disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate
sunset yellow fcf
CAS: 2783-94-0
Molecular Formula: C16H13N2NaO7S2
disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate - Names and Identifiers
| Name | sunset yellow fcf |
| Synonyms | C.I. 15985 Gelborange S Food Yellow 3 SUNSET YELLOW Water Yellow 2 Food yellow No.5 Fodd yellow No.5 sunset yellow fcf SUNSET YELLOW FCF C.I. Food Yellow 3 Sunset Yellow FCF,Food Yellow 3 C.I. Food Yellow 3, disodium salt 1-(Phenylazo)-2-naphthol-4',6-disulfonic acid disodium 1-(p-Sodiosulfophenylazo)-2-hydroxynaphthalene-6-sulfonic acid sodium Sodium (E)-6-hydroxy-5-((4-sulfonatophenyl)diazenyl)naphthalene-2-sulfonate 6-Hydroxy-5-[2-(4-sulfophenyl)diazenyl]-2-naphthalenesulfonic Acid SodiuM Salt disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate disodium (5E)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate |
| CAS | 2783-94-0 |
| EINECS | 220-491-7 |
| InChI | InChI=1/C16H12N2O7S2.2Na/c19-15-8-1-10-9-13(27(23,24)25)6-7-14(10)16(15)18-17-11-2-4-12(5-3-11)26(20,21)22;;/h1-9,17H,(H,20,21,22)(H,23,24,25);;/q;2*+1/p-2/b18-16+; |
disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate - Physico-chemical Properties
| Molecular Formula | C16H13N2NaO7S2 |
| Molar Mass | 432.4 |
| Density | 0.474-0.588[at 20℃] |
| Melting Point | 390°C (dec.) |
| Boling Point | 162.4°C |
| Water Solubility | 5-10 g/100 mL at 24 ºC |
| Solubility | Soluble in water (6.9%,0 ℃), glycerin, propylene glycol, slightly soluble in ethanol, insoluble in oil. |
| Appearance | Orange red powder or granule |
| Color | Orange-red |
| Maximum wavelength(λmax) | ['480 nm'] |
| Merck | 14,9001 |
| pKa | 0[at 20 ℃] |
| Storage Condition | Amber Vial, Refrigerator |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| MDL | MFCD00036437 |
| Physical and Chemical Properties | Orange-red powder or granules. Odorless. Strong hygroscopicity. Light-resistant and heat-resistant. Stable in citric acid, tartaric acid. It changed to brownish red in case of alkali. Soluble in water, neutral and acidic aqueous solution is orange yellow, alkaline red-brown, soluble in concentrated sulfuric acid to orange liquid, diluted with water yellow. Soluble in glycerol, propylene glycol. Slightly soluble in ethanol. |
disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 2 |
| RTECS | QK2450000 |
| HS Code | 32129000 |
| Toxicity | LD50 in rats, mice (g/kg): >10, >6 orally (Gaunt, 1967) |
disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate - Reference
| Reference Show more | 1. Liu Fang, Zhu Shuangshuang, Wang Hongying, etc. Rapid determination of protein content in milk [J]. Journal of Preventive Medicine of PLA, 2018, 036(012):1616-1618. 2. Liao, Qiaobo, et al. "Catalyst-free and efficient fabrication of high crystalline differentiated covalent organic frameworks for selective guest adsorption." Journal of Materials Chemistry A 7.32 (2019): 18959-18970.https:// doi.org/10.1039/C9TA06214A 3. Li, Qi, Wei Liu, and Xiashi Zhu. "Green Choline Amino Acid Ionic Liquid Aqueous Two-Phase Extraction Coupled with HPLC for Analysis Sunset Yellow in Beverages." Food Analytical Methods 12.11 (2019): 2527-2534. 4. [IF=10.588] Chaofan Zheng et al."Modified magnetic chitosan microparticles as novel superior adsorbents with huge “force field” for capturing food dyes."J Hazard Mater. 2019 Apr;367:492 5. [IF=12.732] Qiaobo Liao et al."Catalyst-free and efficient fabrication of highly crystalline fluorinated covalent organic frameworks for selective guest adsorption."J Mater Chem A. 2019 Aug;7(32):18959-18970 6. [IF=5.221] Niu Huimin et al."Electrochemiluminescence Detection Sunset Yellow by Graphene Quantum Dots."Front Chem. 2020 Jun;0:505 7. [IF=2.081] Fu-Xia Yang et al."Rapid Determination of Sunset Yellow in Soft Drinks using Silicon Nanoparticles Synthesized under Mild Conditions."Anal Sci. 2021 Dec;37(12):1749-1755 |
disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate - Nature
Open Data Verified Data
orange-red powder. Soluble in water yellow orange clear solution, insoluble in oil, almost insoluble in ethanol, in concentrated sulfuric acid red orange, diluted yellow. The aqueous solution of concentrated hydrochloric acid does not change color, when concentrated sodium hydroxide is brown red, with acid dye characteristics, can make the animal fiber direct dyeing.
Last Update：2024-01-02 23:10:35
disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate - Preparation Method
Open Data Verified Data
after diazotization with p-aminobenzenesulfonic acid, coupling with 2-naphthol-6-sulfonic acid under alkaline conditions, the resulting pigment may be precipitated with salt, filtered, and purified.
Last Update：2022-01-01 10:08:58
disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate - Introduction
No smell. Soluble in water (6.9%, 0 ℃), glycerin, propylene glycol, slightly soluble in ethanol, insoluble in grease. The aqueous solution is yellow-orange. It is stable in citric acid and tartaric acid, and fades during reduction. 0-1% aqueous solution is orange yellow. Light resistance, heat resistance, acid resistance is very strong, alkali resistance is good, but the alkali is reddish brown.
Last Update：2022-10-16 17:24:12
disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate - Use
Open Data Verified Data
It is mainly used for the coloring of food and medicine, and can also be used for the production of aluminum salt lake pigments.
Last Update：2022-01-01 10:08:58
disodium (5Z)-6-oxo-5-[(4-sulfonatophenyl)hydrazono]-5,6-dihydronaphthalene-2-sulfonate - Reference Information
| color index | 15985 |
| biological field application | Medical devices; treating bone metabolic diseases,dermatological disorders,mitochondrial diseases,respiratory illness |
| LogP | -0.244-0.046 at 25-26℃ |
| (IARC) carcinogen classification | 3 (Vol. 8, Sup 7) 1987 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| food colorant | sunset yellow is also called orange, sunset yellow and sunset yellow. Edible synthetic pigment, orange-red powder or granules, odorless, insoluble in grease, slightly soluble in ethanol, easily soluble in water, glycerin, propylene glycol, the aqueous solution is orange, light resistance, heat resistance, good acid resistance, in citric acid, stable in tartaric acid, dark in alkali, reddish brown, fading during reduction, and high safety. Used as a food colorant, can be used for pastry coloring, the use limit is 0.1 g/kg. It is obtained by diazotization of p-aminobenzenesulfonic acid and 2-naphthol-6-sulfonate. The product is salted out with sodium chloride and then refined. |
| content analysis | method is the same as "amaranth (17004)", but the millimolar mass of sunset yellow in the calculation formula is 0.1131g (not 0.1511). |
| toxicity | ADI 0~2.5 mg/kg(FAO/WHO,2001). LD50>2.0g/k (rat, oral). Norway and Finland are not allowed to use food. |
| usage limit | GB 2760-2002(g/kg): jelly 0.025; juice (flavor) drinks, carbonated drinks, prepared wine, candy, pastries, canned watermelon sauce, green plum, lactic acid bacteria drinks, vegetable protein drinks, shrimp (flavor) slices, biscuit sandwich, kumquat, licorice olive, peach slices, plum, dried mango, apricot, all 0.1; solid beverage 0.1 (diluted), puffed food, fried snacks, 0.1 (in sunset yellow); candy coating, red and green silk, 0.20; Ultra-high temperature flavor milk, flavor yogurt, 0.05. |
| use | edible yellow pigment. used as food colorant, medicine and cosmetics colorant as food colorant, China stipulates that it can be used in candy coating and red and green silk, with a maximum usage of 0.20 g/kg; In a variety of beverages, prepared wine, candy, pastries, canned watermelon sauce, green plum and shrimp (flavor) tablets, the maximum usage is 0.10 g/kg; The maximum usage in ice cream is 0.09 g/kg. as a food colorant, China stipulates that it can be used in candy coating and red and green silk, with a maximum usage of 0.20 g/kg; In a variety of beverages, prepared wine, candy, pastries, canned watermelon paste, green plum and shrimp (flavor) tablets, the maximum usage is 0.10 g/kg; The maximum usage in ice cream is 0.09 g/kg. It is used for coloring food, medicine, and cosmetics, and is also a raw material for making aluminum salt lakes. |
| production method | after diazotization of p-aminobenzenesulfonic acid, it is coupled with 2-naphthol -6-sulfonic acid under alkaline conditions, and the resulting pigment is precipitated, filtered and refined with salt. (1) preparation of sunset yellow. Add 11-12 p-aminobenzenesulfonic acid, then slowly add sodium carbonate to completely dissolve it and filter; cool to 0-5 ℃, then add p-aminobenzenesulfonic acid 1.5-1.8 times the amount (mass) of hydrochloric acid, stir evenly and stand, precipitate fine 1-naphthylamine -4-sulfonic acid crystals, and cool to below 5 ℃. Slowly add 1:2 (mass) sodium nitrite solution at 3-5 ℃ for diazotization to obtain diazonium solution. After the reaction, the feed liquid is strongly acidic (blue) to Congo red test paper. Dissolve sodium 2-naphthol -6-sulfonate in 20 times the amount (mass) 75-80 ℃ water, then add some sodium carbonate (1/5 of the total amount), dissolve and filter. The filtrate is put into the reaction kettle, then the rest of sodium carbonate is added, stirred and cooled to 5-8 ℃; At 10-15 ℃ and PH8-9, diazo liquid is slowly added for coupling reaction for several hours. After the reaction is completed (2-naphthol -6,8-sodium disulfonate is slightly excessive), raise the temperature to 50-60 ℃, add refined sodium chloride, stir, cool it naturally to room temperature, and let it stand to precipitate crystallization; Dissolve the crystallization in 15 times the amount (mass) of clean water at 70 ℃, add an appropriate amount of sodium carbonate to make the solution slightly alkaline, and add refined salt after filtering, stir and adjust PH to 6.5-7.0 with hydrochloric acid. The finished product is obtained by standing, crystallizing, separating and drying. (2) Preparation of sunset yellow aluminum lake. Aluminum hydroxide is prepared from aluminum salt such as aluminum chloride, aluminum sulfate and alkali such as sodium carbonate, and then added to sunset yellow aqueous solution to precipitate the product. Preparation of Sunset Yellow Add p-aminobenzenesulfonic acid to 11-12 times the amount (mass) of water at 60-65 ℃, then slowly add human sodium carbonate to completely dissolve it, filter and cool to 0-5 ℃, then add p-aminobenzenesulfonic acid 1.5-1.8 times the amount (mass) of hydrochloric acid, stir and stand evenly, precipitate fine 1-naphthylamine -4-sulfonic acid and cool to below 5 ℃. Slowly add 1:2 (mass) sodium nitrite solution at 3~5 ℃ for diazotization to obtain diazonium solution. After the reaction, the feed liquid is strongly acidic (blue) to Congo red test paper. Dissolve sodium 2-naphthol -6-sulfonate in 20 times the amount (mass) 75~80 ℃ water, then add some sodium carbonate (1/5 of the total amount), dissolve and filter. The filtrate is put into the reaction kettle, and then the rest of the sodium carbonate is added, stirred and cooled to 5~8 ℃; then at 10~15 ℃ and the Ph value is 8~9, the diazo liquid is slowly added for coupling reaction for several hours. After the reaction is completed (2-naphthol -6,8-disulfonate sodium is slightly excessive), raise the temperature to 50~60 ℃, add refined sodium chloride, stir, let it cool naturally to room temperature, and let it stand to precipitate crystals; The crystallization is stirred and dissolved in 15 times the amount (mass) of clean water at 70 ℃, and an appropriate amount of sodium carbonate is added to make the solution slightly alkaline. After filtration, the refined salt is added, stir and adjust the Ph value to 6.5~7.0 with hydrochloric acid, stand for crystallization, separate and dry to obtain the finished product. Preparation of Sunset Yellow Aluminum Lake The aluminum hydroxide is prepared from aluminum salts such as aluminum chloride, aluminum sulfate, etc. and bases such as sodium carbonate, and then sunset yellow aqueous solution is added to precipitate the product. After diazotization of p-aminobenzene sulfonic acid, it is coupled with sodium 2-naphthol -6-sulfonate, and the resulting pigment is salted out by sodium chloride and then refined. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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