Product Name

  • Name

    Pyrroloquinoline quinone

  • EINECS 200-001-8
  • CAS No. 72909-34-3
  • Article Data28
  • CAS DataBase
  • Density 1.963 g/cm3
  • Solubility
  • Melting Point
  • Formula C14H6N2O8
  • Boiling Point 1018.6 °C at 760 mmHg
  • Molecular Weight 330.21
  • Flash Point 569.8 °C
  • Transport Information
  • Appearance
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 72909-34-3 (Pyrroloquinoline quinone)
  • Hazard Symbols
  • Synonyms 2,7,9-Tricarboxy-4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline;4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid;Coenzyme PQQ;Methoxatin;Methoxatine;PQQ;Pyrroloquinoline quinone;
  • PSA 174.72000
  • LogP 0.55030

Synthetic route

trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate
74447-88-4

trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
With sodium carbonate In water at 30℃; for 24h;100%
With water; potassium carbonate In water at 25 - 80℃; Green chemistry; Industrial scale;91%
With potassium carbonate In water at 25 - 80℃; for 12h;91%
5,5-Dimethoxy-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester
78939-40-9

5,5-Dimethoxy-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
With potassium carbonate In water at 85℃; for 4h;98%
4,5-Dihydro-4,5-dioxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester
80721-47-7

4,5-Dihydro-4,5-dioxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Stage #1: 4,5-Dihydro-4,5-dioxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester With lithium hydroxide; water In tetrahydrofuran at 0 - 17℃; for 31.5h;
Stage #2: With hydrogenchloride; potassium chloride In tetrahydrofuran; water at 0℃; for 1h; pH=5.3 - 6;
Stage #3: With sulfuric acid In water at 20℃; for 2.5h;		97%
With lithium hydroxide In tetrahydrofuran; water at 25℃; for 6h;89%
With lithium hydroxide In tetrahydrofuran for 6.5h;89%
4,5-dihydroxy-4,5-dioxo-1H-pyrrolo{2,3-f}quinoline-2,7,9-tricarboxylic acid
79127-57-4

4,5-dihydroxy-4,5-dioxo-1H-pyrrolo{2,3-f}quinoline-2,7,9-tricarboxylic acid

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
With dihydrogen peroxide at 35℃; for 24h;86.5%
With acetate and phosphate buffer; potassium chloride; oxygen In water; dimethyl sulfoxide at 30℃; Rate constant; Kinetics; Mechanism;
5-Methoxy-1H-pyrrolo<2,3-f>quinoline-2,7,9-tricarboxylic acid
116451-31-1

5-Methoxy-1H-pyrrolo<2,3-f>quinoline-2,7,9-tricarboxylic acid

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In 1,2-dichloro-ethane at 25℃; for 24h;19.01%
5-Methoxy-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester
133706-80-6

5-Methoxy-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 69 percent / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 0.5 h / -3 °C
2: 63 percent / LiOH*H2O / tetrahydrofuran; H2O / 20.5 h / Ambient temperature; purification with conc. H2SO4
View Scheme
Multi-step reaction with 2 steps
1: copper(II) acetate monohydrate / water / 1 h / -5 °C
2: lithium hydroxide monohydrate / water; tetrahydrofuran / 32 h / 16 °C
View Scheme
6-amino-5-methoxy-2-ethoxycarbonylindole
107575-60-0

6-amino-5-methoxy-2-ethoxycarbonylindole

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 73 percent / CH2Cl2 / 8 h / Ambient temperature
2: 94.5 percent / Cu(OAc)2*H2O, HCl(g)/air / CH2Cl2
3: 69 percent / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 0.5 h / -3 °C
4: 63 percent / LiOH*H2O / tetrahydrofuran; H2O / 20.5 h / Ambient temperature; purification with conc. H2SO4
View Scheme
Multi-step reaction with 3 steps
1.1: dichloromethane / 12 h / 20 °C
1.2: 8 h / 20 °C
2.1: copper(II) acetate monohydrate / water / 1 h / -5 °C
3.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 32 h / 16 °C
View Scheme
6-(Formylamino)-5-methoxyindol-2-carbonsaeure-ethylester
119825-27-3

6-(Formylamino)-5-methoxyindol-2-carbonsaeure-ethylester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 84.5 percent / 18percent aq. HCl / acetone / 4 h / 80 °C
2: 73 percent / CH2Cl2 / 8 h / Ambient temperature
3: 94.5 percent / Cu(OAc)2*H2O, HCl(g)/air / CH2Cl2
4: 69 percent / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 0.5 h / -3 °C
5: 63 percent / LiOH*H2O / tetrahydrofuran; H2O / 20.5 h / Ambient temperature; purification with conc. H2SO4
View Scheme
Multi-step reaction with 4 steps
1.1: 1-(3-sulfopropyl)pyridinium phosphotungstate; benzylamine / 1.5 h / 140 °C / Microwave irradiation
2.1: dichloromethane / 12 h / 20 °C
2.2: 8 h / 20 °C
3.1: copper(II) acetate monohydrate / water / 1 h / -5 °C
4.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 32 h / 16 °C
View Scheme
4-oxo-pent-2-enedioic acid dimethyl ester
78939-37-4

4-oxo-pent-2-enedioic acid dimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 73 percent / CH2Cl2 / 8 h / Ambient temperature
2: 94.5 percent / Cu(OAc)2*H2O, HCl(g)/air / CH2Cl2
3: 69 percent / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 0.5 h / -3 °C
4: 63 percent / LiOH*H2O / tetrahydrofuran; H2O / 20.5 h / Ambient temperature; purification with conc. H2SO4
View Scheme
Multi-step reaction with 5 steps
1: CH2Cl2 / 7 h / 25 °C
2: dry hydrogen chloride / CH2Cl2 / 10 h
3: 60 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.17 h / 0 °C
4: 92 percent / p-tuluenesulfonic acid / methanol / 4 h / Heating
5: 98 percent / 0.5 M K2CO3 / H2O / 4 h / 85 °C
View Scheme
Multi-step reaction with 3 steps
1.1: dichloromethane / 12 h / 20 °C
1.2: 8 h / 20 °C
2.1: copper(II) acetate monohydrate / water / 1 h / -5 °C
3.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 32 h / 16 °C
View Scheme
Multi-step reaction with 5 steps
1: sulfuric acid / dichloromethane / 5 h / Reflux
2: potassium carbonate / 2-methyltetrahydrofuran / 5 h / Reflux
3: zinc; acetic acid / 10 h / 50 °C
4: sodium hydroxide / 24 h / 25 °C
5: ammonium cerium (IV) nitrate / 1,2-dichloro-ethane / 24 h / 25 °C
View Scheme
cis-6,7,8,9-Tetrahydro-9-hydroxy-5-methoxy-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester

cis-6,7,8,9-Tetrahydro-9-hydroxy-5-methoxy-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94.5 percent / Cu(OAc)2*H2O, HCl(g)/air / CH2Cl2
2: 69 percent / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 0.5 h / -3 °C
3: 63 percent / LiOH*H2O / tetrahydrofuran; H2O / 20.5 h / Ambient temperature; purification with conc. H2SO4
View Scheme
ethyl 5-hydroxyindole-2-carboxylate
24985-85-1

ethyl 5-hydroxyindole-2-carboxylate

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 94 percent / Fremy's salt, KH2PO4 / acetonitrile; H2O / 0.5 h / 20 °C
2: 47 percent / Et3N / tetrahydrofuran / 1 h / 20 °C
3: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min
4: 85 percent / trifluoroacetic acid / 1 h / 20 °C
5: 82 percent / chlorobenzene / 4 h / 131 °C
6: LiOH
View Scheme
Multi-step reaction with 7 steps
1: 94 percent / Fremy's salt, KH2PO4 / acetonitrile; H2O / 0.5 h / 20 °C
2: 47 percent / Et3N / tetrahydrofuran / 1 h / 20 °C
3: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min
4: Et3N, MnO2 / CH2Cl2
5: 85 percent / trifluoroacetic acid / 1 h / 20 °C
6: 82 percent / chlorobenzene / 4 h / 131 °C
7: LiOH
View Scheme
4-Hydroxy-5-oxo-5H-indole-2-carboxylic acid ethyl ester
98126-24-0

4-Hydroxy-5-oxo-5H-indole-2-carboxylic acid ethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 47 percent / Et3N / tetrahydrofuran / 1 h / 20 °C
2: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min
3: 85 percent / trifluoroacetic acid / 1 h / 20 °C
4: 82 percent / chlorobenzene / 4 h / 131 °C
5: LiOH
View Scheme
Multi-step reaction with 6 steps
1: 47 percent / Et3N / tetrahydrofuran / 1 h / 20 °C
2: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min
3: Et3N, MnO2 / CH2Cl2
4: 85 percent / trifluoroacetic acid / 1 h / 20 °C
5: 82 percent / chlorobenzene / 4 h / 131 °C
6: LiOH
View Scheme
2-Benzyloxycarbonylamino-4-nitro-pentanedioic acid dimethyl ester
204922-65-6

2-Benzyloxycarbonylamino-4-nitro-pentanedioic acid dimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 47 percent / Et3N / tetrahydrofuran / 1 h / 20 °C
2: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min
3: 85 percent / trifluoroacetic acid / 1 h / 20 °C
4: 82 percent / chlorobenzene / 4 h / 131 °C
5: LiOH
View Scheme
Multi-step reaction with 6 steps
1: 47 percent / Et3N / tetrahydrofuran / 1 h / 20 °C
2: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min
3: Et3N, MnO2 / CH2Cl2
4: 85 percent / trifluoroacetic acid / 1 h / 20 °C
5: 82 percent / chlorobenzene / 4 h / 131 °C
6: LiOH
View Scheme
6-Chloro-4-hydroxy-7-[methoxycarbonyl-(4-methoxycarbonyl-2-oxo-2,3-dihydro-oxazol-5-yl)-methyl]-5-oxo-5H-indole-2-carboxylic acid ethyl ester
98126-30-8

6-Chloro-4-hydroxy-7-[methoxycarbonyl-(4-methoxycarbonyl-2-oxo-2,3-dihydro-oxazol-5-yl)-methyl]-5-oxo-5H-indole-2-carboxylic acid ethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / chlorobenzene / 4 h / 131 °C
2: LiOH
View Scheme
2-Benzyloxycarbonylamino-4-[2-ethoxycarbonyl-5-hydroxy-4-oxo-1,4-dihydro-indol-(7Z)-ylidene]-pentanedioic acid dimethyl ester

2-Benzyloxycarbonylamino-4-[2-ethoxycarbonyl-5-hydroxy-4-oxo-1,4-dihydro-indol-(7Z)-ylidene]-pentanedioic acid dimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min
2: 85 percent / trifluoroacetic acid / 1 h / 20 °C
3: 82 percent / chlorobenzene / 4 h / 131 °C
4: LiOH
View Scheme
Multi-step reaction with 5 steps
1: 1.) N-chlorosuccinimide, triethylamine; 2.) DDQ, Et3N / 1.) methylene chloride, 20 deg C, 30 min; 2.) methylene chloride, 20 deg C, 90 min
2: Et3N, MnO2 / CH2Cl2
3: 85 percent / trifluoroacetic acid / 1 h / 20 °C
4: 82 percent / chlorobenzene / 4 h / 131 °C
5: LiOH
View Scheme
(Z)-4-[(Z)-Benzyloxycarbonylimino]-2-(6-chloro-2-ethoxycarbonyl-4-hydroxy-5-oxo-5H-indol-7-yl)-pent-2-enedioic acid dimethyl ester

(Z)-4-[(Z)-Benzyloxycarbonylimino]-2-(6-chloro-2-ethoxycarbonyl-4-hydroxy-5-oxo-5H-indol-7-yl)-pent-2-enedioic acid dimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / trifluoroacetic acid / 1 h / 20 °C
2: 82 percent / chlorobenzene / 4 h / 131 °C
3: LiOH
View Scheme
2-Benzyloxycarbonylamino-4-(6-chloro-2-ethoxycarbonyl-4-hydroxy-5-oxo-5H-indol-7-yl)-pentanedioic acid dimethyl ester
98126-27-3, 98126-28-4

2-Benzyloxycarbonylamino-4-(6-chloro-2-ethoxycarbonyl-4-hydroxy-5-oxo-5H-indol-7-yl)-pentanedioic acid dimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3N, MnO2 / CH2Cl2
2: 85 percent / trifluoroacetic acid / 1 h / 20 °C
3: 82 percent / chlorobenzene / 4 h / 131 °C
4: LiOH
View Scheme
3-Amino-4,5-dihydroxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid 2-ethyl ester 7,9-dimethyl ester
80721-45-5

3-Amino-4,5-dihydroxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid 2-ethyl ester 7,9-dimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89 percent / concd. HCl, aq. NaNO2 / 0.33 h / 0 °C
2: HOAc, 50percent aq. H3PO2 / 1 h / Ambient temperature
3: 89 percent / aq. LiOH / tetrahydrofuran / 6.5 h
View Scheme
Multi-step reaction with 3 steps
1: NaNO2, concd HCl / 30 h / 0 °C
2: 1.) 50percent hypophosphorous acid, 2.) aq. basic potassium ferricyanide / 1.) acetic acid, 25 deg C, 20 min
3: 89 percent / LiOH / H2O; tetrahydrofuran / 6 h / 25 °C
View Scheme
3-Diazo-4,5-dioxo-4,5-dihydro-3H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid 2-ethyl ester 7,9-dimethyl ester
80721-46-6

3-Diazo-4,5-dioxo-4,5-dihydro-3H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid 2-ethyl ester 7,9-dimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HOAc, 50percent aq. H3PO2 / 1 h / Ambient temperature
2: 89 percent / aq. LiOH / tetrahydrofuran / 6.5 h
View Scheme
Multi-step reaction with 2 steps
1: 1.) 50percent hypophosphorous acid, 2.) aq. basic potassium ferricyanide / 1.) acetic acid, 25 deg C, 20 min
2: 89 percent / LiOH / H2O; tetrahydrofuran / 6 h / 25 °C
View Scheme
3-Nitro-4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid 2-ethyl ester 7,9-dimethyl ester
80721-44-4

3-Nitro-4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid 2-ethyl ester 7,9-dimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / H2 / PtO2 / methanol / 3 h
2: 89 percent / concd. HCl, aq. NaNO2 / 0.33 h / 0 °C
3: HOAc, 50percent aq. H3PO2 / 1 h / Ambient temperature
4: 89 percent / aq. LiOH / tetrahydrofuran / 6.5 h
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / H2 / 10percent Pd/C / methanol / 4 h / 760 Torr
2: NaNO2, concd HCl / 30 h / 0 °C
3: 1.) 50percent hypophosphorous acid, 2.) aq. basic potassium ferricyanide / 1.) acetic acid, 25 deg C, 20 min
4: 89 percent / LiOH / H2O; tetrahydrofuran / 6 h / 25 °C
View Scheme
trimethyl 4,5-dimethoxy-1H-pyrrolo<2,3-f>quinoline-2,7,9-tricarboxylate
78891-39-1

trimethyl 4,5-dimethoxy-1H-pyrrolo<2,3-f>quinoline-2,7,9-tricarboxylate

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / AgO, HNO3 / tetrahydrofuran / 0.17 h / Ambient temperature
2: 75 percent / LiOH, H2O / tetrahydrofuran / 5 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 66 percent / AgO, 6 N HNO3 / tetrahydrofuran / 0.17 h
2: 75 percent / H2O, LiOH / tetrahydrofuran / 5.5 h
View Scheme
dimethyl 7,8-dimethoxy-6-<3-methoxy-3-oxo-2-(phenylhydrazono)propyl>-5-nitro-2,4-quinolinedicarboxylate
78891-38-0

dimethyl 7,8-dimethoxy-6-<3-methoxy-3-oxo-2-(phenylhydrazono)propyl>-5-nitro-2,4-quinolinedicarboxylate

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 62 percent / H2, HCl / 10percent Pd/C / methanol
2: 60 percent / AgO, HNO3 / tetrahydrofuran / 0.17 h / Ambient temperature
3: 75 percent / LiOH, H2O / tetrahydrofuran / 5 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 66 percent / H2, 5percent HCl / 5percent Pd/C / methanol / 2 h / Ambient temperature
2: 66 percent / AgO, 6 N HNO3 / tetrahydrofuran / 0.17 h
3: 75 percent / H2O, LiOH / tetrahydrofuran / 5.5 h
View Scheme
dimethyl 2-ketoglutarate
13192-04-6

dimethyl 2-ketoglutarate

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Br2 / CH2Cl2 / Heating
2: Et3N / diethyl ether / 20 h / 25 °C
3: CH2Cl2 / 7 h / 25 °C
4: dry hydrogen chloride / CH2Cl2 / 10 h
5: 60 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.17 h / 0 °C
6: 92 percent / p-tuluenesulfonic acid / methanol / 4 h / Heating
7: 98 percent / 0.5 M K2CO3 / H2O / 4 h / 85 °C
View Scheme
3-bromo-2-oxopentane-1,5-dioic acid dimethyl ester
148728-48-7

3-bromo-2-oxopentane-1,5-dioic acid dimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N / diethyl ether / 20 h / 25 °C
2: CH2Cl2 / 7 h / 25 °C
3: dry hydrogen chloride / CH2Cl2 / 10 h
4: 60 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.17 h / 0 °C
5: 92 percent / p-tuluenesulfonic acid / methanol / 4 h / Heating
6: 98 percent / 0.5 M K2CO3 / H2O / 4 h / 85 °C
View Scheme
6-Formylamino-5-methoxy-1H-indole-2-carboxylic acid methyl ester
78939-35-2

6-Formylamino-5-methoxy-1H-indole-2-carboxylic acid methyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 79 percent / hydrochloric acid / acetone; H2O / 1 h / Heating
2: CH2Cl2 / 7 h / 25 °C
3: dry hydrogen chloride / CH2Cl2 / 10 h
4: 60 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.17 h / 0 °C
5: 92 percent / p-tuluenesulfonic acid / methanol / 4 h / Heating
6: 98 percent / 0.5 M K2CO3 / H2O / 4 h / 85 °C
View Scheme
9-Hydroxy-5-methoxy-6,7,8,9-tetrahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester
78939-38-5

9-Hydroxy-5-methoxy-6,7,8,9-tetrahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dry hydrogen chloride / CH2Cl2 / 10 h
2: 60 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.17 h / 0 °C
3: 92 percent / p-tuluenesulfonic acid / methanol / 4 h / Heating
4: 98 percent / 0.5 M K2CO3 / H2O / 4 h / 85 °C
View Scheme
Multi-step reaction with 3 steps
1: copper(II) acetate monohydrate; formic acid / 48 h / 25 °C
2: ammonium cerium (IV) nitrate / acetonitrile; water / 2 h / -5 °C
3: potassium carbonate / water / 12 h / 25 - 80 °C
View Scheme
6-amino-5-methoxy-2-methoxycarbonylindole
78939-36-3

6-amino-5-methoxy-2-methoxycarbonylindole

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: CH2Cl2 / 7 h / 25 °C
2: dry hydrogen chloride / CH2Cl2 / 10 h
3: 60 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.17 h / 0 °C
4: 92 percent / p-tuluenesulfonic acid / methanol / 4 h / Heating
5: 98 percent / 0.5 M K2CO3 / H2O / 4 h / 85 °C
View Scheme
Multi-step reaction with 4 steps
1: dichloromethane / 25 °C / Green chemistry; Industrial scale
2: copper(II) acetate monohydrate; formic acid / 25 °C / Green chemistry; Industrial scale
3: ammonium cerium (IV) nitrate / acetonitrile / -5 °C / Green chemistry; Industrial scale
4: potassium carbonate; water / water / 25 - 80 °C / Green chemistry; Industrial scale
View Scheme
Multi-step reaction with 4 steps
1: dichloromethane / 16 h / 25 °C
2: copper(II) acetate monohydrate; formic acid / 48 h / 25 °C
3: ammonium cerium (IV) nitrate / acetonitrile; water / 2 h / -5 °C
4: potassium carbonate / water / 12 h / 25 - 80 °C
View Scheme
5-methoxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester
78939-39-6

5-methoxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 60 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.17 h / 0 °C
2: 92 percent / p-tuluenesulfonic acid / methanol / 4 h / Heating
3: 98 percent / 0.5 M K2CO3 / H2O / 4 h / 85 °C
View Scheme
Multi-step reaction with 2 steps
1: ammonium cerium (IV) nitrate / acetonitrile / -5 °C / Green chemistry; Industrial scale
2: potassium carbonate; water / water / 25 - 80 °C / Green chemistry; Industrial scale
View Scheme
Multi-step reaction with 2 steps
1: ammonium cerium (IV) nitrate / acetonitrile; water / 2 h / -5 °C
2: potassium carbonate / water / 12 h / 25 - 80 °C
View Scheme
methyl 4-(acetylamino)-o-anisate
4093-29-2

methyl 4-(acetylamino)-o-anisate

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 98 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
2: 80 percent / manganese (IV) oxide / CHCl3; methanol / 20 h / Ambient temperature
3: 73 percent / NaOMe / methanol / 2 h / -15 °C
4: 87 percent / xylene / 4 h / Heating
5: 85 percent / HCl / methanol / 6 h / Heating
6: 2.) HCl / 1.) CH2Cl2, room temp., 12 h; 2.) 12 h, ether
7: 1.) BBr3; 2.) MeOH, H2SO4 (96percent) / 1.) CH2Cl2, room temp., 140 h; 2.) reflux, 48 h
8: 93 percent / benzoyl t-butyl nitroxide / methanol; CHCl3 / 16 h / Ambient temperature
View Scheme
Multi-step reaction with 10 steps
1: 98 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
2: 80 percent / manganese (IV) oxide / CHCl3; methanol / 20 h / Ambient temperature
3: 73 percent / NaOMe / methanol / 2 h / -15 °C
4: 87 percent / xylene / 4 h / Heating
5: 85 percent / HCl / methanol / 6 h / Heating
6: 2.) HCl / 1.) CH2Cl2, room temp., 12 h; 2.) 12 h, ether
7: 8.7 mg / NH4NO3 / trifluoroacetic acid / 3.75 h / Ambient temperature
8: 93 percent / H2 / 10percent palladium-on-charcoal / methanol / 20 h
9: 73 percent / MnO2 / aq. H2SO4 / 0.75 h / 0 °C
View Scheme
methyl 4-acetamido-2-hydroxybenzoate
4093-28-1

methyl 4-acetamido-2-hydroxybenzoate

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 97 percent / potassium carbonate / acetone / 8 h / Heating
2: 98 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
3: 80 percent / manganese (IV) oxide / CHCl3; methanol / 20 h / Ambient temperature
4: 73 percent / NaOMe / methanol / 2 h / -15 °C
5: 87 percent / xylene / 4 h / Heating
6: 85 percent / HCl / methanol / 6 h / Heating
7: 2.) HCl / 1.) CH2Cl2, room temp., 12 h; 2.) 12 h, ether
8: 1.) BBr3; 2.) MeOH, H2SO4 (96percent) / 1.) CH2Cl2, room temp., 140 h; 2.) reflux, 48 h
9: 93 percent / benzoyl t-butyl nitroxide / methanol; CHCl3 / 16 h / Ambient temperature
View Scheme
Multi-step reaction with 11 steps
1: 97 percent / potassium carbonate / acetone / 8 h / Heating
2: 98 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
3: 80 percent / manganese (IV) oxide / CHCl3; methanol / 20 h / Ambient temperature
4: 73 percent / NaOMe / methanol / 2 h / -15 °C
5: 87 percent / xylene / 4 h / Heating
6: 85 percent / HCl / methanol / 6 h / Heating
7: 2.) HCl / 1.) CH2Cl2, room temp., 12 h; 2.) 12 h, ether
8: 8.7 mg / NH4NO3 / trifluoroacetic acid / 3.75 h / Ambient temperature
9: 93 percent / H2 / 10percent palladium-on-charcoal / methanol / 20 h
10: 73 percent / MnO2 / aq. H2SO4 / 0.75 h / 0 °C
View Scheme
serin
302-84-1

serin

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

C15H7N3O7
132847-84-8

C15H7N3O7

Conditions
ConditionsYield
In water at 30℃; for 24h; pH = 9.7;100%
With air; cetyltrimethylammonim bromide at 30℃;55%
aminoguanidine sulfate
996-19-0

aminoguanidine sulfate

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

4,5-dihydroxy-4,5-dioxo-1H-pyrrolo{2,3-f}quinoline-2,7,9-tricarboxylic acid
79127-57-4

4,5-dihydroxy-4,5-dioxo-1H-pyrrolo{2,3-f}quinoline-2,7,9-tricarboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate for 24h;100%
at 30℃; Mechanism; pH 10;
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

4,5-dihydroxy-4,5-dioxo-1H-pyrrolo{2,3-f}quinoline-2,7,9-tricarboxylic acid
79127-57-4

4,5-dihydroxy-4,5-dioxo-1H-pyrrolo{2,3-f}quinoline-2,7,9-tricarboxylic acid

Conditions
ConditionsYield
With phenylhydrazine hydrochloride In methanol at 50℃; for 0.166667h;100%
With thiophenol In acetonitrile for 2h;84%
With acetate buffer; thiophenol In water; acetonitrile at 30℃;84 % Spectr.
With methylhydrazine In various solvent(s) at 30℃; Rate constant; anaerobic conditions;
With hydrogenchloride; ascorbic acid In water at 12 - 20℃; for 23h; pH=2.96;3.35 g
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

glycine
56-40-6

glycine

C15H7N3O7
132847-84-8

C15H7N3O7

Conditions
ConditionsYield
In water at 30℃; for 24h; pH = 6.6;100%
at 30℃; Rate constant; Mechanism; Product distribution; pH = 9.1; other pH values; other aminoacids;
With phosphate buffer pH 6.5; bovine serum In water Rate constant; Ambient temperature; pH range of 3.0 - 9.0;
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

3H-3,7,8,13-Tetraaza-benzo[a]cyclopenta[c]anthracene-2,4,6-tricarboxylic acid

3H-3,7,8,13-Tetraaza-benzo[a]cyclopenta[c]anthracene-2,4,6-tricarboxylic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature;96%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

6,7-Dimethoxy-quinoxaline-2,3-diamine

6,7-Dimethoxy-quinoxaline-2,3-diamine

C24H14N6O8

C24H14N6O8

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature;95%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

dimethyl sulfate
77-78-1

dimethyl sulfate

trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate
74447-88-4

trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Schlenk technique; Inert atmosphere;91%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; Inert atmosphere;57%
With potassium carbonate In N,N-dimethyl-formamide at 25℃;
With hydrogenchloride; potassium carbonate In water; N,N-dimethyl-formamide at 20 - 50℃; for 72.5h; Large scale;
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

4,5-dihydroxy-1H-pyrrolo[2,3-f]chinoline-2,7,9-tricarboxylic acid trilithium salt

4,5-dihydroxy-1H-pyrrolo[2,3-f]chinoline-2,7,9-tricarboxylic acid trilithium salt

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 15 - 20℃; for 24h;90.5%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

trilithium pyrroloquinoline quinone

trilithium pyrroloquinoline quinone

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 15 - 20℃; for 24h;90.5%
With lithium hydroxide In water at 0 - 5℃; for 2h;10 mg
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

5-Diazo-4,5-dihydro-4-oxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure

5-Diazo-4,5-dihydro-4-oxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure

Conditions
ConditionsYield
With phosphate buffer; toluene-4-sulfonic acid hydrazide In tetrahydrofuran 1.) 2 h, 10 deg C, 2.) 3 h, room temperature;88%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid disodium salt

4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid disodium salt

Conditions
ConditionsYield
With sodium hydroxide at 25℃; for 3h; Reagent/catalyst;88%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

ethylenediamine
107-15-3

ethylenediamine

1H-1,4,7,8-Tetraaza-cyclopenta[l]phenanthrene-2,9,11-tricarboxylic acid

1H-1,4,7,8-Tetraaza-cyclopenta[l]phenanthrene-2,9,11-tricarboxylic acid

Conditions
ConditionsYield
With CTAB micellar system at 50℃; for 1h; Mechanism; further α,ω-diaminoalkanes;87%
With CTAB micellar system at 50℃; for 1h;87%
O-phospho-DL-serine
17885-08-4

O-phospho-DL-serine

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

C16H10N3O11P
144219-06-7

C16H10N3O11P

Conditions
ConditionsYield
In water at 30℃; for 24h; pH = 9.6;86%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

4,5-dihydroxy-1H-pyrrolo[2,3-f]chinoline-2,7,9-tricarboxylic acid dilithium salt

4,5-dihydroxy-1H-pyrrolo[2,3-f]chinoline-2,7,9-tricarboxylic acid dilithium salt

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 15 - 20℃; for 24h;83.9%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

4,5-dihydroxy-1H-pyrrolo[2,3-f]chinoline-2,7,9-tricarboxylic acid lithium salt

4,5-dihydroxy-1H-pyrrolo[2,3-f]chinoline-2,7,9-tricarboxylic acid lithium salt

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 15 - 20℃; for 24h;83.9%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

4,5-dihydroxy-1H-pyrrole[2,3-f]chinoline-2,7,9-tricarboxylic acid, dilithium salt

4,5-dihydroxy-1H-pyrrole[2,3-f]chinoline-2,7,9-tricarboxylic acid, dilithium salt

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 15 - 20℃; for 24h;83.9%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

4,5-dihydroxy-1H-pyrrole[2,3-f]chinoline-2,7,9-tricarboxylic acid, lithium salt
1246998-46-8

4,5-dihydroxy-1H-pyrrole[2,3-f]chinoline-2,7,9-tricarboxylic acid, lithium salt

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 15 - 20℃; for 24h;83.9%
betaine
107-43-7

betaine

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

C14H6N2O8*C5H11NO2

C14H6N2O8*C5H11NO2

Conditions
ConditionsYield
In ethanol at 25 - 30℃; for 24h;81%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

D,L-histidine
71-00-1

D,L-histidine

C19H11N5O7
144219-04-5

C19H11N5O7

Conditions
ConditionsYield
In water at 30℃; for 24h; pH = 6.7;80%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

2-Amino-1-phenylethanol
7568-93-6

2-Amino-1-phenylethanol

C15H7N3O7
132847-84-8

C15H7N3O7

Conditions
ConditionsYield
With cetyltrimethylammonim bromide In water at 30℃; for 24h; pH = 10.4;78%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

›Tyr
556-02-5, 556-03-6, 34537-57-0, 55520-40-6, 96946-98-4, 60-18-4

›Tyr

A

(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

B

C15H7N3O7
132847-84-8

C15H7N3O7

Conditions
ConditionsYield
With air; cetyltrimethylammonim bromide at 30℃;A n/a
B 77%
...Expand
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

›Tyr
556-02-5, 556-03-6, 34537-57-0, 55520-40-6, 96946-98-4, 60-18-4

›Tyr

C15H7N3O7
132847-84-8

C15H7N3O7

Conditions
ConditionsYield
In water at 30℃; for 24h; carbonate buffer, pH = 10.0;77%
3-methoxy-2-aminopropionic acid
19794-53-7

3-methoxy-2-aminopropionic acid

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

C17H11N3O8
144219-05-6

C17H11N3O8

Conditions
ConditionsYield
In water at 30℃; for 24h; pH = 9.8;72%
pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

Trp
54-12-6

Trp

C15H7N3O7
132847-84-8

C15H7N3O7

Conditions
ConditionsYield
In water at 30℃; for 24h; pH = 6.7;71%
DL-threonine
72-19-5, 80-68-2, 144-98-9, 632-20-2, 2676-21-3, 7004-04-8, 24830-94-2, 28954-12-3, 36676-50-3

DL-threonine

pyrroloquinoline quinone
72909-34-3

pyrroloquinoline quinone

C15H7N3O7
132847-84-8

C15H7N3O7

Conditions
ConditionsYield
With air; cetyltrimethylammonim bromide at 30℃;70%
In water at 30℃; for 24h; pH = 10.2;70%

Pyrroloquinoline quinone Specification

The Pyrroloquinoline quinone with the cas number 72909-34-3 is also called 2,7,9-Tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione. The systematic name is 4,5-Dihydro-4,5-dioxo-1-H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid. This chemical belongs to the following product categories: (1)All Inhibitors; (2)Inhibitors. It should be stored at 2-8°C. It is orange-red solid. This chemical is a pyrrolo-quinoline having two adjacent keto-groups at the 4 and 5 positions and three acidic carboxyl groups. It is a coenzyme of some DEHYDROGENASES.

The properties of the chemical are: (1)ACD/LogP: -0.65; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -5.73; (4)ACD/LogD (pH 7.4): -5.8; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 10; (10)#H bond donors:  4  ; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 130.86 Å2; (13)Index of Refraction: 1.801; (14)Molar Refractivity: 71.98 cm3; (15)Molar Volume: 168.2 cm3; (16)Polarizability: 28.53×10-24cm3; (17)Surface Tension: 134.8 dyne/cm; (18)Enthalpy of Vaporization: 155.84 kJ/mol; (19)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)c1c3c(nc(C(=O)O)c1)C(=O)C(=O)c2cc(C(=O)O)nc23
(2)InChI: InChI=1/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)
(3)InChIKey: MMXZSJMASHPLLR-UHFFFAOYAP

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