Paeoniflorin

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  • Identifiers

    CAS number
    23180-57-6

    Molecular formula
    C23H28O11

    SMILES
    C[C@]12C[C@@]3([C@@H]4C[C@]1([C@@]4([C@H](O2)O3)COC(=O)C5=CC=CC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 62.16%
    Sweet 39.24%
    Balsamic 21.72%
    Cooling 21.06%
    Vanilla 20.32%
    Spicy 19.13%
    Milky 18.89%
    Woody 17.59%
    Clean 17.46%
    Bitter 17.41%

     

    Flavor
    Bitter 77.99%
    Fatty 35.3%
    Bland 28.47%
    Sweet-like 27.83%
    Odorless 27.41%
    Metallic 22.37%
    Cedarleaf 21.28%
    Naphthalic 20.22%
    Alkaline 19.85%
    Cauliflower 19.65%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.0

    pKa est.
    5.84 (weak acid)

    Molecular weight
    480.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    1857°C

    Flash point

    • 200.2 ˚C est.

  • Synonyms

    • Paeoniflorin
    • Peoniflorin
    • 23180-57-6
    • NSC-178886
    • 21AIQ4EV64
    • DTXSID2042648
    • [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
    • ((1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-9,10-dioxatetracyclo(4.3.1.02,5.03,8)decan-2-yl)methyl benzoate
    • RefChem:45627
    • DTXCID401478399
    • 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-lH-3,4-dioxacyclobuta(cd) pentalen-1a(2H)-yl-beta-D-glucopyranoside
    • 245-476-2
    • Paeonia moutan
    • ((2S,2aR,2a1S,3aR,4R,5aR)-4-Hydroxy-2-methyl-2a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methyl benzoate
    • b-D-Glucopyranoside,(1aR,2S,3aR,5R,5aR,5bS)-5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl
    • Paeoniflorin (>80%)
    • MFCD00869331
    • NSC 178886
    • paeonilflorin
    • UNII-21AIQ4EV64
    • CCRIS 6494
    • Paeoniflorin RS
    • NSC178886
    • s2410
    • Paeoniflorin CRS
    • YKRGDOXKVOZESV-WRJNSLSBSA-N
    • .BETA.-D-GLUCOPYRANOSIDE, (1AR,2S,3AR,5R,5AR,5BS)-5B-((BENZOYLOXY)METHYL)TETRAHYDRO-5-HYDROXY-2-METHYL-2,5-METHANO-1H-3,4-DIOXACYCLOBUTA(CD)PENTALEN-1A(2H)-YL
    • .beta.-D-Glucopyranoside, (1aR,2S,3aR,5R,5aR,5bS)-5b-[(benzoyloxy)methyl]tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl
    • EINECS 245-476-2
    • Paeoniflorin (Standard)
    • PAEONIFLORIN [USP-RS]
    • SCHEMBL549033
    • CHEBI:7889
    • orb1306020
    • CHEMBL4303209
    • HY-N0293R
    • Paeoniflorin, analytical standard
    • Paeoniflorin, >=98% (HPLC)
    • GLXC-13167
    • HMS3884D17
    • HY-N0293
    • MSK157242
    • AKOS025311455
    • CCG-269549
    • EBC-461042
    • MP08290
    • AS-12193
    • beta-D-Glucopyranoside, (1aS,2R,3aR,5R,5aR,5bS)-5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl
    • NS00027374
    • C09959
    • AB01566855_01
    • 180P576
    • Q7124104
    • BRD-K83631119-001-02-1
    • ((2S,2aR,2a1S,3aR,4R,5aR)-4-Hydroxy-2-methyl-2a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methylbenzoate
    • .BETA.-D-GLUCOPYRANOSIDE, 5B-((BENZOYLOXY)METHYL)TETRAHYDRO-5-HYDROXY-2-METHYL-2,5-METHANO-1H-3,4-DIOXACYCLOBUTA(CD)PENTALEN-1A(2H)-YL, (1AR-(1A.ALPHA.,2.BETA.,3A.ALPHA.,5.ALPHA.,5A.ALPHA.,5B.ALPHA.))-
    • [(1aR,2S,3aR,5R,5aR,5bS)-1a-(beta-D-Glucopyranosyloxy)-5-hydroxy-2-methyltetrahydro-1H-2,5-methano-3,4-dioxacyclobuta[cd]pentalen-5b(3aH)-yl]methyl benzoate
    • [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
    • [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl benzoate
    • [hydroxy-methyl-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-[?]yl]methyl benzoate
    • 5b-((Benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-lH-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl-beta-D-glucopyranoside
    • 9[(Benzoyioxy)methyl]-1-(?-D-glucopyranosyloxy)-4,8-epoxy-6-methyl-7-oxaticyclo[4,3,0,0]nonane
    • beta-D-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, (1aR-(1a-alpha,2-beta,3a-alpha,5-alpha,5a-alpha,5b-alpha))-
    • beta-d-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, (1aR-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))-
    • 23180-57-6

  • Applications

    Paeoniflorin, CAS 23180-57-6, is primarily used in pharmaceutical research and development of herbal products as a natural bioactive constituent that has been studied for activity in biological systems; it is used as an analytical reference standard for quality control of Paeoniae radix extracts; it is employed in cosmetic and personal care formulations as a plant-derived extract ingredient; it can serve as an intermediate/precursor in the synthesis of related glycosides for medicinal chemistry research; and it is used as a reagent in pharmacognosy and analytical studies of herbal materials.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 41.75
    methanol 240.31
    isopropanol 14.68
    water 1.74
    ethyl acetate 33.21
    n-propanol 26.91
    acetone 125.79
    n-butanol 15.98
    acetonitrile 46.77
    DMF 651.5
    toluene 2.44
    isobutanol 8.76
    1,4-dioxane 94.5
    methyl acetate 40.83
    THF 201.37
    2-butanone 48.27
    n-pentanol 7.07
    sec-butanol 7.77
    n-hexane 0.05
    ethylene glycol 80.62
    NMP 276.68
    cyclohexane 0.19
    DMSO 811.04
    n-butyl acetate 7.58
    n-octanol 5.87
    chloroform 31.54
    n-propyl acetate 10.67
    acetic acid 429.34
    dichloromethane 35.92
    cyclohexanone 57.51
    propylene glycol 56.84
    isopropyl acetate 16.02
    DMAc 342.5
    2-ethoxyethanol 139.21
    isopentanol 7.75
    n-heptane 0.14
    ethyl formate 60.62
    1,2-dichloroethane 20.72
    n-hexanol 4.69
    2-methoxyethanol 435.86
    isobutyl acetate 4.22
    tetrachloromethane 2.26
    n-pentyl acetate 9.76
    transcutol 122.47
    n-heptanol 5.91
    ethylbenzene 0.77
    MIBK 15.41
    2-propoxyethanol 81.32
    tert-butanol 9.53
    MTBE 4.73
    2-butoxyethanol 43.59
    propionic acid 47.61
    o-xylene 1.5
    formic acid 485.81
    diethyl ether 11.27
    m-xylene 1.43
    p-xylene 0.95
    chlorobenzene 4.55
    dimethyl carbonate 74.72
    n-octane 0.09
    formamide 514.74
    cyclopentanone 130.53
    2-pentanone 38.67
    anisole 9.19
    cyclopentyl methyl ether 18.86
    gamma-butyrolactone 179.3
    1-methoxy-2-propanol 192.45
    pyridine 44.55
    3-pentanone 21.11
    furfural 169.18
    n-dodecane 0.11
    diethylene glycol 131.57
    diisopropyl ether 1.42
    tert-amyl alcohol 5.95
    acetylacetone 106.69
    n-hexadecane 0.13
    acetophenone 15.25
    methyl propionate 46.57
    isopentyl acetate 6.23
    trichloroethylene 61.47
    n-nonanol 6.03
    cyclohexanol 6.61
    benzyl alcohol 15.09
    2-ethylhexanol 2.31
    isooctanol 3.85
    dipropyl ether 5.11
    1,2-dichlorobenzene 4.96
    ethyl lactate 21.4
    propylene carbonate 56.14
    n-methylformamide 348.56
    2-pentanol 5.05
    n-pentane 0.11
    1-propoxy-2-propanol 34.22
    1-methoxy-2-propyl acetate 28.74
    2-(2-methoxypropoxy) propanol 33.35
    mesitylene 0.81
    ε-caprolactone 54.51
    p-cymene 0.86
    epichlorohydrin 178.61
    1,1,1-trichloroethane 7.69
    2-aminoethanol 97.16
    morpholine-4-carbaldehyde 351.77
    sulfolane 261.75
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 30.1
    n-hexyl acetate 11.79
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 54.78
    sec-butyl acetate 4.91
    tert-butyl acetate 13.68
    decalin 0.08
    glycerin 199.97
    diglyme 118.76
    acrylic acid 94.13
    isopropyl myristate 3.47
    n-butyric acid 61.23
    acetyl acetate 36.83
    di(2-ethylhexyl) phthalate 6.45
    ethyl propionate 12.48
    nitromethane 714.87
    1,2-diethoxyethane 17.18
    benzonitrile 11.41
    trioctyl phosphate 4.94
    1-bromopropane 3.53
    gamma-valerolactone 383.93
    n-decanol 3.79
    triethyl phosphate 5.71
    4-methyl-2-pentanol 2.86
    propionitrile 19.41
    vinylene carbonate 74.76
    1,1,2-trichlorotrifluoroethane 196.39
    DMS 15.38
    cumene 0.5
    2-octanol 2.96
    2-hexanone 10.24
    octyl acetate 6.27
    limonene 1.41
    1,2-dimethoxyethane 133.86
    ethyl orthosilicate 4.69
    tributyl phosphate 4.87
    diacetone alcohol 42.15
    N,N-dimethylaniline 5.78
    acrylonitrile 53.14
    aniline 9.77
    1,3-propanediol 116.99
    bromobenzene 3.17
    dibromomethane 12.1
    1,1,2,2-tetrachloroethane 34.2
    2-methyl-cyclohexyl acetate 6.02
    tetrabutyl urea 9.14
    diisobutyl methanol 1.56
    2-phenylethanol 10.63
    styrene 1.14
    dioctyl adipate 8.23
    dimethyl sulfate 138.06
    ethyl butyrate 9.01
    methyl lactate 94.02
    butyl lactate 15.64
    diethyl carbonate 6.66
    propanediol butyl ether 41.79
    triethyl orthoformate 7.9
    p-tert-butyltoluene 0.84
    methyl 4-tert-butylbenzoate 18.75
    morpholine 123.83
    tert-butylamine 2.04
    n-dodecanol 2.39
    dimethoxymethane 290.68
    ethylene carbonate 52.07
    cyrene 58.29
    2-ethoxyethyl acetate 25.05
    2-ethylhexyl acetate 3.91
    1,2,4-trichlorobenzene 7.53
    4-methylpyridine 25.19
    dibutyl ether 3.49
    2,6-dimethyl-4-heptanol 1.56
    DEF 67.11
    dimethyl isosorbide 54.4
    tetrachloroethylene 20.88
    eugenol 23.22
    triacetin 26.02
    span 80 26.4
    1,4-butanediol 29.1
    1,1-dichloroethane 9.62
    2-methyl-1-pentanol 3.85
    methyl formate 281.75
    2-methyl-1-butanol 6.96
    n-decane 0.21
    butyronitrile 14.69
    3,7-dimethyl-1-octanol 3.69
    1-chlorooctane 1.27
    1-chlorotetradecane 0.46
    n-nonane 0.16
    undecane 0.15
    tert-butylcyclohexane 0.06
    cyclooctane 0.09
    cyclopentanol 14.91
    tetrahydropyran 25.21
    tert-amyl methyl ether 4.46
    2,5,8-trioxanonane 76.66
    1-hexene 0.29
    2-isopropoxyethanol 39.33
    2,2,2-trifluoroethanol 136.79
    methyl butyrate 18.77

    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