1,3-Isobenzofurandion, Reaktionsprodukte mit Methylchinolin und Chinolin

CI 47000 · E104 · KI204 · yellow204 · CI NO 47005 · CHINA YELLOW · petrolyellowc · abcolyellowss

Identifikatoren & physikalische Daten

CAS No.	8003-22-3
Summenformel	C18H11NO2
Durchschnittliche Molmasse	273,3 g/mol
Monoisotopische Masse	273,07897859 g/mol
SMILES	O=C1c2ccccc2C(=O)C1c1ccc2ccccc2n1
InChIKey	IZMJMCDDWKSTTK-UHFFFAOYSA-N
PubChem CID	6731
ChEMBL	CHEMBL1486465
ChEBI	CHEBI:53700
EC No.	201-453-9
DTXSID	DTXSID00873130
Lokaler Name	1,3-Isobenzofurandion, Reaktionsprodukte mit Methylchinolin und Chinolin

Chemische & physikalische Eigenschaften

XLogP	3,4
Polarare Oberfläche (TPSA)	47
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	1
Schwere Atome	21
Formalladung	0
Komplexität	422
Stoffklassen	Dyes -> Other Dyes
Kosmetika	Cosmetic colorantHair dyeing
Duftstoffe	Fragrance Ingredient (C.I. Solvent yellow 33) -> IFRA transparency List
LogP (Verteilungskoeffizient)	log Kow = 4.10
Lebensmittelzusatzstoffe	Drugs, Cosmetics -> FDA Regulatory Status of Color Additives
Color/Form	Bright greenish yellowYellow brown in concentrated H2SO4, yellow flocculent precipitate in dilutionYellow-gold powder
Löslichkeit	less than 1 mg/mL at 66 °F (NTP, 1992)In water, 0.169 mg/L at 25 °CIn ethylene glycol monomethyl ether, 3 mg/mLethanol, 0.3 mg/mLSoluble in acetone, benzene, toluene and xyleneslightly soluble in ethyl acetate, linseed oil, mineral oil, paraffin wax and stearic acid50g/L in organic solvents at 20 ℃5.438mg/L at 25℃
Decomposition	When heated to decomposition it emits toxic fumes of /oxides of nitrogen/.
Schmelzpunkt	320 °F (Sublimes) (NTP, 1992)241 °C240C
Dampfdruck	0.00000001 [mmHg]0Pa at 25℃
Physical Description	D & c yellow 11 appears as bright greenish yellow solid or canary yellow powder. (NTP, 1992)Wet SolidDry PowderYellow powder or granulesBright greenish yellow or canary yellow solid[CAMEO]
Siedepunkt	250℃[at 101 325 Pa]
Dichte	0.274[at 20℃]
Lagerbedingungen	room temp
Aggregatzustand	Solid
Farbe	Yellow to Dark Yellow
Merck	13,8164
Henry-Konstante	1.6×108 mol/(m3Pa) at 25℃, HSDB (2015)
Hauptanwendungen	diagnostic assay manufacturinghematologyhistology
Kosmetik-Inhaltsstoffe Funktionen	HAIR DYEINGCOLORANT
InChI	1S/C18H11NO2/c20-17-12-6-2-3-7-13(12)18(21)16(17)15-10-9-11-5-1-4-8-14(11)19-15/h1-10,16H
InChIKey	IZMJMCDDWKSTTK-UHFFFAOYSA-N
SMILES	O=C1C(c2ccc3ccccc3n2)C(=O)c4ccccc14
LogP (Verteilungskoeffizient)	3.55 at 25℃
CAS Datenbank	8003-22-3(CAS DataBase Reference)
EPA chemische Informationen	C.I. Solvent Yellow 33 (8003-22-3)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH315 (100%): 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 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
Regulatorische Informationen	Chemical: C.I. Solvent Yellow 33Regulation (EC) No 1333/2008 (amended)C.I. Solvent Yellow 33 is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of C.I. Solvent Yellow 33 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)C.I. Solvent Yellow 33: Does not have an individual approval but may be used under an appropriate group standard
Weitere Sicherheitsinformationen	IMAP assessments - Quinoline Yellow, spirit-soluble: Human health tier II assessment
Brandgefahren	Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Gefahrenübersicht	Demonstrates a high potential for skin sensitization, with positive patch test results from soaps, facial cosmetics, and in beauticiansCauses liver changes in animal studies[NTP] A skin and strong eye irritantTargets the liver and kidney[Aldrich MSDS]
FDA-Anforderungen	All batches of this color additive when used in externally applied drugs shall meet the specifications, uses and restrictions, and labeling regulations contained in 21 CFR Part 74 and be certified in accordance with regulations in 21 CFR Part 80.All batches of this color additive when used in coloring externally applied cosmetics shall meet the specifications, uses and restrictions, and labeling regulations contained in 21 CFR Part 74 and be certified in accordance with regulations in 21 CFR Part 80.
Reaktive Gruppe	Amines, Phosphines, and Pyridines
Air and Water Reactions	Insoluble in water.
Hazard Classes and Categories	Skin Irrit. 2 (100%)Carcinogenicity - category 2
Brandbekämpfung	Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Erste Hilfe	EYES: 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.
Freisetung ohne Brand	SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.
Entsorgungsverfahren	SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant lifeand conformance with environmental and public health regulations.
Personal Protective Equipment (PPE)	RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Umweltverhalten	TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3800(SRC), determined from a log Kow of 4.10(2) and a regression-derived equation(3), indicates that D&C Yellow No. 11 is expected to have moderate mobility in soil(SRC). The estimated pKa of D&C Yellow No. 11 is 5.28(4), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of the neutral species from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.1X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(6). D&C Yellow No. 11 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). Biodegradation data in soil were not available(SRC, 2012).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3800(SRC), determined from a log Kow of 4.10(2)and a regression-derived equation(3), indicates that D&C Yellow No. 11 is expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 6.1X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). An estimated pKa of 5.28(6) indicates D&C Yellow No. 11 will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(7), an estimated BCF of 61(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegadation data in water were not available(SRC, 2012).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), D&C Yellow No. 11, which has an estimated vapor pressure of 2.73X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase. Particulate-phase D&C Yellow No. 11 may be removed from the air by wet or dry deposition(SRC). D&C Yellow No. 11 contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
Unerwünschte Wirkungen	Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ongoing Test Status	The 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.[Available from, as of June 21, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=8003-22-3]
Soil Adsorption/Mobility	The Koc of D&C Yellow No. 11 is estimated as 3800(SRC), using a log Kow of 4.10(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that D&C Yellow No. 11 is expected to have slight mobility in soil. The estimated pKa of D&C Yellow No. 11 is 5.28(4), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).
Human Toxicity Excerpts	/HUMAN EXPOSURE STUDIES/ The quinoline color D & C Yellow No. 11 was added to a standard test series. Of 88 patients tested with 1% in PEG, four showed unexplained positive test reactions. One patient had a "flare-up" reaction after 14 days. At rechallenge he reacted to a dilution down to 0.00001%. Simultaneous reaction with the chemically related commonly used food color Quinoline Yellow (E 104) suggests cross-sensitivity./HUMAN EXPOSURE STUDIES/ Repeat insult patch testing of the quinoline dyes, D & C Yellow No. 10 (Acid Yellow No. 3) and D & C Yellow No. 11 (Solvent Yellow No. 33) demonstrated that concentrations as high as 1,000 ppm of the former induced no delayed contact hypersensitivity, whereas, concentrations of 20 ppm and 10 ppm of D & C Yellow No. 11 induced delayed hypersensitivity reactions in human volunteer panelists. No definitive hypersensitivity resulted from testing with 5 ppm of this dye. 2 persons who had been demonstrated to have reacted allergically to the use of a soap bar that contained D & C Yellow No. 11 did not react to the ad libitum use of a soap bar in which this dye was replaced with D & C Yellow No. 10./HUMAN EXPOSURE STUDIES/ /Investigators/ reported that 14 of 56 /volunteers subjected/ to repeat insult patch tests with 20 percent Solvent Yellow 33 in petroleum showed a strong positive reaction when challenged or during the 9th or 10th induction patch. Two years later 9 of the 14 positive subjects were rechallenged with 20 percent Solvent Yellow 33 in petroleum3 showed a positive reaction after a first 48-hr patch, and 2 more were positive after the second 48-hr patch./HUMAN EXPOSURE STUDIES/ /Investigators/ describe contact dermatitis due to solvent yellow 33 in 11 of 149 volunteers who developed a sensitization reaction when tested with solvent yellow 33 concentrations of 16.4 ppm in a modified Draize test.For more Human Toxicity Excerpts (Complete) data for D & C Yellow no. 11 (10 total), please visit the HSDB record page.
Artificial Pollution Sources	D&C Yellow No. 11's production and use in lacquers and resins, in hydrocarbon solvents, in externally applied drugs and cosmetics(1) and in wool dye(2) may result in its release to the environment through various waste streams. Its use as a smoke colorant(1) will result in its direct release to the environment(SRC).
Carcinogen Classification	D & C Yellow No. 11TR-463: Toxicology and Carcinogenesis Studies of D&C Yellow No. 11 (CASRN 8003-22-3) in F344 Rats (Feed Studies) (1997 )12/05/95Some EvidenceChemical Not Tested in Species/Sex
Environmental Bioconcentration	An estimated BCF of 61 was calculated in fish for D&C Yellow No. 11(SRC), using a log Kow of 4.10(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).
Volatilization from Water/Soil	The Henry's Law constant for D&C Yellow No. 11 is estimated as 6.1X10-14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that D&C Yellow No. 11 is expected to be essentially nonvolatile from water and moist soil surfaces(2). D&C Yellow No. 11 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7X10-9 mm Hg(SRC), determined from a fragment constant method(3).
Non-Human Toxicity Excerpts	/LABORATORY ANIMALS: Acute Exposure/ D&C Yellow no. 11 was found to consist predominantly of quinophthalone together with other minor components, though not 6'-methylquinophthalone. Quinophthalone was found to be a strong sensitizer in guinea pigs by means of a modified testing technique, and its threshold concentration for induction and challenge was 10 ppm. Purified D&C Yellow no. 10, which was found to consist of 6 derivatives of sodium sulfonated quinophthalone, did not sensitize or elicit a cross-reaction in quinophthalone-sensitized guinea pigs even at a challenge concentration of 5%. Commercial D&C Yellow no. 10 contained 0.95-170 ppm of quinophthalone, and it is suggested that skin sensitization by D&C Yellow no. 10 is caused by contaminating quinophthalone./LABORATORY ANIMALS: Acute Exposure/ Using the modified Buehler method, /investigators/ applied 50 percent Solvent Yellow 33 in 95 percent ethanol with a 24-hr occluded patch to Hartley Strain female guinea pigs. The animals were treated once weekly for 3 consecutive weeks (induction phase), rested for 2 weeks, and challenged with another 24-hr occluded patch containing 1, 3, or 10 percent Solvent Yellow 33 in 95 percent ethanol, Twenty-four hours after the patches were removed, the treated areas were depilated and evaluated on a scale of 0 to 4 for erythema and edema. The lowest score of 0 indicates no reaction, and the highest score of 4 indicates strong erythema (beet red), with or without edema, eschar formation, or skin damage. Control animals were treated with 95 percent ethanol. /Investigators/ noted that the induction dose of Solvent Yellow 33 was minimally irritating. The skin sensitization reaction elicited by the challenge was statistically significant only for the 10 percent concentration11 of 13 animals (85 percent) responded with a score of 1 (barely perceptible erythema). Only 15 to 20 percent of the controls responded with a score of 1. Thus, Solvent Yellow 33, under the conditions of the rest, was a weak sensitizer./LABORATORY ANIMALS: Acute Exposure/ The eye irritation test using 100 mg of Solvent Yellow 33 or Solvent Yellow 33/Solvent Green 3 powder placed in one eye of each of three rabbits showed that Solvent Yellow 33 was minimally irritating and that Solvent Yellow 33/Solvent Green 3 mixture was nonirritating to rabbit eyes./LABORATORY ANIMALS: Acute Exposure/ In a study to test for primary dermal irritation, 500 mg of Solvent Yellow 33 was applied to two abraded and two unabraded sites on six rabbits for 24 hr, Evaluation of the test site immediately after removal of the dye revealed only barely perceptible erythema that was resolved by 72 hr. The Primary Irritation Score was 0.02, indicating that Solvent Yellow 33 was practically nonirritating. The results of a similar test using Solvent Yellow 33/Solvint Green 3 mixture produced a score of 0.08.For more Non-Human Toxicity Excerpts (Complete) data for D & C Yellow no. 11 (18 total), please visit the HSDB record page.
Environmental Abiotic Degradation	D&C Yellow No. 11 is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). D&C Yellow No. 11 does contains chromophores that absorb at wavelengths >290 nm(1) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
Probable Routes of Human Exposure	NIOSH (NOES Survey 1981-1983) has statistically estimated that 14,314 workers (4,310 US(1). Occupational exposure to D&C Yellow No. 11 may occur through inhalation of dust and dermal contact with this compound at workplaces where D&C Yellow No. 11 is produced or used(SRC). Aerosolized D&C Yellow No. 11 particles <10 um concentration range of <0.04-029 mg/cu m were measured in some of the general work areas in a US colored smoke munitions production plant. With fill and press operations cordoned off by protective acrylic curtains, a range 0.6-5.8 mg/cu m was reported. D&C Yellow No. 11 content of filters placed in various plant locations were as follows (% dye of mass collected): inside reamer, 41reamer operator 1, 43fill and press area, 45cubicle (weighing of "pure" dye), 84corridor near fill and press, 0(2). Use data indicate that the general population may be exposed to D&C Yellow No. 11 via dermal contact with consumer products containing this compound(SRC).Respirable D&C Yellow No. 11 content in the breathing zones of 8 areas in a US colored smoke munitions production plant were (in ug): weighing cubicle, 409operator 1, 33.9hallway near weighing cubicle, 3.6operator 2, 136.3exterior corridor near fill and press, 26.2inside fill and press, 542.4inside reamer enclosure, 936outside fill and press, 93.5(1).
Wassergefährdungsklasse (WGK)	3
TSCA-Inventar-Status	TSCA listed
RTECS-Nr.	GC5796000
R-Sätze (R)	22-36/37/38-36/38
Gefahrensymbole	Xn,Xi
Sicherheitshinweise (S)	24/25-36-26-37/39
Lagerklasse	11 - Combustible Solids
Gefahrstoffdaten	8003-22-3(Hazardous Substances Data)
Gefahrenklasse	Eye Irrit. 2Skin Irrit. 2STOT SE 3

Anwendungen & Verwendung

Verwenden

It is used in cosmetic composition for application to the skin, lips, and/or body surface. Dyes and metabolites, Environmental Testing.

Herstellung & Synthese

synthetische

the dye: (a) 2-Methylquinolineand Phthalic anhydride in 200 ℃ in the presence of Zinc chloride condensation; (b) 2-Methylquinolineand Diethyl phthalatein the 100 ℃ were hot. (c) 3 – (2 – quinolin – ylmethylidene) – 2 – benzo [c] furanone and Sodium ethoxide in 240 ~ 250 ℃ were hot. Late dye: 2-Methylquinolineand 2,6-DimethylquinolinePhthalic anhydride mixture and in 190 ~ 220 ℃ were hot.