Biopterin

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  • Identifiers

    CAS number
    22150-76-1

    Molecular formula
    C9H11N5O3

    SMILES
    C[C@@H]([C@@H](C1=CN=C2C(=N1)C(=O)NC(=N2)N)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 79.54%
    Savory 23.75%
    Bitter 20.65%
    Cooked 19.42%
    Roasted 19.19%
    Milky 18.51%
    Meaty 17.8%
    Burnt 16.9%
    Nutty 15.8%
    Popcorn 14.12%

     

    Flavor
    Bitter 75.09%
    Odorless 53.61%
    Bland 28.18%
    Mild 24.82%
    Sweet-like 23.03%
    Very mild 22.12%
    Bread crust 18.97%
    Yeast 18.51%
    Nitrile 18.4%
    Taco 18.38%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.4

    pKa est.
    8.98 (weak base)

    Molecular weight
    237.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1262°C

    Flash point

    • 314.35 ˚C est.

    Solubility expt.

    • 0.7 mg/mL

  • Synonyms

    • 6-Biopterin
    • L-Biopterin
    • 22150-76-1
    • biopterin
    • L-Erythro-Biopterin
    • (-)-Biopterin
    • E54CTM794Y
    • NSC-339699
    • CHEBI:63931
    • DTXSID30912041
    • 4(1H)-Pteridinone, 2-amino-6-(1,2-dihydroxypropyl)-, (S-(R*,S*))-
    • 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one
    • CHEBI:15373
    • L Biopterin
    • 2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-1,4-dihydropteridin-4-one
    • 6 Biopterin
    • L erythro Biopterin
    • RefChem:917204
    • GlyTouCan:G34146ZD
    • 2-Amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone
    • DTXCID201341069
    • G34146ZD
    • 244-807-8
    • 2-Amino-6-((1S,2R)-1,2-dihydroxypropyl)-4(1H)-pteridinone
    • 2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4(1H)-pteridinone
    • MFCD00036787
    • 2-amino-6-((1R,2S)-1,2-dihydroxypropyl)pteridin-4(1H)-one
    • 4(1H)-Pteridinone, 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-
    • 2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine
    • 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one
    • 2-amino-6-((1R,2S)-1,2-dihydroxypropyl)pteridin-4(3H)-one
    • 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]pteridin-4(3H)-one
    • (1R,2S)-1-(2-AMINO-4-HYDROXYPTERIDIN-6-YL)PROPANE-1,2-DIOL
    • NSC 339699
    • UNII-E54CTM794Y
    • 2-AMINO-6-((1R,2S)-1,2-DIHYDROXYPROPYL)-4(1H)-PTERIDINONE
    • 4(1H)-PTERIDINONE, 2-AMINO-6-((1R,2S)-1,2-DIHYDROXYPROPYL)-
    • L-erythro biopterin
    • EINECS 244-807-8
    • BIOPTERIN [MI]
    • (1'R,1'S) Biopterin
    • 6-Biopterin, >=97%
    • SCHEMBL258466
    • orb1299675
    • SCHEMBL5541270
    • SCHEMBL18662632
    • SCHEMBL29400382
    • GLXC-07348
    • (L-erythro)-2-Amino-6-(1,2-dihydroxypropyl)-4(3H)-pteridinon
    • L-erythro-Biopterin,NSC 339699
    • EBC-66031
    • MFCD29763933
    • s5577
    • Sapropterin Impurity 15 (Biopterin)
    • AKOS025312532
    • AKOS028109358
    • AKOS030254292
    • CCG-266851
    • CS-6962
    • FB03838
    • AC-28999
    • AS-70364
    • SY226840
    • 6-(L-erythro-1,2-dihydroxypropyl)-pterin
    • HY-102015
    • B6302
    • EN300-7365623
    • 150B761
    • Q408256
    • Z3245415986
    • 2-amino-6-(L-erythro-1,2-dihydroxypropyl)-4(3H)-Pteridinone
    • 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3H-pteridin-4-one
    • 2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]pteridin-4(8H)-one
    • (S-(R*,S*))-2-Amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one
    • [S-(R*,S*)]-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-Pteridinone
    • 4(3H)-Pteridinone, 2-amino-6-(L-erythro-1,2-dihydroxypropyl)-
    • 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-3,4-dihydropteridin-4-one
    • 22150-76-1

  • Applications

    Biopterin (CAS 22150-76-1) is primarily used in biochemical and pharmaceutical research as a reagent and analytical reference standard; as a pteridine-derived compound it serves as a model and potential precursor for the synthesis of compounds related to the tetrahydrobiopterin cofactor and enzymes such as nitric oxide synthase and phenylalanine/tyrosine hydroxylases; it is used as a calibration standard for LC-MS/HPLC methods to quantify pterins in biological samples; it may function as an intermediate in the synthesis of pteridine-based structures for drug discovery and development and as a reference material in enzymatic assays; use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.04
    methanol 0.13
    isopropanol 0.02
    water 0.12
    ethyl acetate 0.0
    n-propanol 0.05
    acetone 0.0
    n-butanol 0.04
    acetonitrile 0.01
    DMF 0.26
    toluene 0.0
    isobutanol 0.02
    1,4-dioxane 0.0
    methyl acetate 0.0
    THF 0.04
    2-butanone 0.01
    n-pentanol 0.02
    sec-butanol 0.03
    n-hexane 0.0
    ethylene glycol 0.31
    NMP 3.76
    cyclohexane 0.0
    DMSO 2.64
    n-butyl acetate 0.02
    n-octanol 0.0
    chloroform 0.0
    n-propyl acetate 0.01
    acetic acid 0.14
    dichloromethane 0.0
    cyclohexanone 0.03
    propylene glycol 0.47
    isopropyl acetate 0.0
    DMAc 0.74
    2-ethoxyethanol 0.2
    isopentanol 0.03
    n-heptane 0.0
    ethyl formate 0.01
    1,2-dichloroethane 0.0
    n-hexanol 0.03
    2-methoxyethanol 0.82
    isobutyl acetate 0.0
    tetrachloromethane 0.0
    n-pentyl acetate 0.01
    transcutol 0.16
    n-heptanol 0.02
    ethylbenzene 0.0
    MIBK 0.0
    2-propoxyethanol 0.27
    tert-butanol 0.02
    MTBE 0.0
    2-butoxyethanol 0.15
    propionic acid 0.08
    o-xylene 0.0
    formic acid 1.99
    diethyl ether 0.0
    m-xylene 0.0
    p-xylene 0.0
    chlorobenzene 0.0
    dimethyl carbonate 0.01
    n-octane 0.0
    formamide 1.34
    cyclopentanone 0.06
    2-pentanone 0.01
    anisole 0.0
    cyclopentyl methyl ether 0.01
    gamma-butyrolactone 0.1
    1-methoxy-2-propanol 0.31
    pyridine 0.01
    3-pentanone 0.01
    furfural 0.25
    n-dodecane 0.0
    diethylene glycol 0.78
    diisopropyl ether 0.0
    tert-amyl alcohol 0.03
    acetylacetone 0.0
    n-hexadecane 0.0
    acetophenone 0.01
    methyl propionate 0.01
    isopentyl acetate 0.02
    trichloroethylene 0.0
    n-nonanol 0.01
    cyclohexanol 0.02
    benzyl alcohol 0.01
    2-ethylhexanol 0.02
    isooctanol 0.01
    dipropyl ether 0.01
    1,2-dichlorobenzene 0.0
    ethyl lactate 0.07
    propylene carbonate 0.04
    n-methylformamide 0.21
    2-pentanol 0.01
    n-pentane 0.0
    1-propoxy-2-propanol 0.18
    1-methoxy-2-propyl acetate 0.03
    2-(2-methoxypropoxy) propanol 0.19
    mesitylene 0.0
    ε-caprolactone 0.05
    p-cymene 0.01
    epichlorohydrin 0.03
    1,1,1-trichloroethane 0.0
    2-aminoethanol 0.44
    morpholine-4-carbaldehyde 0.42
    sulfolane 1.72
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.02
    n-hexyl acetate 0.0
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 0.15
    sec-butyl acetate 0.0
    tert-butyl acetate 0.0
    decalin 0.0
    glycerin 3.17
    diglyme 0.24
    acrylic acid 0.16
    isopropyl myristate 0.0
    n-butyric acid 0.05
    acetyl acetate 0.0
    di(2-ethylhexyl) phthalate 0.02
    ethyl propionate 0.01
    nitromethane 0.07
    1,2-diethoxyethane 0.01
    benzonitrile 0.01
    trioctyl phosphate 0.01
    1-bromopropane 0.0
    gamma-valerolactone 0.22
    n-decanol 0.0
    triethyl phosphate 0.05
    4-methyl-2-pentanol 0.01
    propionitrile 0.01
    vinylene carbonate 0.03
    1,1,2-trichlorotrifluoroethane 0.54
    DMS 0.01
    cumene 0.0
    2-octanol 0.01
    2-hexanone 0.01
    octyl acetate 0.0
    limonene 0.01
    1,2-dimethoxyethane 0.12
    ethyl orthosilicate 0.04
    tributyl phosphate 0.02
    diacetone alcohol 0.07
    N,N-dimethylaniline 0.01
    acrylonitrile 0.03
    aniline 0.01
    1,3-propanediol 0.48
    bromobenzene 0.0
    dibromomethane 0.0
    1,1,2,2-tetrachloroethane 0.0
    2-methyl-cyclohexyl acetate 0.03
    tetrabutyl urea 0.04
    diisobutyl methanol 0.01
    2-phenylethanol 0.02
    styrene 0.0
    dioctyl adipate 0.01
    dimethyl sulfate 0.08
    ethyl butyrate 0.02
    methyl lactate 0.15
    butyl lactate 0.07
    diethyl carbonate 0.02
    propanediol butyl ether 0.15
    triethyl orthoformate 0.03
    p-tert-butyltoluene 0.0
    methyl 4-tert-butylbenzoate 0.04
    morpholine 0.02
    tert-butylamine 0.01
    n-dodecanol 0.0
    dimethoxymethane 0.03
    ethylene carbonate 0.02
    cyrene 0.56
    2-ethoxyethyl acetate 0.01
    2-ethylhexyl acetate 0.02
    1,2,4-trichlorobenzene 0.0
    4-methylpyridine 0.01
    dibutyl ether 0.0
    2,6-dimethyl-4-heptanol 0.01
    DEF 0.04
    dimethyl isosorbide 0.34
    tetrachloroethylene 0.01
    eugenol 0.08
    triacetin 0.01
    span 80 0.1
    1,4-butanediol 0.1
    1,1-dichloroethane 0.0
    2-methyl-1-pentanol 0.02
    methyl formate 0.05
    2-methyl-1-butanol 0.04
    n-decane 0.0
    butyronitrile 0.01
    3,7-dimethyl-1-octanol 0.0
    1-chlorooctane 0.0
    1-chlorotetradecane 0.0
    n-nonane 0.0
    undecane 0.0
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.06
    tetrahydropyran 0.0
    tert-amyl methyl ether 0.01
    2,5,8-trioxanonane 0.23
    1-hexene 0.0
    2-isopropoxyethanol 0.05
    2,2,2-trifluoroethanol 0.14
    methyl butyrate 0.01

    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