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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 342
実験および物理化学的性質
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.
Physical Description
Dry Powder
Yellow-red, orange, or deep red solid; [HSDB] Orange powder; [MSDSonline]
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)
- 闪点
- 222 °C · 222 °C
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 1 g/l · <1g/l
- 酸解離定数(Pka)
- pK (18°) 9.51
- 外見
- 粉
- 色
- 赤茶色
- 水溶解度
- 1 g/L · <1 g/L (20 °C)
- Merck
- 14 · 14,8064
- BRN
- 1914036 · 1914036
- Henry's Law Constant
- 1.2 · 1.2×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- InChI
- 1S/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H
- InChIKey
- GUEIZVNYDFNHJU-UHFFFAOYSA-N
- SMILES
- Oc1ccc(O)c2C(=O)c3ccccc3C(=O)c12
- LogP
- 4.2 at · 4.2 at 25℃
- CAS データベース
- 81 · 81-64-1(CAS DataBase Reference)
- NISTの化学物質情報
- 9 · 9,10-Anthracenedione, 1,4-dihydroxy-(81-64-1)
- EPAの化学物質情報
- Quinizarin (81-64-1)
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
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
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.
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
- risk_code
- 36/37/38-43-50/53
- 化審法
- (4)-704, (5)-5055
- 安衛法
- 変異原性物質
- hazard_code
- Xi,N
- safety_code
- 22-24/25-36/37-26-61-60
- packing_group
- III
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1
- ストレージクラス
- 13 - Non Combustible Solids
- 有毒物質データの
- 81-64-1(Hazardous Substances Data)
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
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.
応用分野
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.]
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: 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
関連ノート
読み込み中…