Piperonylic Acid

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  • Identifiers

    CAS number
    94-53-1

    Molecular formula
    C8H6O4

    SMILES
    C1OC2=C(O1)C=C(C=C2)C(=O)O

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1329.0
    • Carbowax: 2177.0

  • Odor profile

    Phenolic 51.97%
    Balsamic 49.13%
    Vanilla 45.65%
    Sweet 45.61%
    Odorless 38.75%
    Powdery 35.57%
    Spicy 35.45%
    Creamy 34.87%
    Aromatic 34.52%
    Coumarinic 28.76%

    Scent© AI

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    6.92 (neutral)

    Molecular weight
    166.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    348°C

    Melting point expt.

    • 229 °C

    Flash point est.
    178.24 ˚C

  • Synonyms

    • PIPERONYLIC ACID
    • 94-53-1
    • 1,3-Benzodioxole-5-carboxylic acid
    • Benzo[d][1,3]dioxole-5-carboxylic acid
    • Heliotropic acid
    • 3,4-Methylenedioxybenzoic acid
    • Protocatechuic acid methylene ether
    • benzo[1,3]dioxole-5-carboxylic acid
    • 3,4-(Methylenedioxy)benzoic acid
    • 2H-1,3-Benzodioxole-5-Carboxylic Acid
    • 5-Benzodioxolecarboxylic acid
    • MFCD00005830
    • 3,4-Dioxymethylenebenzoic acid
    • 3,4-Methylene dioxybenzoic acid
    • NSC 10072
    • Benzoic acid, 3,4-(methylenedioxy)-
    • QX3V1NO0KH
    • EINECS 202-342-8
    • AI3-05972
    • NSC-10072
    • PIPERONYLIC ACID [MI]
    • DTXSID6059104
    • CHEBI:107644
    • 1,3-dioxaindane-5-carboxylic acid
    • PIPERONYLIC ACID-2,2-D2
    • benzo(d)(1,3)dioxole-5-carboxylic acid
    • UNII-QX3V1NO0KH
    • piperonylsaure
    • 4ddk
    • 0HN
    • Spectrum_001164
    • Piperonylic acid, 99%
    • Spectrum3_001022
    • Spectrum4_001152
    • 5Benzodioxolecarboxylic acid
    • 5-carboxy-1,3-benzodioxole
    • BSPBio_002803
    • KBioGR_001723
    • KBioSS_001644
    • SPECTRUM500580
    • 3,4Dioxymethylenebenzoic acid
    • SCHEMBL142318
    • 3,4Methylene dioxybenzoic acid
    • CHEMBL573781
    • 1,3Benzodioxole5carboxylic acid
    • PIPERONYLIC ACID [INCI]
    • 3,4-methylenedioxy-benzoic acid
    • DTXCID7048902
    • KBio2_001644
    • KBio2_004212
    • KBio2_006780
    • KBio3_002023
    • VDVJGIYXDVPQLP-UHFFFAOYSA-
    • Benzoic acid,4-(methylenedioxy)-
    • BDBM153299
    • benzoic acid, 3,4-methylenedioxy-
    • 3, 4-(Methylenedioxy)benzoic acid
    • 3,4-(Methylenedioxy)-Benzoic acid
    • Benzoic acid, 3,4(methylenedioxy)
    • CS-D1455
    • NSC10072
    • STR05605
    • BBL011979
    • STK397540
    • 1,3-Benzodioxole -5-carboxylic acid
    • 1,3-benzodioxole-5-carbonsäure
    • AKOS000113163
    • benzo[1,3]-dioxole-5-carboxylic acid
    • BS-3899
    • CCG-214272
    • FB34327
    • PB47803
    • SDCCGMLS-0065919.P001
    • SDCCGMLS-0065919.P002
    • Benzo[d][1,3]dioxole-5-carboxylicacid
    • Benzo[d][I,3]dioxole-5-carboxylic acid
    • NCGC00095970-01
    • NCGC00095970-02
    • AC-11342
    • HY-41404
    • SY004612
    • 1,3-Benzodioxole-5-carboxylic acid, 9CI
    • Piperonylic acid, purum, >=97.0% (T)
    • DB-011499
    • NS00040406
    • P0459
    • EN300-20111
    • F16336
    • 3,4-(Methylenedioxy)benzoic acid;Piperonylic acid
    • AE-562/40258182
    • BRD-K52148119-001-01-5
    • BRD-K52148119-001-02-3
    • Q27185967
    • F3318-0150
    • Z104476884
    • 3,4-Methylenedioxybenzoic acid; 1,3-Benzodioxole-5-carboxylic acid
    • InChI=1/C8H6O4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H,9,10)
    • 202-342-8

  • Applications

    Piperonylic acid (CAS 94-53-1, 3,4-methylenedioxycinnamic acid) is a versatile intermediate for synthesis and research: it serves as a building block to access methylenedioxyphenyl derivatives for pharmaceuticals, agrochemicals, flavors and fragrances (via ester/amide formation, acid chloride activation, reduction or decarboxylation, and cross-coupling workflows), as an analytical reference standard for HPLC/GC quantification of methylenedioxy compounds in botanicals and foods, and, notably, as a mechanism-based inhibitor of the plant cytochrome P450 enzyme cinnamate 4-hydroxylase (C4H) to modulate phenylpropanoid/monolignol metabolism in studies of lignin biosynthesis, cell-wall remodeling, defense responses and biomass saccharification; its carboxylic acid handle also enables labeling, prodrug and conjugate design, or incorporation as a functional comonomer precursor in materials.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 52.86
    methanol 134.38
    isopropanol 32.27
    water 6.77
    ethyl acetate 37.66
    n-propanol 31.25
    acetone 112.62
    n-butanol 25.69
    acetonitrile 63.02
    DMF 233.27
    toluene 8.78
    isobutanol 18.9
    1,4-dioxane 120.35
    methyl acetate 59.81
    THF 133.38
    2-butanone 55.01
    n-pentanol 20.28
    sec-butanol 21.23
    n-hexane 0.95
    ethylene glycol 39.29
    NMP 190.2
    cyclohexane 2.45
    DMSO 198.13
    n-butyl acetate 16.23
    n-octanol 30.69
    chloroform 11.58
    n-propyl acetate 20.64
    acetic acid 57.85
    dichloromethane 36.54
    cyclohexanone 52.0
    propylene glycol 18.38
    isopropyl acetate 23.27
    DMAc 231.36
    2-ethoxyethanol 82.29
    isopentanol 22.66
    n-heptane 3.29
    ethyl formate 35.2
    1,2-dichloroethane 30.93
    n-hexanol 15.03
    2-methoxyethanol 132.13
    isobutyl acetate 8.61
    tetrachloromethane 2.77
    n-pentyl acetate 20.82
    transcutol 198.32
    n-heptanol 20.33
    ethylbenzene 6.7
    MIBK 20.87
    2-propoxyethanol 51.08
    tert-butanol 42.25
    MTBE 23.28
    2-butoxyethanol 50.07
    propionic acid 26.69
    o-xylene 11.4
    formic acid 84.02
    diethyl ether 35.45
    m-xylene 8.82
    p-xylene 9.36
    chlorobenzene 10.61
    dimethyl carbonate 43.85
    n-octane 2.6
    formamide 203.96
    cyclopentanone 87.78
    2-pentanone 35.19
    anisole 30.42
    cyclopentyl methyl ether 39.32
    gamma-butyrolactone 108.45
    1-methoxy-2-propanol 70.68
    pyridine 64.19
    3-pentanone 30.88
    furfural 96.51
    n-dodecane 2.78
    diethylene glycol 64.94
    diisopropyl ether 10.18
    tert-amyl alcohol 26.48
    acetylacetone 53.13
    n-hexadecane 3.06
    acetophenone 34.63
    methyl propionate 43.1
    isopentyl acetate 14.7
    trichloroethylene 39.8
    n-nonanol 28.72
    cyclohexanol 20.85
    benzyl alcohol 30.03
    2-ethylhexanol 11.63
    isooctanol 17.0
    dipropyl ether 18.73
    1,2-dichlorobenzene 12.87
    ethyl lactate 19.04
    propylene carbonate 37.96
    n-methylformamide 118.88
    2-pentanol 16.04
    n-pentane 1.75
    1-propoxy-2-propanol 30.96
    1-methoxy-2-propyl acetate 29.49
    2-(2-methoxypropoxy) propanol 57.53
    mesitylene 7.18
    ε-caprolactone 48.37
    p-cymene 8.02
    epichlorohydrin 107.95
    1,1,1-trichloroethane 10.86
    2-aminoethanol 43.5
    morpholine-4-carbaldehyde 197.05
    sulfolane 117.13
    2,2,4-trimethylpentane 1.03
    2-methyltetrahydrofuran 64.82
    n-hexyl acetate 31.29
    isooctane 0.94
    2-(2-butoxyethoxy)ethanol 83.31
    sec-butyl acetate 13.15
    tert-butyl acetate 25.36
    decalin 1.56
    glycerin 44.82
    diglyme 146.92
    acrylic acid 32.79
    isopropyl myristate 16.93
    n-butyric acid 25.32
    acetyl acetate 29.11
    di(2-ethylhexyl) phthalate 18.21
    ethyl propionate 21.34
    nitromethane 185.96
    1,2-diethoxyethane 52.02
    benzonitrile 25.72
    trioctyl phosphate 14.61
    1-bromopropane 10.8
    gamma-valerolactone 128.78
    n-decanol 22.13
    triethyl phosphate 15.31
    4-methyl-2-pentanol 11.4
    propionitrile 31.42
    vinylene carbonate 37.75
    1,1,2-trichlorotrifluoroethane 54.28
    DMS 28.33
    cumene 5.83
    2-octanol 16.13
    2-hexanone 21.3
    octyl acetate 22.6
    limonene 10.0
    1,2-dimethoxyethane 120.14
    ethyl orthosilicate 14.38
    tributyl phosphate 14.14
    diacetone alcohol 40.36
    N,N-dimethylaniline 27.38
    acrylonitrile 51.55
    aniline 22.95
    1,3-propanediol 51.63
    bromobenzene 8.71
    dibromomethane 14.52
    1,1,2,2-tetrachloroethane 25.98
    2-methyl-cyclohexyl acetate 16.95
    tetrabutyl urea 28.53
    diisobutyl methanol 10.18
    2-phenylethanol 22.76
    styrene 8.35
    dioctyl adipate 25.1
    dimethyl sulfate 69.31
    ethyl butyrate 18.87
    methyl lactate 33.26
    butyl lactate 18.15
    diethyl carbonate 15.32
    propanediol butyl ether 42.95
    triethyl orthoformate 16.91
    p-tert-butyltoluene 7.54
    methyl 4-tert-butylbenzoate 40.45
    morpholine 115.5
    tert-butylamine 18.77
    n-dodecanol 17.36
    dimethoxymethane 143.7
    ethylene carbonate 30.07
    cyrene 59.6
    2-ethoxyethyl acetate 38.02
    2-ethylhexyl acetate 11.4
    1,2,4-trichlorobenzene 17.25
    4-methylpyridine 44.26
    dibutyl ether 24.53
    2,6-dimethyl-4-heptanol 10.18
    DEF 69.06
    dimethyl isosorbide 80.26
    tetrachloroethylene 20.33
    eugenol 41.29
    triacetin 40.76
    span 80 36.26
    1,4-butanediol 27.46
    1,1-dichloroethane 15.05
    2-methyl-1-pentanol 16.72
    methyl formate 93.89
    2-methyl-1-butanol 18.37
    n-decane 4.24
    butyronitrile 23.71
    3,7-dimethyl-1-octanol 20.53
    1-chlorooctane 12.02
    1-chlorotetradecane 6.07
    n-nonane 3.73
    undecane 3.37
    tert-butylcyclohexane 1.17
    cyclooctane 1.66
    cyclopentanol 29.63
    tetrahydropyran 47.56
    tert-amyl methyl ether 20.44
    2,5,8-trioxanonane 117.07
    1-hexene 3.49
    2-isopropoxyethanol 47.77
    2,2,2-trifluoroethanol 38.51
    methyl butyrate 25.5

    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

Botanical

Name CAS Botanical Proportion
Pepper, black 1 8006-82-4 Piper nigrum L., fam. Piperaceae 0.1%
Eucalyptus lehmanni (Uruguay) Eucalyptus lehmanni Preiss, fam. Myrtaceae 1.4%
Cinnamomum micranthum (China) Cinnamomum mecranthum (Hayata) Hayata, fam. Lauraceae 0.24%
Cinnamomum parthenoxylon (Vietnam) 1b Cinnamomum parthenoxylon (Jack) Nees, fam. Lauraceae 0.05%
Lemongrass (Burkina Faso) 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 0.3%