The Introduction of Quinones:

Quinone contains two carbonyl groups, >C=O, either adjacent or separated by a vinylene group, ―CH = CH―, in a six-membered unsaturated ring. In a few quinones, the carbonyl groups are located in different rings. Quinones are not aromatic compounds but are conjugated cyclic diketones. Quinones and the related aromatic arenols are readily interconverted, and their chemistry is largely interdependent. Quinones are yellow pigments and are highly unstable, being both strong electrophiles and potent oxidants.

Quinones are usually prepared by the oxidation of aromatic amines, polyhydric phenols, and polynuclear hydrocarbons. The most important characteristic reaction of quinones is the reduction to the corresponding dihydroxy form. In an acidic solution, p-benzoquinone is reduced reversibly to hydroquinone. Quinones are considered potent genotoxins because of their ability to generate reactive oxygen species and also create DNA adducts leading to gene mutation. In addition, quinones may lead to paralysis of the medullary centers and coma. Albuminuria and hematuria may occur.

Quinones are a ubiquitous class of compounds found in several natural products, including plants, fungi, and bacteria. Most of these naturally occurring quinones are synthesized via the shikimate or polyketide pathways, which are absent in animals. In mammals, quinones can be formed via the metabolism of endogenous substances, xenobiotics, and drugs. Quinones have several beneficial effects. Quinones are electron carriers that play a role in photosynthesis. As vitamins, they represent a class of molecules that prevent and treat several illnesses, such as osteoporosis and cardiovascular diseases. Quinones, through their antioxidant activity, improve general health conditions.

 

Fig 1 Quinones

Classification of Quinones:

 

There are three main groups of quinones: the benzoquinones (1,4-benzoquinone and 1,2-benzoquinone), the naphthoquinones, and the anthraquinones.

--Benzoquinones: Benzoquinones are a class of natural quinones found chiefly in higher plants, fungi, bacteria and animal kingdom.  All of them have in common a benzene ring with C = O groups. Benzoquinone appears as a yellowish-colored crystalline solid with a pungent, irritating odor. Examples of benzoquinones are: embelin, rapanone, and primin. They are involved in important biological functions such as bioenergetic transport, oxidative phosphorylation and electron transport processes. Benzoquinone is found in bacterial fermentations and may readily be identified by its characteristic ultraviolet and infrared spectra. Poisonous by ingestion or inhalation of benzoquinone vapors. May severely damage skin, eyes and mucous membranes.

--Naphthoquinones: The structural base of naphthoquinones, as their name implies, is the naphthenic ring, that is, naphthoquinones are a group of aromatic compounds derived from naphthalene, characterized by a conjugated cyclic dione structure that can exist in either a 1,4 or 1,2 arrangement. Naphthoquinone is the major bioactive compound isolated from the alkanet plant. Examples of naphthoquinones are plumbagin, lawsona and juglone. Naturally occurring naphthoquinones and their synthetic derivatives constitute a significant group of bioactive substances. Vitamins K1 and K2 play a crucial role in hemostasis and facilitate bone mineralization and have been extensively studied with regard to their biological activities. In addition, it was found that some naphthoquinone compounds have anticancer activity.

--Anthraquinones: Anthraquinones are characterized by having the anthracene ring as their structural base; that is, a set of three benzene rings linked by their sides. Anthraquinones typically occur in their glycosidic forms. Examples of anthraquinones are barbaloin, alizarin and chrysophanol. Biosynthetic pathways such as the polyketide pathway, chorismite, and O-succinylbenzoic acid pathway were utilized to produce anthraquinones. These metabolites exist as O- and C-glycosides and aglycons in the aerial parts and roots. Anthraquinones are widespread in nature but are most often associated with plants. Anthraquinones possess a lot of applications as they are used in the textile industry. 9,10-Anthraquinone is used as a bird repellent on seeds and also as a gas generator in satellite balloons. Fungal anthraquinones are widely used as dyes for natural and synthetic fibers. Further, anthraquinones also find applications as semiconductors in microelectronics. Many of them possess antibacterial, antiparasitic, insecticidal, fungicidal, and antiviral properties. They are also used as anticancer agents. Anthraquinones are active components of many plant blends which are used as medicines and exhibit laxative, diuretic, estrogenic, and immunomodulatory effects.

 

Product Description:

 

Natural or synthetic quinones show biological and pharmacological activity against microbes and parasites (rhein- and saprorthoquinone, atovaquone). Our range of quinones is meticulously formulated to provide exceptional reactivity and versatility. These high-purity reactants serve as powerful oxidizing agents, facilitating a wide array of chemical reactions. Laxative effects were reported for the sennosides as well as the inhibitory activity of principal mediators of inflammation (arnebinone and arnebifuranone). Quinone representatives emodin and juglone, have therapeutic potential for tumor treatment, and tanshinone for the prevention and treatment of cardiovascular diseases. Whether you require them for pharmaceutical synthesis, polymerization, or organic chemistry applications, our quinone products can meet your requirements. Unlock the limitless potential of chemistry with our quinone Products. You can experience reliability, excellence, and innovation by choosing ALL Chemistry.

 

Product Category

CAS Number

Product Name

Purity

Molecular Formula

Quinones

117-02-2

Rubiadin

99%

C15H10O4

Quinones

24502-78-1

Acetylshikonin

>98%

C18H18O6

Quinones

5162-01-6

Arnebin 1

>95%

C21H22O6

Quinones

568-72-9

Tanshinone IIA

98%

C19H18O3

Quinones

33440-64-1

BI-Lawsone

95%

C20H10O6

Quinones

518-82-1

Emodin

95%

C15H10O5

Quinones

481-74-3

Chrysophanol

≥98%

C15H10O4

Quinones

478-43-3

Rhein

>98%

C15H8O6

Quinones

303-98-0

Coenzyme Q10

>98%

C59H90O4

Quinones

517-89-5

Shikonin

>98%

C16H16O5

Please contact us for further information if you have a purchase requirement, including pricing, samples, and technical specifications. We look forward to providing our quinone products. In addition, ALL Chemistry provides a seamless one-stop process development service, ALL Chemistry can provide synthesis and fine chemical services if the existing products can't meet your needs, we have expertise in the synthesis of a broad array of customized molecules, and we offer lab scale custom synthesis, biosynthesis, bioconjugation and analytical services.

Product Advantage:

 

Provide quality-guaranteed products, all products are provided with a quality analysis report (COA), use advanced instruments such as MS(Mass Spectrometry), HPLC and NMR (Nuclear Magnetic Resonance) for quality inspection.

Professional and reliable packaging ensures the safety and stability of products from transportation, storage to use.

ALL Chemistry provides quinone products with a purity greater than 95%.

ALL Chemistry guarantees the confidence to put our products in a risk-free environment for worldwide scientists and researchers.

Access our expertise and technical support from anywhere, anytime.

 

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