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HCID 6780생성일: 2026년 10월 23일

Anthraquinone

안트라퀴논 · 9,10-안트라센디온 · 9,10-다이옥소안트라센 · 9,10-다이하이드로-9,10-다이케토안트라센 · 9,10-안트라센다이온 · 9,10-안트라퀴논 · 안트라다이온 · 코르비트

https://huagongshe.com/ko/chemical/6780

Anthraquinone 분자 구조식

식별자 및 물리적 특성

CAS No.84-65-1
분자식C14H8O2
평균 분자량208.21 g/mol
단동위원소 질량208.0524295 g/mol
SMILESO=C1c2ccccc2C(=O)c2ccccc21
InChIKeyRZVHIXYEVGDQDX-UHFFFAOYSA-N
PubChem CID6780
ChEMBLCHEMBL55659
ChEBICHEBI:40448
EC No.201-549-0
DTXSIDDTXSID3020095
현지명안트라퀴논

화학 및 물리적 성질

XLogP3.4
극성 표면적34.1
수소 결합 공여자 수0
수소 결합 수용자 수2
회전 가능 결합 수0
무거운 원자 수16
형식 전하0
복잡도261
물질 분류Other Classes -> Aromatic KetonesDyeSemi-Volatile Organic Compound (SVOC) and(or) Waste-water effluent contaminant
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
농약RepellantsActive substance -> EU Pesticides database: Not approvedPesticide (Anthraquinone) -> USDA PDB
LogP(분배 계수)log Kow = 3.393.28
냄새Aromatic odor (technical)
밀도1.438 at 68 °F (NTP, 1992) - Denser than waterwill sink1.42-1.44 at 20 °C/4 °C1.4 g/cm³1.42-1.44 @ 20°C
Color/FormLight yellow, slender monoclinic prisms by sublimation in vacuo. Almost colorless, orthorhombic, bipyramidal crystals from sulfuric acid and water.Yellow rhombic needles from alcohol, benzeneYellow-green crystals
용해도less than 1 mg/mL at 73 °F (NTP, 1992)0.44 g/100 g alc at 25 °C2.25 g/100 g boiling alc0.11 g/100 g ether at 25 °C0.61 g/100 g chloroform at 20 °C0.26 g/100 g benzene at 20 °C0.30 g/100 g toluene at 25 °CSOL IN CONCN SULFURIC ACIDSoluble in acetoneIn water, 1.353 mg/L at 25 °CSolubility in water: very poor0.00007g/L
인화점365 °F (NTP, 1992)185 °C365 °F (185 °C) (Closed cup)185 °C c.c.
끓는 점714 to 718 °F at 760 mmHg (NTP, 1992)377 °C at 760 mm Hg380 °C376.9 °C @760 [mm Hg]379-381 °C (lit.)
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
녹는점547 °F (sublimes) (NTP, 1992)286 °CLiquid Molar Volume = 0.193625 cu m/kmolIG Heat of Formation = -9.52X10+7 J/kmolHeat Fusion at Melting Point = 3.2552X10+7 J/kmol284-286 °C (lit.)
증기 밀도7.16 (vs air)
증기압1 mm Hg ( 190 °C)
굴절률1.5681 (estimate)
저장 조건no restrictions.
물리적 상태가루
색상황록색에서 카키색, 황갈색까지
용해도23&C에서 <0.1g/100mL
Merck14,687
BRN390030
헨리 상수4.2×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
안정성안정적인. 강한 산화제와 호환되지 않습니다. 타기 쉬운.
주요 응용음식 및 음료제약
InChI1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H
InChIKeyRZVHIXYEVGDQDX-UHFFFAOYSA-N
SMILESO=C1c2ccccc2C(=O)c3ccccc13
LogP(분배 계수)3.39-3.4 at 30℃
NIST9,10-Anthraquinone(84-65-1)
EPAAnthraquinone (84-65-1)

화학적 성질

Anthraquinone is a combustible, light yellow to green crystalline solid. Soluble in ethanol, ether and acetone, insoluble in water. It may be prepared by reacting benzene with phthalic anhydride. The compoundis the basis of a range ofdyestuffs.

안전 및 규제

GHS 분류DangerH350: May cause cancer [Danger Carcinogenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 4.1% (10 of 242) of reports.H317 (80.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]
규제 정보Chemical: 9,10-AnthracenedioneHazard Traits - Carcinogenicity9,10-Anthracenedione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9,10-Anthracenedione 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)Anthraquinone is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2008/986Status: Active Update: 10-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/2211
기타 안전 정보IMAP assessments - 9,10-Anthracenedione: Human health tier II assessment
화재 위험This chemical is combustible. (NTP, 1992)
화재 가능성Conbustible when exposed to heat or flame.
건강 유해성SYMPTOMS: Symptoms following exposure to this compound may include skin and eye irritation, allergic skin reaction and skin sensitization. It may cause discoloration of the urine.
유해성 요약May cause skin irritation and sensitization[Merck Index] Toxic by ingestionFound in certain plants, e.g., Rhamnus berriesA skin irritant[HSDB] An irritant and possible skin sensitizer[CAMEO] An irritant[ICSC] No results for 84-65-1[EC/RN Number] AND dermatitis, allergic contact[mesh][PubMed] Allergic dermatitis reported[RTECS] Antraquuinone, insoluble in water and lipids, is biologically inert. [Ullmann] An irritant[MSDSonline]
반응성 그룹Hydrocarbons, Aromatic
Special ReportsZWAVING JHRECENT DEVELOPMENTS IN THE ANALYSIS OF ANTHRAQUINONE DERIVATIVESPHARMACOLOGY 20(SUPPL 1) 65 (1980). A REVIEW & DISCUSSION ON RECENT DEVELOPMENTS IN THE ANALYSIS OF ANTHRAQUINONE DERIVATIVES.FRIEDMANN CASTRUCTURE-ACTIVITY RELATIONSHIPS OF ANTHRAQUINONES IN SOME PATHOLOGICAL CONDITIONSPHARMACOLOGY 20(SUPPL 1) 113 (1980). A REVIEW ON THE STRUCTURE-ACTIVITY RELATIONSHIPS OF ANTHRAQUINONES IN SOME PATHOLOGICAL CONDITIONS.ANTON R ET ALPHARMACOLOGY 20 (SUPPL 1): 104 (1980). A REVIEW & DISCUSSION ON THE THERAPEUTIC USE OF NATURAL ANTHRAQUINONE FOR OTHER THAN LAXATIVE ACTIONS.
TSCA 요건Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Anthraquinone is included on this list.Manufacturers and processors of anthraquinone are required to conduct specific chemical tests as required under TSCA section 4.
Reactivity ProfileANTHRAQUINONE is incompatible with strong oxidizing agents. (NTP, 1992)
대기 기준This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Anthraquinone is produced, as an intermediate or a final product, by process units covered under this subpart.
Chemical DangersDecomposes on burning. This produces toxic fumes.
소화Fires involving this compound should be controlled using a dr chemical, carbon dioxide or Halon extinguisher. A water spray can also be use. (NTP, 1992)Use water spray, powder, foam, carbon dioxide.
응급 조치Fresh air, rest.Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth.
응급 처치EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
안전 보관Store in an area without drain or sewer access.
소화 절차To fight fire use water, foam, carbon dioxide, water spray or mist, dry chemical.
비화재 누출 대응SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
처리 방법SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
누출 처리Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers.
Preventive MeasuresSRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Eye PreventionWear safety goggles.
Fire PreventionNO open flames.
Skin PreventionProtective gloves.
상호 작용Anthraquinone seems to inhibit the function of certain enzymes in the S-9 mix (rat liver homogenate) by which 3-amino-1-methyl-5H-pyrido(2,3-b)indol, 2-acetylaminofluorene and benzo(a)pyrene are activated. Ina mutation assay (according to Ames with some modification) anthraquinone decreased markedly the mutagenicities of the mutagens mentioned above (test strains: S.typhimurium TA 98, TA 100assay with metabolic activation).
생태독성 수치LC50 Lepomis macrochirus (Bluegill) >5 mg/L/24 hrStaticLC50 Pimephales promelas (Fathead minnow) 2,650 mg/L/96 hr /Conditions of bioassay not specified in source examined/EC50 Lemna gibba (Duckweedgrowth inhibition) 1.5 mg/L/7 daysrenewal, under photosynthetically active radiationrenewal, under simulated solar radiationrenewal, after photomodification
환경 거동TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 2,755-17,416, determined in five European reference soils(2), indicates that anthraquinone is expected to have slight mobility or be immobile in soil(SRC). Volatilization of anthraquinone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.35X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 1.16X10-7 mm Hg(3), and water solubility, 1.35 mg/L(4). Anthraquinone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Direct photolysis is possible on sunlit solid surfaces(5). Biodegradation of anthraquinone is expected to be a major fate process for this compound in soil68% of added anthraquinone was biodegraded by a mixed soil population within 12 weeks(6). A mixed bacterial population, isolated from a coal-tar contaminated soil, biodegraded anthraquinone even faster with only 6.5% of the initial concentration of anthraquinone remaining after 3 days(7). A BOD/ThOD of 54% and a CO2/ThCO2 of 41% were measured in a biodegradation study using a garden soil inoculum and a 58-day incubation period(8). Rapid degradation, apparently due to microbial activity, has been reported for different soils with half-lives of 7-10 days(5).AQUATIC FATE: Based on a classification scheme(1), Koc values of 2755-17416, determined in five European reference soils(2), indicate that anthraquinone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.35X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 1.16X10-7 mm Hg(4), and water solubility, 1.35 mg/L(5). According to a classification scheme(6), an estimated BCF of 12(SRC), from its log Kow of 3.39(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Anthraquinone is stable to aqueous environmental hydrolysis, but sensitive to light with a reported direct photolysis half-life of about 9 minutes in aqueous solution(9).AQUATIC FATE: Biodegradation of anthraquinone in the water column is expected to be a major fate process. Over a three day period, 82% of the added anthraquinone (at 10 mg/L) was degraded by river water, 91% was degraded by sea water(1). Biodegradation using mixed cultures from seawater degraded anthraquinone 50% over 10 daysmetabolite concentration was low but included mainly benzoic and phthalic acids(2). Mixed bacterial populations from groundwater were able to completely degrade anthraquinone within 5 days(3). From 50-100% degradation has been reported using activated sludge as an inoculum and a three week incubation period(4-9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), anthraquinone, which has a vapor pressure of 1.16X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase anthraquinone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be about 11 days(SRC), calculated from its rate constant of 1.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Anthraquinone absorbs at wavelengths >290nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). Anthraquinone is sensitive to light in aqueous solution with a reported half-life of about 9 minutes(6) which suggests direct photolysis in air may be important(SRC). Particulate-phase anthraquinone may be removed from the air by wet or dry deposition(SRC)anthraquinone has been detected in rain water from several storm events(5).
유해 작용IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.
Plant Concentrations2 of 6 samples of mosses collected near a chemical factory in Czechoslovakia and 3 of 6 samples of needles from the same area contained anthraquinone(mosses = 1756.8 to 4054.1 ng/gneedles = 459.5 to 1918.9 ng/g)(1).
Animal Concentrations2 of 5 earthworm samples collected near a chemical factory in Czechoslovakia contained anthraquinone(concentrations = 473 to 4715.9 ng/g)(1).
Signs and SymptomsCough.Pain. Redness.
Ongoing Test StatusThe following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=84-65-1]
Effluent ConcentrationsAnthraquinone was emitted at concns of 24.3 and 4.4 ug/km, resepectively, during particulate emission tests (simulating urban driving conditions) of tailpipes of non-catalyst (average of 1965 Mercury Monterey, 1969 Ford Mustang, 1970 Buick Skylark, 1972 Chevrolet Caprice, 1974 Ford Pinto, and 1976 Volkswagen Beetle) and catalyst cars (average of 1977 Chevrolet Vega, 1980 Honda Civic 150, 1980 Honda 1500, 1980 Toyota Corolla, Datsun 200 SX, 1983 Chevrolet Malibu CL, and 1983 Dodge Omni), and at a concn of 23.5 ug/km from tailpipes of heavy-duty diesel trucks (average of a 1987 GMC truck, two-axle, and a 1987 Ford Dump truck, three-axle)(1). Particulate samples obtained from an automobile using a diesel engine contained anthraquinone at unreported concns(2). Diesel emission particulates from a Volkswagen Rabbit contained anthraquinone(3). Particulate emissions from a representative small aircraft gas turbine engine contained detectable quantities of anthraquinone in 5 of 8 different sampling conditions (concns of 0.06-58.49 ng/cu mdetection limit = 0.01 ug)(4). Organic extracts of emissions from burning cereal straw contained anthraquinone at 995 ug/kg fuel(5). Particulate samples from the exhaust of a flame retention head residential oil burner combusting No. 2 fuel oil contained anthraquinone(6).Anthraquinone was detected in 2 of 4 extracts of MM5 air sampling trains from 4 different municipal waste incinerators (concentration = 2.9-9.0 ug/ml)(1). Flyash extracts from municipal incinerators contained anthraquinone in 3 of 5 sites(2). Anthraquinone was identified in the flyash of an Ontario municipal incinerator at unreported concentrations(3). Anthraquinone was not detected in tire wear particles and was present at concentrations of 0.31 and 0.41 ug/g in brake lining particles and road dust particles, respectively(4).Anthraquinone was detected in leachate (concentration = 0.7 ug/l) from central Texas lignite under conditions meant to replicate rainfall leaching of coal piles(1). Tap water (pH = 9) exposed to test panels coated with a commercial coal tar contained anthraquinone(2). Anthraquinone was detected in pulping liquors from processes using this compound as a catalyst for the delignification of woodin black liquors n=14, concentration = 3.0-170 mg/Lin alkaline pulping liquors n = 6, concentration = 0.5-11.5 mg/Lin wash liquors n = 5, concentration = 0.13-0.75in filtrates from bleaching n = 5, concentration = 0.04-0.66(3). Anthraquinone was detected at concentrations of 49-110 ppb in the raw wastewater of a dye manufacturing plantit was not detected in the final effluent of the same plant(4). Anthraquinone was detected in 235 samples obtained from superfund sitesdata were compiled from CLP Analytical Results Database(5).Anthraquinone was detected in particulate emissions collected from the tailpipes of diesel and gasoline vehicles at conc of 1.3 to 130 ug/g (extract mass) in Japan(1). An anthraquinone conc of 2.8 ug/cu m was detected in smoke particulate matter collected from a controlled burn of forest litter in the Amazon(2).
ICSC Environmental DataThe substance is harmful to aquatic organisms. The substance may cause long-term effects in the aquatic environment.
Soil Adsorption/MobilityUsing an HPLC screening technique and five European reference soils, Koc values ranging from 2,755 to 17,416 were determined for anthraquinone(1). According to a suggested classification scheme(2), these Koc values suggest that anthraquinone has slight mobility or is immobile in soil(SRC). Laboratory trials with BBA soils did not reveal any leaching potential(3). Results of a 23-day soil column leaching study have shown that anthraquinone has the potential to reach ground water under recharge conditions similar to those in arid and semi-arid climates(4).
Atmospheric ConcentrationsSOURCE DOMINATED: Anthraquinone was detected in one of eight air samples (concentration = 44.5 ng/cu m) near a chemical factory in Czechoslovakia(1). Air samples from a freeway tunnel in Japan contained a conc of 52 ug/g (extract mass)(2). Anthraquinone was detected in air samples collected in the potroom of an aluminum reduction plant at a concentration of 297 ng/cu m(3).URBAN/SUBURBAN: Organic extracts from airborne particulate matter collected in Barcelona, Spain contained anthraquinone at 9, not detected, 26, and 21 pg/cu m during the spring, summer, fall, and winter, respectively(1). Atmospheric aerosol samples were collected in Barcelonaanthraquinone was present in the summer sample at 82 pg/cu m and in the winter sample at 75 pg/cu m(2). Anthraquinone was detected in airborne particulate matter in Duisburg, Germany from February to April, 1982 (concentration = 0.22-1.89 ng/cu m(3). Ambient air levels of anthraquinone in Toronto, Ontario were reported as 0.9 to 1.3 pg/cu m(4). 2 of 7 sites in the US sampled for ambient air particulates (Upland, CALake Charles, LA) contained anthraquinone at unreported concentrations(5). Mean gas and particulate-phase concentrations of anthraquinone were measured in Portland, OR during February and April, 1984 and February and April, 1985 (gas concentration = 2.5 ng/cu mparticulate concn = 0.59 ng/cu m)(6). Urban air particles from St. Louis, MO contained anthraquinone at unreported concentrations(7). An anthraquinone concentration of 0.3 ng/cu m was detected in ambient air samples collected from Los Angeles, CA during a smog episode on Sept 8, 1993(8). Atmospheric particulate samples collected from 12 sites in southern California in 1995 contained anthraquinone concentrations of 0.011 to 0.218 ng/cu m(9).RURAL/REMOTE: Airborne particulate matter sampled near Chacaltaya, Bolivia (remote location) and Antwerp, Belgium (urban location) contained anthraquinone in 6 of 6 samples (Bolivia, n = 2, concentration = 0.064-0.065 ug/1000 cu mBelgium, n = 4, concentration = 0.57-1.0 ug/1000 cu mdetection limit = 0.02 ug/1000 cu m)(1). An anthraquinone concentration of 2.8 ug/g (total weight mass) was reported for a Japanese rural air sample(2).
수질 위해 등급(WGK)1
TSCA 등재 상태TSCA listed
RTECS 번호CB4725000
운송 번호(UN)3077
독성LD50 orally in Rabbit: > 5000 mg/kg
관세 코드2914 61 00
위험 문구(R)43-36/37/38
위험 표시Xi
안전 문구(S)36/37-37/39-26-24
포장분류III
위험 등급9Carc. 1BSkin Sens. 1
기존화학 물질KE-01826
자연 발화 온도650 °C
저장 분류6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터84-65-1(Hazardous Substances Data)

용도

용도

안트라퀴논은 설사약으로 사용된다. 장기적인 사용과 남용은 대장흑피증을 일으킨다.

출처

Anthraquinones naturally occur in some plants (eg. aloe, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and insects, where they serve as a basic skeleton for their pigments. Natural anthraquinone derivatives tend to have laxative effects.

용도

Anthraquinone is used in paper industry as a catalyst to increase the pulp production yield and to improves the fiber strength through reduction reaction of cellulose to carboxylic acid. It is also used as a precursor for dye formation.

일반 설명

Anthraquinone is a polycyclic aromatic hydrocarbon derived from anthracene or phthalic anhydride. Anthraquinone is used in the manufacture of dyes, in the textile and pulp industries, and as a bird repellant.

제조 및 합성 방법

제조 방법

Anthraquinone is obtained by oxidation of anthracene using sodium dichromate plus sulfuric acid, and is purified by dissolving in concentrated sulfuric acid at 130 °C and pouring into boiling water, whereupon anthraquinone separates as pure solid, and is recovered by filtration. Further purification may be accomplished by sublimation or crystallization from nitrobenzene, aniline or tetrachloroethane.

Anthraquinone|Huagongshe