HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,3,8-Trihydroxy-6-methylanthrachinon
RHUBARB EXTRACT · EMODINE · EMODOL · 1,3,8-TRIHYDROXY-6-METHYLANTHRAQUINONE · 1,3,8-TRIHYDROXY-6-METHYL-9-10-ANTHRACENEDIONE · Ecdyson · FRANGULA EMODIN · 1,6,8-Trihydroxy-3-Methylanthraquinone
Identifikatoren & physikalische Daten
| CAS No. | 518-82-1 |
|---|---|
| Summenformel | C15H10O5 |
| Durchschnittliche Molmasse | 270,24 g/mol |
| Monoisotopische Masse | 270,05282342 g/mol |
| SMILES | Cc1cc(O)c2c(c1)C(=O)c1cc(O)cc(O)c1C2=O |
| InChIKey | RHMXXJGYXNZAPX-UHFFFAOYSA-N |
| PubChem CID | 3220 |
| ChEMBL | CHEMBL289277 |
| ChEBI | CHEBI:42223 |
| EC No. | 208-258-8 |
| DTXSID | DTXSID5025231 |
| Lokaler Name | 1,3,8-Trihydroxy-6-methylanthrachinon |
Chemische & physikalische Eigenschaften
| XLogP | 2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 94,8 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 434 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Lipide | Polyketides [PK] -> Aromatic polyketides [PK13] -> Anthracenes and phenanthrenes [PK1304] |
| Geruch | Orange crystals |
| Color/Form | Orange needles from alcohol or by sublimation at 12 mm |
| Löslichkeit | less than 1 mg/mL at 66 °F (NTP, 1992)Practically insoluble in watersoluble in alcohol, aqueous alkali hydroxide solutions (cherry red color), sodium carbonate and ammonia solutions.Solubility @ 25 °C (g/100 ml of satd solution): ether 0.140chloroform 0.071carbon tetrachloride 0.010carbon bisulfide 0.009benzene 0.041soluble in ethanolmoderately soluble in aqueous alkali solutionsSoluble in alcoholinsoluble in waterDMSO: soluble<0.1 g/100 mL at 19 ºC |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | Sublimes (NTP, 1992)373.35°C (rough estimate) |
| Decomposition | When heated to decomp it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 493 to 495 °F (NTP, 1992)256-257 °CBrick red monoclinic needlesmp: 207 °C /3-Methyl ether/Pale yellow needlesmp: 225 °C /Trimethyl ether/266 - 268 °C255 °C (dec.)(lit.) |
| Physical Description | Emodin appears as orange needles or powder. (NTP, 1992)Solid |
| Stability/Shelf Life | This chemcial may be sensitive to prolonged exposure to light. Solns of this chemical in water, DMSO, 95% ethanol or acetone should be stable for 24 hr under normal lab conditions (RAD). |
| Collision Cross Section | 154.6 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID5025231]158.74 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]161.3 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]156.4 Ų [M-H]- |
| Dichte | 1.3280 (rough estimate) |
| Brechungsindex | 1.5000 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 6.39±0.20(Predicted) |
| Farbe | orange |
| Biologische Quelle | Frangula bark |
| Merck | 14,3561 |
| BRN | 1888141 |
| Hauptanwendungen | food and beverages |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
| 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 |
| InChIKey | RHMXXJGYXNZAPX-UHFFFAOYSA-N |
| SMILES | Cc1cc(O)c2C(=O)c3c(O)cc(O)cc3C(=O)c2c1 |
| LogP (Verteilungskoeffizient) | 3.641 (est) |
| CAS Datenbank | 518-82-1(CAS DataBase Reference) |
| EPA chemische Informationen | Emodin (518-82-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (92.3%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 52 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Brandpotenzial | Flash point data for this chemical are not availablehowever, it is probably combustible. |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and irritating fumes. (NTP, 1992) |
| FDA-Anforderungen | 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 amended21 U.S.C. 321-392). |
| Reaktive Gruppe | Ketones |
| Reactivity Profile | EMODIN may be sensitive to prolonged exposure to light. Probably a weak acid due to the phenolic functional groups. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (92.3%) |
| Brandbekämpfung | Fires involving this material can be controlled with a carbon dioxide, dry chemical or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Brandbekämpfungsverfahren | Fires involving this material can be controlled with a carbon dioxide, dry chemical or Halon extinguisher. |
| Lagerbedingungen | You should store this material under refrigerated temperatures and protect it from light. |
| Reinigungsverfahren | 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. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: 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 surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)Where the neat chemical is weighed and diluted, wear a NIOSH approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). |
| Gesundheitliche Auswirkungen | Chronic use can cause disturbances in electrolyte balance, especially potassium deficiency, and fluid imbalance. Emodin may also cause damage to kidney cells. (A3043, A3044) |
| Expositionspfade | Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) |
| Toxizitätsübersicht | Emodin is moderately cytotoxic and can inhibit the growth of many cell types by interfering with the cell cycle, possibly by stimulating the expression of p53 and p21. Alternatively, it may do this by creating DNA strand breaks and/or non-covalently binding to DNA and inhibiting the catalytic activity of topoisomerase II. It may also induce apoptosis by inhibiting the electron transport chain, producing reactive oxygen species. Emodin is a strong inhibitor of tyrosine-protein kinase Lck and other tyrosine kinase receptors, which likely contributes to its growth suppressing activity. It may act as a chemopreventive agent by activating DNA repair machinery. Emodin can also inhibit metastasis by interfering with the activity of matrix metalloproteinases, either directly or through through inhibition of focal adhesion kinase, mitogen-activated protein kinase, and RAC-alpha serine/threonine-protein kinase activation, and partial inhibition of transcription factor AP-1 and nuclear factor NF-kappa-B (NF-kB) transcriptional activities. Emodin exerts its purgative effects by acting directly or indirectly on colon epithelial cells. This activates the underlying smooth muscle cells, leading to muscle contractility. Possible mechanisms for this effect includes enhancing the hormone motilin, activating muscarinic receptors by triggering the release of acetylcholine, stimulating the protein kinase C-alpha pathway for increased calcium sensibility, inhibiting the secretion of the hormone somatostatin, increasing fluid electrolyte accumulation in the distal ileum and colon, and inhibiting the activity of Na+/K+-ATPase and/or potassium channels. Emodin's antiinflammatory action is due to its specific inhibition of the transcription factor NF-kB. It also regulates angiogenesis by inhibiting the enzymes casein kinase II and nitric oxide synthase and has shown potent estrogen receptor binding affinity. Emodin can induce the microsomal enzyme cytochrome P-450 1A1, perpetuating its own metabolic activation. (A3043, A3044, A3045, A3046, A3047, A3048, A3049, A3050, A3051, A3052, A3053, A3054) |
| Signs and Symptoms | Emodin has purgative properties and causes diarrhea. (A3043) |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=518-82-1] |
| Natural Pollution Sources | 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. |
| Carcinogen Classification | EmodinTR-493: Toxicology and Carcinogenesis Studies of Emodin (CASRN 518-82-1) in F344/N Rats and B6C3F1 Mice (Feed Studies) (2001 )05/21/99No EvidenceEquivocal Evidence |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ This compound has caused gastrointestinal effects in experimental animals./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... The effect of emodin on hepatic fibrosis in rats /was investigated/. The rat hepatic fibrosis model was induced by the subcutaneous injection of 40% CCl4 (twice a week for 6 weeks) dissolved in olive oil. The emodin-treated rats were treated with low-dose, intermediate-dose and high-dose emodin (20, 40 and 80 mg/kg body weight, once a day for 42 days) dissolved in 0.5% sodium carboxymethylcellulose (CMC), except receiving CCl4. Control group received only olive oil and 0.5% CMC... Compared with model group, the emodin-treated rats showed (1) liver functions were improved, alanine transaminase (ALT) and alkaline phosphatase (AKP) were obviously reduced, and total protein (TP) and albumin (ALB) were significantly increased(2) serum hyaluronic acid and laminin were markedly reduced(3) liver hydroxyproline was significantly decreased(4) the degrees of fibrosis were reduced. The changes of parameters mentioned above were significant (P < 0.05 or P < 0.01). Emodin has effect on hepatic fibrosis in rats. The hepatoprotective of emodin /SRP: may effect liver fibrosis/./LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ... Emodin and cassiamin B /were examined as cancer chemopreventive agents/ ... These compounds exhibited the remarkable anti-tumor promoting effect on two-stage carcinogenesis test of mouse skin tumors induced by 7,12-dimethylbenz[a]anthracene as an initiator and 12-O-tetradecanoylphorbol-13-acetate (TPA) as a promoter by both topical application. Furthermore, emodin exhibited potent inhibitory activity on two-stage carcinogenesis test of mouse skin tumors induced by nitric oxide donor, (+/-)-(E)-methyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexeneamide as an initiator and TPA as a promoter./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ EMOD /emodin/ was administered in feed to timed-mated Sprague-Dawley (CD) rats (0, 425, 850, and 1,700 ppmgestational day (gd) 6 to 20), and Swiss albino (CD-1) mice (0, 600, 2,500or 6,000 ppmgd 6 to 17). Ingested dose was 0, 31, 57, and 80-144 mg EMOD/kg/day (rats) and 0, 94, 391, and 1,005 mg EMOD/kg/day (mice). ...There were no maternal deathsdiscolored, soft or loose feces were observed at the high dose in mice. In rats, maternal body wt decreased at the high dose (gd 9, 12)wt gain was reduced at the mid (gd 6-9) and high dose (gd 6-96-20). Maternal body wt (gestation) and wt gain (corrected for gravid uterine weight (GUW)) exhibited a decreasing trend. In mice, maternal body wt and wt gain decreased at the high dose. Prenatal mortality, live litter size, fetal sex ratio, and morphological development were unaffected in both rats and mice. At the high dose, rat average fetal body wt/litter was unaffected, but was significantly reduced in mice. The rat maternal LOAEL was 1,700 ppm based on maternal body weight and weight gainthe NOAEL was 850 ppm. The rat developmental toxicity NOAEL was greater than 1,700 ppma LOAEL for rat developmental toxicity was not established. In mice, the maternal toxicity LOAEL was 6,000 ppm based on reduction of maternal body wt and wt gainthe NOAEL was 2,500 ppm. The developmental toxicity LOAEL was 6000 ppm, based on reduction of fetal body wtthe NOAEL was 2,500 ppm.For more Non-Human Toxicity Excerpts (Complete) data for EMODIN (10 total), please visit the HSDB record page. |
| Antidote and Emergency Treatment | SKIN CONTACT: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Respirator Recommendation.EYE CONTACT: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup ... may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. |
| Toxicity Data | LD50: 35 mg/kg (Intraperitoneal, Mouse) (L135) |
| Non-Human Toxicity Values | LD50 Mouse ip 35 mg/kg |
| F | 8-10-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29146990 |
| RTECS-Nr. | CB7920600 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-37/39-36/37 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 518-82-1(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Verwenden
Emodin has been used:to investigate its regulatory mechanisms on lipopolysaccharide (LPS)-induced inflammatory injury in myocarditisas a reference standard for the development and validation of high performance liquid chromatography (HPLC)-photodiode array (PDA) assay methodto inhibit Tau aggregationfor direct binding assay