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High purity Pyrroloquinoline Quinone Acid 99% PQQ
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Pyrroloquinoline quinone CAS72909-34-3 Methoxatin 1H-Pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylicacid, 4,5-dihydro-4,5-dioxo- CAS no 72909-34-3 PQQ disodium salt
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CAS No.:72909-34-3 pyrroloquinoline quinine
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72909-34-3 Usage

Purification Methods

Efflorescent yellow-orange needles of PQQ are formed on recrystallising from H2O by addition of Me2CO, or better from a supersaturated aqueous solution, as it forms an acetone adduct. [Forrest et al. Nature 280 843 1979.] It has also been purified by passage through a C-18 reverse phase silica cartridge or a silanized silica gel column in aqueous solution whereby methoxantin remains behind as a red-orange band at the origin. This band is collected and washed thoroughly with dilute aqueous HCl (pH 2) and is then eluted with MeOH/H2O (7:3) and evaporated in vacuo to give the coenzyme as a red solid. It has also been purified by dissolving it in aqueous 0.5M K2CO3 and acidified to pH 2.5 whereby PQQ precipitates as a deep red solid which is collected and dried in vacuo. Methoxantin elutes at 3.55 retention volumes from a C18 _Bondapak column using H2O/MeOH (95:5) + 0.1% AcOH pH 4.5. It has UV max at 247 and 330nm (shoulder at 270nm) in H2O and max at 250 and 340nm in H2O at pH 2.5. With excitation at ex 365nm it has a max emission at 483nm. The 13C NMR has : 113.86, 122.76, 125.97, 127.71, 130.68, 137.60, 144.63, 146.41, 147.62, 161.25, 165.48, 166.45, 173.30 and 180.00ppm. When a solution in 10% aqueous MeCO is adjusted to pH 9 with aqueous NH3 and kept at 25o for 30minutes, the acetone adduct is formed; UV has max at 250, 317 and 360nm (H2O, pH 5.5), and with ex at 360nm it has max fluorescence at max at 465nm; and the 13C NMR [(CD3)2SO, TMS] has : 29.77, 51.06, 74.82, 111.96, 120.75, 121.13, 125.59, 126.88, 135.21, 139.19, 144.92, 161.01, 161.47, 165.17, 168.61, 190.16 and 207.03ppm. It also forms a methanol adduct. When it is reacted with Me2SO4/K2CO3 in dry Me2NCHO at 80o for 4hours, it forms the trimethyl ester which has m 265-267o(dec) [260-263o(dec) also reported] after recrystallisation from hot MeCN (orange crystals) with UV max at 252 and 344nm (H2O) and 251, 321 and 373nm (in MeOH; MeOH adduct ). [Duine et al. Eur J Biochem 108 187 1980, Duine et al. Adv Enzymology 59 169 1987, Corey & Tramontano J Am Chem Soc 103 5599 1981, Gainor & Weinreb J Org Chem 46 4319 1981, Hendrickson & de Vries J Org Chem 17 1148 1982, McKenzie et al. J Chem Soc, Chem Commun 1372 1983.]

Uses

PQQ has been reported to function as a water soluble vitamin/cofactor and as an antioxidant. Pyrroloquinoline quinone (PQQ) disodium salt is proposed for use due to its nutritive value in the United States (U.S.) in foods, such as energy, sport, and isotonic drinks; non-milk based meal replacement beverages; water (bottled, enhanced, fortified); milk-based meal replacement beverages; cereal and granola bars; and energy, meal replacement, and fortified bars. PQQ is also intended for use in dietary supplements.

Uses

A cofactor of microbial quinoprotein enzyme, and imidazopyrroline. A redox/cofactor found in a a class of enzymes called quinoproteins

Chemical Properties

Orange-Red Solid

Description

Pyrroloquinoline quinone (PQQ) is a novel biofactor for which a proposition can be made for physiological importance. PQQ was first recognized as an enzyme cofactor in bacteria. It has recently been tentatively identified as a component of interstellar dust. Thus, PQQ may have been present throughout early biological conception and evolution. PQQ is also a potent plant growth factor. Consequently, for animals and humans, there has been constant exposure to PQQ. In animals, PQQ is reported to participate in a range of biological functions with apparent survival benefits (e.g., improved neonatal growth and reproductive performance). There are also benefits from PQQ supplementation related to cognitive, immune, and antioxidant functions, as well as protection from cardiac and neurological ischemic events. Although PQQ is not currently viewed as a vitamin, its involvement in cell signaling pathways, particularly those important to mitochondriogenesis in experimental animal models, may eventually provide a rationale for defining PQQ as vital to life. For humans, such evidence suggests there may be similar parallels or benefits from improving PQQ status.
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)

72909-34-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name pyrroloquinoline quinone

1.2 Other means of identification

Product number -
Other names 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:72909-34-3 SDS

72909-34-3Synthetic 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

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%
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

C15H7N3O7
132847-84-8

C15H7N3O7

Conditions
ConditionsYield
In water at 30℃; for 24h; pH = 6.7;71%
Conditions
ConditionsYield
With air; cetyltrimethylammonim bromide at 30℃;70%
In water at 30℃; for 24h; pH = 10.2;70%
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