2,5-Dimethoxybenzoquinone
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-05678 |
| CAS | 3117-03-1 |
| Molecular Weight | 168.15 |
| Molecular Formula | C8H8O4 |
| Purity | >98.0%(GC) |
Online Inquiry
Description
2,5-Dimethoxybenzoquinone is a natural product found in Phyllostachys nigra, Gloeophyllum sepiarium, and other organisms.
Specification
| Synonyms | 2,5-Dimethoxy-1,4-benzoquinone; Thermophillin |
| Storage | Store under inert gas |
| IUPAC Name | 2,5-dimethoxycyclohexa-2,5-diene-1,4-dione |
| Canonical SMILES | COC1=CC(=O)C(=CC1=O)OC |
| InChI | InChI=1S/C8H8O4/c1-11-7-3-6(10)8(12-2)4-5(7)9/h3-4H,1-2H3 |
| InChI Key | RMMPZDDLWLALLJ-UHFFFAOYSA-N |
Properties
| Appearance | Light yellow to Brown powder to crystal |
| Boiling Point | 311.1ºC at 760 mmHg |
| Melting Point | 289 °C |
| Density | 1.24 g/cm3 |
Reference Reading
1.Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis.
Ishikawa NK1, Tahara S2, Namatame T2, Farooq A2, Fukushi Y2. Braz J Microbiol. 2014 Mar 10;44(4):1285-90. eCollection 2013.
Enokipodins A, B, C, and D are antimicrobial sesquiterpenes isolated from the mycelial culture medium of Flammulina velutipes, an edible mushroom. The presence of a quaternary carbon stereocenter on the cyclopentane ring makes enokipodins A-D attractive synthetic targets. In this study, nine different cytochrome P450 inhibitors were used to trap the biosynthetic intermediates of highly oxygenated cuparene-type sesquiterpenes of F. velutipes. Of these, 1-aminobenzotriazole produced three less-highly oxygenated biosynthetic intermediates of enokipodins A-D; these were identified as (S)-(-)-cuparene-1,4-quinone and epimers at C-3 of 6-hydroxy-6-methyl-3-(1,2,2-trimethylcyclopentyl)-2-cyclohexen-1-one. One of the epimers was found to be a new compound.
2.Modulation of quinone PCET reaction by Ca2+ ion captured by calix[4]quinone in water.
Kim YR1, Kim RS, Kang SK, Choi MG, Kim HY, Cho D, Lee JY, Chang SK, Chung TD. J Am Chem Soc. 2013 Dec 18;135(50):18957-67. doi: 10.1021/ja410406e. Epub 2013 Dec 5.
Calix[4]arene-triacid-monoquinone (CTAQ), a quinone-containing water-soluble ionophore, was utilized to investigate how proton-coupled electron transfer (PCET) reactions of quinones were influenced by redox-inactive metal ions in aqueous environment. This ionophoric quinone derivative captured a Ca(2+) ion that drastically altered the voltammetric behavior of quinone, showing a characteristic response to pH and unique redox wave separation. Spectroelectrochemistry verified significant stabilization of the semiquinone, and electrocatalytic currents were observed in the presence of Ca(2+)-free CTAQ. Using digital simulation of cyclic voltammograms to clarify how the thermodynamic properties of quinones were altered, a simple scheme was proposed that successfully accounted for all the observations. The change induced by Ca(2+) complexation was explained on the basis of the combined effects of the electrostatic influence of the captured metal ion and hydrogen bonding of water molecules with the support of DFT calculation.
3.Effect of human glutathione S-transferase hGSTP1-1 polymorphism on the detoxification of reactive metabolites of clozapine, diclofenac and acetaminophen.
Dragovic S1, Venkataraman H, Begheijn S, Vermeulen NP, Commandeur JN. Toxicol Lett. 2014 Jan 13;224(2):272-81. doi: 10.1016/j.toxlet.2013.10.023. Epub 2013 Oct 31.
Recent association studies suggest that genetically determined deficiencies in GSTs might be a risk factor for idiosyncratic adverse drug reactions resulting from the formation of reactive drug metabolites. hGSTP1-1 is polymorphic in the human population with a number of single nucleotide polymorphisms that yield an amino acid change in the encoded protein. Three allelic variants of hGSTP1-1 containing an Ile105Val or Ala114Val substitution, or a combination of both, have been the most widely studied and showed different activity when compared to wild-type hGSTP1-1*A (Ile105/Ala114). In the present study, we studied the ability of these allelic variants to catalyze the GSH conjugation of reactive metabolites of acetaminophen, clozapine, and diclofenac formed by bioactivation in in vitro incubations by human liver microsomes and drug metabolizing P450 BM3 mutants. The results show that effects of the change of amino acid at residue 105 and 114 on conjugation reactions were substrate dependent.
4.Interaction of bisphenol A 3,4-quinone metabolite with glutathione and ribonucleosides/deoxyribonucleosides in vitro.
Wu Q1, Fang J1, Li S1, Wei J1, Yang Z1, Zhao H1, Zhao C1, Cai Z2. J Hazard Mater. 2016 Mar 7. pii: S0304-3894(16)30230-8. doi: 10.1016/j.jhazmat.2016.03.015. [Epub ahead of print]
Bisphenol A is a monomer used in the manufacture of polycarbonate plastic products, epoxy resin-based food can liners and flame retardants. To determine the genotoxic potential of bisphenol A, the mechanism of the reactions between the reactive electophilic bisphenol A 3,4-quinone (BPAQ) with glutathione and ribonucleosides/deoxyribonucleosides were studied. The obtained results demonstrated that BPAQ reacted with 2'-deoxyguanosine (dG)/guanosine (G), 2'-deoxyadenosine (dA)/adenosine (A), but not with 2'-deoxycytidine (dC)/cytidine (C) and thymidine (T)/uridine (U) in aqueous acetic acid. The reactions were accompanied by loss of deoxyribose, and the rate of depurination by deoxyribonucleoside adducts were faster than that of ribonucleoside adducts. In mixtures of ribonucleosides and deoxyribonucleosides treated with BPAQ, reactions occurred more readily with dG/G than dA/A. The structures of the modified bases were confirmed by electrospray ionization tandem mass spectrometry (ESI-MS/MS).
Recommended Products
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
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:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
