1,3-Isobenzofurandion, Reaktionsprodukte mit Methylchinolin und Chinolin

Bright greenish yellow

Yellow brown in concentrated H2SO4, yellow flocculent precipitate in dilution

Yellow-gold powder

less than 1 mg/mL at 66 °F (NTP, 1992)

In water, 0.169 mg/L at 25 °C

In ethylene glycol monomethyl ether, 3 mg/mL; ethanol, 0.3 mg/mL

Soluble in acetone, benzene, toluene and xylene; slightly soluble in ethyl acetate, linseed oil, mineral oil, paraffin wax and stearic acid

320 °F (Sublimes) (NTP, 1992)

241 °C

D & c yellow 11 appears as bright greenish yellow solid or canary yellow powder. (NTP, 1992)

Wet Solid; Dry Powder

Yellow powder or granules

Bright greenish yellow or canary yellow solid; [CAMEO]

Warning

H315 (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.

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

Chemical: C.I. Solvent Yellow 33

Regulation (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

Demonstrates a high potential for skin sensitization, with positive patch test results from soaps, facial cosmetics, and in beauticians; Causes liver changes in animal studies; [NTP] A skin and strong eye irritant; Targets the liver and kidney; [Aldrich MSDS]

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.

Skin Irrit. 2 (100%)

Carcinogenicity - category 2

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.

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.

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 quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

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)

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).

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]

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 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 petroleum; 3 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.

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).

D & C Yellow No. 11

TR-463: Toxicology and Carcinogenesis Studies of D&C Yellow No. 11 (CASRN 8003-22-3) in F344 Rats (Feed Studies) (1997 )

12/05/95

Some Evidence

Some Evidence

Chemical Not Tested in Species/Sex

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).

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).

/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 concentration; 11 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.

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).

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, 41; reamer operator 1, 43; fill and press area, 45; cubicle (weighing of "pure" dye), 84; corridor 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, 409; operator 1, 33.9; hallway near weighing cubicle, 3.6; operator 2, 136.3; exterior corridor near fill and press, 26.2; inside fill and press, 542.4; inside reamer enclosure, 936; outside fill and press, 93.5(1).

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.

/Investigators/ exposed male F344/N rats to (14)C-solvent yellow aerosols (160 nmol solvent yellow/liter air) or a mixture of (14)C-solvent yellow and unlabeled solvent green (340 nmol solvent yellow and 370 nmol solvent green/liter air) for 60 min. ... The major pathway for excretion of solvent yellow and solvent yellow metabolites was the feces (74% of the initial body burden); the t1/2 for excretion was 14 hr. Urinary (14)C accounted for 14% of the initial body burden and the t1/2 for excretion was 10 hr. ...

/Investigators/ observed external color changes in Fischer 344 albino rats administered a single dose of 5,000 mg/kg of Solvent Yellow 33 or Solvent Yellow 33/Solvent Green 3 mixture by gavage. The color changes, which first appeared on day 2 after dosing, were observed throughout a 14-day observation period. The males were light green and the females were yellow. In the absence of vomiting, this observation indicates that the dyes may be excreted through the skin.

/Investigators/ exposed male F344/N rats to (14)C-solvent yellow aerosols (160 nmol solvent yellow/liter air) or a mixture of (14)C-solvent yellow and unlabeled solvent green (340 nmol solvent yellow and 370 nmol solvent green/liter air) for 60 min. After either exposure, solvent yellow was rapidly cleared from the respiratory tract, with a t1/2 of 2-3 hr. Solvent green was retained in the lungs with a minimum estimated t1/2 for clearance of 22 days. Solvent green was not detected in other tissues during the 70-hr post-exposure period. After either exposure, high-pressure liquid chromatography analysis of tissues extracts indicated that 40 to 75% of the (14)C in liver and kidney consisted of solvent yellow metabolites. Greater than 90% of the (14)C in the lungs was unmetabolized solvent yellow. The major pathway for excretion of solvent yellow and solvent yellow metabolites was the feces (74% of the initial body burden) ... Urinary (14)C accounted for 14% of the initial body burden ... Over 90% of the (14)C excreted in the urine was solvent yellow metabolites. Very little solvent yellow (2%) was metabolized to (14)CO2. By 72 hr after exposure, only 10% of the initial (14)C deposited remained in the body.

The disposition of 2-(2-quinolyl)-1,3-indandione (D. C. yellow #11, DCY) in male Fischer rats dosed intravenously or by feeding was determined. For rats given (14)C-DCY in the feed (0.00044-0.41% of the diet), recovery of radioactivity during the 24-hr dosing period and the 72-hr period thereafter ranged from 89.1 to 93.9% for feces and from 4.98 to 6.25 for urine. Tissues contained only trace amounts. Following intravenous dosing with (14)C-DCY (0.93 mg/kg), radioactivity distributed readily into most tissues; maximum amounts were present at 5 min, the earliest time of assay. Maximum amounts of radioactivity in fat, skin, and gut tissue, however, were present at 30 min after dosing. These three tissues also had relatively long alpha phases for the elimination of radioactivity. In 24 hr after intravenous dosing, rats excreted 81.1% of the dose in the feces and 16.0% of the dose in the urine. For rats fitted with biliary cannulas, 54.5% of the dose, all of which was metabolites of (14)C-DCY, was recovered in the bile in 4 hr. Associated with the rapid and extensive biliary excretion of metabolites of intravenously administered (14)C-DCY was the appearance of large amounts of radioactivity in the feces and also, at intermediate time points, in the liver, gut contents, and gut tissue. In conclusion, rats rapidly distribute, metabolize, and excrete (14)C-DCY.

Solvent Yellow 33 is also rapidly absorbed from the lung after repeated exposures; less than 0.2 percent of the quantity deposited after each exposure is retained (i.e., 99.8 percent is absorbed within 16 hr).

Permitted for use as an inert ingredient in non-food pesticide products; [EPA] A synthetic dye used in spirit lacquers, polystyrenes, polycarbonates, polyamides, acrylic resins, colored smokes, externally applied drugs and cosmetics, and occasionally in hydrocarbon solvents; [Merck Index]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

The major military use is in M18 colored smoke grenades that are deployed as a means of communication. Solvent Yellow 33 is also used in spirit lacquers, polystyrenes, polycarbonates, pulyamide and acrylic resins, and occasicnally in hydrocarbon solvents.

In spirit lacquers, polystyrenes, polycarbonates, polyamides, and acrylic resins. In colored smokes. Occasionally in hydrocarbon solvents. In externally applied drugs and cosmetics.

Used to color spirit lacquers, polystyrenes, polycarbonates, polyamides, cosmetics and smoke.

Used to dye wool; the aluminum salt is used as a pigment, finding application in cosmetics ... rarely used as a biological stain /Quinoline Yellow S/

2023: 500,000 - <1,000,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#8040]

The chemical for the dye exists as three tautomeric structures in equilibrium between resonance forms: (a) 2-(2-quinolyl)-1,3-indandione (CAS No. 83-08-9); (b) 3-hydroxy-2-(2-quinolinyl)-1H-inden-1-one (CAS No.5662-02-2); and (c) 2-(2(1H)-quinolinylidene)-1H-indene-1,3-(2H)-dione (CAS No. 5662-03-3). Based on chemical principles the main tautomeric structure in solution is structure (b).

Food additives

Fragrance Ingredients

Food Additives -> COLOUR -> JECFA Functional Classes

Cosmetics -> Cosmetic colorant; Hair dyeing

Synthetic Dye and Pigment Manufacturing

1H-Indene-1,3(2H)-dione, 2-(2-quinolinyl)-: ACTIVE

C.I. Solvent Yellow 33: ACTIVE

Synthetic dye consisting principally of quinaphthalone (2-(2-quinolinyl)-1H-indene-1,3-(2H)-dione)