yellow root
Curcumin
CAS: 458-37-7
Molecular Formula: C21H20O6
yellow root - Names and Identifiers
| Name | Curcumin |
| Synonyms | E100 haidr E-100 halad Halad Haidr Halud YO-KIN haldar souchet curcuma curouma gelbwurz Curcumin C.I. 75300 kachs haldi yellow root safra d'inde terra merita merita earth yellow ginger indian saffron tumeric yellow Natural Yellow 3 diferuloylmethane C.I. Natural Yellow 3 Curcumin, Natural Yellow 3, Diferuloylmethane 5-dione,1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptadiene-3 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione 5-dione,1,7-bis(4-hydroxy-3-methoxyphenyl)-,(e,e)-6-heptadiene-3 6-Heptadiene-3,5-dione,1,7-bis(4-hydroxy-3-methoxyphenyl)-,(E,E)-1 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (E,E)- (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one |
| CAS | 458-37-7 |
| EINECS | 207-280-5 |
| InChI | InChI=1/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-13,22,24-25H,1-2H3/b7-3+,8-4+,16-13- |
| InChIKey | VFLDPWHFBUODDF-FCXRPNKRSA-N |
yellow root - Physico-chemical Properties
| Molecular Formula | C21H20O6 |
| Molar Mass | 368.38 |
| Density | 0.93 |
| Melting Point | 183 °C |
| Boling Point | 418.73°C (rough estimate) |
| Flash Point | 208.9±23.6 °C |
| Water Solubility | Slightly soluble (hot) |
| Solubility | Insoluble in water and ether, soluble in ethanol and glacial acetic acid. |
| Vapor Presure | 6.43E-15mmHg at 25°C |
| Vapor Density | 13 (vs air) |
| Appearance | Orange-yellow crystalline powder |
| Color | orange |
| Odor | Odorless |
| Maximum wavelength(λmax) | ['430nm'] |
| Merck | 14,2673 |
| BRN | 2306965 |
| pKa | 8.09(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.4155-1.4175 |
| MDL | MFCD00008365 |
| Physical and Chemical Properties | Density 0.93 melting point 183°C refractive index 1.4155-1.4175 water-soluble sweet solution (hot) |
| Use | Widely used in food, dishes, cakes, candy, canned drinks and cosmetics, medicine coloring |
yellow root - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | MI5230000 |
| TSCA | Yes |
| HS Code | 29145000 |
| Hazard Note | Irritant |
| Toxicity | LD50 Oral-Rat-12.200 mg/kg |
yellow root - Reference Information
| Plant source: | Turmeric |
| color index | 75300 |
| pH indicator color change ph range | yellow (7.8) to red-brown (9.2) |
| Concentration | 1 mCi/ml |
| Solvent | Ethanol |
| Specific Activity | 5-15 Ci/mmol |
| main applications | Cosmetics, drug-eluting stents, inhibition of formation of skin-wrinkles, treating alzheimer's disease, skin diseases, coronary restenosis, diabetes, obesity, leukemia, neurofibromas, cancer, antimicrobial, antiviral, antiinflammatory, antiprostate cancer |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Plant extract | Curcumin, also known as curcumin and acid yellow, is extracted from the roots of ginger plants such as turmeric, curcuma, mustard, curry, and turmeric. The main chain is unsaturated aliphatic and aromatic groups. It is a rare pigment with diketone in the plant kingdom and is a diketone compound, it is a commonly used seasoning and food pigment, non-toxic, with choleretic, anti-infection, paroxysmal contraction of the uterus, lowering blood cholesterol, antiviral, antibacterial, antioxidant (stronger than α-tocopherol), anticoagulant, Various pharmacological effects such as lowering blood lipids and anti-atherosclerosis. In 1985, Indian scholar Kuttan first proposed the anti-cancer effect of curcumin. In recent years, curcumin has an inhibitory mechanism on the production, proliferation and metastasis of various tumor cells. The National Cancer Institute of the United States lists it as a third-generation tumor treatment drug. After compatibility with mitomycin C, the dosage of mitomycin C is reduced, and the nephrotoxicity and bone marrow suppression caused by mitomycin C alone can be reduced, which can improve the effect of mitomycin C in the treatment of breast cancer. Curcumin has protective effects on liver damage induced by various toxic substances such as carbon tetrachloride, aflatoxin B1, paracetamol and cyclophosphamide in vivo and in vitro, significantly reduces alkaline phosphatase and r-glutamyl transpeptidase (r-GT) activities in alcoholic liver damage (ALI) animals, and prevents the occurrence of experimental fatty liver. |
| identification test | solubility insoluble in water and ether; Soluble in ethanol and glacial acetic acid. Measured according to OT-42 method. The melting range is 179~182 ℃. Measured by conventional methods. The ethanol solution of the color reaction A sample should be pure yellow and light green fluorescence; if the ethanol extraction solution is added with concentrated sulfuric acid, it will produce deep purple red. Color reaction B treated the sample with hydrochloric acid in aqueous solution or dilute ethanol solution until it began to appear slightly orange. Divide this mixture into two parts, and add a small amount of boric acid powder or crystals in one part. Compared with the part without boric acid, its color becomes significantly red. Several pieces of filter paper can also be impregnated in the ethanol solution of pigment, dried at 100 ℃, and then moistened with a dilute solution of boric acid (with a few drops of hydrochloric acid). It should be cherry red after drying.. Chromatography takes 5ml of test solution (0.01g sample dissolved in 1mL of 95% ethanol) and drops it on thin layer chromatography (microcrystalline cellulose, 0.1mm) and puts it in a development tank containing 3-methyl -1-butanol/ethanol/water/ammonia (4:4:2:1) mixture to raise the solvent front by 10-15cm. After one day and night, it was observed under ultraviolet light: there were three yellow spots with Rf between 0.2 and 0.4; Rf of other spots was 0.6~0.8; All spots showed yellow fluorescence under ultraviolet light. 6.95% ethanol solution has a maximum absorption peak at 425nm. |
| content analysis | weigh the sample correctly about 0.08g, move it into a 200ml volumetric flask with ethanol, and shake it until dissolved. Shake well after constant volume with ethanol. A 100-fold dilution was prepared with ethanol. Put into a 1cm absorption cell (GT-29), measure the absorbance (A) at 425nm, and calculate the content of total pigment substance in the sample-A × 20000./W × 1607 according to the following formula, where A is the absorbance of the sample and W is the sample amount (g). The determination shall not be delayed to avoid browning and inaccuracy. |
| toxicity | LD50 Oral-Rat-12.200 mg/kg |
| use limit | GB 2760-96: carbonated drinks, candy, ice cream, jelly, 0.01 g/kg. |
| use | edible yellow pigment. China has been used for dried turnips and curry powder for a long time. Japan is used for pickles, ham, sausage and sugar stains of apples, pineapples and chestnuts. Widely used in food, dishes, pastries, candies, canned beverages, and coloring cosmetics and medicine. it can be used as a feed colorant. according to regulations in our country, it can be used for candy, jelly, ice cream and carbonated drinks with a maximum usage of 0.01 g/kg. as a food colorant, China stipulates that it can be used for candy, jelly, ice cream and carbonated drinks, with a maximum usage of 0.01 g/kg. a natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and antioxidant properties. Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) ac Reported to inhibit production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Potent inhibitor of EGFR tyrosine kinase and IB kinase. Inhibits inducible nit ric oxide synthase (iNOS)), cycloxygenase and lipoxygenase. Easy penetrates into the cytoplasm of cells, accumulating in membranous structures such as plasma membrane, endoplasmic reticulum and nucle ar envelope. Curcumin is currently being examined as a possible therapeutic for the treatment of Alzheimers disease (Chem. and Eng. News 90(31), 44 (2012)). pure natural food colorant with strong coloring power and good heat resistance, good light resistance. manufacturing turmeric test paper, pH 8~9; Determination of boron acid-base indicator, pH7.8 (yellow) ~ 9.2 (red brown). The color reaction measures beryllium, zirconium and magnesium, borate and reagents. A natural phenolic substance, anti-tumor and anti-inflammatory substance, and has antioxidant properties, can induce cancer cell apoptosis. |
| production method | water is used as solvent to extract turmeric powder of 0.175-0.36mm for 60-75min at 70-80 ℃ with 8 times the amount of 1% sodium hydroxide solution. after filtration, the filter residue is leached twice again, and the solvent dosage and time can be reduced in turn. Merge the filtrate for three times and add sodium bisulfite solution with 0.8% liquid amount, after concentration, use hydrochloric acid to adjust the pH value to 3~4; let it stand and layer, discard the supernatant, and the lower layer precipitates and filters to obtain a semi-solid mixture of curcumin, turmeric and turmeric resin; use 70% at 70°C The mixture is dissolved in ethanol, filtered while hot to remove the turmeric resin that is insoluble in ethanol, the filtrate is extracted with petroleum ether, and the petroleum ether phase is distilled under reduced pressure to recover the petroleum ether to obtain turmeric butter, curcumin was obtained by distillation of residual ethanol phase under reduced pressure, and the yield could reach 0.5% ~ 1.5%. Organic solvent extraction of curcumin can be dissolved in ethanol, ether, acetone or dichloromethane and other solvents. One of them can be used to extract curcumin and curcumin from turmeric powder of 0.16~0.32mm. After separation and concentration, ginger butter is extracted and separated with petroleum ether. The residual phase is distilled under reduced pressure to obtain curcumin, and the yield is generally 0.55% ~ 1.5%. Step-by-step extraction The turmeric powder is distilled by steam at 100~105 ℃ for 4~6h to obtain ginger butter, and the filter residue is soaked in 1% sodium hydroxide solution at 80 ℃ for 25min. Filtration, neutralization and acidification of the filtrate with hydrochloric acid, filtration to obtain crude curcumin, and refining to obtain the finished product. (1) water as solvent extraction. At 70-80 ℃, the turmeric powder of 0.175-.036mm is extracted with 8 times of 1% sodium hydroxide solution for 60-75min, and the filter residue is extracted twice after filtration. The solvent dosage and time can be reduced in turn. Merge filtrates for 3 times, add sodium bisulfite solution with 0.8% liquid volume, and adjust the PH to 3-4 with hydrochloric acid after concentration. After standing for stratification, the supernatant is discarded, the lower layer precipitates and filters to obtain a semi-solid mixture of curcumin, turmeric butter and turmeric resin; dissolve the mixture with 70% ethanol at 70°C, filter while hot to remove the turmeric resin that is insoluble in ethanol, and then use petroleum ether to extract and separate ginger butter. The petroleum ether phase is distilled under reduced pressure to recover the petroleum ether to obtain turmeric butter, and the residual ethanol phase is distilled under reduced pressure to obtain curcumin, the yield can reach 0.5%-1.5%.(2) Organic solvent extraction. Curcumin can be dissolved in ethanol, ether, acetone or dichloromethane and other solvents. One of them can be used to extract curcumin and curcumin from turmeric powder of 0.16-0.32mm. After separation and concentration, ginger butter is extracted and separated with petroleum ether. The residual phase is distilled under reduced pressure to obtain curcumin, and the yield is generally 0.55%-1.5%. (3) Step-by-step extraction. Turmeric powder was distilled by steam for 4-6h at 100-105 ℃ to obtain ginger butter, and the filter residue was soaked in 1% sodium hydroxide solution at 80 ℃ for 25min. Filtration, neutralization and acidification of the filtrate with hydrochloric acid, filtration to obtain crude curcumin, and refining to obtain the finished product. the rhizome of turmeric (Curcuma longa or c. domastic) is dried into powder, extracted with 95% ethanol or propylene glycol or glacial acetic acid (according to FAO/WHO,1992 only acetone, methanol, ethanol or light gasoline), and then dried after desolventizing, concentration, crystallization and purification. It is obtained by the reaction of vanillin and acetylacetone. Dissolve vanillin with anhydrous ethyl acetate, then add tributyl borate and the complex formed by acetylacetone and B2O3, then add n-butylamine dropwise, stir for 4-5h after dripping, and leave overnight. The next day, 0.4N hydrochloric acid at 60 ℃ was added and stirred for 1h, and the reaction was complete with 50 ℃ water bath. The water layer of the reaction product is separated, washed 3-4 times with water, curcumin is filtered out, and the crude product is obtained by washing 2-3 times with ethyl acetate, and the finished product is recrystallized with ethanol. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:41:30
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