenedione, 1,4-dihydroxy-
名称をさらに表示
キニザリン1,4-ジヒドロキシ-9,10-アントラキノンC.I.ソルベントオレンジ861,4-ジヒドロキシアントラセン-9,10-ジオンスモークピグメント1,4-ジヒドロキシアントラキノン1,4-ジヒドロキシ-9,10-アントラセンジオン9,10-ジヒドロ-9,10-ジオキソアントラセン-1,4-ジオール1,4‐ジヒドロキシアントラキノンキニザリン標準品ソルベントオレンジ86DSD ACID1,4-DHAQQUINAZARINQuinizalin4-Dihydroxyanthraquinone
Anthraquinone, 1,4-dihydroxy-1,4-Dioxyanthraquinone1,4-Doa1,4-DIHYDROXY-9,10-ANTHRACENEDIONEC.I. 58050DTXSID80444648S496ZV3CSCI 58050

データベース識別子

CAS
81-64-1
PubChem CID
6688
DTXSID
DTXSID8044464
ChEMBL
CHEMBL17594
ChEBI
CHEBI:37487
UNII
8S496ZV3CS
EC Number
201-368-7
Nikkaji
J3.861J、J710.748J

物性

構造計算による物性

XLogP
3.7
極性表面積
74.6 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
0
重原子数
18

実験および物理化学的性質

Chemical ClassesDyes -> Anthraquinone Dyes
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Color/Form · 2 件

ORANGE CRYSTALS FROM ACETIC ACID; ORANGE PLATES FROM ETHER; DEEP RED NEEDLES FROM ALCOHOL, BENZENE, TOLUENE, XYLENE

YELLOW RED LEAFLETS FROM ETHER; RED CRYSTALS FROM TOLUENE, ACETIC ACID

Solubility · 5 件

MODERATELY SOL IN ALCOHOL WITH RED COLOR

SOL IN ETHER WITH BROWN COLOR & YELLOW FLUORESCENCE

SOL WITH VIOLET COLOR IN AQ ALKALIES & IN AMMONIA

1 G SOL IN ABOUT 13 G OF BOILING GLACIAL ACETIC ACID

For more Solubility (Complete) data for 1,4-DIHYDROXY-9,10-ANTHRACENEDIONE (6 total), please visit the HSDB record page.

Flash Point222 °C
Melting Point196 °C

物理化学的性質

融点
195 · 195-200 °C
沸点
450 °C · 450 °C
比重(密度)
1.3032 · 1.3032 (rough estimate)
蒸気密度
8.3 · 8.3 (vs air)
蒸気圧
1 mm · 1 mm Hg ( 196.7 °C)
屈折率
1.543 · 1.5430 (estimate)

化学的性質

化学的特性orange to red-brown crystalline powder

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 0.3% (7 of 2238) of reports.

Warning

H315 (90.9%): 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 2238 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

危険有害性情報

Regulatory Information · 4 件

Chemical: 9,10-Anthracenedione, 1,4-dihydroxy-

9,10-Anthracenedione, 1,4-dihydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9,10-Anthracenedione, 1,4-dihydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 14-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20342

9,10-Anthracenedione, 1,4-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA mutagen and irritant; Effects in high-dose animal studies include changes in renal tubules and weight loss; [RTECS] Emergency treatment: irritants; [HSDB] An irritant; [MSDSonline]
Hazard Classes and Categories · 2 件

Skin Irrit. 2 (90.9%)

Hazardous to the aquatic environment (Acute) - Category 1

毒性情報

Non-Human Toxicity Excerpts · 4 件

ACUTE TOXICITY OF 1,4-DIHYDROXYANTHRAQUINONE WAS TESTED IN ANIMALS & DID NOT SENSITIZE MANY, BUT PRODUCED A VERY SEVERE REACTION IN THOSE AFFECTED.

1,4-DIHYDROXYANTHRAQUINONES DID NOT ALTER COLONIC WATER ABSORPTION BUT RESTRICTED SODIUM ABSORPTION & CAUSED AN APPARENT RELEASE OF POTASSIUM INTO THE LUMEN.

IN VITRO STUDY INDICATED ANTHRAQUINONE DYES TO BE INHIBITORS OF MITOCHONDRIA ADENINE NUCLEOTIDE TRANSLOCATION & OXIDATIVE PHOSPHORYLATION. MOST OF THE DYES INHIBITED MITOCHONDRIAL (14)C-ADP UPTAKE IN A PARTIALLY COMPETITIVE-NONCOMPETITIVE MANNER.

QUINIZARIN GLUCOSIDE TETRAACETATE WAS RENDERED MUTAGENIC TO SALMONELLA TYPHIMURIUM BY ENZYME EXTRACTS OF RAT CECAL BACTERIA (APPARENTLY BY AGLYCONE FORMATION).

安全データ

wgk
2
tsca
TSCA listed
rtecs
CB6600000
ridadr
UN 3077 9 / PGIII
毒性
LD50 orally in Rabbit: > 5000 mg/kg
hs_code
2914 69 80

化学と産業

薬理情報

Mechanism of Action · 1 件

LAXATIVE EFFECTS OF 6 ANTHRAQUINONES WERE RELATED TO THEIR ABILITY TO UNCOUPLE PHOSPHORYLATION IN BOTH PLANT (PHASEOLUS AUREUS) & ANIMAL (GUINEA PIGS INTESTINE) MITOCHONDRIA. THE STRUCTURAL REQUIREMENTS WERE: A RIGID PLANAR STRUCTURE AND AT LEAST 1 OH GROUP, PREFERENTIALLY IN POSITION 1, 1 AND 8, 2, 3, 6, AND 7.

用途と製造

Uses · 5 件

Used as an antioxidant in synthetic lubricants and a fungicide for control of powdery mildew; [HSDB] Used in the fuel and textile processing industries and as a coloring agent and intermediate; [IUCLID]

Petroleum Production and Refining [Category: Industry]

ANTIOXIDANT IN SYNTHETIC LUBRICANTS

IN THE SYNTHESIS OF EXPERIMENTAL ANTITUMOR AGENTS

FUNGICIDE FOR CONTROL OF POWDERY MILDEW

U.S. Production2023: 75,000 - <500,000 lb
Industry UsesIntermediate
Methods of Manufacturing · 1 件

...BY DIAZOTIZING P-CHLOROANILINE, CONDENSING WITH PHTHALIC ANHYDRIDE, & HYDROLYZING: BRITISH PATENT 373,999, CA 27, 3946 (1933); BY TREATING ANTHRAQUINONE WITH AMMONIUM PERSULFATE IN SULFURIC ACID: WACKER, J PRAKT CHEM [2] 54, 90 (1896). BY HEATING P-CHLOROPHENOL, PHTHALIC ANHYDRIDE & EITHER SULFURIC ACID OR ALUMINUM CHLORIDE: REYNOLDS, BIGELOW, J AM CHEM SOC 48, 420 (1926); US PATENT 1,845,632, CA 26, 2203; ORG SYN COLL VOL I, 476 (NEW YORK, 1941).

General Manufacturing Information · 4 件

Synthetic Dye and Pigment Manufacturing

9,10-Anthracenedione, 1,4-dihydroxy-: ACTIVE

THE CONDENSATION OF ALKYLENEDIAMINES WITH QUINIZARIN GAVE COMPD MARKEDLY ACTIVE AGAINST BOTH LEUKEMIAS & SOLID TUMORS IN MICE.

1,4-DIHYDROXYANTHRAQUINONE IS FUNGICIDE @ 4000 PPM FOR CONTROL OF POWDERY MILDEW (ERYSIPHE POLYGONI) ON INOCULATED CRANBERRY BEAN SEEDLINGS.

応用分野 · 4 件

解説1,4-ジヒドロキシアントラキノンの別名.アントラキノン染料の重要な中間物.無水フタル酸とかp-クロロフェノールの縮合,環化によってつくる.

用途溶剤、指示薬

使用1,4-Dihydroxyanthraquinone, also known as quinizarin, is of great importance in manufacturing disperse, acid, and vat dyes.

一般的な説明1,4-Dihydroxyanthraquinone is an organic dye molecule with an aromatic structure. It is a derivative of anthraquinone bearing hydroxyl moieties. They may find uses in pharmacological, biochemical and dye industries. Anthraquinone dye are resistant to degradation.

調製方法

純化方法Crystallise quinizarin from glacial acetic acid. [Beilstein 8 H 450, 8 IV 3260.]

サプライヤー50 社

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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: Quinizarin is a dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups It has a role as a dye.

関連反応

29 件

関連ノート

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