Emodin
- Iupac Name：1,3,8-trihydroxy-6-methylanthracene-9,10-dione
- CAS No.: 518-82-1
- Molecular Weight：270.24
- Modify Date.: 2022-11-05 08:21
- Introduction: 1. The product can be used as a laxative. As it is susceptible to oxidative damage within the body, its diarrhea activity is actually very weak. However, it can be compounded with glucose to form a glycoside with diarrhea activity. Both emodin-1-O-β-D-glucoside and emodin-8-O-β-D-glucoside are glycosides formed through combination of emodin and glucose. The only different between the two are the binding sites. The two glycosides coexist in Radix et Rhizoma Rhei.2. intermediate;health products material.
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1. Names and Identifiers
- 1.1 Name
- Emodin
- 1.2 Synonyms
1,3,8-trihydroxy-6-methyl-9,10-anthraquinone 1,3,8-TRIHYDROXY-6-METHYL-9-10-ANTHRACENEDIONE 1,3,8-Trihydroxy-6-methylanthracene-9,10-dione 1,3,8-Tri-hydroxy-6-methyl-anthra-quinone 1,3,8-TRIHYDROXY-6-METHYLANTHRAQUINONE 6-METHYL-1,3,8-TRIHYDROXYANTHRAQUINONE 6-METHYL-1,3,8-TRIHYDROXYANTHROQUINONE 9,10-ANTHRACENEDIONE, 1,3,8-TRIHYDROXY-6-METHYL- Alatinone Archin Ecdyson EINECS 208-258-8 Emdin EMODIN 99 emodin from frangula bark EMODINE EMODOL MFCD00001207 schuttgelb
- 1.3 CAS No.
- 518-82-1
- 1.4 CID
- 3220
- 1.5 EINECS(EC#)
- 208-258-8
- 1.6 Molecular Formula
- C15H10O5 (isomer)
- 1.7 Inchi
- InChI=1S/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
- 1.8 InChkey
- RHMXXJGYXNZAPX-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O
- 1.10 Isomers Smiles
- CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O
2. Properties
- 2.1 Density
- 1.583
- 2.1 Melting point
- 253-257℃
- 2.1 Boiling point
- 493 to 495° F (NTP, 1992)
- 2.1 Refractive index
- 1.5000 (estimate)
- 2.1 Flash Point
- 322.8 °C
- 2.1 Precise Quality
- 270.05300
- 2.1 PSA
- 94.83000
- 2.1 logP
- 1.88720
- 2.1 Solubility
- DMSO: soluble
- 2.2 Appearance
- red-orange powder
- 2.3 Storage
- Keep Cold.
- 2.4 Color/Form
- orange
- 2.5 Decomposition
- When heated to decomp it emits acrid smoke and irritating fumes.
- 2.6 Odor
- Orange crystals
- 2.7 Physical
- PHYSICAL DESCRIPTION: Orange needles or powder. (NTP, 1992)
- 2.8 pKa
- 6.39±0.20(Predicted)
- 2.9 Water Solubility
- DMSO: soluble | <0.1 g/100 mL at 19 oC
- 2.10 Spectral Properties
- Absorption max (ethanol): 222, 252, 265, 289, 437 nm (log E = 4.55, 4.26, 4.27, 4.34, 4.10)
Maximum absorbance: 521 (309) nm in 0.1 N sodium hydroxide
MASS: 80649 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
IR: 3:900F (The Aldrich Handbook of Organic Chemicals and Biochemicals, Aldrich Chemical Co., Inc., NY, NY; Aldrich Library of Infrared Spectra, Aldrich Chemical Co., Milwaukee, WI)
- 2.11 Stability
- Stable under normal temperatures and pressures.
- 2.12 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 General Description
- Orange needles or powder.
- 3.2 GHS Classification
- Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 34 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
H315 (94.12%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (94.12%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (91.18%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
- 3.3 Usage
- 1. The product can be used as a laxative. As it is susceptible to oxidative damage within the body, its diarrhea activity is actually very weak. However, it can be compounded with glucose to form a glycoside with diarrhea activity. Both emodin-1-O-β-D-glucoside and emodin-8-O-β-D-glucoside are glycosides formed through combination of emodin and glucose. The only different between the two are the binding sites. The two glycosides coexist in Radix et Rhizoma Rhei.2. intermediate;health products material.
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R36/37/38
- 4.1 Safety Statements
- S26;S37/39
- 4.1 Exposure Standards and Regulations
- Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392). [
- 4.2 Fire Hazard
- Flash point data for Emodin are not available; however, Emodin is probably combustible.
- 4.3 Hazard Declaration
- H315-H319-H335
- 4.3 Cleanup Methods
- If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated sufaces with acetone followed by washing with a soap and water soln. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
- 4.4 DisposalMethods
- SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
- 4.5 RIDADR
- NONH for all modes of transport
- 4.5 Fire Fighting Procedures
- Fires involving this material can be controlled with a carbon dioxide, dry chemical or Halon extinguisher.
- 4.6 FirePotential
- Flash point data for this chemical are not available; however, it is probably combustible.
- 4.7 Caution Statement
- P261-P305 + P351 + P338
- 4.7 Formulations/Preparations
- This compound occurs either free or combined with a sugar in a glucoside in rhubarb, cascara sagrada, aloes and other plants. A synthetic product is also available.
- 4.8 WGK Germany
- 3
- 4.8 RTECS
- CB7920600
- 4.8 Report
-
EPA Genetic Toxicology Program.
- 4.9 Safety
-
Poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:?
Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39-36/37
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
F: 8-10-23
- 4.10 Specification
-
? Emodin , with CAS number of 518-82-1, can be called 1,3,8-Trihydroxy-6-methylanthraquinone ; 6-Methyl-1,3,8-trihydroxyanthraquinone ; C.I. 75440 ; C.I. Natural Yellow 14 ; 1,3,8-Trihydroxy-6-methylanthraquinone ; 1,3,8-trihydroxy-6-methylanthra-9,10-quinone . Emodin (CAS NO.518-82-1)? is a purgative resin from rhubarb and the buckthorn. The term may also refer to any one of a series of principles isomeric with the emodin of rhubarb. When heated to decomposition Emodin emits acrid smoke and irritating fumes.
- 4.11 Toxicity
-
| 1. |
??? |
mmo-sat 50?μg/plate
|
??? |
BCSTB5 ?? Biochemical Society Transactions. 5 (1977),1489. |
| 2. |
??? |
mma-sat 10?μg/plate
|
??? |
MUREAV ?? Mutation Research. 125 (1984),135. |
| 3. |
??? |
ipr-mus LD50:35?mg/kg
|
??? |
JAFCAU ?? Journal of Agricultural and Food Chemistry. 27 (1979),1342. |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
Specific target organ toxicity \u2013 single exposure, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
518-82-1Total: 15 Synthesis Route
9. Other Information
- 9.0 Uses
-
Emodin has been used:
- to investigate its regulatory mechanisms on lipopolysaccharide (LPS)-induced inflammatory injury in myocarditis
- as a reference standard for the development and validation of high performance liquid chromatography (HPLC)-photodiode array (PDA) assay method
- to inhibit Tau aggregation
- for direct binding assay
- 9.1 Merck
- 14,3561
- 9.2 BRN
- 1888141
- 9.3 Radix et Rhizoma Rhei
- Radix et Rhizoma Rhei is the dry root or rhizome of Rheum palmatum L, Rheum officinale Baill, and Rheum tanguticum Maxim. ex Balf. in the genus Rheum of the family Polygonaceae. Rheum tanguticum Maxim. ex Balf has slender pinnate leaves with three deep lobes and dense inflorescence branches, often erect, clinging to the stem, which are the main difference of it from Rheum palmatum L. The main difference between Rheum tanguticum Maxim. ex Balf. and the other two species mentioned above are its lobed leaves with big serrate or broadly triangular margin, large and yellow-white flowers, oval-shaped flower buds and patulous branches. There are about 60 Rheum species all over the world, of which about 50 are in China.
Morphological Characteristics: herbaceous perennial about two meters high. Rhizomes and roots are fleshy and yellowish-brown in color. The stem is erect, smooth, hairless and hollow. The basal leaf has a fleshy, long and sturdy petiole, about as long as the leaf blade. The leaf blade is broadly ovate or nearly round in shape, up to 40 cm in diameter, palmate-cleft with three to five (or to seven) lobes and each lobe sometimes also palmate-cleft or serrate. The leaf base is slightly heart-shaped. The stem leaf is small, shortly stalked. The ocrea is membranous and densely pubescent.
Habitat and distribution: Grow in mountain areas, forest margins or grassland, wild or cultivated and distributed in Shaanxi, southeastern Gansu, Qinghai, western Sichuan, northwestern Yunnan and Eastern Tibet.
Cultivation: suitable for growing in places with cool and moist climate and with deep soil layer that contains humus-rich sandy loam or calcareous loam, rather than growing in cold places with high temperature and humidity.
Harvest: harvest during September to October, select plants that have grown more than three years, dig up the rhizomes and roots, remove the leaves, stems, rootlets, scrape the bark and buds, and then dried in air or in an oven, or sliced and dried.
Figure 1 is an image of the Radix et Rhizoma Rhei
- 9.4 Chemical constituents
- There have been more than 130 compounds isolated and characterized from a variety species of Rheum, including anthraquinones and anthraquinone glycosides, anthrones, bianthrones and bianthrone glycosides, stilbenes and stilbene glycosides, gallate, naphthalene derivatives, chromanones and chromanone glycosides, banzylethylketone, tannins and so on. Among them the anthraquinones are the most important and representative ingredients. Free anthraquinones mainly include rhein, emodin, physcion, aloe-emodin, and chrysophanol. And anthraquinone glycosides mainly include chrysophanol-1-glucoside, chrysophanol-8-glucoside, emodin-1-glucoside, emodin-8-glucoside, physcion-8-glucoside, physcion-8-gentiobiosiden, aloe-emodin-8-glucoside, aloe-emodin-3-glucoside, and rhein-8-glucoside. Bianthrone glycosides include sennosides A, B, C, D, E, and F. Stilbenes and stilbene glycosides include rhaponticin, rhapontigenin and de-oxyrhaponticin.
Radix et Rhizoma Rhei contains a variety of tannins, both hydrolyzable tannins and condensed tannins[4]. Hydrolyzable tannins and its related compounds contain a variety of pentagalloylglucose and 1-O-galloyl-6-O-cinnamoyl-β-D-glucose. Condensed tannins and its related compounds contain catechin, epicatechin and its polymers. In addition, Radix et Rhizoma Rhei also contains a variety of banzylethylketone glycosides.
- 9.5 Production method
- Emodin is a plant laxative widely present in plant organs such as roots of Radix et Rhizoma Rhei, bark and root bark of buckthorn and cassia seeds. Emodin can be extracted from roots and rhizomes of Radix et Rhizoma Rhei. It also can be obtained by synthesis, for example, using 2-methyl-anthraquinone, or 3, 5-nitro-phthalic anhydride and m-cresol as the raw material.
- 9.6 Antitumor effect
- Pharmacological studies have found that anthraquinone derivatives in Radix et Rhizoma Rhei, rhein, emodin and aloe-emodin showed obvious inhibitory effect on cancers, especially on cancers such as melanoma, P388 leukemia and Ehrlich ascites carcinoma. The polysaccharides contained in Radix et Rhizoma Rhei could markedly inhibit the cells of sarcoma S180. And a concentration of 10 μg/ml emodin could reduce the maximum growth density and the mitotic index of human lung cancer cell line A-549, and apparently decreased the incorporation of tritiated thymidine and the level DNA content. It was also found that the drug could relatively increase the number of cells at the G1 and S stages and decreased the number of aneuploid cells as well as the number of cells at the G2/M phase, with a sinistral displacement of the peak in the DNA histogram. These results suggested that emodin has an obvious inhibitory effect on human lung cancer A-549 cells. The antitumor mechanism of Radix et Rhizoma Rhei is presently considered to be the inhibition of respiration and DNA biosynthesis of cancer cells. It is also believed that rhein and emodin may destroy the cancer cells directly.
- 9.7 Diuretic effect
- Both rhein and emodin have evident diuretic effect. The urine volume increased to peak two to four hours after dosing, and in the meanwhile the amounts of Na+ and K+ discharges were also reached to the peak. Aloe-emodin and chrysophanol were less effective in diuretic property as compared with rhein and emodin. The mechanism is contributed to the inhibitory effect of rhein and emodin on renal medullary Na+, K+-ATPase. The Na+ re-absorption in renal tubules is mainly active transport which needs energy from ATP hydrolysis catalyzed by the Na+, K+-ATPase. When the enzyme is inhibited, Na+ re-absorption would decrease because of insufficient energy supply, which leads to water discharge increase along with the increase of Na+ discharge. When distal convoluted tubule Na+ increases, promote Na+-K+ exchange would be promoted, resulting in increase in K+ discharge.
- 9.8 Chemical Properties
- red-orange powder
- 9.9 Uses
- Occurs mostly as the rhamnoside (see Frangulin) in rhubarb root. Cathartic.
- 9.10 Uses
- antibacterial, antineoplastic, cathartic, tyrosine kinase inhibitor
- 9.11 General Description
- Orange needles or powder.
- 9.12 Air & Water Reactions
- Insoluble in water.
- 9.13 Reactivity Profile
- Emodin may be sensitive to prolonged exposure to light. Probably a weak acid due to the phenolic functional groups.
- 9.14 Health Hazard
- ACUTE/CHRONIC HAZARDS: When heated to decomposition Emodin emits acrid smoke and irritating fumes.
- 9.15 Fire Hazard
- Flash point data for Emodin are not available; however, Emodin is probably combustible.
- 9.16 Biological Activity
- Naturally occurring anthraquinone that displays a range of biological activities. Exhibits anti-inflammatory, antitumor and neuroprotective effects.
- 9.17 Usage
- A protein tyrosine kinase inhibitor
10. Computational chemical data
- Molecular Weight: 270.24g/mol
- Molecular Formula: C15H10O5
- Compound Is Canonicalized: True
- XLogP3-AA: 2.7
- Exact Mass: 270.05282342
- Monoisotopic Mass: 270.05282342
- Complexity: 434
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 3
- Hydrogen Bond Acceptor Count: 5
- Topological Polar Surface Area: 94.8
- Heavy Atom Count: 20
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwYMAAAAAAAADBQAAAGgAACAAADASAmAAyBoAAAgCIAqBSAAACAAAkIAAAiAEGCMgIJzaCFRKAcUAl4BUImYeL7PTO4AADCAAYAADAAAYQADAAAAAAAAAAAA==
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