517-82-8

Basic information

• Product Name: echinochrome A
• Synonyms: echinochrome A
• CAS NO: 517-82-8
• Molecular Formula: C₁₂H₁₀O₇
• Molecular Weight: 532.408
• Mol File: 517-82-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 220° (some decompn)
• Boiling Point: 329.41°C (rough estimate)
• Flash Point: 87.4°C
• Appearance: /
• Density: 1.3494 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4455 (estimate)
• PKA: 5.10±0.58(Predicted)
• CAS DataBase Reference: echinochrome A(CAS DataBase Reference)
• NIST Chemistry Reference: echinochrome A(517-82-8)
• EPA Substance Registry System: echinochrome A(517-82-8)

Safety Data

• Hazardous Substances Data: 517-82-8(Hazardous Substances Data)

Usage

General Description

Echinochrome A is a naturally occurring chemical compound found in sea urchins and certain other marine organisms. It is a bicyclic polyphenol that exhibits strong antioxidant and anti-inflammatory properties. Echinochrome A has been shown to have potential benefits for human health, including the ability to protect against oxidative stress and reduce inflammation. It has also been investigated for its potential use in pharmaceuticals, particularly in the treatment of various diseases and conditions related to oxidative damage and inflammation. Research into the therapeutic potential of echinochrome A is ongoing, and this compound shows promise as a valuable natural resource for the development of new drugs and therapies.

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

• 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 
• 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 
• 409318-60-1 3-ethyl-3-hydroxy-6,7-diisopropoxy-5,8-dimethoxy-1,4-naphthoquinone 
• 99861-25-3 3-ethyl-1,2,4-trimethoxybenzene 
• 158526-26-2 6,7-dichloro-2,5,8-trihydroxy-1,4-naphthoquinone 
• 1027560-79-7 2-ethyl-3,6,7-triisopropoxy-5,8-dimethoxy-naphthalene-1,4-diol 
• 14918-69-5 2,3-dichloro-5,8-dihydroxy-[1,4]naphthoquinone 

Relevant articles and documents

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.

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