Pyrroloquinoline Quinone

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  • Identifiers

    CAS number
    72909-34-3

    Molecular formula
    C14H6N2O8

    SMILES
    C1=C(C2=C(C(=O)C(=O)C3=C2NC(=C3)C(=O)O)N=C1C(=O)O)C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 71.63%
    Burnt 28.55%
    Sour 24.12%
    Nutty 23.0%
    Caramellic 22.33%
    Winey 20.66%
    Clean 19.75%
    Bitter 19.11%
    Cooked 18.01%
    Sharp 16.99%

     

    Flavor
    Bitter 57.81%
    Odorless 54.14%
    Very mild 31.54%
    Nutty 25.46%
    Mild 24.54%
    Bland 22.82%
    Yeast 20.74%
    Nitrile 20.64%
    Bread crust 20.61%
    Faint 20.44%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    3.45 (weak acid)

    Molecular weight
    330.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1174°C

    Flash point

    • 396.6 ˚C est.

  • Synonyms

    • pyrroloquinoline quinone
    • 72909-34-3
    • methoxatin
    • Coenzyme pqq
    • Pyrrolo-quinoline quinone
    • Pqq coenzyme
    • Pqq cofactor
    • 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
    • 4,5-dioxo-1H,4H,5H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
    • 2,7,9-Tricarboxypyrroloquinoline quinone
    • DTXSID3041162
    • CHEBI:18315
    • 47819QGH5L
    • pyrroloquinolinedione tricarboxylic acid
    • 2,7,9-Tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione
    • 1H-Pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-
    • Coenzyme, PQQ
    • Cofactor, PQQ
    • PQQ, Coenzyme
    • Quinone, Pyrroloquinoline
    • Pyrrolo Quinoline Quinone
    • Quinone, Pyrrolo-Quinoline
    • 2,4,6-tricarboxylic-pyrrolo(2,3-5,6)quinoline 8,9-quinone
    • 2,4,6-tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone
    • 4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid
    • 4,5-dioxo-1H,4H,5H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid
    • 1H-Pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-
    • 4,5-dihydro-4,5-dioxo-1H-pyrrolo(2,3-5,6)quinoline-2,7,9-tricarboxylic acid
    • 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-5,6]quinoline-2,7,9-tricarboxylic acid
    • RefChem:871130
    • 4,5-Dihydro-4,5-dioxo-1-H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid
    • DTXCID1021162
    • 2,7,9-Tricarboxy-1H-Pyrrolo-(2,3-f)Quinoline-4,5-Dione
    • 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
    • Methoxatine
    • PQQ
    • MFCD00043125
    • Pyrroloquinoline-quinone
    • PQQ;Methoxatin
    • C14H6N2O8
    • 4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
    • 4,5-Dihydro-4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid
    • UNII-47819QGH5L
    • Methoxantin
    • Pyroquinoline Quinone
    • Pyrroloquinoline dione
    • Pyrroloquinolinequinone(PQQ)
    • SCHEMBL37975
    • orb1301578
    • orb3025137
    • Pyrroloquinoline Quinone (PQQ)
    • CHEMBL1235421
    • SCHEMBL21049248
    • SCHEMBL29350225
    • GLXC-26180
    • BDBM50575553
    • MSK158015
    • AKOS015920260
    • CS-W009276
    • DB03205
    • EBC-616001
    • FD21985
    • GS-6613
    • MSK158015-100W
    • Pyrroloquinoline dione tricarboxylic acid
    • MSK158015-1000W
    • PYRROLOQUINOLINE QUINONE [WHO-DD]
    • PYRROLOQUINOLINEDIONE TRICARBOXYLATE
    • SY025685
    • DB-055694
    • HY-100196
    • NS00068569
    • P2781
    • Pyrroloquinoline quinone, >=95.0% (HPLC)
    • C00113
    • 909M343
    • F079870
    • Q414583
    • Pyrroloquinoline quinone Solution in Water, 1000ug/mL
    • Pyrroloquinoline quinone Solution in Water, 100ug/mL
    • 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylicacid
    • 2,7,9-TRICARBOXY-4,5-DIHYDRO-4,5-DIOXO-1H-PYRROLO(2,3-F)QUINOLINE
    • 4,5-Dioxo-4,5-dihydro-1H-pyrrolo-[2,3-f]quinoline-2,7,9-tricarboxylic acid
    • 72909-34-3

  • Applications

    Pyrroloquinoline Quinone (CAS 72909-34-3) is a redox-active biochemical cofactor used to support enzyme-catalyzed oxidation–reduction reactions, with applications in industrial biocatalysis for the synthesis of fine chemicals and pharmaceutical intermediates. In cosmetics and personal care, it is explored as an antioxidant ingredient and stabilizer in formulations. In laboratory and industrial settings, it serves as a biochemical reagent and redox probe for enzymatic assays and process development. It is also investigated as a mediator or additive in electrochemical biosensors and enzyme-based sensing platforms. Additionally, it is considered for microbial bioprocessing to enable sustainable, enzyme-driven steps in manufacturing routes. All applications are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.26
    methanol 4.94
    isopropanol 2.26
    water 0.26
    ethyl acetate 0.45
    n-propanol 3.12
    acetone 0.33
    n-butanol 1.67
    acetonitrile 0.16
    DMF 37.01
    toluene 0.2
    isobutanol 1.28
    1,4-dioxane 1.81
    methyl acetate 0.87
    THF 4.77
    2-butanone 1.64
    n-pentanol 0.86
    sec-butanol 2.38
    n-hexane 0.02
    ethylene glycol 10.49
    NMP 45.9
    cyclohexane 0.02
    DMSO 45.63
    n-butyl acetate 0.88
    n-octanol 1.46
    chloroform 0.01
    n-propyl acetate 0.47
    acetic acid 0.56
    dichloromethane 0.02
    cyclohexanone 1.55
    propylene glycol 7.71
    isopropyl acetate 0.36
    DMAc 52.76
    2-ethoxyethanol 13.57
    isopentanol 1.0
    n-heptane 0.05
    ethyl formate 0.55
    1,2-dichloroethane 0.06
    n-hexanol 0.8
    2-methoxyethanol 37.63
    isobutyl acetate 0.09
    tetrachloromethane 0.01
    n-pentyl acetate 1.12
    transcutol 11.99
    n-heptanol 1.82
    ethylbenzene 0.13
    MIBK 0.34
    2-propoxyethanol 15.27
    tert-butanol 1.65
    MTBE 0.41
    2-butoxyethanol 11.12
    propionic acid 2.12
    o-xylene 0.3
    formic acid 5.3
    diethyl ether 0.66
    m-xylene 0.14
    p-xylene 0.12
    chlorobenzene 0.02
    dimethyl carbonate 1.89
    n-octane 0.04
    formamide 14.23
    cyclopentanone 2.76
    2-pentanone 0.82
    anisole 0.47
    cyclopentyl methyl ether 1.61
    gamma-butyrolactone 3.89
    1-methoxy-2-propanol 28.91
    pyridine 1.88
    3-pentanone 0.96
    furfural 3.15
    n-dodecane 0.04
    diethylene glycol 18.74
    diisopropyl ether 0.13
    tert-amyl alcohol 2.03
    acetylacetone 0.53
    n-hexadecane 0.04
    acetophenone 0.77
    methyl propionate 2.17
    isopentyl acetate 0.5
    trichloroethylene 0.05
    n-nonanol 1.57
    cyclohexanol 1.34
    benzyl alcohol 0.97
    2-ethylhexanol 0.5
    isooctanol 0.98
    dipropyl ether 1.33
    1,2-dichlorobenzene 0.03
    ethyl lactate 2.35
    propylene carbonate 0.72
    n-methylformamide 12.85
    2-pentanol 1.03
    n-pentane 0.03
    1-propoxy-2-propanol 10.94
    1-methoxy-2-propyl acetate 2.49
    2-(2-methoxypropoxy) propanol 6.52
    mesitylene 0.09
    ε-caprolactone 2.44
    p-cymene 0.19
    epichlorohydrin 1.48
    1,1,1-trichloroethane 0.01
    2-aminoethanol 13.32
    morpholine-4-carbaldehyde 23.54
    sulfolane 13.4
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.88
    n-hexyl acetate 1.19
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 10.39
    sec-butyl acetate 0.26
    tert-butyl acetate 0.41
    decalin 0.02
    glycerin 24.66
    diglyme 13.28
    acrylic acid 2.29
    isopropyl myristate 0.5
    n-butyric acid 1.07
    acetyl acetate 0.1
    di(2-ethylhexyl) phthalate 0.62
    ethyl propionate 0.81
    nitromethane 1.25
    1,2-diethoxyethane 1.88
    benzonitrile 0.23
    trioctyl phosphate 0.81
    1-bromopropane 0.06
    gamma-valerolactone 8.95
    n-decanol 1.12
    triethyl phosphate 0.76
    4-methyl-2-pentanol 0.36
    propionitrile 0.5
    vinylene carbonate 0.57
    1,1,2-trichlorotrifluoroethane 3.47
    DMS 0.93
    cumene 0.09
    2-octanol 1.15
    2-hexanone 0.52
    octyl acetate 0.91
    limonene 0.24
    1,2-dimethoxyethane 9.84
    ethyl orthosilicate 0.67
    tributyl phosphate 0.55
    diacetone alcohol 2.91
    N,N-dimethylaniline 0.76
    acrylonitrile 1.0
    aniline 0.94
    1,3-propanediol 11.82
    bromobenzene 0.01
    dibromomethane 0.01
    1,1,2,2-tetrachloroethane 0.09
    2-methyl-cyclohexyl acetate 0.46
    tetrabutyl urea 1.98
    diisobutyl methanol 0.29
    2-phenylethanol 0.97
    styrene 0.1
    dioctyl adipate 0.78
    dimethyl sulfate 4.34
    ethyl butyrate 0.84
    methyl lactate 8.82
    butyl lactate 3.05
    diethyl carbonate 0.57
    propanediol butyl ether 8.37
    triethyl orthoformate 1.19
    p-tert-butyltoluene 0.17
    methyl 4-tert-butylbenzoate 2.15
    morpholine 7.88
    tert-butylamine 0.49
    n-dodecanol 0.73
    dimethoxymethane 14.12
    ethylene carbonate 0.51
    cyrene 5.93
    2-ethoxyethyl acetate 1.89
    2-ethylhexyl acetate 0.43
    1,2,4-trichlorobenzene 0.06
    4-methylpyridine 1.16
    dibutyl ether 0.82
    2,6-dimethyl-4-heptanol 0.29
    DEF 6.44
    dimethyl isosorbide 5.28
    tetrachloroethylene 0.08
    eugenol 3.07
    triacetin 1.29
    span 80 4.16
    1,4-butanediol 3.79
    1,1-dichloroethane 0.01
    2-methyl-1-pentanol 0.55
    methyl formate 2.88
    2-methyl-1-butanol 1.32
    n-decane 0.07
    butyronitrile 0.3
    3,7-dimethyl-1-octanol 0.53
    1-chlorooctane 0.17
    1-chlorotetradecane 0.08
    n-nonane 0.05
    undecane 0.05
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 2.14
    tetrahydropyran 1.11
    tert-amyl methyl ether 0.86
    2,5,8-trioxanonane 9.62
    1-hexene 0.08
    2-isopropoxyethanol 4.79
    2,2,2-trifluoroethanol 0.66
    methyl butyrate 0.96

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction