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
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
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
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
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
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