Haloquinone
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01313 |
| CAS | 80902-01-8 |
| Molecular Weight | 296.27 |
| Molecular Formula | C17H12O5 |
Online Inquiry
Description
It is produced by the strain of Streptomyces venezuelae subsp. xanthophaeus Tu 2115. It is a quinone antibiotic. It has strong anti-bacterial activity on Halobacteria, and also has effects on gram-positive bacteria and mycoplasma.
Specification
| Synonyms | 3-Acetyl-1,8-dihydroxy-2-methyl-9,10-phenanthrenequinone; 9,10-Phenanthrenedione, 3-acetyl-1,8-dihydroxy-2-methyl- |
| IUPAC Name | 3-acetyl-1,8-dihydroxy-2-methylphenanthrene-9,10-dione |
| Canonical SMILES | CC1=C(C=C2C3=C(C(=CC=C3)O)C(=O)C(=O)C2=C1O)C(=O)C |
| InChI | InChI=1S/C17H12O5/c1-7-10(8(2)18)6-11-9-4-3-5-12(19)13(9)16(21)17(22)14(11)15(7)20/h3-6,19-20H,1-2H3 |
| InChI Key | CPYFLMXPZMBECD-UHFFFAOYSA-N |
Properties
| Appearance | Dark Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycoplasma |
| Boiling Point | 614.2 °C at 760 mmHg |
| Melting Point | 226 °C |
| Density | 1.454 g/cm3 |
| Solubility | Soluble in Ethanol, Chloroform, Methanol |
Reference Reading
1. Mechanistic Study on Oxidative DNA Damage and Modifications by Haloquinoid Carcinogenic Intermediates and Disinfection Byproducts
Ben-Zhan Zhu, Miao Tang, Chun-Hua Huang, Li Mao, Jie Shao Chem Res Toxicol. 2021 Jul 19;34(7):1701-1712. doi: 10.1021/acs.chemrestox.1c00158. Epub 2021 Jun 18.
Haloquinones (XQs) are a group of carcinogenic intermediates of the haloaromatic environmental pollutants and newly identified chlorination disinfection byproducts (DBPs) in drinking water. The highly reactive hydroxyl radicals/alkoxyl radicals and quinone enoxy/ketoxy radicals were found to arise in XQs and H2O2 or organic hydroperoxides system, independent of transition-metal ions. However, it was not clear whether these haloquinoid carcinogens and hydroperoxides can cause oxidative DNA damage and modifications, and if so, what are the underlying molecular mechanisms. We found that 8-oxodeoxyguanosine (8-oxodG), DNA strand breaks, and three methyl oxidation products could arise when DNA was treated with tetrachloro-1,4-benzoquinone and H2O2 via a metal-independent and intercalation-enhanced oxidation mechanism. Similar effects were observed with other XQs, which are generally more efficient than the typical Fenton system. We further extended our studies from isolated DNA to genomic DNA in living cells. We also found that potent oxidation of DNA to the more mutagenic imidazolone dIz could be induced by XQs and organic hydroperoxides such as t-butylhydroperoxide or the physiologically relevant hydroperoxide 13S-hydroperoxy-9Z,11E-octadecadienoic acid via an unprecedented quinone-enoxy radical-mediated mechanism. These findings should provide new perspectives to explain the potential genotoxicity, mutagenesis, and carcinogenicity for the ubiquitous haloquinoid carcinogenic intermediates and DBPs.
2. Haloquinone Chloroimides as Toxic Disinfection Byproducts Identified in Drinking Water
Shuo Xu, Shaoyang Hu, Lizhong Zhu, Wei Wang Environ Sci Technol. 2021 Dec 21;55(24):16347-16357. doi: 10.1021/acs.est.1c01690. Epub 2021 Dec 9.
Haloquinone chloroimides (HQCs) are suspected to be highly toxic contaminants, and their production during drinking water disinfection is predicted. However, HQC disinfection byproducts (DBPs) have not been reported in drinking water to date because of analytical limitations. In this study, we developed an analytical method to detect five HQCs, including 2,6-dichloroquinone-4-chloroimide (2,6-DCQC), 2,6-dibromoquinone-4-chloroimide (2,6-DBQC), 2-chloroquinone-4-chloroimide (2-CQC), 3-chloroquinone-4-chloroimide (3-CQC), and 2,6-dichloroquinone-3-methyl-chloroimide (2,6-DCMQC). This method combined a derivatization reaction of HQCs with phenol in alkaline solutions to produce halogenated indophenols, a solid-phase extraction pretreatment using hydrophilic-lipophilic balanced (HLB) cartridges, and a multiple reaction monitoring (MRM) method for quantification. The method was demonstrated to be sensitive and accurate with recoveries of 71-85% and limits of detection of 0.1-0.2 ng/L for the five tested HQCs. Using this method, five tested HQCs were identified in drinking water samples from nine water treatment plants and water distribution systems as new DBPs at concentrations of up to 23.1 ng/L. The cytotoxicity of the five tested HQCs in HepG2 cells was higher than or comparable to that of 2,6-dichloro-1,4-benzoquinone (2,6-DCBQ), an emerging DBP that was hundreds to thousands of times more toxic than regulated DBPs. This study presents the first analytical method for HQC DBPs in drinking water and the first set of occurrence and cytotoxicity data of HQC DBPs.
3. Toward the Total Synthesis of Alpkinidine: Synthesis of Haloquinone CE Ring System Synthons and Attempted Nucleophilic Bisannulation
Marco Buccini, Louisa Tham, Francis Dhoro, Brian W Skelton, Craig M Williams, Matthew J Piggott ACS Omega. 2022 Jun 1;7(23):19080-19092. doi: 10.1021/acsomega.2c02116. eCollection 2022 Jun 14.
Model chemistry involving the bisannulation of 2,3-dichloro-1,4-naphthoquinone with the ester enolate derived from ethyl o-nitrophenylacetic acid, which rapid assembled the ABCD ring system of a pentacyclic pyrroloacridine, has been applied to the attempted synthesis of the marine natural product alpkinidine. The reaction of ethyl o-nitrophenylacetic acid with 6,7-dichloro-2-methylisoquinoline-1,5,8(2H)-trione, required to extend the model strategy to alpkinidine, was unfruitful, giving only complex mixtures. Efforts to direct the regiochemistry of the key Michael substitution step using 6-bromo-2-methylisoquinoline-1,5,8(2H)-trione afforded an adduct sharing the complete carbon skeleton of alpkinidine, but this could not be elaborated to the natural product.
Recommended Products
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-03755 | Actinomycin D | 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 ╳
