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Home > Encyclopedia > Quinoline Yellow

Quinoline Yellow

pharmaceutical raw materials
Quinoline Yellow structure

Quinoline Yellow 

structure
  • CAS No:

    8004-92-0

  • Formula:

    C18H9NNa2O8S2

  • Chemical Name:

    Quinoline Yellow

  • Synonyms:

    D&CYellow#10;D&CYellow#11;D&CYELLOWNO.10;FD&CYELLOWNO.10;Acid yellow 3 (C.I. 47005);2-(1,3-Dioxoindan-2-yl)quinolinedisulfonic acid sodium salt;2-(2-Quinolyl)-1,3-indandione disulfonic acid disodium salt;c.i.foodyellow13

  • Categories:

    Cosmetic Ingredient  >  Cosmetic Colorant

Description

Yellow to orange-brown powder

Quinoline Yellow Basic Attributes

477.38

476.956482

616-849-0

0QYP77F82G

TSCA listed

DTXSID0041721|DTXSID70873122

Yellow to orange-brown

32129000

Characteristics

412 nm

178.19000

3.36740

Yellow to orange-brown Powder

240 °C

225 g/L (20 ºC)

4.11X10-22 mm Hg at 25 °C (est)

LD50 in rats (g/kg): >2 orally (Lu, Lavalle)

Odorless

3.4×1014mol/(m3Pa) at 25℃, HSDB (2015)

Hydroxyl radical reaction rate constant = 2.34X10-12 cu cm/molec-sec at 25 °C (est)

Hygroscopic, Refrigerator, under inert atmosphere

Safety Information

NONH for all modes of transport

3

Xn,Xi

24/25-36-26-22

GC5796000

Xn,Xi

22-36/37/38

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.

All batches of this color additive when used for coloring 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 for coloring 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.|All batches of this color additive when used for coloring contact lenses 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.|A batch of this straight color may be certified, in accordance with 21 CFR Part 82, for use in drugs and cosmetics, if such batch conforms to the requirements of 21 CFR 82.5 and to the specifications in 21 CFR Part 82.

Not Classified

D&C Yellow No. 10 was detected in both the influent and effluent of the Mill Creek wastewater treatment plant, Cincinnati, OH, that receives wastewater from a factory that produces xanthene, triarylamine, and other food and cosmetic dyes, indicating resistance to both degradation and removal by sorption. Influent concentration was 160 ppb and effluent concentration was 44 ppb(1).

Toxicity

LD50 Rat oral 2000 mg/kg|LD50 Dog oral >1000 mg/kg bw

A personal or family history of atopy was frequent among the cases, so /the authors/ recommend that those who have such a history should not become beauticians.

D&C Yellow No. 10's production and use as a wool dye(1) and shampoo colorant(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: D&C Yellow No. 10 is expected to have high mobility in soil(SRC) as it is a water-soluble anionic dye(1). Volatilization of D&C Yellow No. 10 from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-20 atm-cu m/mole(SRC), using a fragment constant estimation method(2). D&C Yellow No. 10 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.0X10-22 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). D&C Yellow No. 10 exhibited <25% elimination in 42 days using an activated sludge inoculum in a modified static test(4), indicating that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: D&C Yellow No. 10 is not expected to adsorb to suspended solids and sediment(SRC) based upon irs anionic nature(1). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 2.9X10-20 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -2.47(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). D&C Yellow No. 10 exhibited <25% elimination in 42 days using an activated sludge inoculum in a modified static test(7), indicating that biodegradation is not an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), D&C Yellow No. 10, which has an estimated vapor pressure of 4.0X10-22 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase D&C Yellow No. 10 may be removed from the air by wet or dry deposition(SRC). D&C Yellow No. 13 absorbs at wavelengths >412 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

D&C Yellow No. 10 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. 10 absorbs at wavelengths >412 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for D&C Yellow No. 10(SRC), using an estimated log Kow of -2.47(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

D&C Yellow No. 10 is expected to have high mobility in soil and to not adsorb strongly to suspened solids and sediments(SRC) as it is a water-soluble anionic dye(1). D&C Yellow No. 10 was detected in both the influent and effluent of the Mill Creek wastewater treatment plant, Cincinnati, OH, from a factory that produces xanthene, triarylamine, and other food and cosmetic dyes(2).

The Henry's Law constant for D&C Yellow No. 10 is estimated as 2.9X10-20 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that D&C Yellow No. 10 is expected to be essentially nonvolatile from water and soil surfaces(2). D&C Yellow No. 10 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.0X10-22 mm Hg(SRC), determined from a fragment constant method(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 174,651 workers (97,348 of these were female) were potentially exposed to D&C Yellow No. 10 sodium in the US(1). Occupational exposure to D&C Yellow No. 10 may occur through inhalation and dermal contact with this compound at workplaces where D&C Yellow No. 10 is produced or used. Use data indicate that the general population may be exposed to D&C Yellow No. 10 via dermal contact with consumer products containing this compound(SRC).

Drug Information

The uptake, fate and excretion of quinoline yellow, a coloring in sweets and soft drinks, in the rat were studied. In the isolated perfused liver, 70% of the dose was excreted into the bile within 3 hr. Similar results were obtained after i.v. injection into anesthetized animals. When given by gavage, only approximately 1% was excreted in bile and urine within 4-5 hr. Quinoline yellow administered orally to rats was quantitatively excreted, the excretion being mainly fecal. ... Very little quinoline yellow is absorbed from the gastrointestinal tract of the rat. No evidence of metabolism was obtained.|Quinoline Yellow is absorbed from the gastro-intestinal tract to only a small extent in rats and dogs, and most of an orally administered dose is excreted unchanged.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/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/ 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/ In a clinical study in which 330 patients with recurrent urticaria were investigated for possible triggering factors, 30 % of individuals indicated that their condition was worsened by consumption of certain foods, while 18 % mentioned drinks as possible triggering factors. Quinoline Yellow was one of an extensive number of food additives investigated in provocation tests in a number of patients, others included azo dyes, benzoates, antioxidants, sorbic acid, carotene, canthaxanthin, annatto and nitrite. The additives were given orally by capsule, Quinoline Yellow being administered at levels of 1, 5 or 10 mg per individual to 91 patients. The dosing regime was over several hours and it is assumed that increasing doses were administered sequentially. Of the 91 patients tested, 13 % showed positive evidence of sensitivity reactions, as manifest by a flare-up of urticaria, while 15 % showed uncertain reactions and 72 % were negative. The incidence of positive reactions to Quinoline Yellow was comparable to that found for a number of other food additives tested.|/CASE REPORTS/ ... A patient, extremely sensitive to D & C Yellow No. 11 with a positive patch test reaction down to 0.00001%, also reacted to Quinoline Yellow at a test concentration of 0.1%. To establish if any cross-reactivity occurs between the two compounds, a high pressure liquid chromatograph was used for analysis, purification and separation of the two colors. The patient was then patch tested with the two colors and the pure fraction of Quinoline Yellow. The test results confirm a true sensitivity to Quinoline Yellow and to D & C Yellow No. 11, and may indicate cross-reactivity between the colors.|For more Human Toxicity Excerpts (Complete) data for D&C Yellow No. 10 (7 total), please visit the HSDB record page.

C.I. acid yellow 3

Quinoline Yellow Use and Manufacturing

Methods of Manufacturing

By 2-(2-quinolinyl)-2, 3-dihydro-1, 3-indendione or by containing about 2/3 of 2-(2-quinolinyl)-2, 3-dihydro- 1, 3-Indendione and 1/3 of 2-[2-(6-methylquinolinyl)]-2, 3-dihydro-1, 3-indendione are obtained by sulfonation.

Uses

Textile dye for wool, nylon, silk.Paper dye.Barium salt in printing inks.Color for food, drugs, cosmetics.Food yellow coloring.


Dyes


Quinoline yellow, is a yellow powder used in lipstick, lotion, soap, shampoo, bubble bath, ingested drugs, and applied drugs applications.

Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7968]

Synthetic dye and pigment manufacturing|C.I. Acid Yellow 3: ACTIVE|The color additive D&C Yellow No. 10 is a mixture of the sodium salts of the mono- and disulfonic acids of 2-(2-quinolinyl)-1H-indene-1,3 (2H)-dione consisting principally of the sodium salts of 2-(2,3-dihydro-1,3-dioxo-1H-indene-2-yl)-6-quinolinesulfonic acid and 2-(2,3-dihydro-1,3-dioxo-1H-indene-2-yl)-8-quinolinesulfonic acid with lesser amounts of the disodium salts of the disulfonic acids of 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione.|Color additives were initially regulated in the United States under the U.S. Department of Agriculture's (USDA) Bureau of Chemistry. In 1906, the Food and Drugs Act was passed by Congress, which prohibited the use of poisonous or deleterious colors in confectionery and the coloring or staining of food to conceal damage or inferiority. In 1927, responsibility of the Food and Drugs Act was transferred to FDA. Increasing government oversight, the Federal Food, Drug, and Cosmetic Act (FFDCA) was passed in 1938 and established the three following categories for colors: FD&C: colors used in foods, drugs and cosmetics; D&C: colors used in drugs and cosmetics when in contact with mucous membranes or ingested; and Ext. D&C: colors used in products applied externally.|D&C Yellow No. 13 is a water soluble anionic dye.|The name D&C Yellow No. 10 can be used only when applied to batches of color that have been certified according to the United States certification regulations. The CFTA Adopted Name for non-certified batches of this color is Acid Yellow 3.

A screening method for the detection of artificial colors (naphthol yellow, tartrazine, quinoline yellow, Sunset yellow, Allura red, amaranth, azorubine, Ponceau 4R and Red 2G) in saffron is described. The method involves removal of crocins by precipitation of crocetin (pH 0.1, 90 °C) before adsorption of the artificial colors on polyamide SPE cartridges (pH 2). After washing with methanol, acetone and methanol, elution was done with a methanol:ammonia solution (95:5 v/v), and detection was performed by derivative spectrometry. Sample pretreatment changes the UV-Vis saffron extract profile in such a way that second derivative spectra can be used to identify the presence of added colors. Erythrosine, which was found to be pH dependent, could not be detected under the above conditions. The lowest detectable amount for each color was strongly dependent on chemical structure. The recovery of carminic acid was very low possibly due to irreversible retention on the polyamide. This procedure can replace the current ISO TLC method (2003) and be used alternatively or in combination with HPLC procedures adopted in the same standard.|Acid Blue 9, Acid Violet 17, Quinoline Yellow, Acid Red 51, Acid Red 87, and Acid Red 92 along with N-benzyl-N-ethylaniline sulfonic acid (BEASA), a synthetic precursor, were identified and measured in colored wastewater samples from a municipal treatment plant. Continuous flow fast-atom bombardment mass spectrometry was used to analyze BEASA. Liquid chromatography with ultraviolet detection was used to analyze the other dyes, but its lack of selectivity required prior isolation of the analytes from interfering compounds by solid-phase extraction onto C18 extraction disks and onto cartridges packed with strong anion-exchange resins...

Cosmetics -> Cosmetic colorant; Hair dyeing

Food Additives -> COLOUR;

Computed Properties

Molecular Weight:477.4
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:1
Exact Mass:476.95649716
Monoisotopic Mass:476.95649716
Topological Polar Surface Area:178
Heavy Atom Count:31
Complexity:853
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes

Drug Function and Efficacy

After long-term use, sudden cessation of tobacco product use can lead to withdrawal syndrome, including 4 or more of the following symptoms: restlessness or depression, insomnia, irritability, frustration or anger, anxiety, inattention, restlessness or impatience, slowed heart rate, appetite or weight gain. The craving for smoking, which has been identified as a clinically relevant symptom, is also an important part of the withdrawal syndrome during nicotine withdrawal. Clinical studies have shown that nicotine replacement products can help smokers give up smoking. The toxicity of nicotine, as one of the components of tobacco, has been widely demonstrated. The most common symptoms of nicotine overdose are nausea and vomiting. Symptoms of severe acute poisoning include: weak and irregular pulse, difficulty breathing, and whole body convulsions. There is no evidence that nicotine causes genetic toxicity. The carcinogenicity of tobacco is mainly related to substances produced by the high-temperature decomposition of tobacco, which does not occur in nicotine preparations.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

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