Sudan red is divided into four types: I, II, III and IV.
Sudan red I (Sudan)
Chemical name: 1- phenylazo -2- naphthol
Molecular structure: C6H5N = NC 10H6OH/> molecular weight: 248.28.
Sudan II
Chemical name:1-[(2,4-dimethylbenzene) azo ]-2- naphthol
Sudan Red No.3
Chemical name: 1-{[4- (phenylazo) phenyl] diazo }-2- naphthol (1-{[4- (phenylazo) phenyl] azo ]-2- naphthol)
Sudan Red No.4
Chemical name: 1-{ {2- methyl -4-[(2- methyl-phenyl) azo] phenyl }-2- naphthol (1-{ {2- methyl -4-[(2- methylphenyl) azo] phenyl} azo]-
In vivo metabolism
Sudan red microsomes and cytoplasmic reductase entering the body are metabolized into corresponding amines in the body, and are metabolized by microbial reductase in gastrointestinal tract, liver and extrahepatic tissues. Mutagenic and carcinogenic amines in Sudan red produce some metabolites found in mutagenic experiments in vitro and carcinogenic experiments in animals. Sudan Red I can reduce and metabolize aniline and 1- amino -2- naphthol (1- amino -2- naphthol) in vivo. The metabolism of Sudan II in vivo may produce dimethylaniline (2,4-dimethylaniline) and 1- amino -2- naphthol. The metabolism of Sudan III in vivo produces 4-(4- aminoazobenzene) aminoazobenzene, 1- amino -2- naphthol, aniline, p-phenylenediamine (p- phenylenediamine) and 1-4 aminophenylazo -2- naphthol [1-(4-).
a sum of money
Sudan red is a synthetic industrial dye. 1995, the European Union (EU) and other countries have banned it from being added to food as a pigment. However, due to its bright dyeing, India and other countries allowed Sudan Red I. In 2005, the European Union tested Sudan Red for the red pepper powder imported from India and the processing of Sudan Red I 2.8-3,500mg/kg Chili powder. This substance has also been detected in some other foods, such as Sudan red I 0.7- 170 mg/kg. It has been reported that Sudan II, III and IV can also be detected in Chili powder, such as Chili powder, Chili sauce and Chili powder with Sudan IV content of 230 mg/kg and 380 mg/kg. Generally, Sudan Red No.1 was detected on February 18. The British Food Standards Agency (FSA) warned consumers about foods containing Sudan red pigment, and published a list of products that may contain Sudan red I on its website.
& lt/ European Condiment Council of European Condiment Association (expert committee), the average person in Europe eats 50-500 mg of red pepper powder every day, and the detected amount of Sudan I in red pepper powder is 2.8-3,500mg/kg. It is estimated that the per capita intake of Sudan I in Europe is 0. 14-1750 micrograms per day. The expert committee of the French European Condiment Association submitted a report. The daily per capita consumption of pepper (including red pepper and Chili powder) and the highest consumption of Sudan Red No.1 are 77 and 264mg respectively. The detection amount of Chili powder is 2.8-3500 mg/kg. It is estimated that the average daily intake of Sudan Red I in Europe is 0.2 -270 micrograms, and the maximum intake is 0.7-924 micrograms. ..
Sudan red does not exist naturally in food, but in many foods, there are some amines naturally. According to some research reports, 0.6-30.9mg/kg aniline can be detected in fresh fruits and vegetables, 22mg/kg aniline in Chinese cabbage and carrot, and 30.9mg/kg aniline in black tea and garlic juice. 7.2mg/kg toluidine was detected in radish, and 1. 1mg/kg toluidine was detected in celery and cabbage.
risk assessment
1 phenylazo 2 naphthol
IARC (International Agency for Research on Cancer) classifies Sudan Red I into three types of carcinogens, namely animal carcinogens. It is impossible to determine human carcinogens mainly based on the results of in vitro and experimental animals. Liver is the main target organ of Sudan Red I carcinogenicity, but it may also lead to tumors of bladder, spleen and other organs.
Sudan red I has mutagenic effect on l 5 178y TK+/- cells of S-9 salmonella and Salmonella typhi mutant mice. The micronucleus test of rat bone marrow was positive; Increase sister chromatid exchange in CHO cells. Comet test shows that it can cause DNA breakage in mouse stomach and colon cells.
Sudan red I is allergic and can cause human dermatitis. Indian women use "Kumkums" brand cosmetics on their foreheads. However, there are also reports of allergic contact dermatitis caused by smearing "Kumkum". By gas chromatography analysis, there are three kinds of seven brands of "Combs" that can detect Sudan Red No.1 with different concentrations.
Aniline, a metabolite of Sudan Red I, is toxic. According to the sensitivity endpoint of hemoglobin toxicity, the lowest observed adverse reaction level (LOAEL) is 7 mg/kg/day, but the maximum NOAEL has not been found in the chronic toxicity test. Based on LOAEL 7mg/kg/ day, the safety limit (MOS) is 0.7× 10-6 mg/kg body weight/day, and the exposure route is through food, air and drinking water. Studies have shown that the human body ingests 0.4mg/kg aniline many times a day, which can cause hemoglobin poisoning.
The genotoxicity classification of aniline in vitro and in vivo is classified as carcinogen by IARC, which is uncertain. Animal experiments showed that the incidence of spleen tumors in rats fed with aniline (72mg/kg) increased significantly for 104 weeks.
The metabolite is 1- amino -2- naphthol. Mutation of T 100 gene of Salmonella typhimurium can induce bladder tumor.
Sudan Red No.2
Carcinogens of IARC Sudan II and its metabolite 2,4-dimethylaniline can be divided into three types. Is there any evidence of cancer? In animal experiments, the incidence of lung cancer in female mice with high dose of 2,4-dimethylaniline (30mg/kg) was significantly higher than that in the control group. Although the detection range of Sudan Ⅱ, Ⅲ and Ⅳ in EU Chili powder may be similar to Sudan Ⅰ in food detection.
Sultan III
IARC will be classified as the third carcinogen, but its main metabolite, 4- aminoazobenzene (4- aminoazobenzene), is classified as the second carcinogen that induces Sudan III, and humans may be carcinogens. Animal experiments show that the dose of 4- aminoazobenzene is 80-400mg/kg for 104 weeks, and the incidence of liver cancer in rats is high.
Sultan IV
IARC is listed as the third carcinogen Sudan IV, but its main metabolites o-toluidine and o-aminoazotoluene are listed as the second carcinogen, which may be carcinogens. Animal experiments showed that the incidence of multiple organ sarcoma, fibrosarcoma and osteosarcoma in rats increased in 150mg/kgBW- toluidine 100- 104 weeks, and bladder cancer appeared in dogs given 5mg/kgBW o-azobenzene for 30 months.
Sudan Red Incident
Sudan prohibits the use of industrial dyes as food additives. In 2005, Sudan red in EU food was found in many foods in China, including the famous fast food company KFC Sudan red, which triggered a discussion on food safety in China.
background
Sudan Red I was approved as a food additive in the United States on 19 18, but the license was later cancelled, but it is still used for color enhancement in some brands of Worcestershire, curry powder, Chili powder and Chili sauce.
In May 2003, France reported that imported Chili powder contained Sudan Red I, and then EU member states issued a warning, demanding that the imported Chili products prohibited by member states contain Sudan Red I from June 2003. The British Food Standards Agency also issued two warnings in June 2004, saying that Laziza international and food experts found Sudan Red I and Sudan Red 4 dyes in Chili sauce and Chili bean products.
Event occurrence
Europe
In 2005, Premier Foods reported to the British Environmental Health Department that it imported Sudan I dye from India. In 2002, Chili sauce and other seasonings produced by 5 tons of Chili powder were sold in many downstream grocery stores. 18 On February 24th, the British Food Standards Agency confirmed the pollution, used Premier Foods to track the supply of raw materials, and listed the grocers of 575 kinds of foods containing Sudan Red I in four batches, warning consumers not to eat them, so as to reduce the risk and possibly lead to the risk of cancer. All these foods must be taken off the shelves at noon on February 24, and they need to be returned unconditionally. The British Food Standards Agency said that this was the largest food recall in British history. It is estimated that the losses suffered by the British food industry may exceed1500 million pounds.
Following the food warning issued by the United Kingdom, on February 23rd, 2005, the General Administration of Quality Supervision, Inspection and Quarantine of China issued the Emergency Notice on Strengthening the Inspection and Supervision of Food Containing Sudan Red (No.), demanding that domestic food (especially imported food) be prevented from being sold and eaten in stock.
On March 29th, China urgently needed to establish a national standard for the determination of Sudan red in food, and formally implemented it.
Sudan red exists in many foods, including KFC's "New Orleans Roasted Chicken Wings, Mai Spicy Chicken Leg Burger", "The Best Chicken Flower in the World" and Heinz's "Guilin Chili Sauce".
1 phenylazo 2 naphthol
The English name of IUPAC is 1- phenylazo -2- naphthol.
identify
Si Nuo. 842-07 -9
Smile OC 1 = C(N = NC3 = CC = CC
= C3)C2 = C(C = CC = C2)C = C 1
nature
Formula c16h12n2obr/>; The molar mass is 248.2836 g mol-1
A flaky crystal with dark red or dark yellow appearance.
Density 0.3
The melting point is131-133 C.
Sublimation at boiling point of 202 C.
The solubility in water is 0.0 1g/ 100mL.
thermodynamics
Standard enthalpy of formation change
δ fho298246.0kj/mol
Unless otherwise specified, the data are in international system units and standard conditions (25°C, 100 kPa). describe
Chemical framework and references
Sudan I (Sudan I, molecular formula: C 16H 12N2O), also known as Sudan Red, is an industrial oil-soluble dye, which is called solvent yellow 14 solvent yellow R in industrial application.
Benzazo 2- naphthol, a chemical called Sudan Red I, has different nicknames and trade names in the product catalogues of different manufacturers (see below).
Industrial application
Sultan I am colored wax, grease, gasoline, solvent, shoe polish, and can also be used to color fireworks. In daily contact, household red floor wax or red shoe polish usually contains Sudan Red No.1..
The industrial production of Sudan Red I is diazotized with aniline in hydrochloric acid and sodium nitrite, and then connected with 2- naphthol.
Toxicity of
According to the data of MSDS in April 2004, the evidence is limited, and I am not carcinogenic to Sudan Red.
The International Agency for Research on Cancer (IARC) listed me as the third carcinogen. These substances lack sufficient direct evidence of carcinogenicity to human body, but they have potential carcinogenic risks.
But research shows that Sudan Red I can cause cancer in animals. In the laboratory experiment, the mouse injected with Sudan red intraperitoneally is a mouse with liver tumor. The dye was injected directly into the bladder, and the bladder tumor began to grow. The oral test is still negative. So far, no cancer has been reported. The whole experiment proved that Sudan, I increased the risk of cancer. On this basis, the EU has banned the use of Sudan I as a food additive since 1995.
A possible carcinogenic mechanism in Sudan decomposes the gene mutation of liver cells caused by aniline in human body, which increases the risk of cancer in human beings. At the same time, if exposed to aniline in large quantities, Fe(II) of aniline may be oxidized to combine with hemoglobin in Fe(III), leading to methemoglobinemia in people who cannot combine hemoglobin with oxygen.
I only add Sudan red to add color, because this dye is very effective, so the actual consumption is very small, and the added food will not cause immediate diseases, and the potential impact on health and the subsequent cancer risk are not high.
Sudan Red 19 18 I have been approved as a food additive in the United States, but the license was later revoked in the United States, but it is still used for color enhancement in some brands of Worcester sauce, curry powder, Chili powder and Chili sauce.
In May, 2003, France reported that imported Chili powder contained Sudan I, and then EU member states issued a warning, demanding that the imported Chili products prohibited by member states contain Sudan I from June 17, 2003. The British Food Standards Agency also issued two warnings, saying that Laziza international and food experts found Sudan I and Sudan IV dyes in Chili sauce and Chili bean products.
On February 24th, 2005, Premier Foods reported that it had been working in the environmental sanitation department in the UK in 2002. The company imported Sudan Red I dye from India and sold spices such as Chili sauce to many downstream food suppliers. 18 On February 24th, the British Food Standards Agency confirmed the pollution, used Premier Foods to track the supply of raw materials, and listed the grocers of 575 kinds of foods containing Sudan Red I in four batches, warning consumers not to eat them, so as to reduce the risk and possibly lead to the risk of cancer. All these foods must be taken off the shelves at noon on February 24, and they need to be returned unconditionally. The British Food Standards Agency said that this was the largest food recall in British history. It is estimated that the losses suffered by the British food industry may exceed1500 million pounds.
On February 23, 2005, the General Administration of Quality Supervision, Inspection and Quarantine of China issued the Emergency Notice on Strengthening the Inspection and Supervision of Foods Containing Sudan I, requiring that foods sold in China, especially imported foods, must be stocked to prevent foods containing Sudan I from being used in the market.
On March 29th, China made great efforts to formulate the detection method of Sudan red dye in national standard food, and formally implemented it.
Sudan red is found in many foods, including KFC New Orleans roast chicken wings, spicy chicken leg hamburgers, the world's five best chicken rice flowers, Heinz food Guilin Chili sauce, and stall spicy Chili products.
According to the standard analyte containing Sudan I provided by the Fourth Sub-committee of the EU Health and Consumer Protection Committee, it was extracted with acetonitrile and filtered. The filtrate was detected by quantitative standard curve method or standard addition method, and the detection wavelengths were 432nm, 478nm and 520nm respectively.
Reversed-phase high performance liquid chromatography analysis, qualitative and quantitative variable wavelength ultraviolet-visible photometric detector.
In order to prove Sudan red, I compared the peaks of samples and standard samples by liquid chromatography-electrospray ionization mass spectrometry.
Ambiguous name
Sudan red 1 is one of the Sudan red series dyes. Chemist Dida named it Sudan red in 1896. After that, it was impossible to study how to name this dye with Sudan red. Sudan I have nothing to do with African countries, Sudan, but Sudan has had a negative impact because of the food safety panic caused by Sudan Red I. The Sudanese ambassador to the UK wrote to the British Food Standards Agency, hoping that this would clarify the country, avoid the negative impact and affect the food export to Sudan [1].
Other names and trade names
1- phenylazo -2- naphthol, as a commodity, usually uses the following trade names or nicknames (registered trademarks of some chemical suppliers):
Artur orange r
Benzene 1- azo -2- naphthol/>; Brazilian orange oil
Huang Hui Youcheng River
Karkogas medium
Calcogas orange NC
Carcau Oil Orange 7078
Campbelline oil orange
Carmina fu
Ceres orange r
aurantius
CI 12055 CI solvent yellow 14
Loose yellow PP
Dunkel Gelb
Orange me
Fast oil orange BR/> Fast oil orange me
Sunflower orange
Send me oranges.
Fetrange 4A
Grasal orange
Grasan orange diameter
Sidak Oil Orange
Lacquer orange VG
Motion diameter
Diameter of petroleum orange
Orange oil pan
Orange insoluble OLG
Orange 3RA is soluble in oil.
& gt orange red pigment
Fat-soluble orange r
Organic alcohol orange
Dongfang petroleum orange PS
Gasoline orange
1- (phenylazo) 2- naphthol/>; Plastic orange F4A
Pyro orange
Resin alcohol orange r
Resonance orange g
Sansheng orange g
Scharlach B.
Sirotra orange tr
Solvent yellow 14
Somalia orange me
1 phenylazo 2 naphthol
SpiritOrange
Spirits orange
Spirit makes me yellow.
Stearic orange
the Sudan
Sudan orange diameter
Sultan orange ridge
Sudan orange ra new
Tertrogras orange SV
Toyo oil orange
Wa Kisakol orange GL
Waxy yellow me
Lenolin yellow IM
Woxiaolin Yellow River Intellectual Property
Waxy yellow
Sudan (1)
Sudan Red 1 Sudan Yellow
Solvent yellow 14 BR/> oil-soluble yellow diameter
Oil soluble orange