キニザリン
Quinizarin
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基本情報
- CAS
81-64-1- 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補完中
- 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
- 形式電荷
- 0
- 複雑度
- 342
実験および物理化学的性質
Chemical ClassesDyes -> Anthraquinone Dyes
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Color/Form
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
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
Vapor Pressure0.00000002 [mmHg]
Physical Description
Dry Powder
Yellow-red, orange, or deep red solid; [HSDB] Orange powder; [MSDSonline]
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
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
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
Skin Irrit. 2 (90.9%)
Hazardous to the aquatic environment (Acute) - Category 1
毒性情報
Non-Human Toxicity Excerpts
ACUTE TOXICITY OF 1,4-DIHYDROXYANTHRAQUINONE WAS TESTED IN ANIMALS & DID NOT SENSITIZE MANY, BUT PRODUCED A VERY SEVERE REACTION IN THOSE AFFECTED.
化学と産業
薬理情報
Mechanism of Action
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
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
...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
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.
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