517-82-8

Usage

Uses

Used in Pharmaceutical Industry:
Echinochrome A is used as a therapeutic agent for its potential in treating diseases and conditions related to oxidative damage and inflammation. Its strong antioxidant and anti-inflammatory properties make it a promising candidate for pharmaceutical applications.
Used in Antioxidant Applications:
Echinochrome A is used as an antioxidant to protect against oxidative stress, which is implicated in various diseases and aging processes. Its ability to neutralize free radicals and reduce oxidative damage makes it a valuable component in health supplements and treatments.
Used in Anti-Inflammatory Applications:
Echinochrome A is used as an anti-inflammatory agent to reduce inflammation, which is a common factor in many chronic diseases and conditions. Its potential to alleviate inflammation could contribute to the management and treatment of inflammatory disorders.
Used in Research and Development:
Echinochrome A is used as a subject of research for exploring its therapeutic potential and understanding its mechanisms of action. Ongoing studies aim to uncover new applications and optimize its use in drug development and therapy.

InChI:InChI=1/C12H10O7/c1-2-3-6(13)4-5(8(15)7(3)14)10(17)12(19)11(18)9(4)16/h14,16-19H,2H2,1H3

Synthetic route

2-ethyl-5,8-dihydroxy-3,6,7-trimethoxy-[1,4]naphthoquinone (133039-72-2) → echinochrome A (517-82-8)

Conditions	Yield
With aluminium trichloride In nitrobenzene at 80℃; for 4h;	91%

3-ethyl-3-hydroxy-6,7-diisopropoxy-5,8-dimethoxy-1,4-naphthoquinone (409318-60-1) → echinochrome A (517-82-8)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 25℃;	41%

3-ethyl-1,2,4-trimethoxybenzene (99861-25-3) + dibenzoyloxy-maleic acid-anhydride → echinochrome A (517-82-8)

Conditions	Yield
at 180℃; in einer AlCl3-NaCl-Schmelze;

1,4-dimethoxy-2,3-diisopropoxybenzene (409318-58-7) → echinochrome A (517-82-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 59 percent / s-BuLi; TMEDA / tetrahydrofuran / 2 h / -78 °C 2: 0.33 h / 150 °C 3: CAN / diethyl ether; H2O 4: 0.35 g / air / 7 h 5: 41 percent / BBr3 / CH2Cl2 / -78 - 25 °C View Scheme

2-ethyl-3-isopropoxy-4-hydroxy-4-(2',5'-dimethoxy-3',4'-diisopropoxyphenyl)-2-cyclobuten-2-one (409318-57-6) → echinochrome A (517-82-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 0.33 h / 150 °C 2: CAN / diethyl ether; H2O 3: 0.35 g / air / 7 h 4: 41 percent / BBr3 / CH2Cl2 / -78 - 25 °C View Scheme

2-ethyl-3,6,7-triisopropoxy-5,8-dimethoxy-[1,4]naphthoquinone (944549-64-8) → echinochrome A (517-82-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.35 g / air / 7 h 2: 41 percent / BBr3 / CH2Cl2 / -78 - 25 °C View Scheme

2-ethyl-3,6,7-triisopropoxy-5,8-dimethoxy-naphthalene-1,4-diol (1027560-79-7) → echinochrome A (517-82-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: CAN / diethyl ether; H2O 2: 0.35 g / air / 7 h 3: 41 percent / BBr3 / CH2Cl2 / -78 - 25 °C View Scheme

2,3-dichloro-5,8-dihydroxy-[1,4]naphthoquinone (14918-69-5) → echinochrome A (517-82-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 66 percent / MnO2, conc. H2SO4 / 2 h / Ambient temperature 2: 40 percent / 2-methyl-propan-2-ol / Heating 3: 81 percent / 3 h / Heating 4: 74 percent / CsF, Al2O3 / 8 h / 90 - 95 °C 5: 91 percent / AlCl3 / nitrobenzene / 4 h / 80 °C View Scheme

3-ethyl-1,2,4-trimethoxybenzene (99861-25-3) → echinochrome A (517-82-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 61 percent / AlCl3, NaCl / 0.08 h / 190 °C 2: 81 percent / 3 h / Heating 3: 74 percent / CsF, Al2O3 / 8 h / 90 - 95 °C 4: 91 percent / AlCl3 / nitrobenzene / 4 h / 80 °C View Scheme

2,5,8-trihydroxy-6,7-dichloro-1,4-naphthoquinone (158526-26-2) → echinochrome A (517-82-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 40 percent / 2-methyl-propan-2-ol / Heating 2: 81 percent / 3 h / Heating 3: 74 percent / CsF, Al2O3 / 8 h / 90 - 95 °C 4: 91 percent / AlCl3 / nitrobenzene / 4 h / 80 °C View Scheme

2,5,8-trihydroxy-6,7-dichloro-3-ethyl-1,4-naphthoquinone (187149-22-0) → echinochrome A (517-82-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / 3 h / Heating 2: 74 percent / CsF, Al2O3 / 8 h / 90 - 95 °C 3: 91 percent / AlCl3 / nitrobenzene / 4 h / 80 °C View Scheme

6,7-dichloro-2-ethoxy-3-ethyl-5,8-dihydroxy-1,4-naphthoquinone (187149-23-1) → echinochrome A (517-82-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / CsF, Al2O3 / 8 h / 90 - 95 °C 2: 91 percent / AlCl3 / nitrobenzene / 4 h / 80 °C View Scheme

methanol (67-56-1) + C12H7Cl3O4 (888019-56-5) → 6-hydroxy-2,7-dichloro-3-ethylnaphthazarin (1093132-36-5) + 7-hydroxy-2,6-dichloro-3-ethylnaphthazarin (1093132-35-4) + echinochrome A (517-82-8)

Conditions	Yield
Stage #1: methanol; C12H7Cl3O4 With aluminum oxide; cesium fluoride Stage #2: Acidic conditions;

2-ethyl-5,8-dihydroxy-3,6,7-trimethoxy-[1,4]naphthoquinone (133039-72-2) → echinochrome A (517-82-8) + 2,5,8-trihydroxy-6,7-dimethoxy-3-ethyl-1,4-naphthaquinone (14990-99-9) + 2,6-dihydroxy-7-methoxy-3-ethylnaphthazarin + 2,7-dihydroxy-6-methoxy-3-ethylnaphthazarin

Conditions	Yield
Acidic conditions;

echinochrome A (517-82-8) → 2-bromo-3,5,6,7,8-pentahydroxy-1,4-naphthoquinone

Conditions	Yield
With bromine In tetrachloromethane at 20℃; for 48h; Irradiation;	65%

diazomethane (186581-53-3, 908094-01-9) + echinochrome A (517-82-8) → 2,5,8-trihydroxy-6,7-dimethoxy-3-ethyl-1,4-naphthaquinone (14990-99-9)

Conditions	Yield
With diethyl ether

diazomethane (186581-53-3, 908094-01-9) + echinochrome A (517-82-8) → 2,6-dihydroxy-7-methoxy-3-ethylnaphthazarin

Conditions	Yield
With diethyl ether

echinochrome A (517-82-8) + orthoformic acid triethyl ester (122-51-0) → 2,5,6-triethoxy-3-ethyl-5,8-dihydroxy-1,4-naphthoquinone

Conditions	Yield
Heating;

diazomethane (186581-53-3, 908094-01-9) + diethyl ether (60-29-7) + echinochrome A (517-82-8) → 2(or 6)-ethyl-5,8-dihydroxy-3,6,7(or 2,3,7)-trimethoxy-<1,4>naphthoquinone

diazomethane (186581-53-3, 908094-01-9) + diethyl ether (60-29-7) + echinochrome A (517-82-8) → 3.5.7.(or 6).8-tetrahydroxy-6(or 7)-methoxy-2-ethyl-naphthoquinone-(1.4)

diazomethane (186581-53-3, 908094-01-9) + diethyl ether (60-29-7) + echinochrome A (517-82-8) → 3.5.8-trihydroxy-6.7-dimethoxy-2-ethyl-naphthoquinone-(1.4)

echinochrome A (517-82-8) + water (7732-18-5) → 5.7.8-trihydroxy-1.2.3.4-tetraoxo-6-ethyl-tetralin

Conditions	Yield
beim Behandeln mit neutralisierter wss.NaOCl-Loesung;

diethyl ether (60-29-7) + echinochrome A (517-82-8) + Ag2O → 5.7.8-trihydroxy-1.2.3.4-tetraoxo-6-ethyl-tetralin

diethyl ether (60-29-7) + echinochrome A (517-82-8) + PbO2 → 5.7.8-trihydroxy-1.2.3.4-tetraoxo-6-ethyl-tetralin

echinochrome A (517-82-8) → 2-amino-3,5,6,7,8-pentahydroxy-1,4-naphthoquinone

Conditions	Yield
Multi-step reaction with 5 steps 1: bromine / tetrachloromethane / 48 h / 20 °C / Irradiation 2: diethyl ether / 20 °C 3: sodium azide / dimethyl sulfoxide / 3 h / 65 °C 4: water / Acidic conditions 5: hydrogen bromide / water / 3 h / 100 °C View Scheme

echinochrome A (517-82-8) → 2-amino-5,8-dihydroxy-3,6,7-trimethoxy-1,4-naphthoquinone

Conditions	Yield
Multi-step reaction with 4 steps 1: bromine / tetrachloromethane / 48 h / 20 °C / Irradiation 2: diethyl ether / 20 °C 3: sodium azide / dimethyl sulfoxide / 3 h / 65 °C 4: water / Acidic conditions View Scheme

echinochrome A (517-82-8) → C13H11N3O7

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine / tetrachloromethane / 48 h / 20 °C / Irradiation 2: diethyl ether / 20 °C 3: sodium azide / dimethyl sulfoxide / 3 h / 65 °C View Scheme

echinochrome A (517-82-8) → 2-bromo-3,6,7-trimethoxynaphthazarin

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine / tetrachloromethane / 48 h / 20 °C / Irradiation 2: diethyl ether / 20 °C View Scheme

Upstream product

• 409318-60-1 3-ethyl-3-hydroxy-6,7-diisopropoxy-5,8-dimethoxy-1,4-naphthoquinone 
• 67-56-1 methanol 
• 888019-56-5 C₁₂H₇Cl₃O₄ 
• 133039-72-2 2-ethyl-5,8-dihydroxy-3,6,7-trimethoxy-[1,4]naphthoquinone 
• 187149-23-1 6,7-dichloro-2-ethoxy-3-ethyl-5,8-dihydroxy-1,4-naphthoquinone 
• 187149-22-0 6,7-dichloro-3-ethyl-2,5,8-trihydroxy-1,4-naphthoquinone 
• 158526-26-2 6,7-dichloro-2,5,8-trihydroxy-1,4-naphthoquinone 
• 99861-25-3 3-ethyl-1,2,4-trimethoxybenzene 
• 14918-69-5 2,3-dichloro-5,8-dihydroxy-[1,4]naphthoquinone 
• 1027560-79-7 2-ethyl-3,6,7-triisopropoxy-5,8-dimethoxy-naphthalene-1,4-diol 
• 944549-64-8 2-ethyl-3,6,7-triisopropoxy-5,8-dimethoxy-[1,4]naphthoquinone 
• 409318-57-6 2-ethyl-3-isopropoxy-4-hydroxy-4-(2',5'-dimethoxy-3',4'-diisopropoxyphenyl)-2-cyclobuten-2-one 
• 409318-58-7 1,4-dimethoxy-2,3-diisopropoxybenzene 

Relevant academic research and scientific papers

Squaric acid ester-based total synthesis of echinochrome A

The total synthesis of echinochrome A is described. Both key intermediates 5 and 8 were efficiently prepared from diisopropyl squarate 7. Nucleophilic addition of aryllithium 8 to 5, followed by thermal ring-expansion/cyclization of the 1,2-adduct 4, furnished hydroquinone 3. Oxidation and full deprotection of 3 gave the title compound.

Synthesis of some hydroxynaphthazarins and their cardioprotective effects under ischemia-reperfusion in vivo

A series of hydroxynaphthazarins has been synthesized. Some of them were found in in vivo experiments to be protectors of myocardium under ischemia-reperfusion and to reduce the infarction zone by 50% without any adverse effect. All compounds exhibit a moderate or small toxicity and are active in low doses.

Cytotoxic activity of intermediates and side products of echinochrome synthesis

The cytotoxic activity of the principal intermediates and side products of echinochrome synthesis toward gametes of the sea urchin Strogylocentrotus intermedius was studied. Di-and trichloro naphthazarin derivatives with two vicinal Cl atoms were the most