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HCID 6688Erstellt: 23. Oktober 2026

1,4-Dihydroxyanthrachinon

QUINIZARINE · QUINIZARIN · DSD ACID · Solvent Orange 86 · 1,4-dihydroxyanthracene-9,10-dione · 1,4-DHAQ · QUINAZARIN · Quinizalin

https://huagongshe.com/de/chemical/6688

Molekülstruktur von 1,4-Dihydroxyanthrachinon

Identifikatoren & physikalische Daten

CAS No.81-64-1
SummenformelC14H8O4
Durchschnittliche Molmasse240,21 g/mol
Monoisotopische Masse240,04225874 g/mol
SMILESO=C1c2ccccc2C(=O)c2c(O)ccc(O)c21
InChIKeyGUEIZVNYDFNHJU-UHFFFAOYSA-N
PubChem CID6688
ChEMBLCHEMBL17594
ChEBICHEBI:37487
EC No.201-368-7
DTXSIDDTXSID8044464
Lokaler Name1,4-Dihydroxyanthrachinon

Chemische & physikalische Eigenschaften

XLogP3,7
Polarare Oberfläche (TPSA)74,6
H-Brücken-Donoren2
H-Brücken-Akzeptoren4
Frei drehbare Bindungen0
Schwere Atome18
Formalladung0
Komplexität342
StoffklassenDyes -> Anthraquinone Dyes
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Color/FormORANGE CRYSTALS FROM ACETIC ACIDORANGE PLATES FROM ETHERDEEP RED NEEDLES FROM ALCOHOL, BENZENE, TOLUENE, XYLENEYELLOW RED LEAFLETS FROM ETHERRED CRYSTALS FROM TOLUENE, ACETIC ACID
LöslichkeitMODERATELY SOL IN ALCOHOL WITH RED COLORSOL IN ETHER WITH BROWN COLOR & YELLOW FLUORESCENCESOL WITH VIOLET COLOR IN AQ ALKALIES & IN AMMONIA1 G SOL IN ABOUT 13 G OF BOILING GLACIAL ACETIC ACIDFor more Solubility (Complete) data for 1,4-DIHYDROXY-9,10-ANTHRACENEDIONE (6 total), please visit the HSDB record page.<1g/l<1 g/L (20 ºC)
Flammpunkt222 °C
Schmelzpunkt196 °C195-200 °C
Dampfdruck0.00000002 [mmHg]1 mm Hg ( 196.7 °C)
Physical DescriptionDry PowderYellow-red, orange, or deep red solid[HSDB] Orange powder[MSDSonline]
Stability/Shelf LifeBLACK PPT WITH CO2SUBLIMES @ HIGH VACUUM
Collision Cross Section148.9 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID8044464]
Other Experimental PropertiesUV: 1-545 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /1,5-Dihydroxyanthraquinone/
Siedepunkt450 °C
Dichte1.3032 (rough estimate)
Dampfdichte8.3 (vs air)
Brechungsindex1.5430 (estimate)
LagerbedingungenStore below +30°C.
pKa (Säurekonstante)pK (18°) 9.51
Aggregatzustandpowder
Farbered-brown
Merck14,8064
BRN1914036
Henry-Konstante1.2×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
InChI1S/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
InChIKeyGUEIZVNYDFNHJU-UHFFFAOYSA-N
SMILESOc1ccc(O)c2C(=O)c3ccccc3C(=O)c12
LogP (Verteilungskoeffizient)4.2 at 25℃
CAS Datenbank81-64-1(CAS DataBase Reference)
NIST chemische Informationen9,10-Anthracenedione, 1,4-dihydroxy-(81-64-1)
EPA chemische InformationenQuinizarin (81-64-1)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 0.3% (7 of 2238) of reports.WarningH315 (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
Regulatorische InformationenChemical: 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/203429,10-Anthracenedione, 1,4-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard
GefahrenübersichtA mutagen and irritantEffects in high-dose animal studies include changes in renal tubules and weight loss[RTECS] Emergency treatment: irritants[HSDB] An irritant[MSDSonline]
Hazard Classes and CategoriesSkin Irrit. 2 (90.9%)Hazardous to the aquatic environment (Acute) - Category 1
Non-Human Toxicity ExcerptsACUTE 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).
Wassergefährdungsklasse (WGK)2
TSCA-Inventar-StatusTSCA listed
UN-TransportnummerUN 3077 9 / PGIII
Zollcode2914 69 80
RTECS-Nr.CB6600000
R-Sätze (R)36/37/38-43-50/53
ToxizitätLD50 orally in Rabbit: > 5000 mg/kg
GefahrensymboleXi,N
Sicherheitshinweise (S)22-24/25-36/37-26-61-60
VerpackungsgruppeIII
Lagerklasse13 - Non Combustible Solids
Gefahrstoffdaten81-64-1(Hazardous Substances Data)
GefahrenklasseAquatic Acute 1Aquatic Chronic 1

Anwendungen & Verwendung

Beschreibung

Chinizarin bildet aus Eisessig gelbrote Blättchen mit einem Schmelzpunkt von 200-202 ℃ oder tiefrote Nadeln mit einem Schmelzpunkt von 194-196 ℃ aus Alkohol, Benzol, Toluol und Xylol. Ein Gramm löst sich in 13 g siedendem Eisessig. Es ist in Wasser, Alkohol, Ether, Toluol, Xylol und Benzol löslich. Die alkoholische Lösung ist rot, während die Ether-Lösung braun ist und gelbe Fluoreszenz zeigt. In Alkalien und Ammoniak löst sich die Verbindung und ergibt eine violette Lösung. Chinizarin findet Verwendung bei der Herstellung einer großen Anzahl von Anthrachinonfarbstoffen.

Verwenden

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