Emodin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04483 |
| CAS | 518-82-1 |
| Molecular Weight | 270.24 |
| Molecular Formula | C15H10O5 |
| Purity | 95% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04483 | 50 g | $249 | In stock |
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Add to cartDescription
Emodin is an anthraquinone found naturally in the roots and barks of numerous plants. It exerts antiproliferative effects in cancer cells that are regulated by different signaling pathways. It has anti-cancer, anti-depressant and anti-microbial effects.
Specification
| Synonyms | Emodol; Frangula emodin; HSDB 7093; NSC 408120; NSC 622947; 3-methyl-1,6,8-trihydroxyanthraquinone; 1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione; 1,6,8-Trihydroxy-3-methylanthraquinone; 4,5,7-Trihydroxy-2-methylanthraquinone; Archin; Frangulic Acid; Rheum Emodin; Schuttgelb |
| Storage | Store at 2-8°C |
| IUPAC Name | 1,3,8-trihydroxy-6-methylanthracene-9,10-dione |
| Canonical SMILES | CC1=CC(=C2C(=C1)C(=O)C3=CC(=CC(=C3C2=O)O)O)O |
| 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 |
| InChI Key | RHMXXJGYXNZAPX-UHFFFAOYSA-N |
| Source | Emodin is a mycotoxin and naturally occurring anthraquinone present in the roots and barks of numerous plants, such as rhubarb. It is an active ingredient of Chinese herbs, including Rheum officinale and Polygonam cuspidatum. Emodin is also produced as a secondary metabolite by molds and lichens such as Aspergillus wentii. |
Properties
| Appearance | Orange to Dark Orange Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Bacteria |
| Boiling Point | 586.9°C at 760 mmHg |
| Melting Point | 258-260°C |
| Flash Point | 322.8±23.6 °C |
| Density | 1.583 g/cm3 |
| Solubility | Slightly soluble in Chloroform, DMSO, Methanol |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | 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 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'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. |
| Toxicity | LD50: 35 mg/kg (Intraperitoneal, Mouse). |
Reference Reading
1.[Research progress in anti-tumor effect of emodin].
Lin WF, Wang C, Ling CQ. Zhongguo Zhong Yao Za Zhi. 2015 Oct;40(20):3937-40.
Emodin is one of the main active ingredient of Rheum palmatum, and has anti-inflammatory, anti-bacterial, anti-viral and other effects. In recent years, it arouse concern since it has a significant anti-tumor effect with low toxicity. In this paper we mainly report the anti-cancer effects of emodin according to the studies of the past five years, including four parts such as inhibit tumor growth, inhibit migration and invasion, enhance the efficacy of combination therapy, increase chemosensitivity and attenuated side effects. We hope that our work may provide a reference for further study.
2.Erratum to "Aloe-Emodin Protects RIN-5F (Pancreatic β-cell) Cell from Glucotoxicity via Regulation of Pro-Inflammatory Cytokine and Downregulation of Bax and Caspase 3" [Biomol. Ther. 24 (2016) 49-56].
Alshatwi AA1, Subash-Babu P1. Biomol Ther (Seoul). 2016 May 1;24(3):346. doi: 10.4062/biomolther.2016.346.
The authors request to change the corresponding author's name as Ali A Alshatwi* from P. Subash-Babu in author list.
3.IDH2 knockdown sensitizes tumor cells to emodin cytotoxicity in vitro and in vivo.
Ku HJ1, Kwon OS1, Kang BS1, Lee DS1, Lee HS1, Park JW1. Free Radic Res. 2016 Apr 17:1-24. [Epub ahead of print]
Although reactive oxygen species (ROS) work as second messengers at sublethal concentrations, higher levels of ROS can kill cancer cells. Since cellular ROS levels are determined by a balance between ROS generation and removal, the combination of ROS generators and the depletion of reducing substances greatly enhance ROS levels. Emodin (1,3,8-trihydroxy-6-methyl anthraquinone), a natural anthraquinone derivative from the root and rhizome of numerous plants, is a ROS generator that induces apoptosis in cancer cells. The major enzyme to generate mitochondrial NADPH is the mitochondrial isoenzyme of NADP+-dependent isocitrate dehydrogenase (IDH2). In this report, we demonstrate that IDH2 knockdown effectively enhances emodin-induced apoptosis of mouse melanoma B16F10 cells through the regulation of ROS generation. Our findings suggest that suppression of IDH2 activity results in perturbation of the cellular redox balance and, ultimately, exacerbates emodin-induced apoptotic cell death in B16F10 cells.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C15H10O5
Molecular Weight (Monoisotopic Mass): 270.0528 Da
Molecular Weight (Avergae Mass): 270.2369 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C15H10O5
Molecular Weight (Monoisotopic Mass): 270.0528 Da
Molecular Weight (Avergae Mass): 270.2369 Da
LC-MS/MS Spectrum - DI-ESI-qTof , Positive
Experimental Conditions
Instrument Type: DI-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C15H10O5
Molecular Weight (Monoisotopic Mass): 270.0528 Da
Molecular Weight (Avergae Mass): 270.2369 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C15H10O5
Molecular Weight (Monoisotopic Mass): 270.0528 Da
Molecular Weight (Avergae Mass): 270.2369 Da
13C NMR Spectrum
Experimental Conditions
Solvent: H2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
