6-METHYL-1,3,8-TRIHYDROXYANTHROQUINONE
Emodin
CAS: 518-82-1
Molecular Formula: C15H10O5
6-METHYL-1,3,8-TRIHYDROXYANTHROQUINONE - Names and Identifiers
| Name | Emodin |
| Synonyms | Emodin C.I. 75440 C.I. Natural Yellow 14 emodin from frangula bark 6-METHYL-1,3,8-TRIHYDROXYANTHRAQUINONE 1,3,8-Trihydroxy-6-methylanthraquinone 6-METHYL-1,3,8-TRIHYDROXYANTHROQUINONE 1,3,8-TRIHYDROXY-6-METHYLANTHRAQUINONE 6-Methyl-1,3,8-trihydroxyanthraquinone 1,3,8-TRIHYDROXY-6-METHYL-9-10-ANTHRACENEDIONE 9,10-ANTHRACENEDIONE, 1,3,8-TRIHYDROXY-6-METHYL- |
| CAS | 518-82-1 |
| EINECS | 208-258-8 |
| InChI | InChI=1/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3 |
| InChIKey | RHMXXJGYXNZAPX-UHFFFAOYSA-N |
6-METHYL-1,3,8-TRIHYDROXYANTHROQUINONE - Physico-chemical Properties
| Molecular Formula | C15H10O5 |
| Molar Mass | 270.24 |
| Density | 1.3280 (rough estimate) |
| Melting Point | 255°C (dec.)(lit.) |
| Boling Point | 373.35°C (rough estimate) |
| Water Solubility | <0.1 g/100 mL at 19 ºC |
| Solubility | Almost insoluble in water, soluble in ethanol and alkali solution. |
| Appearance | Orange-yellow long needle-like crystals (orange in acetone and yellow in methanol) |
| Color | orange |
| Merck | 14,3561 |
| BRN | 1888141 |
| pKa | 6.39±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Sensitive | Sensitive to light and air |
| Refractive Index | 1.5000 (estimate) |
| MDL | MFCD00001207 |
| Physical and Chemical Properties | Orange needle-like crystals. Melting Point 256-257 °c (259-260 °c). Soluble in ethanol, slightly soluble in ether, chloroform, benzene, insoluble in water. Soluble in caustic aqueous solution, sodium carbonate solution, ammonia solution in the cherry red. |
| Use | Pharmaceutical intermediates intermediate; health products material |
6-METHYL-1,3,8-TRIHYDROXYANTHROQUINONE - 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. S37/39 - Wear suitable gloves and eye/face protection S36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 3 |
| RTECS | CB7920600 |
| FLUKA BRAND F CODES | 8-10-23 |
| HS Code | 29146990 |
6-METHYL-1,3,8-TRIHYDROXYANTHROQUINONE - Reference Information
| Plant source: | Rhubarb |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| uses | emodin is a natural compound extracted from Chinese herbal medicines such as rhubarb and polygonum cuspidatum. it has many pharmacological effects such as anti-inflammatory, anti-virus and anti-tumor. Emodin is mainly used for antifeedant, anti-inflammatory, anti-mutation, antiseptic, anti-cancer (chest), anti-ulcer, anti-virus, cathartic, gonadotropic, anti-epidemic, insecticide, laxative, antispasmodic, hemostatic. This product can be used as a laxative. Although emodin has laxative activity, it is easy to be oxidized and destroyed in the body. In fact, the laxative effect is very weak. If it is combined with sugar to form glycosides, it can play a laxative effect. Emodin-1-O-β-D-glucoside and emodin-8-O-β-D-glucoside are glycosides that bind emodin and glucose. The two are only different in binding positions and exist in rhubarb. pharmaceutical intermediate intermediate; Health products material inhibits NF-κB activation and adhesion molecule expression. Casein kinase 2(CK2) inhibitors. |
| rhubarb | rhubarb is the dry rhizome of Rheum palmatum L., Rheum tanguticum Maxim. ex Balf. or Rheum officinale Baill. of medicinal rhubarb. The main difference between Tanggu extra-large yellow and palm-leaf rhubarb is that the leaves are deep 3-lobed and slender and feathery. Inflorescence branches tightly, often erect, close to the stem. The main difference between medicinal rhubarb and the above two rhubarb is that the leaves are lobed, the lobed slices are large-toothed or wide-triangular, the flowers are larger, yellow-white, and the flower buds are oval. There are about 60 species of rhubarb in the world and about 50 species in China. Form: Rhubarb is a tall perennial herb, about 2m high. Rhizomes and roots are thick and yellowish brown. Stems erect, smooth and glabrous, hollow. The basal leaves have long, fleshy thick stalks, about the same length as the leaves, the leaves are broadly ovate or nearly round, the diameter can reach 40cm, palmately half-lobed, lobes 3~5(-7), each 1 The lobes are sometimes feathered or coarsely toothed, and the base is slightly heart-shaped; the cauline leaves are smaller, with short stalks; the stipules are sheath-shaped, membranous, and densely pubescent. Habitat and distribution: born in mountain forest edge or grass slope, wild or cultivated. Distributed in Shaanxi, southeastern Gansu, Qinghai, western Sichuan, northwestern Yunnan and eastern Tibet. Cultivation: It is suitable for cool and humid climate, cold-resistant, and afraid of high temperature and humidity; it is better to plant sandy loam and calcareous loam with deep soil and rich humus. collection: from September to October, plants that have grown for more than 3 years are selected, rhizomes are excavated, stems and leaves, branches and roots are cut off, coarse skin and terminal buds are scraped off, air-dried, dried or sliced in the sun. Figure 1 is a picture of rhubarb. |
| Chemical composition of rhubarb | More than 130 compounds have been isolated and identified from various rhubarb, including anthraquinones and their glycosides, anthracenones, Dianthrone and its glycosides, stilbene and its glycosides and gallate, naphthalene derivatives, chromanone and its glycosides, phenylbutanone, tannins, etc. Among them, anthraquinones are important representative components. Free anthraquinone mainly includes rhein, emodin, physcion (Physcion), aloe-emodin (Aloe-emodin), chrysophanol (Chrysophanol), etc. Anthraquinone glycosides mainly include: chrysophane-1-glucoside, chrysophane-8-glucoside, emodin-1-glucoside, emodin-8-glucoside, physcion-8-glucoside, physcion-8-glucoside, physcion-8-gentiosides, aloe-emodin-8-glucoside, aloe-emodin-3-glucoside, rhein-8-glucoside, etc. Dianthrone glycosides include sennoside (Sennoside)A,B,C,D,E,F, etc. Stilbene and its glycosides include rhubarb glycoside (Rhaponticin), rhubarb glycoside (Rhapontigenin) and deoxyrhubarb glycoside (De-oxyrhaponticin). Rhubarb contains a variety of tannins that are hydrolyzable tannins and condensed tannins [4]. Hydrolyzed tannins and related compounds include a variety of galloyl glucose and 1-0galloyl-6-0-cinnamoyl-β-D-glucose (1). Condensation tannins and their related compounds include catechins, epicatechins and their multimers. In addition, rhubarb also contains a variety of phenylbutanone glycoside compounds. |
| anti-tumor effect | pharmacological studies have found that rhubarb anthraquinone derivatives, rhein, emodin and aloe emodin have obvious anti-cancer effects, and the more sensitive ones are melanoma, P388 leukemia and Ehrlich ascites cancer. Rhubarb polysaccharide has obvious inhibitory effect on sarcoma S180. Emodin concentration of 10 μg/mL can reduce the maximum growth density, division index and the incorporation of thymidine by tritium labeling method of human lung cancer A- 549 cells. The DNA content of the cells was significantly reduced. It was also found that this drug could increase G1 and S phase cells relatively, G2 M phase and aneuploid cells relatively reduced, and the peak value of the group diagram was left-handed and appeared on the lower channel. It shows that emodin has obvious inhibitory effect on the division of human lung cancer A- 549 cells. The anti-tumor mechanism of rhubarb is currently believed to inhibit the respiration of cancer cells and the biosynthesis of DNA. Some people think that rhein and emodin have a direct destructive effect on cancer cells. |
| diuretic effect | rhein and emodin have obvious diuretic effect. the increase of urine output reaches a peak 2~4 hours after taking the medicine, and the excretion of Na and k also reaches a peak. Aloe-emodin and chrysophanol have weak effects. The mechanism of action is due to the inhibitory effect of rhein and emodin on Na -K-ATPase in renal medulla. The reabsorption of Na in the renal tubules is mostly active transport, which requires the decomposition of ATP by Na -K-ATPase to provide energy. When this enzyme is inhibited, the energy source is insufficient, the reabsorption of Na is reduced, and Na carries water and is excreted diuresis. When the tubule Na increases, Na -K exchange is promoted, and K excretion also increases. |
| production method | emodin is widely found in plant laxatives, such as the rhizome of rhubarb, the bark and root bark of rhamnus, and the seeds of cassia. Emodin can be extracted from the rhizome of rhubarb. Emodin can also be prepared by synthesis, for example, with 2-methylanthraquinone, or with 3, 5-dinitrophthalic anhydride and m-cresol as raw materials, which can produce emodin. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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