C.I. Food Orange 5
beta-Carotene
CAS: 7235-40-7;116-32-5
Molecular Formula: C40H56
C.I. Food Orange 5 - Names and Identifiers
| Name | beta-Carotene |
| Synonyms | Carotin SOLATENE CI 40800 -Carotene β-Carotene C.I. 75130 PROVITAMIN A Provitanin A beta carotene beta-Carotene PROVITAMIN A1 Beta Carotene TRANS-B-CAROTENE C.I. Food Orange 5 beta,beta-carotene TRANS-BETA-CAROTENE all-trans-beta,beta-Carotene beta, beta-all-trans-Carotene (9cis,13cis)-beta,beta-carotene 1,1'-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-cyclohexen 1,3,5,7,9,11,13,15,17-Octadecanonene,3,7,12,16-tetramethyl-1,18-cyclohex-1-ene,2,6,6-trimethyl- (all-E)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis(2,6,6-trimethylcyclohexene) |
| CAS | 7235-40-7 116-32-5 |
| EINECS | 230-636-6 |
| InChI | InChI=1/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26u,31-17-,32-18+,33-21-,34-22+ |
| InChIKey | OENHQHLEOONYIE-JLTXGRSLSA-N |
C.I. Food Orange 5 - Physico-chemical Properties
| Molecular Formula | C40H56 |
| Molar Mass | 536.89 |
| Density | 1.000 |
| Melting Point | 178-179 °C |
| Boling Point | 644.94°C (rough estimate) |
| Flash Point | 103°C |
| Water Solubility | Soluble in hexane, dimethyl sulfoxide, benzene, chloroform, cyclohexane. Insoluble in water. |
| Solubility | Soluble in carbon disulfide, benzene, chloroform. Insoluble in water, propylene glycol, glycerin, almost insoluble in methanol and ethanol. |
| Vapor Presure | 0.004Pa at 25℃ |
| Appearance | Dark red or dark red, shiny rhombic hexahedron or crystalline powder |
| Color | red to purple |
| Merck | 14,1853 |
| BRN | 1917416 |
| Storage Condition | -20°C |
| Stability | Stable, but sensitive to air, heat and light. Store at -20C under nitrogen. Pyrophoric - may ignite spontaneously in air at room temperature. |
| Sensitive | Air & Light Sensitive |
| Refractive Index | 1.5630 (estimate) |
| MDL | MFCD00001556 |
| Physical and Chemical Properties | Melting point 178-179°C |
| Use | Mainly used in food, health care products and drugs |
C.I. Food Orange 5 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R44 - Risk of explosion if heated under confinement R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S7 - Keep container tightly closed. S15 - Keep away from heat. S18 - Handle and open container with care. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 1 |
| RTECS | FI0329500 |
| FLUKA BRAND F CODES | 1-8-10-16 |
| TSCA | Yes |
| HS Code | 32030019 |
C.I. Food Orange 5 - Reference Information
| LogP | 6.5 at 40℃ and pH6.5 |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | β-carotene belongs to carotenoids, it is ubiquitous in nature and is the most stable natural pigment, is a fat-soluble compound in Orange, glossy rhombohedral or crystalline powder, mainly from green plants and yellow, orange fruit and other natural food. A dilute solution of β-carotene is orange-yellow to yellow, orange in color with increasing concentration, and may be slightly reddish due to different polarity of the solvent. |
| Food Source | the richest sources of beta-carotene are green leafy vegetables and yellow or orange fruits such as carrots, spinach, lettuce, potato, sweet potato, broccoli, cantaloupe, etc. Beta-carotene is fat-soluble and its fortified dosage forms are usually in the form of capsules and gums. |
| physiological function and function | the antioxidant activity of β-carotene is mainly manifested in its ability to scavenge free radicals. The β-carotene molecule contains multiple double bonds, which are easily oxidized in the presence of light, heat, oxygen and radical ions with strong activity, thus protecting the body from being destroyed. There are a large number of lipid peroxidation and free radical reactions in the organism, which lead to the decline of cell function, the aging of the body and the occurrence of diseases. The presence of β-carotene can reduce lipid peroxidation. Therefore, the activity of carotenoids in scavenging free radicals and quenching singlet oxygen has received widespread attention. |
| efficacy | 1. The rod cells in the retina contain rhodopsin and have the function of dark vision. The appropriate amount of β-carotene can promote the normal content of rhodopsin, so as to avoid the dark field adaptation caused by the lack of vitamin A, and also avoid the damage to the eyes caused by the bright light after the dark field. In addition, it can also prevent night blindness, dry eye, corneal ulcer and corneal softening; 2. Health care of skin tissue. VA is necessary to maintain the integrity of all epithelial tissues, and β-carotene can be converted into VA in the human body. Therefore, the intake of a certain amount of beta carotene, to maintain the normal body surface, digestive tract, respiratory tract, genitourinary tract, endocrine tract goods are of great significance, can avoid the skin, keratinization, skin diseases such as epidermal cell scaly and hyperkeratotic skin xerosis. Beta-carotene also has a good effect on the stability of cell membranes. It may also be used for the treatment of inflammation due to sun exposure ". 3. Anti-aging. Beta-carotene can increase the activity of red blood cells. Peroxide free radicals can accelerate the aging of the human body, people Image called the "garbage" of the body ". And beta-carotene can neutralize the body's peroxide free radicals, so that it plays a role in delaying aging; 4. Resistance to adverse environment. Often in the dark room, light, high temperature or deep water environment, as well as radiation workers, and often watch TV, should be additionally supplemented with beta carotene, in order to resist the adverse environment. |
| Application | β-carotene is the most common and stable natural pigment in nature, because of its large number of agricultural products, unique physiological and nutritional benefits, has been incorporated into the "United States Pharmacopoeia" in 1985, as food additives and nutritional supplements, more to the "A excellent nutritional pigment" identity by the United Nations Food and Agriculture Organization (FAO) and World Health Organization (WHO) Joint Expert Committee on Food Additives recommended in 52 countries and regions in the world approved the application. In our country, β-carotene is mainly used as natural pigment and nutrition enhancer. |
| extraction process | supercritical CO2 extraction technology has been widely used in the separation and extraction of various carotenoids. Maclas et al. extracted β-carotene from microalgae as raw material. The process conditions were as follows: extraction pressure 40MPa, extraction temperature 60 ℃,CO2: flow rate 1g/min, extraction time 5H, the β-carotene yield was 1.5ms/g dry basis. The amount of β-carotene dissolved in CO2 is limited, so it is necessary to find a suitable entrainer, which can effectively improve the yield after pretreatment. In addition, there are several new extraction methods, such as ultrasonic-assisted extraction, microwave-assisted extraction and enzymolysis-assisted extraction. (1) ultrasonic assisted extraction method is the use of petroleum ether acetone, methanol acetone or tetrahydrofuran, etc. on the repeated extraction of microalgae, ultrasonic assisted extraction of all-trans beta carotene. (2) microwave-assisted extraction is the extraction of microalgae or other raw materials with appropriate solvent under microwave conditions. The extraction yield and extraction time are better than Soxhlet extraction method, however, this method has the disadvantage that the microwave heating speed is fast, which may affect the structure and yield of the product. (3) enzymatic assisted extraction method is the use of pectinase cellulase to destroy the cell wall and cell membrane, can play to reduce the amount of organic solvent, save production time, improve the extraction efficiency, however, the limitation of enzyme activity in organic solvents should be considered. |
| content analysis | accurately weigh sample 0.08g, according to the method in OT-15-(Method 2 in spectrophotometry) determination of its absorbance, (Alpha) 2500, the maximum absorption wavelength is about 477nm. Or according to GB 12389-90, carotene paper chromatography. |
| toxicity | ADI is not specified (FAO/WHO,2001). LD50 21.5g/kg (mouse, oral). GRAS(FDA,§ 182.5243,2000). Ames test, micronucleus test, mouse sperm abnormality test and original Phage induction test were all negative (from Dunaliella salina). ADI 0-5 mg/kg(FAO/WHO,2001). LD50>8000mg/kg (oil solution, dog, oral). GRAS(FDA,§ 182.5245,2000). |
| usage limit | GB 2760-1996(g/kg; As colorant): Cream, puffed food, 0.2; margarine 0.1; Shortening, biscuits, 0.05; Bao Bao Le 10.0; Plant fat powder 0.05; Bread, ice cream, cake, beverage, jelly, candy, ice cream, Popsicle, all GMP. GB 14880-94(μg/kg; As a nutrition enhancer; Based on retinol equivalent, 1 μg/β-carotene = 0.167 retinol equivalent): sesame oil, salad oil, margarine, 4000~8000; Dairy products, infant food, 3000 9000; Milk and milk drinks 600 1000; Liquid milk 780. GB2760-96(g/kg): flavored yogurt 0.50g/kg; Solid beverage 3~5 mg/kg; Fortified β-carotene beverage 20~40mg/kg; Other kinds of food, GMF. FAO/WHO,1984: various edible oils, margarine, processed cheese, GMP; Canned green beans, cold drinks, 100mg/kg; Pickled cucumber, 300mg/kg; Special cheese 600mg/kg. EEC,1990: Limited to vitamin A source, not for infant food as a pigment. GB 14880-94: same as "01040, vitamin A Oil". According to Japan (1998), it is not allowed to be used for kelp, meat, fresh fish, cetacean, tea and Laver, beans, vegetables and sprouts. FDA,§ 73.95,2000: Subject to GMP. |
| Use | as a Nutrition Fortifier and food colorant. China's provisions can be used for all kinds of food, according to the production needs of the appropriate amount of use. edible orange pigment; Nutrition Fortifier. Mainly used in margarine, noodles, cakes, beverages and health food. as a dietary Vitamin Nutrition Fortifier and colorant. nutritional supplements and pigments. According to China's Ministry of Health promulgated the "Food Nutrition Fortifier use health standards (1993)", can be used for cream and puffed food, the maximum use of 0.2g/kg. The physiological action of 0.6 μg of this product is equivalent to 1 International unit (I. U.) of vitamin A. Is widely used as a yellow pigment instead of oil-soluble tar pigment, such as for the original contains carotene cream, cheese, mayonnaise, etc., and is widely used in other edible oils, margarine, shortening, cakes, bread, etc. When used in oily foods, often dissolved in cottonseed oil and other edible oil or suspension preparation (content of 30%). After dilution, even when used, the oxidation of β-carotene can be prevented. Antioxidants such as α-tocopherol, stearyl ascorbate, and BHA are generally added. Used as a pigment to add less, such as for margarine is 1.37mg/kg. In the fruit juice with vitamin C, can improve the stability. It is mainly used in food, health care products and medicines An antioxidant, which can be used as a pro-oxidant or antioxidant due to its inhibition of free radical-induced peroxidation in vitro. Dietary supplement for mice to reduce hearing loss and hair cell damage. |
| production method | 1. The extraction of natural β-carotene from natural substances is usually produced by three methods: plant extraction, Dunaliella Salina extraction and fermentation. China mainly adopts Dunaliella Salina extraction method and fermentation method, and plant extraction method has been eliminated in China. 2. Synthesis of intermediates 3, 8-dimethyl-3, 5, 7-tridecene-1, 9-diacetylphenyl lithium and 4-(2,6, the preparation of 6-trimethyl-1-cyclohexen-1-yl)-2-methyl-2-buten-1-aldehyde is described in U.S. patent no. 2917539. Industrial products are generally made of β-carotene edible oil solution or suspension, emulsion and can be dispersed in water powder. In order to improve its stability, antioxidants, emulsifiers, dispersants may be added, and trans/cis isomers may be contained in different ratios. 1 organic solvents such as petroleum ether can be used to extract from carrot, pepper or silkworm sand. The soap of the gasoline layer at the time of extraction of the lutein was simply washed once with an equal amount of 1% sodium chloride solution to remove the soluble lipid compound, and the layer was left to stand to remove the lower aqueous phase. The gasoline layer was distilled under reduced pressure to recover the gasoline to obtain a yellow waxy residue, which was dissolved in petroleum ether and rapidly filtered. The filtrate was passed through an activated alumina column, eluted with a mixture of petroleum ether: acetone = 8:2 (volume ratio), and the solvent was recovered by distillation under reduced pressure to obtain an oily crude β-carotene. Recrystallization with anthracene-ethanol was performed to obtain the finished crystals. This method is limited by resources, it is not possible to large-scale production. (2) chemical synthesis method the chemical synthesis method is the Grignard reaction method of Roche company in Sweden and the Witting reaction synthesis method of Base company in Germany. Grignard reaction synthesis method is based on β-ionone as raw material, then get β-C14, β-C16, β-C19 aldehyde, then by Grignard to two molecules of β-C19 aldehyde condensation synthesis β-C40 diphenol, and then after dehydration, obtained by hydrogenation. Based on beta-ionone, The overall yield was 21%. Β-carotene was also synthesized from β-ionone by Wittig reaction via vinyl-β-Violet, C15 + C10 + C15. The yield was 25% based on C15 enol. The reaction formula is detailed in the literature. Synthesis although the route is longer, but more economic, nutritional value and color stability are good. 3 extracted from Dunaliella Salina is the growth of marine plankton in salt field, the single cell algae, under artificial control conditions can be a large number of reproduction. China has a long shoreline, rich in potential resources and good prospects for development. In the national "seventh five-year" public relations project, the following two technological routes are put forward. (1) petroleum ether extraction process. The wet Dunaliella Salina powder was extracted with solvent oil No. 6 at 50 ° C. For about 20min with stirring. After filtration, the residue was extracted twice more. The filtrate is concentrated by thin film evaporation, crystallized, filtered and vacuum dried to obtain the finished product, and the extraction rate is about 80%. (2) vegetable oil extraction process. The extraction is carried out with vegetable oil 2 times as much as the dry Dunaliella Salina powder for 30-60min at 75 °c with stirring. The oil solution of β-carotene was obtained by centrifugal separation by a three-foot centrifuge and centrifugal sedimentation by a disc centrifuge. 4. Fermentation method the red yeast cells containing β-carotene were cultured by the alternative fermentation method. The relative density of 1.06-1.07 wort as the culture medium, by high temperature sterilization with inoculation of 2%-3% red yeast, at 26 ℃ and PH5-6 under the condition of ventilation culture for 48h, the fermentation broth was separated by high speed centrifugation for 15min, washed with distilled water, and dried at 50 C to obtain dry yeast cells. Stem cells were first treated with 2-3mol/L hydrochloric acid and then boiled in boiling water for 2-3min. The cells were separated by high-speed centrifugation and washed twice with water to obtain cell debris. The stem cell fragments were soaked with acetone, and the cell fragments were separated by high-speed centrifugation to obtain β-carotene extract. After vacuum concentration by Rotary thin film evaporator, β-carotene concentrate was obtained by extraction with chloroform. Finally, it was concentrated under reduced pressure and spray-dried to obtain the finished product. The following types are included. From carrots (Daucus carota) a dry product of meat straight roots, Carrot carotenoids extracted with hot oil or slightly warm hexane, acetone or carbon dioxide. Algae carotenes, or called halophyta carotenes, extracted from algae (Dunaliella salina and Dunaliella naliella bardawil) with carbon dioxide, oil or organic solvents. The resulting unsaponifiable matter was separated from Palm oil of Elaeis quinine by adsorption on silica gel followed by separation with hexane, and then extracted with hot aqueous ethanol to obtain Palm oil carotene. Generally, edible-grade vegetable oils are prepared as emulsified products or suspensions of fats and oils, which may contain emulsifiers, emulsion stabilizers and even antioxidants (tocopherols). When added to oil and fat, it is appropriate to increase the solubility of heat; Solid can be dispersed in water powder excipients. organic solvents such as petroleum ether can be used to extract from carrot, pepper or silkworm sand. Extraction of chlorophyll in the gasoline layer unsaponifiable matter, with the same amount of 1% sodium chloride solution stirred and washed once to remove soluble lipid compounds, static stratification to gasoline layer, the yellow waxy residue was recovered by vacuum distillation of gasoline, dissolved with petroleum ether and rapidly filtered; The filtrate was passed through an activated alumina column and eluted with a mixture prepared by a volume ratio of petroleum ether: acetone = 8:2, after recovering the solvent by vacuum distillation, the crude oil carotene is obtained, and then the product is recrystallized from anthracene/ethanol. Dunaliella Salina extracted from Dunaliella salina is a marine plankton that grows in salt fields. It is a single-celled algae that can be propagated in large quantities under artificially controlled conditions. There are two process routes as follows. Petroleum ether extraction process at 50 ℃ with 6# solvent oil extraction of wet salt algae powder about 20min, filtered filter residue after extraction 2 times, the filtrate by thin film evaporation concentration, crystallization, filtration, the product was obtained by vacuum drying, and the extraction rate was about 80%. Vegetable oil extraction process at 75 deg C with 2 times the dry salt algae powder of vegetable oil stirring extraction 30~60min, by three foot centrifuge centrifugal separation, then the oil solution of β-carotene was obtained by centrifugal sedimentation through a disc centrifuge. The wort with relative density of 1.06~1.07 was used as the culture medium, and the red yeast was inoculated with 2%~ 3% after high temperature sterilization, it was cultured under the condition of 26 ~ C and pH 5~6 for 48h. The fermentation broth was separated by high speed centrifugation for 15min, washed with distilled water, and dried at 50 C to obtain dry yeast cells. The stem cells were first treated with 2-3 mo1/L hydrochloric acid, then boiled in boiling water for 2-3min, separated by high-speed centrifugation, and washed twice with water to obtain cell debris. Dry cell fragments were soaked with acetone, cell fragments were separated by high-speed centrifugation to obtain p-carotene extract, vacuum concentrated by Rotary thin-film evaporator, and extracted with chloroform to obtain β-carotene concentrate, and finally concentrated under reduced pressure, spray-drying gave the finished product. Chemical synthesis method Grignard reaction synthesis method is based on β-ionone as raw material, has been β-C14, β-C16, β-C19 aldehyde, and then by Grignard reaction to two molecules of β-C19 aldehyde synthesis of β-C40 diphenol, after dehydration, the product is obtained by hydrogenation, Based on β-ionone, the overall yield was 21%. Can also be synthesized by Wittig reaction, also with β-ionone as raw material, by vinyl-β-Violet alcohol, C15 + C10 + C15 synthesis of products, C15 enol, the yield was 25%. See references for the reaction formulas. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-22 11:05:26
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