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72909-34-3

Basic Information
CAS No.: 72909-34-3
Name: Pyrroloquinoline quinone
Article Data: 28
Molecular Structure:
Molecular Structure of 72909-34-3 (Pyrroloquinoline quinone)
Formula: C14H6N2O8
Molecular Weight: 330.21
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;
EINECS: 200-001-8
Density: 1.963 g/cm3
Boiling Point: 1018.6 °C at 760 mmHg
Flash Point: 569.8 °C
Safety: 22-24/25
PSA: 174.72000
LogP: 0.55030
Synthetic route
74447-88-4

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

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%
78939-40-9

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

72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
With potassium carbonate In water at 85℃; for 4h;98%
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

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%
79127-57-4

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

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;
116451-31-1

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

72909-34-3

pyrroloquinoline quinone

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In 1,2-dichloro-ethane at 25℃; for 24h;19.01%
133706-80-6

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

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
107575-60-0

6-amino-5-methoxy-2-ethoxycarbonylindole

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
119825-27-3

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

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
78939-37-4

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

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

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
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  • Pyrroloquinoline quinone CAS NO.: 72909-34-3

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    Pyrroloquinoline quinone CAS NO.: 72909-34-3

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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