Zizanene

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  • Identifiers

    CAS number
    20085-19-2

    Molecular formula
    C15H24

    SMILES
    CC1=C[C@@H]2[C@H](CC1)C(=CC[C@@H]2C(C)C)C

    Retention indicies (RI)

    • DB5: 1485.8
    • Carbowax: 1690.0

  • Odor profile

    Woody 82.01%
    Spicy 64.43%
    Herbal 60.93%
    Green 51.95%
    Fresh 48.61%
    Citrus 46.73%
    Terpenic 41.8%
    Dry 37.43%
    Pine 34.48%
    Oily 31.04%

    Scent© AI

  • Properties

    XLogP3-AA
    4.1

    pKa est.
    10.06 (weak base)

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    261°C

    Flash point est.
    97.25 ˚C

  • Synonyms

    • Zizanene
    • (+)-alpha-amorphene
    • Amorphene
    • alpha-Amorphene
    • QMAYBMKBYCGXDH-KFWWJZLASA-N
    • DTXSID601020740
    • 20085-19-2
    • Q67880158
    • (1R,4aS,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene

  • Applications

    Zizanene (CAS 20085-19-2) is a sesquiterpene hydrocarbon occurring naturally in vetiver oil and some other woody tropical essential oils; in practice it is used mainly as a fragrance raw material to deliver and reinforce dry-woody, earthy and slightly smoky facets, adding depth and substantivity to vetiver accords in fine fragrances, aftershaves, personal care and home care; analytically, zizanene is employed as a reference/marker compound for GC–MS profiling and quantitation of the sesquiterpene fraction of vetiver oil to support traceability and quality control; in research it serves as a model molecule for studies of sesquiterpene biosynthesis and odor structure–activity, and as a precursor/starting point to prepare oxidized derivatives (e.g., zizanal, zizanoic acid) used in vetiver reconstitution; additionally, thanks to its hydrophobicity and moderate volatility, zizanene can act as a low-level odor modulator to round out woody–amber compositions without imposing a strong signature, with use subject to prevailing fragrance safety guidelines and storage recommended under inert gas, cool and dark to limit oxidation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 58.2
    methanol 19.74
    isopropanol 71.43
    water 0.02
    ethyl acetate 211.7
    n-propanol 77.24
    acetone 165.8
    n-butanol 111.66
    acetonitrile 74.07
    DMF 94.48
    toluene 498.81
    isobutanol 72.17
    1,4-dioxane 506.25
    methyl acetate 143.9
    THF 916.97
    2-butanone 234.21
    n-pentanol 75.49
    sec-butanol 84.03
    n-hexane 124.53
    ethylene glycol 3.24
    NMP 148.0
    cyclohexane 289.63
    DMSO 80.71
    n-butyl acetate 483.67
    n-octanol 126.63
    chloroform 501.95
    n-propyl acetate 153.34
    acetic acid 33.58
    dichloromethane 462.04
    cyclohexanone 429.22
    propylene glycol 10.6
    isopropyl acetate 183.38
    DMAc 129.1
    2-ethoxyethanol 60.07
    isopentanol 115.26
    n-heptane 260.01
    ethyl formate 78.94
    1,2-dichloroethane 296.36
    n-hexanol 250.19
    2-methoxyethanol 71.02
    isobutyl acetate 147.54
    tetrachloromethane 129.6
    n-pentyl acetate 215.8
    transcutol 425.24
    n-heptanol 118.4
    ethylbenzene 216.22
    MIBK 178.31
    2-propoxyethanol 187.4
    tert-butanol 109.47
    MTBE 256.39
    2-butoxyethanol 121.54
    propionic acid 41.82
    o-xylene 235.87
    formic acid 2.97
    diethyl ether 318.63
    m-xylene 293.41
    p-xylene 249.67
    chlorobenzene 292.17
    dimethyl carbonate 45.5
    n-octane 72.99
    formamide 7.11
    cyclopentanone 428.16
    2-pentanone 231.09
    anisole 235.08
    cyclopentyl methyl ether 425.2
    gamma-butyrolactone 269.73
    1-methoxy-2-propanol 91.24
    pyridine 442.17
    3-pentanone 196.2
    furfural 181.06
    n-dodecane 48.15
    diethylene glycol 57.91
    diisopropyl ether 143.79
    tert-amyl alcohol 108.09
    acetylacetone 203.82
    n-hexadecane 56.98
    acetophenone 183.69
    methyl propionate 129.1
    isopentyl acetate 408.53
    trichloroethylene 444.19
    n-nonanol 127.55
    cyclohexanol 176.68
    benzyl alcohol 106.88
    2-ethylhexanol 256.7
    isooctanol 109.94
    dipropyl ether 479.73
    1,2-dichlorobenzene 223.39
    ethyl lactate 46.12
    propylene carbonate 175.42
    n-methylformamide 28.16
    2-pentanol 96.35
    n-pentane 113.49
    1-propoxy-2-propanol 207.46
    1-methoxy-2-propyl acetate 287.27
    2-(2-methoxypropoxy) propanol 168.71
    mesitylene 196.25
    ε-caprolactone 307.58
    p-cymene 237.31
    epichlorohydrin 353.83
    1,1,1-trichloroethane 344.17
    2-aminoethanol 11.28
    morpholine-4-carbaldehyde 189.32
    sulfolane 213.94
    2,2,4-trimethylpentane 52.37
    2-methyltetrahydrofuran 653.72
    n-hexyl acetate 289.05
    isooctane 51.18
    2-(2-butoxyethoxy)ethanol 202.02
    sec-butyl acetate 141.48
    tert-butyl acetate 214.93
    decalin 107.65
    glycerin 12.6
    diglyme 355.41
    acrylic acid 25.45
    isopropyl myristate 164.47
    n-butyric acid 106.06
    acetyl acetate 134.72
    di(2-ethylhexyl) phthalate 118.93
    ethyl propionate 141.07
    nitromethane 56.64
    1,2-diethoxyethane 393.78
    benzonitrile 178.68
    trioctyl phosphate 86.68
    1-bromopropane 365.29
    gamma-valerolactone 331.94
    n-decanol 106.24
    triethyl phosphate 115.89
    4-methyl-2-pentanol 81.73
    propionitrile 111.95
    vinylene carbonate 134.87
    1,1,2-trichlorotrifluoroethane 99.25
    DMS 149.68
    cumene 146.58
    2-octanol 93.52
    2-hexanone 185.25
    octyl acetate 181.13
    limonene 324.93
    1,2-dimethoxyethane 224.77
    ethyl orthosilicate 129.11
    tributyl phosphate 102.16
    diacetone alcohol 140.33
    N,N-dimethylaniline 165.16
    acrylonitrile 80.24
    aniline 197.05
    1,3-propanediol 30.87
    bromobenzene 400.24
    dibromomethane 412.19
    1,1,2,2-tetrachloroethane 339.2
    2-methyl-cyclohexyl acetate 247.3
    tetrabutyl urea 135.22
    diisobutyl methanol 159.22
    2-phenylethanol 203.74
    styrene 235.17
    dioctyl adipate 178.99
    dimethyl sulfate 53.03
    ethyl butyrate 300.63
    methyl lactate 34.01
    butyl lactate 99.52
    diethyl carbonate 161.76
    propanediol butyl ether 83.74
    triethyl orthoformate 209.01
    p-tert-butyltoluene 227.05
    methyl 4-tert-butylbenzoate 185.38
    morpholine 432.99
    tert-butylamine 107.89
    n-dodecanol 89.94
    dimethoxymethane 142.7
    ethylene carbonate 126.62
    cyrene 111.98
    2-ethoxyethyl acetate 228.73
    2-ethylhexyl acetate 392.15
    1,2,4-trichlorobenzene 256.06
    4-methylpyridine 411.68
    dibutyl ether 307.17
    2,6-dimethyl-4-heptanol 159.22
    DEF 175.19
    dimethyl isosorbide 335.78
    tetrachloroethylene 202.94
    eugenol 134.41
    triacetin 181.1
    span 80 162.64
    1,4-butanediol 13.92
    1,1-dichloroethane 286.37
    2-methyl-1-pentanol 94.5
    methyl formate 27.35
    2-methyl-1-butanol 101.79
    n-decane 83.02
    butyronitrile 162.84
    3,7-dimethyl-1-octanol 154.1
    1-chlorooctane 185.8
    1-chlorotetradecane 85.62
    n-nonane 87.01
    undecane 60.44
    tert-butylcyclohexane 89.94
    cyclooctane 140.77
    cyclopentanol 142.88
    tetrahydropyran 778.13
    tert-amyl methyl ether 188.61
    2,5,8-trioxanonane 265.68
    1-hexene 237.81
    2-isopropoxyethanol 71.82
    2,2,2-trifluoroethanol 10.04
    methyl butyrate 160.83

    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
Clove bud (Malagasy) 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison (E.caryophyllata Thunb.) 0.05%
Muhuhu Brachylaena hutchinsii Hutch. (Synchodendron hutchii Hutch.), Asteraceae 16.5%
Peppermint (USA) 3 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 0.1%
Peppermint (Greece) 1 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 0.1%
Peppermint (Greece) 2 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 0.1%
Dysoxylum richii leaf (Fiji) Dysoxylum richii (A. Gray) C.D.C. 4.05%
Basil (Israel) 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.01%
Pistacia lentiscus (Israel) 1b leaf 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 2.74%
Pistacia lentiscus (Israel) 1a fruit 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.17%
Myrtle flower (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.09%
Tea Tree (Australia) 7 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.01%
Cistus (Spain) 2 8016-26-0 Cistus ladaniferus L. var. maculatus Dun, fam. Cistaceae 1.0%
Eucalyptus maidenii (Burundi) Eucalyptus maidenii F. Muell., fam. Myrtaceae 0.2%
Ylang Ylang 3 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.5%
Ylang Ylang (Colombia) 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.2%
Phoebe 1 Phoebe porosa Mez. (syn. Oreodaphne porosa Nees et Mart.), fam. Lauraceae 0.55%
Phoebe 2 Phoebe porsa Mez. (syn. Oreodaphne prosa Nees & Mart.), fam. Lauraceae 0.3%
Alseuosmia macrophylla Alseuosmia macrophylla A. Cunn, fam. Alseuosmiaceae 9.6%
Bay, West Indian 3 8015-73-4 Pimenta racemosa var. racemosa (P. Miller) J.W. Moore, fam. Myrtaceae 0.2%
Eugenia banderensis leaf (Cuba) Eugenia banderensis Urb., fam. Myrtaceae 5.04%
St. John's wort (India) 84082-80-4 Hypericum perforatum L., fam. Guttiferae (Hypericaceae) 0.05%
Pepper, black (India) 3 8006-82-4 Piper nigrum L., fam. Piperaceae 1.0%
Sage, dalmatian (New Zealand) 1a 8022-56-8 Salvia officinalis L., fam. Lamiaceae (Labiatae) 0.82%
Sage, dalmatian (New Zealand) 1b 8022-56-8 Salvia officinalis L., fam. Lamiaceae (Labiatae) 2.23%
Ylang Ylang leaf (Cameroon) 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson, fam. Annonaceae 0.4%
Tea Tree (Australia) 9 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.29%
Parsley herb (Cuba) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.02%
Cabore (Brazil) Micrastur ruficolis, fam. Leguminosae (so-called: officially unknown) 0.2%
Hyptis lanceolata Hyptis lanciolata Poit., fam. Lamiaceae (Labiatae) 1.2%
Basil (Benin) 1a 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 1.4%
Basil (Benin) 1b 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.6%
Ocimum tenuiflorum (Cuba) Ocimum tenuiflorum L., fam. Lamiaceae (Labiatae) 0.1%
Ocimum gratissimum (Cuba) 2a Ocimum gratissimum L., fam. Lamiaceae (Labiatae) 0.1%
Olibanum, African (Oman) 8016-36-2 Boswellia frereana Birdwood, fam. Burseraceae 0.1%
Pistacia lentiscus (Spain) 2 whole plant 90082-83-0 Pistacia lentiscus L., fam. Anarcadiaceae 2.0%
Kewda (India) Pandanus fascicularis Lam., var. fascilarris, fam. Pandanaceae 0.02%
Pistacia lentiscus (Spain) 3 whole plant 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 2.0%
Port Orford Cedarwood Chamaecyparis lawsoniana (A. Murray) Parl., fam. Cupressaceae 1.87%
Manuka (New Zealand) 1 Leptospermum scoparium J.R. et F. Forst., fam. Myrtaceae 0.33%
Sage, dalmatian 10 8022-56-8 Salvia officinalis L., fam. Lamiaceae (Labiatae) 0.25%
Nepeta persica (Iran) Nepeta persica Boiss, fam. Lamiaceae (Labiatae) 0.4%
Licaria salicifolia Licaria salicifolia (Sw.) Kosterm., fam. Lauraceae 0.1%
Aristolochia odoratissima Aristolochia odoratissima L., fam. Aristolochaceae 2.3%
Amorpha fruticosa flower Amorpha fruticosa L., fam. Papilionaceae 0.2%
Amorpha fruticosa leaf Amorpha fruticosa L., fam. Papilionaceae 0.1%
Amorpha fruticosa fruit Amorpha fruticosa L., fam. Papilionaceae 1.4%
Baccharis uncinella (Brazil) Baccharis uncinella DC., fam. Asteraceae (Compositae) 0.4%
Vetiver (Haiti) 84238-29-9 Vetiveria zizanioides Stapf, fam. Poaceae (Gramineae) 0.8%
Ajuga chamaepitys (Iran) Ajuga chamaepitys (L.) Schreb., fam. Lauraceae 1.0%
Teucrium arduini (Serbia/Montenegro) Teucrium arduini L., fam. Lamiaceae (Labiatae) 1.1%