4693-19-0

Basic information

• Product Name: 2',5'-dihydroxyoctanophenone
• Synonyms: 2',5'-dihydroxyoctanophenone;1-(2,5-Dihydroxyphenyl)-1-octanone;1-Octanone, 1-(2,5-dihydroxyphenyl)-;Einecs 225-152-7
• CAS NO: 4693-19-0
• Molecular Formula: C₁₄H₂₀O₃
• Molecular Weight: 236.3068
• EINECS: 225-152-7
• Mol File: 4693-19-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 393.5°Cat760mmHg
• Flash Point: 206°C
• Appearance: /
• Density: 1.089g/cm³
• CAS DataBase Reference: 2',5'-dihydroxyoctanophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2',5'-dihydroxyoctanophenone(4693-19-0)
• EPA Substance Registry System: 2',5'-dihydroxyoctanophenone(4693-19-0)

Safety Data

• Hazardous Substances Data: 4693-19-0(Hazardous Substances Data)

Usage

General Description

2',5'-dihydroxyoctanophenone is a chemical compound with the molecular formula C12H18O3. It is a phenolic ketone and a derivative of octanophenone. 2',5'-dihydroxyoctanophenone is known for its antioxidant and anti-inflammatory properties, and has been studied for potential application in skincare and pharmaceutical products. Additionally, 2',5'-dihydroxyoctanophenone has been investigated for its potential role in treating conditions related to oxidative stress and inflammation, making it a promising candidate for future research and development in the field of medical and cosmetic science.

Upstream product

• 21182-58-1 2-Hydroxy-5-octanoyloxy-octanophenon 
• 111-64-8 n-octanoic acid chloride 
• 124-13-0 Octanal 
• 106-51-4 p-benzoquinone 
• 150-78-7 1,4-dimethoxybezene 
• 124-07-2 Octanoic acid 
• 123-31-9 hydroquinone 

Downstream Products

• 21182-43-4 2-Octyl-benzochinon-(1,4) 
• 21182-53-6 2,5-Bis-(methylamino)-3-octyl-benzochinon-(1.4) 
• 21182-47-8 2,5-dihydroxy-3-octyl-2,5-cyclohexadiene-1,4-dione 
• 895-21-6 2-Octyl-hydrochinon-5-sulfonsaeure 
• 63134-27-0 1-(2,5-dihydroxy-4-octyl-phenyl)-octan-1-one 
• 10551-36-7 2,5-dioctylhydroquinone 
• 1706-69-0 n-octylhydroquinone 
• 63494-67-7 1-(2,5-dihydroxy-phenyl)-octan-1-ol 

Relevant articles and documents

Synthesis and pharmacological evaluation of acylhydroquinone derivatives as potent antiplatelet agents

Platelets are the smallest blood cells, and their activation (platelet cohesion or aggregation) at sites of vascular injury is essential for thrombus formation. Since the use of antiplatelet therapy is an unsolved problem, there are now focused and innovative efforts to develop novel antiplatelet compounds. In this context, we assessed the antiplatelet effect of an acylhydroquinone series, synthesized by Fries rearrangement under microwave irradiation, evaluating the effect of diverse acyl chain lengths, their chlorinated derivatives, and their dimethylated derivatives both in the aromatic ring and also the effect of the introduction of a bromine atom at the terminus of the acyl chain. Findings from a primary screening of cytotoxic activity on platelets by lactate dehydrogenase assay identified 19 non-toxic compounds from the 27 acylhydroquinones evaluated. A large number of them showed IC50 values less than 10 μM acting against specific pathways of platelet aggregation. The highest activity was obtained with compound 38, it exhibited sub-micromolar IC50 of 0.98 ± 0.40, 1.10 ± 0.26, 3.98 ± 0.46, 6.79 ± 3.02 and 42.01 ± 3.48 μM against convulxin-, collagen-, TRAP-6-, PMA- and arachidonic acid-induced platelet aggregation, respectively. It also inhibited P-selectin and granulophysin expression. We demonstrated that the antiplatelet mechanism of compound 38 was through a decrease in a central target in human platelet activation as in mitochondrial function, and this could modulate a lower response of platelets to activating agonists. The results of this study show that the chemical space around ortho-carbonyl hydroquinone moiety is a rich source of biologically active compounds, signaling that the acylhydroquinone scaffold has a promising role in antiplatelet drug research.

Synthesis of antiplatelet ortho-carbonyl hydroquinones with differential action on platelet aggregation stimulated by collagen or TRAP-6

Cardiovascular diseases are the leading cause of death in the world. Platelets have a major role in cardiovascular events as they bind to the damaged endothelium activating and forming thrombi. Although some hydroquinone scaffold-containing compounds have known antiplatelet activities, currently there is a lack of evidence on the antiplatelet activity of hydroquinones carrying electron attractor groups. In this work, we evaluate the antiplatelet effect of a series of ortho-carbonyl hydroquinone derivatives on cytotoxicity and function of human platelets, using collagen and thrombin receptor activator peptide 6 (TRAP-6) as agonists. Our structure-activity relationship study shows that gem-diethyl/methyl substitutions and the addition/modifications of the third ring of ortho-carbonyl hydroquinone scaffold influence on the selective index (IC50 TRAP-6/IC50 Collagen) and the inhibitory capacity of platelet aggregation. Compounds 3 and 8 inhibit agonist-induced platelet aggregation in a non-competitive manner with IC50 values of 1.77 ± 2.09 μM (collagen) and 11.88 ± 4.59 μM (TRAP-6), respectively and show no cytotoxicity. Both compounds do not affect intracellular calcium levels and mitochondrial bioenergetics. Consistently, they reduce the expression of P-selectin, activation of glycoprotein IIb/IIIa, and release of adenosine triphosphate and CD63 from platelet. Our findings may be used for further development of new drugs in platelet-related thrombosis diseases.

Biochemical studies on benzoquinone derivatives. V. Structure-activity relationship between benzoquinone derivatives and inhibition of respiration of rat liver intact mitochondria.

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