5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]naphthalene-1,4-dione
Shikonin
CAS: 517-89-5
Molecular Formula: C16H16O5
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]naphthalene-1,4-dione - Names and Identifiers
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]naphthalene-1,4-dione - Physico-chemical Properties
| Molecular Formula | C16H16O5 |
| Molar Mass | 288.3 |
| Density | 1.373±0.06 g/cm3(Predicted) |
| Melting Point | 148℃ |
| Boling Point | 567.4±50.0 °C(Predicted) |
| Flash Point | 311°C |
| Solubility | Insoluble in water, soluble in ethanol, organic solvents and vegetable oils. Easily soluble in alkaline water, precipitated when exposed to acid. |
| Vapor Presure | 1.04E-13mmHg at 25°C |
| Appearance | Purple flake crystal or crystalline powder |
| pKa | 7.34±0.20(Predicted) |
| Storage Condition | -20°C |
| Refractive Index | 1.642 |
| MDL | MFCD00075680 |
| Physical and Chemical Properties | Purple brown needle crystal, melting point 147 ℃, optical rotation αD20=135 (benzene). Soluble in phenyl ether, acetone, chloroform, methanol, ethanol, glycerin, animal and vegetable oil and alkaline aqueous solution, insoluble in water. The hue varies with the Ph value, the Ph value 4~6 is red, the Ph value 8 is purple, and the Ph value 10~12 is blue. Light resistance, heat resistance, good oxidation resistance, unstable to the reduction dose, and dark purple when exposed to iron ions. It has a certain antibacterial effect. |
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]naphthalene-1,4-dione - Risk and Safety
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R20 - Harmful by inhalation |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | 3077 |
| HS Code | 29146990 |
| Toxicity | 我国自古用于染料并制药(有退热、解毒)。 |
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]naphthalene-1,4-dione - Reference Information
| source plant | Lithospermum is a perennial herb of the family arnebiaceae, lithospermum, Xinjiang [Arnebia euchroma (Roy) John St.] or ArnebiaguttataBunge. The dry root, alias purple Dan, Earth blood, rarmgrass, mountain lithospermum, etc. It mainly contains naphthoquinones and other components, including shikonin, shikonin, shikonin, shikonin, shikonin and other chemical components. In our country has a long history of medicinal, clinical Chinese medicine is mainly used for the treatment of wet rash, purpura, hematuria, turbidity and blood dysentery, heat constipation, burns, eczema, erysipelas and so on. Modern medical research found that the chemical composition of arnebia euchroma complex, with anti-tumor, antibacterial, antiviral, anti-HIV, anti-fertility, antipyretic, hemostatic, hypoglycemic and other extensive pharmacological effects. at present, shikonin is mainly used as medicinal materials: "Soft shikonin", "shikonin", "Inner Mongolia shikonin". Soft Lithospermum: irregular long cylindrical, more twisted, 7 ~ 20cm long, 1~2.5 in diameter. The surface is purplish red or purple-brown, with loose skin, in strip-like form, often overlapping with more than 10 layers, easy to peel off. At the top there are visible branched stem residues. The patient is light, soft and easy to break. Irregular cross-section, Wood is small, yellow-white or yellow. Gas specific, slightly bitter, astringent. 2. D: conical, twisted, branched, 7 ~ 14cm long, 1 ~ 2cm in diameter. The surface is purple-red or purple-black, rough with longitudinal lines, thin skin, easy to peel. Hard and brittle, easy to break. The skin of the cross section was dark purple, and the wood was large, gray-yellow. Micro-aroma, slightly bitter taste. 3. Inner Mongolia Lithospermum: conical or cylindrical, twisted, 6 ~ 20cm long, 0.5 ~ 4cm in diameter. The head of the root was slightly coarse, with 1 to 1 residue at the apical end, with short bristles. The surface is purplish red or dark purple, the skin is slightly thin, and the constant layers are stacked and easy to peel. Hard and brittle, easy to break. The cross section was relatively regular, with purple-red skin and small wood, yellow-white. Gas-specific, astringent. FIG. 1 is a graph of lithospermum. |
| physical and chemical properties | purple flake crystal or crystalline powder, melting point 147 ℃ ~ 149 ℃,[α]D20: 138 degrees (benzene). Insoluble in water, soluble in alcohol, organic solvents and vegetable oils. Soluble in alkaline water, acid precipitation and precipitation. |
| Main components | containing acetyl shikonin, β-hydroxy isovaleryl shikonin, shikonin, shikonin, etc. Deoxyshikonin, β-dimethylpropenyl phthalate shikonin, isobutylphthalein shikonin, shikonin, methyl shikonin, β-sitosterol and caffeic acid fatty alcohol ester; Higher fatty acid esters of shikonin A, shikonin B and caffeic acid. 1. Lithospermum: Containing β,β-dimethylacryloylshikonin (β,β-dimethacryloylshikonin) about 1.7% ~ 3.41%, and containing Shikonin (Shikonin), acetyl Shikonin (Shikonin), isobutyrylshikonin, Isovalerylshikonin, β-hydroxyisovalarylshikonin, deoxyshikonin (De-oxyshikonin), etc. 2. Lithospermum: mainly containing acetyl shikonin, the rest of the composition and soft shikonin similar. The content of shikonin and its derivatives was 3.1%, and the content of was 1.05%. Inner Mongolia shikonin: also contains beta, beta-dimethyl acryloyl shikonin, acetyl shikonin, shikonin and other ingredients. |
| extraction process | FIG. 2 is a process flow chart for extracting shikonin from shikonin. |
| Content determination | (1) chromatographic conditions silica gel high-performance thin-layer plate, the empty plate is first used with ethanol-glacial acetic acid (5: 0.2) push to the front for pretreatment; N-hexane-acetone-chloroform-glacial acetic acid (8: 1: 0.1: 0.1) as the developing solvent; Positioning under natural light. (2) preparation of reference solution precise weighing shikonin, deoxyshikonin, acetyl shikonin, β,β-dimethylacryloylacanin, A solution containing 0.1mg/ml of chloroform was prepared as a control solution. (3) preparation of sample solution 0.2g of lithospermum root powder was accurately weighed, placed in a 50ml plug triangle bottle, 10.0ml of chloroform was added, and extracted by ultrasonic oscillation for 10min, centrifuged, and the supernatant was used as the sample solution. (4) the sample solution and the reference solution are accurately absorbed, respectively, 1~3 μl each, and are placed on the same high-efficiency thin layer plate (pretreatment), and are expanded according to the above chromatographic conditions, taken out, dried, scanning according to thin layer scanning method, λs = 280nm, λr = 400nm, reflective linear scanning; Slit 5mm × 0.4; Scanning speed and paper speed are both 20mm/min. (5) measurement results FIG. 3 shows the content measurement results (%) of shikonin-like compounds in arnebia euchroma. |
| pharmacological action | (1) hypoglycemic effect Lithospermum leaf extract and shikonin (A, B, C) have obvious hypoglycemic effect. (2) bacteriostasis shikonin had inhibitory effect on Jingke 68-1 Virus test tube, and had inhibitory effect on Staphylococcus aureus. The anti-Parainfluenza Virus effect of L-shikonin was studied by hemagglutination reaction and cytopathic method. The results showed that the toxicity of L-shikonin was low in the concentration range used in the experiment, it has a certain anti-influenza virus activity in vitro and a direct killing effect of Parainfluenza Virus. (3) effect on blood coagulation intraperitoneal injection of shikonin components (shikonin, acetyl shikonin) did not affect the blood coagulation time, but could prevent the anticoagulant effect of heparin. (4) anti-tumor effect The Lithospermum extract had a certain inhibitory effect on the late stage of DNA synthesis (G2 phase) of Hela cells. (5) anti-tumor effect shikonin inhibits proliferation, promotes apoptosis and induces cell cycle arrest of drug-resistant human choriocarcinoma cell line (JAR/MTX) in vitro, experiments showed that the concentration of shikonin increased with the increase of the dose and the extension of the action time, the inhibition rate of the growth of choriocarcinoma resistant cells was also significantly increased. (6) effect on hormone secretion effect of shikonin on the function of hypothalamic-pituitary-gonadal axis in adolescent female rats the experiment showed that the serum hormone level of the arnebia euchroma group was significantly lower than that of the negative control group, there was no significant difference compared with the positive control group. The results indicate that shikonin can inhibit the function of hypothalamic-pituitary-gonadal axis in rats. (7) antioxidant effect The effects of shikonin on superoxide radical (O2-) and 1, 1-diphenyl-2-phenylhydrazine radical (DPPH) were determined by researchers. Scavenging ability, and its inhibitory effect on β-carotene/linoleic acid autoxidation system. The results showed that the Lithospermum pigment had strong scavenging ability on DPPH and O2-, and had obvious inhibitory effect on β-carotene/linoleic acid auto-oxidation system, the pharmacological effects of arnebia euchroma may be related to the strong antioxidant capacity of naphthoquinone pigments. |
| toxicity | our country since ancient times for dyes and Pharmaceutical (antipyretic, detoxification). |
| usage limit | GB 2760-2000: fruit juice, ice-cream, Popsicle, fruit wine, biscuits, sandwich biscuits, cakes and cakes in color clothes, both 0.1g/kg. |
| maximum allowable use amount of food additives maximum allowable residue standard | The Chinese name of the additive the Chinese name of the additive is allowed to use the food Chinese name of the additive function maximum allowable use amount (g/kg) maximum allowable residue (g/kg) Lithospermum red fruit wine colorant 0.1 Lithospermum red-flavored beverages (including fruit-flavored beverages, milk-flavored, tea-flavored and other beverages) (fruit-flavored beverages only) coloring agent 0.1 Lithospermum red fruit and vegetable juice (meat) beverage coloring agent 0.1 Lithospermum red baked food filling (biscuit sandwich only) coloring agent 0.1 Lithospermum red biscuit coloring agent 0.1 Lithospermum red cake coloring agent 0.1 Lithospermum Red frozen drinks (except 03.04 edible ice) colorant 0.1 |
| Chemical properties | purple-brown needle-like crystals, melting point 147 ℃, optical rotation αD20=135 ° (benzene). Soluble in benzene ether, acetone, chloroform, methanol, ethanol, glycerol, animal and vegetable oil and alkaline aqueous solution, insoluble in water. Color changes with pH, pH 4~6 red, pH 8 purple, pH 10~12 blue. Light-resistant, heat-resistant, oxidation-resistant, on the reduction of dose instability, iron ions were dark purple. Has a certain antibacterial effect. |
| Use | as a food colorant, China's provisions can be used for fruit juice (taste) drinks, fruit wine, ice cream and popsicles, the maximum amount used was 0.1g/kg. edible purple pigment. It is used for the coloring of canned spicy meat and poultry, and the dosage is 0.35~0.56g/kg. The crushed Lithospermum can be placed in a fine sieve and poured onto it with hot oil at 1 60~170 °c to dissolve the pigment in the oil. The oil flows out through a fine sieve, is mixed with the chili powder in the container, and is thoroughly stirred and then boiled into a mixed sauce for later use. |
| production method | Litho perMUM EUCHROMOM; Macritmia euchroma root ethanol, propylene glycol, edible oil, obtained by extraction of water, etc. Ethanol extraction performance is more stable. Arnebia root is mainly produced in Xinjiang and other places in northwest China. with the root of arnebia euchroma as raw material, extracted with 4 times the amount (mass) of refined soybean oil at 165~1 70 ℃ for 6min, then the extract was extracted twice with ethanol (volume ratio) slightly more than 95% of soybean oil; The ethanol extract was concentrated under a vacuum of 80kPa, and then the insoluble matter was filtered off to obtain a finished product. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:06
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Product Name: R-Shikonin Visit Supplier Webpage Request for quotationCAS: 517-89-5
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Email: 2853786052@qq.com
Mobile: 86+15671228036
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