Bicyclosesquiphellandrene

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  • Identifiers

    CAS number
    54324-03-7

    Molecular formula
    C15H24

    SMILES
    C[C@@H]1CC[C@H](C2=CC(=C)CC[C@H]12)C(C)C

    Retention indicies (RI)

    • DB5: 1489.25

  • Odor profile

    Woody 76.44%
    Spicy 62.41%
    Herbal 56.84%
    Green 46.62%
    Fresh 46.16%
    Citrus 42.13%
    Terpenic 37.28%
    Mint 35.13%
    Dry 35.06%
    Oily 34.4%

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  • Properties

    XLogP3-AA
    4.7

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    274°C

    Flash point est.
    98.48 ˚C

  • Synonyms

    • Bicyclosesquiphellandrene
    • 7E, 9E-Octadecadienoic acid
    • (1S,4R,4aR)-1-Isopropyl-4-methyl-7-methylene-1,2,3,4,4a,5,6,7-octahydronaphthalene
    • CHEBI:192811
    • 54324-03-7
    • (1S,4R,4aR)-4-methyl-7-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene

  • Applications

    Bicyclosesquiphellandrene (CAS 54324-03-7) is a sesquiterpene hydrocarbon typically encountered at trace levels in essential oils, used mainly as a reference and analytical standard in GC-MS/GCxGC for qualitative-quantitative profiling, retention-index calibration, and essential-oil fingerprinting; it is also valuable in fragrance-flavor R&D as a model component to impart woody-resinous, spicy nuances in experimental accords, in chemical ecology to probe plant volatile signaling and plant-insect interactions, and in terpenoid biosynthesis studies to interrogate cyclase mechanisms, enzyme/cell engineering, and isotopic labeling; additionally, it is employed to evaluate terpene stability/oxidation and evaporation kinetics for shelf-life prediction, while large-scale direct commercial use remains limited by availability and high-purity requirements.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 230.67
    methanol 79.03
    isopropanol 312.33
    water 0.02
    ethyl acetate 557.43
    n-propanol 288.81
    acetone 562.72
    n-butanol 378.2
    acetonitrile 247.28
    DMF 364.53
    toluene 1017.23
    isobutanol 255.31
    1,4-dioxane 1286.68
    methyl acetate 379.59
    THF 2662.76
    2-butanone 641.25
    n-pentanol 218.33
    sec-butanol 288.7
    n-hexane 252.57
    ethylene glycol 8.32
    NMP 386.24
    cyclohexane 593.41
    DMSO 240.07
    n-butyl acetate 1256.77
    n-octanol 285.35
    chloroform 1157.44
    n-propyl acetate 366.79
    acetic acid 96.22
    dichloromethane 1177.21
    cyclohexanone 1106.94
    propylene glycol 26.97
    isopropyl acetate 468.71
    DMAc 309.4
    2-ethoxyethanol 149.31
    isopentanol 356.96
    n-heptane 509.13
    ethyl formate 241.57
    1,2-dichloroethane 771.84
    n-hexanol 696.23
    2-methoxyethanol 227.51
    isobutyl acetate 317.14
    tetrachloromethane 275.03
    n-pentyl acetate 498.72
    transcutol 987.6
    n-heptanol 265.34
    ethylbenzene 377.52
    MIBK 446.57
    2-propoxyethanol 517.07
    tert-butanol 417.91
    MTBE 805.63
    2-butoxyethanol 278.08
    propionic acid 119.68
    o-xylene 415.2
    formic acid 7.25
    diethyl ether 942.51
    m-xylene 587.76
    p-xylene 433.14
    chlorobenzene 644.76
    dimethyl carbonate 114.29
    n-octane 129.52
    formamide 19.26
    cyclopentanone 1171.0
    2-pentanone 655.23
    anisole 439.4
    cyclopentyl methyl ether 1061.71
    gamma-butyrolactone 756.88
    1-methoxy-2-propanol 274.59
    pyridine 1079.83
    3-pentanone 473.12
    furfural 440.76
    n-dodecane 74.77
    diethylene glycol 135.62
    diisopropyl ether 360.87
    tert-amyl alcohol 317.59
    acetylacetone 513.49
    n-hexadecane 90.37
    acetophenone 323.44
    methyl propionate 336.39
    isopentyl acetate 1009.77
    trichloroethylene 1097.1
    n-nonanol 259.24
    cyclohexanol 492.68
    benzyl alcohol 223.08
    2-ethylhexanol 581.55
    isooctanol 233.91
    dipropyl ether 1146.01
    1,2-dichlorobenzene 446.46
    ethyl lactate 94.0
    propylene carbonate 444.49
    n-methylformamide 106.46
    2-pentanol 303.84
    n-pentane 267.7
    1-propoxy-2-propanol 561.0
    1-methoxy-2-propyl acetate 645.96
    2-(2-methoxypropoxy) propanol 304.57
    mesitylene 379.72
    ε-caprolactone 726.71
    p-cymene 421.94
    epichlorohydrin 964.25
    1,1,1-trichloroethane 788.71
    2-aminoethanol 33.75
    morpholine-4-carbaldehyde 458.43
    sulfolane 519.28
    2,2,4-trimethylpentane 96.68
    2-methyltetrahydrofuran 1801.45
    n-hexyl acetate 625.42
    isooctane 108.94
    2-(2-butoxyethoxy)ethanol 409.07
    sec-butyl acetate 291.48
    tert-butyl acetate 516.17
    decalin 166.7
    glycerin 30.19
    diglyme 747.91
    acrylic acid 64.55
    isopropyl myristate 295.9
    n-butyric acid 340.62
    acetyl acetate 286.73
    di(2-ethylhexyl) phthalate 202.35
    ethyl propionate 297.82
    nitromethane 170.08
    1,2-diethoxyethane 931.13
    benzonitrile 415.32
    trioctyl phosphate 164.64
    1-bromopropane 880.98
    gamma-valerolactone 880.6
    n-decanol 200.78
    triethyl phosphate 199.47
    4-methyl-2-pentanol 212.69
    propionitrile 353.39
    vinylene carbonate 331.34
    1,1,2-trichlorotrifluoroethane 228.92
    DMS 285.81
    cumene 238.57
    2-octanol 206.1
    2-hexanone 426.91
    octyl acetate 333.1
    limonene 633.48
    1,2-dimethoxyethane 583.63
    ethyl orthosilicate 221.63
    tributyl phosphate 194.58
    diacetone alcohol 338.63
    N,N-dimethylaniline 286.05
    acrylonitrile 247.77
    aniline 454.72
    1,3-propanediol 102.07
    bromobenzene 820.96
    dibromomethane 1008.9
    1,1,2,2-tetrachloroethane 778.98
    2-methyl-cyclohexyl acetate 436.49
    tetrabutyl urea 253.91
    diisobutyl methanol 350.03
    2-phenylethanol 411.9
    styrene 436.23
    dioctyl adipate 314.31
    dimethyl sulfate 119.73
    ethyl butyrate 665.62
    methyl lactate 81.08
    butyl lactate 228.19
    diethyl carbonate 327.16
    propanediol butyl ether 190.22
    triethyl orthoformate 426.72
    p-tert-butyltoluene 417.71
    methyl 4-tert-butylbenzoate 327.39
    morpholine 1208.96
    tert-butylamine 393.19
    n-dodecanol 162.23
    dimethoxymethane 474.89
    ethylene carbonate 327.25
    cyrene 211.74
    2-ethoxyethyl acetate 492.48
    2-ethylhexyl acetate 864.46
    1,2,4-trichlorobenzene 481.39
    4-methylpyridine 1047.2
    dibutyl ether 684.81
    2,6-dimethyl-4-heptanol 350.03
    DEF 460.25
    dimethyl isosorbide 644.87
    tetrachloroethylene 468.6
    eugenol 241.89
    triacetin 328.04
    span 80 315.27
    1,4-butanediol 33.74
    1,1-dichloroethane 784.93
    2-methyl-1-pentanol 231.13
    methyl formate 94.49
    2-methyl-1-butanol 296.54
    n-decane 140.94
    butyronitrile 557.48
    3,7-dimethyl-1-octanol 319.82
    1-chlorooctane 360.02
    1-chlorotetradecane 143.71
    n-nonane 153.3
    undecane 98.34
    tert-butylcyclohexane 148.41
    cyclooctane 246.71
    cyclopentanol 434.0
    tetrahydropyran 2173.98
    tert-amyl methyl ether 484.3
    2,5,8-trioxanonane 488.85
    1-hexene 548.02
    2-isopropoxyethanol 162.0
    2,2,2-trifluoroethanol 23.74
    methyl butyrate 377.77

    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

Botanical

Name CAS Botanical Proportion
Tea Tree (Australia) 9 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.51%
Bupleurum gibraltarium (Spain) Bupleurum gibraltarium Lam., fam. Apiaceae (Umbelliferae) 0.5%
Acinos alpinus oil (Greece) Acinos alpinus (L.) Moench., fam. Lamiaceae (Labiatae) 14.0%
Aristolochia odoratissima Aristolochia odoratissima L., fam. Aristolochaceae 0.4%
Calamus (India) 3 root 8015-79-0 Acorus calamus L., fam. Araceae 1.02%
Spearmint (Mexico) 8008-79-5 Mentha spicata L., fam. Lamiaceae (Labiatae) 2.0%
Nepeta argolica (Greece) 1a chemotype 1 Nepeta argolica Bory & Chaub. ssp. argolica, fam. Lamiaceae (Labiatae) 1.46%
Croton ovalifolius (Venezuela) Croton ovalifolius Vahl, fam. Euphorbiaceae 3.4%
Peppermint (Mexico) 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 1.7%
Osage orange fruit, 1a headspace Maclura pomifera (Raf.) Schneid, fam. Moraceae 0.7%
Elaeoselinum gummiferum Elaeoselinum gummiferum (Desf.) Tutin, fam. Apiaceae (Umbelliferae) 0.01%