(E)-calamenene

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  • Identifiers

    CAS number
    73209-42-4

    Molecular formula
    C15H22

    SMILES
    C[C@@H]1CC[C@H](C2=C1C=CC(=C2)C)C(C)C

    Retention indicies (RI)

    • DB5: 1531.6
    • Carbowax: 1817.67

  • Odor profile

    Spicy 66.43%
    Woody 64.82%
    Herbal 63.84%
    Leathery 35.52%
    Earthy 34.1%
    Dry 32.98%
    Citrus 32.64%
    Green 31.85%
    Phenolic 30.79%
    Fresh 30.35%

    Scent© AI

  • Properties

    XLogP3-AA
    5.1

    Molecular weight
    202.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    272°C

    Flash point est.
    107.97 ˚C

  • Synonyms

    • (E)-calamenene
    • (-)-trans-Calamenene
    • Calamenene, trans-(-)-
    • SUQ88Q1Q6F
    • Calamenene, trans-(+/-)-
    • 4H1Y6V04B0
    • 73209-42-4
    • 35943-92-1
    • Naphthalene, 1,2,3,4-tetrahydro-1,6-dimethyl-4-(1-methylethyl)-, (1R,4S)-
    • Naphthalene, 1,2,3,4-tetrahydro-1,6-dimethyl-4-(1-methylethyl)-, (1R,4S)-rel-
    • UNII-SUQ88Q1Q6F
    • UNII-4H1Y6V04B0
    • (1R,4S)-4-Isopropyl-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene
    • PGTJIOWQJWHTJJ-OLZOCXBDSA-N
    • DTXSID201042908
    • (1R,4S)-1,6-dimethyl-4-propan-2-yl-1,2,3,4-tetrahydronaphthalene

  • Applications

    (E)-Calamenene is a plant-derived terpenoid found in many essential oils and is used primarily as a fragrance ingredient imparting warm woody, herbal-minty facets and mild fixative effects in fine fragrances, soaps, personal care, detergents and candles; analytically it serves as a reference standard and chemotaxonomic marker for profiling and quantifying essential oils by GC-MS; in bioactivity research, (E)-calamenene and its oxygenated derivatives have been reported to show antibacterial and antifungal effects (notably against Gram-positive bacteria), biofilm inhibition, antiparasitic activity, and insect-repellent/insecticidal properties, making it a natural lead for pharmaceutical, veterinary and crop-protection discovery; it is also used as a synthetic intermediate (e.g., to methoxy- or hydroxycalamenene analogs), a subtle flavor/aroma nuance in certain formulations, and a model compound for formulation strategies such as emulsions, encapsulation and cyclodextrin inclusion to address low aqueous solubility and enable controlled release in bio-based green products.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 278.68
    methanol 107.99
    isopropanol 283.55
    water 0.02
    ethyl acetate 782.92
    n-propanol 334.55
    acetone 858.41
    n-butanol 403.52
    acetonitrile 389.41
    DMF 606.5
    toluene 1118.45
    isobutanol 261.19
    1,4-dioxane 1916.97
    methyl acetate 593.85
    THF 3102.0
    2-butanone 882.87
    n-pentanol 289.69
    sec-butanol 277.04
    n-hexane 434.17
    ethylene glycol 11.72
    NMP 569.26
    cyclohexane 726.67
    DMSO 323.31
    n-butyl acetate 1881.23
    n-octanol 329.09
    chloroform 1755.63
    n-propyl acetate 561.29
    acetic acid 118.95
    dichloromethane 2074.0
    cyclohexanone 1523.92
    propylene glycol 31.4
    isopropyl acetate 530.67
    DMAc 452.35
    2-ethoxyethanol 203.98
    isopentanol 353.25
    n-heptane 708.73
    ethyl formate 404.38
    1,2-dichloroethane 1426.38
    n-hexanol 910.21
    2-methoxyethanol 267.65
    isobutyl acetate 478.2
    tetrachloromethane 377.81
    n-pentyl acetate 594.6
    transcutol 906.99
    n-heptanol 306.05
    ethylbenzene 511.2
    MIBK 508.55
    2-propoxyethanol 684.95
    tert-butanol 363.58
    MTBE 896.93
    2-butoxyethanol 322.67
    propionic acid 150.3
    o-xylene 475.26
    formic acid 8.77
    diethyl ether 1289.19
    m-xylene 640.39
    p-xylene 603.11
    chlorobenzene 890.9
    dimethyl carbonate 165.78
    n-octane 188.55
    formamide 27.5
    cyclopentanone 1589.78
    2-pentanone 841.83
    anisole 603.33
    cyclopentyl methyl ether 1244.44
    gamma-butyrolactone 1140.2
    1-methoxy-2-propanol 268.1
    pyridine 1466.66
    3-pentanone 643.94
    furfural 592.15
    n-dodecane 113.02
    diethylene glycol 163.55
    diisopropyl ether 404.09
    tert-amyl alcohol 300.16
    acetylacetone 665.8
    n-hexadecane 135.81
    acetophenone 429.49
    methyl propionate 485.54
    isopentyl acetate 1317.55
    trichloroethylene 1802.9
    n-nonanol 294.83
    cyclohexanol 502.31
    benzyl alcohol 279.98
    2-ethylhexanol 713.92
    isooctanol 255.45
    dipropyl ether 1599.46
    1,2-dichlorobenzene 595.23
    ethyl lactate 112.37
    propylene carbonate 581.66
    n-methylformamide 186.73
    2-pentanol 292.52
    n-pentane 316.67
    1-propoxy-2-propanol 630.99
    1-methoxy-2-propyl acetate 800.4
    2-(2-methoxypropoxy) propanol 295.34
    mesitylene 400.34
    ε-caprolactone 971.46
    p-cymene 505.12
    epichlorohydrin 1448.81
    1,1,1-trichloroethane 1086.78
    2-aminoethanol 41.75
    morpholine-4-carbaldehyde 639.63
    sulfolane 708.32
    2,2,4-trimethylpentane 107.91
    2-methyltetrahydrofuran 2034.73
    n-hexyl acetate 766.59
    isooctane 112.15
    2-(2-butoxyethoxy)ethanol 406.93
    sec-butyl acetate 378.2
    tert-butyl acetate 546.05
    decalin 233.91
    glycerin 32.09
    diglyme 871.58
    acrylic acid 89.27
    isopropyl myristate 356.43
    n-butyric acid 377.31
    acetyl acetate 386.44
    di(2-ethylhexyl) phthalate 219.7
    ethyl propionate 433.57
    nitromethane 273.49
    1,2-diethoxyethane 1195.77
    benzonitrile 513.52
    trioctyl phosphate 188.89
    1-bromopropane 1366.47
    gamma-valerolactone 1243.27
    n-decanol 233.04
    triethyl phosphate 239.33
    4-methyl-2-pentanol 190.71
    propionitrile 480.67
    vinylene carbonate 447.79
    1,1,2-trichlorotrifluoroethane 289.37
    DMS 383.22
    cumene 316.97
    2-octanol 236.36
    2-hexanone 664.06
    octyl acetate 409.86
    limonene 755.26
    1,2-dimethoxyethane 875.34
    ethyl orthosilicate 262.62
    tributyl phosphate 220.01
    diacetone alcohol 345.77
    N,N-dimethylaniline 375.77
    acrylonitrile 367.72
    aniline 489.92
    1,3-propanediol 113.01
    bromobenzene 1147.4
    dibromomethane 1656.57
    1,1,2,2-tetrachloroethane 1181.3
    2-methyl-cyclohexyl acetate 535.36
    tetrabutyl urea 301.47
    diisobutyl methanol 360.65
    2-phenylethanol 517.8
    styrene 603.61
    dioctyl adipate 372.05
    dimethyl sulfate 168.22
    ethyl butyrate 928.0
    methyl lactate 93.3
    butyl lactate 253.78
    diethyl carbonate 452.65
    propanediol butyl ether 195.87
    triethyl orthoformate 529.28
    p-tert-butyltoluene 476.14
    methyl 4-tert-butylbenzoate 353.33
    morpholine 1741.42
    tert-butylamine 325.36
    n-dodecanol 197.55
    dimethoxymethane 675.12
    ethylene carbonate 457.77
    cyrene 243.51
    2-ethoxyethyl acetate 630.06
    2-ethylhexyl acetate 1201.16
    1,2,4-trichlorobenzene 606.98
    4-methylpyridine 1338.75
    dibutyl ether 910.59
    2,6-dimethyl-4-heptanol 360.65
    DEF 657.04
    dimethyl isosorbide 667.91
    tetrachloroethylene 730.62
    eugenol 267.17
    triacetin 375.22
    span 80 309.0
    1,4-butanediol 45.81
    1,1-dichloroethane 1162.14
    2-methyl-1-pentanol 291.59
    methyl formate 175.41
    2-methyl-1-butanol 309.66
    n-decane 197.23
    butyronitrile 710.06
    3,7-dimethyl-1-octanol 326.23
    1-chlorooctane 489.99
    1-chlorotetradecane 205.19
    n-nonane 216.41
    undecane 145.45
    tert-butylcyclohexane 201.08
    cyclooctane 294.12
    cyclopentanol 452.29
    tetrahydropyran 2797.44
    tert-amyl methyl ether 531.09
    2,5,8-trioxanonane 507.18
    1-hexene 898.15
    2-isopropoxyethanol 210.77
    2,2,2-trifluoroethanol 29.43
    methyl butyrate 590.74

    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
Ayou Aydendron barbeyana Mez. (Nectandra globosa Mez.), fam. Lauraceae 1.05%
Clove leaf (Indonesia) 1 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison, fam. Myrtaceae 0.05%
Santolina neapolitana (Italy) Santolina neapolitana Jordan et Fourr., fam. Asteraceae (Compositae) 0.5%
Peppermint (Italy) 10a 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 0.25%
Juniper leaf (France) 8012-91-7 Juniperus communis L., fam. Cupressaceae 0.01%
Blumea brevipes Blumea brevipes (Oliv. & Hiern) Willd., fam. Asteraceae (Compositae) 0.05%
Phoebe 1 Phoebe porosa Mez. (syn. Oreodaphne porosa Nees et Mart.), fam. Lauraceae 1.3%
Vassoura (Brazil) 3 Baccharis dracunculifolia DC., fam. Asteraceae (Compositae) 0.5%
Cangerana (Brazil) Cabralea cangerana Sald. (C. glaberrima A. Juss.), fam. Meliaceae 0.6%
Thyme (Denmark) 8007-46-3 Thymus vulgaris L., fam. Lamiaceae (Labiatae) 0.01%
Eugenia ovalifolia leaf Eugenia ovalifolia Camb., fam. Myrtaceae 0.8%
Manuka (New Zealand) 2 Leptospermum scoparium J.R. et G. Forst., fam. Myrtaceae 14.0%
Rosemary (Brazil) 2 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Kanuka (New Zealand) 1 Kunzea ericoides (A. Rich.) J. Thompson, fam. Myrtaceae 0.2%
Kanuka (New Zealand) 4 Kunzea ericoides (A. Rich.) J. Thompson, fam. Myrtaceae 0.9%
Manuka (New Zealand) 3 Leptospermum scoparium J.R. et G. Forst., fam. Myrtaceae 14.1%
Licaria salicifolia Licaria salicifolia (Sw.) Kosterm., fam. Lauraceae 0.05%
Metrosideros robusta leaf Metrosideros robusta A. Cunn., fam. Myrtaceae 0.9%
Baccharis uncinella (Brazil) Baccharis uncinella DC., fam. Asteraceae (Compositae) 0.1%
Nepeta argolica (Greece) 1b chemotype 2 Nepeta argolica Bory & Chaub. ssp. argolica, fam. Lamiaceae (Labiatae) 0.14%
Sage, ssp. altissima (Cuba) Salvia officinalis L. ssp. altissima, fam. Lamiaceae (Labiatae) 0.01%
Oregano, greek (Himalaya) 84012-24-8 Origanum vulgare L. ssp. vulgare, fam. Lamiaceae (Labiatae) 2.6%
Eucalyptus resinifera (Cuba) Eucalyptus resinifera Smith, fam. Myrtaceae 0.01%
Astronium urundeuva (Brazil) Astronium urundeuva (Allemao) Engl., fam. Anacardiaceae 0.1%
Teucrium polium (Serbia/Montenegro) Teucrium polium L., fam. Lamiaceae (Labiatae) 0.4%
Teucrium scordium (Serbia/Montenegro) 90131-54-7 Teucrium scordium L., fam. Lamiaceae (Labiatae) 0.8%