1,4-다이하이드록시안트라퀴논
Quinizarin
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기본 정보
- CAS
81-64-1- 표준 SMILES
O=C1c2ccccc2C(=O)c2c(O)ccc(O)c21- InChIKey
GUEIZVNYDFNHJU-UHFFFAOYSA-N- 분자식
- C14H8O4
- 평균 분자량
- 240.21 g/mol
- 단동위원소 질량
- 240.04225874
개요
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.
이름 및 식별자
- 우선 이름
- Quinizarin
- IUPAC
- 1,4-dihydroxyanthracene-9,10-dione
- 현지명
- 1,4-다이하이드록시안트라퀴논
- 영어명
- 1,4-Dihydroxyanthraquinone
- 분자식
- C14H8O4
- 분자량
- 240.21
이름 및 동의어
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-
이름 더 보기
1,4-다이하이드록시-9,10-안트라센다이온1,4-다이하이드록시안트라퀴논퀴니자린DSD ACID1,4-DHAQQUINAZARINQuinizalin4-Dihydroxyanthraquinone
Anthraquinone, 1,4-dihydroxy-1,4-Dioxyanthraquinone1,4-Doa1,4-DIHYDROXY-9,10-ANTHRACENEDIONEC.I. 58050DTXSID80444648S496ZV3CSCI 58050
데이터베이스 식별자
- 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
물성
구조 계산 물성보충 중
- XLogP
- 3.7
- 극성 표면적
- 74.6 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 18
- 형식 전하
- 0
- 복잡도
- 342
실험 및 물리화학적 성질
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]
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
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
유해성 정보
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
독성 정보
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.
화학 및 산업
약리 정보
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.
용도 및 제조
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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