Zizanoic acid

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  • Identifiers

    CAS number
    16203-25-1

    Molecular formula
    C15H22O2

    SMILES
    CC1([C@@H]2CC[C@@]3(C2)[C@@H](C1=C)CC[C@@H]3C(=O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Woody 82.13%
    Cedar 47.82%
    Balsamic 45.05%
    Dry 44.28%
    Amber 43.4%
    Spicy 40.55%
    Herbal 36.14%
    Camphoreous 36.03%
    Pine 35.88%
    Vetiver 32.38%

     

    Flavor
    Bitter 31.6%
    Woody 29.05%
    Balsam 23.37%
    Odorless 22.38%
    Cedarleaf 22.12%
    Sandalwood 21.47%
    Ripe apricot 21.43%
    Minty 21.43%
    Fir needle 21.1%
    Herbal 21.02%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.6

    pKa est.
    9.05 (weak base)

    Molecular weight
    234.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    367°C

    Flash point

    • 153.18 ˚C est.

  • Synonyms

    • Zizanoic acid
    • Khusenic acid
    • 16203-25-1
    • (1R,2S,5S,8R)-7,7-dimethyl-6-methylidenetricyclo[6.2.1.01,5]undecane-2-carboxylic acid
    • J14.140B
    • 6W12127I74
    • (3S-(3alpha,3aalpha,6alpha,8aalpha))-Octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-carboxylic acid
    • (1R,2S,5S,8R)-7,7-dimethyl-6-methylidenetricyclo(6.2.1.01,5)undecane-2-carboxylic acid
    • RefChem:52066
    • 240-332-5
    • [3S-(3alpha,3aalpha,6alpha,8aalpha)]-octahydro-7,7-dimethyl-8-methylene-1H-3a,6-methanoazulene-3-car
    • 1H-3a,6-Methanoazulene-3-carboxylic acid, octahydro-7,7-dimethyl-8-methylene-, (3S,3aR,6R,8aS)-
    • (+)-Zizanoic acid
    • Zizaens?ure; Zizanoicacid
    • UNII-6W12127I74
    • 1H-3a.alpha.,6-Methanoazulene-3-carboxylic acid, 2,3.beta.,4,5,6.beta.,7,8,8a.alpha.-octahydro-7,7-dimethyl-8-methylene-
    • EINECS 240-332-5
    • MEGxp0_001824
    • orb1991158
    • SCHEMBL16982358
    • ACon0_000543
    • ACon1_002030
    • 7,7-dimethyl-8-methylideneoctahydro-1h-3a,6-methanoazulene-3-carboxylic acid
    • CHEBI:181165
    • (3S,3aR,6R,8aS)-7,7-Dimethyl-8-methyleneoctahydro-1H-3a,6-methanoazulene-3-carboxylic acid
    • 1H-3A,6-METHANOAZULENE-3-CARBOXYLIC ACID, OCTAHYDRO-7,7-DIMETHYL-8-METHYLENE-, (3S-(3.ALPHA.,3A.ALPHA.,6.ALPHA.,8A.ALPHA.))-
    • AKOS040735640
    • NCGC00179899-01
    • NCGC00179899-02
    • BRD-K27523296-001-01-6
    • Q27265607
    • 1H-3A,6-METHANOAZULENE-3-CARBOXYLIC ACID, OCTAHYDRO-7,7-DIMETHYL-8-METHYLENE-
    • 7,7-DIMETHYL-6-METHYLENETRICYCLO(6.2.1.0(SUP 1,5))UNDECANE-2-CARBOXYLIC ACID
    • 7,7-Dimethyl-6-methylidenetricyclo[6.2.1.0^1,5^]undecane-2-carboxylic acid
    • (3S)-2,3,4,5,6,7,8,8A.ALPHA.-OCTAHYDRO-7,7-DIMETHYL-8-METHYLENE-1H-3A.ALPHA.,6.ALPHA.-METHANOAZULENE-3.ALPHA.-CARBOXYLIC ACID
    • NCGC00179899-02_C15H22O2_1H-3a,6-Methanoazulene-3-carboxylic acid, octahydro-7,7-dimethyl-8-methylene-, (3S,3aR,6R,8aS)-
    • 16203-25-1

  • Applications

    Zizanoic acid (CAS 16203-25-1) is primarily used as a chemical intermediate in organic synthesis, serving as a building block to prepare esters, amides, and other derivatives. It may also function as a precursor for fragrance-related esters or odorant compounds in fragrance development. In polymers and plastics, it can be used as a starting material for functionalized esters that act as plasticizers, surfactants, or resin modifiers after derivatization. In cosmetics and personal care, it may be utilized as a precursor for emollient esters or surfactants, contributing to formulation performance. In coatings, inks, and adhesives, it can serve as a source for specialty esters and crosslinkable intermediates, enabling tailored properties in formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 268.78
    methanol 366.3
    isopropanol 228.72
    water 2.85
    ethyl acetate 380.35
    n-propanol 279.64
    acetone 465.13
    n-butanol 223.05
    acetonitrile 217.58
    DMF 789.01
    toluene 336.53
    isobutanol 169.78
    1,4-dioxane 714.86
    methyl acetate 303.96
    THF 1970.77
    2-butanone 437.36
    n-pentanol 89.04
    sec-butanol 162.42
    n-hexane 8.59
    ethylene glycol 88.12
    NMP 619.51
    cyclohexane 18.72
    DMSO 716.94
    n-butyl acetate 183.62
    n-octanol 36.33
    chloroform 917.1
    n-propyl acetate 133.02
    acetic acid 193.98
    dichloromethane 740.86
    cyclohexanone 542.48
    propylene glycol 101.86
    isopropyl acetate 271.7
    DMAc 426.93
    2-ethoxyethanol 211.73
    isopentanol 177.14
    n-heptane 5.12
    ethyl formate 194.74
    1,2-dichloroethane 538.65
    n-hexanol 127.85
    2-methoxyethanol 551.02
    isobutyl acetate 83.51
    tetrachloromethane 129.09
    n-pentyl acetate 111.0
    transcutol 732.41
    n-heptanol 61.31
    ethylbenzene 99.47
    MIBK 228.3
    2-propoxyethanol 379.56
    tert-butanol 241.75
    MTBE 234.71
    2-butoxyethanol 177.44
    propionic acid 200.79
    o-xylene 142.5
    formic acid 170.8
    diethyl ether 312.36
    m-xylene 201.88
    p-xylene 102.63
    chlorobenzene 335.9
    dimethyl carbonate 252.63
    n-octane 1.73
    formamide 338.63
    cyclopentanone 988.2
    2-pentanone 388.7
    anisole 241.16
    cyclopentyl methyl ether 562.17
    gamma-butyrolactone 978.68
    1-methoxy-2-propanol 485.56
    pyridine 656.58
    3-pentanone 290.87
    furfural 703.04
    n-dodecane 1.05
    diethylene glycol 287.89
    diisopropyl ether 86.64
    tert-amyl alcohol 155.84
    acetylacetone 436.57
    n-hexadecane 1.31
    acetophenone 194.8
    methyl propionate 371.43
    isopentyl acetate 171.71
    trichloroethylene 1104.6
    n-nonanol 35.05
    cyclohexanol 193.89
    benzyl alcohol 170.28
    2-ethylhexanol 57.27
    isooctanol 47.82
    dipropyl ether 90.4
    1,2-dichlorobenzene 263.65
    ethyl lactate 94.04
    propylene carbonate 387.05
    n-methylformamide 526.64
    2-pentanol 138.91
    n-pentane 13.48
    1-propoxy-2-propanol 239.2
    1-methoxy-2-propyl acetate 324.62
    2-(2-methoxypropoxy) propanol 148.52
    mesitylene 99.28
    ε-caprolactone 456.89
    p-cymene 45.31
    epichlorohydrin 1204.65
    1,1,1-trichloroethane 430.87
    2-aminoethanol 174.0
    morpholine-4-carbaldehyde 620.15
    sulfolane 948.84
    2,2,4-trimethylpentane 7.62
    2-methyltetrahydrofuran 745.54
    n-hexyl acetate 131.91
    isooctane 7.93
    2-(2-butoxyethoxy)ethanol 210.06
    sec-butyl acetate 113.27
    tert-butyl acetate 292.73
    decalin 9.89
    glycerin 190.14
    diglyme 450.63
    acrylic acid 205.66
    isopropyl myristate 40.7
    n-butyric acid 285.91
    acetyl acetate 214.44
    di(2-ethylhexyl) phthalate 55.08
    ethyl propionate 155.5
    nitromethane 543.55
    1,2-diethoxyethane 178.18
    benzonitrile 211.95
    trioctyl phosphate 39.87
    1-bromopropane 248.87
    gamma-valerolactone 1043.21
    n-decanol 22.22
    triethyl phosphate 66.69
    4-methyl-2-pentanol 90.5
    propionitrile 239.01
    vinylene carbonate 359.92
    1,1,2-trichlorotrifluoroethane 494.21
    DMS 207.33
    cumene 54.52
    2-octanol 31.93
    2-hexanone 134.29
    octyl acetate 55.31
    limonene 52.9
    1,2-dimethoxyethane 370.64
    ethyl orthosilicate 61.09
    tributyl phosphate 49.77
    diacetone alcohol 300.79
    N,N-dimethylaniline 131.14
    acrylonitrile 316.47
    aniline 377.28
    1,3-propanediol 256.23
    bromobenzene 319.21
    dibromomethane 466.68
    1,1,2,2-tetrachloroethane 749.33
    2-methyl-cyclohexyl acetate 96.86
    tetrabutyl urea 59.9
    diisobutyl methanol 42.91
    2-phenylethanol 190.21
    styrene 120.56
    dioctyl adipate 65.6
    dimethyl sulfate 389.34
    ethyl butyrate 112.43
    methyl lactate 210.34
    butyl lactate 114.39
    diethyl carbonate 84.52
    propanediol butyl ether 139.83
    triethyl orthoformate 87.9
    p-tert-butyltoluene 48.04
    methyl 4-tert-butylbenzoate 158.88
    morpholine 830.71
    tert-butylamine 122.19
    n-dodecanol 14.07
    dimethoxymethane 742.2
    ethylene carbonate 302.33
    cyrene 171.09
    2-ethoxyethyl acetate 220.16
    2-ethylhexyl acetate 120.75
    1,2,4-trichlorobenzene 309.7
    4-methylpyridine 603.89
    dibutyl ether 43.14
    2,6-dimethyl-4-heptanol 42.91
    DEF 332.42
    dimethyl isosorbide 320.06
    tetrachloroethylene 475.31
    eugenol 157.71
    triacetin 148.11
    span 80 120.14
    1,4-butanediol 67.36
    1,1-dichloroethane 483.17
    2-methyl-1-pentanol 78.04
    methyl formate 367.63
    2-methyl-1-butanol 152.41
    n-decane 2.25
    butyronitrile 209.23
    3,7-dimethyl-1-octanol 44.68
    1-chlorooctane 20.58
    1-chlorotetradecane 5.79
    n-nonane 2.02
    undecane 1.49
    tert-butylcyclohexane 9.2
    cyclooctane 7.3
    cyclopentanol 273.19
    tetrahydropyran 658.8
    tert-amyl methyl ether 146.79
    2,5,8-trioxanonane 240.59
    1-hexene 39.24
    2-isopropoxyethanol 134.88
    2,2,2-trifluoroethanol 162.98
    methyl butyrate 172.35

    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