(-)-alpha-Himachalene

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  • Identifiers

    CAS number
    3853-83-6

    Molecular formula
    C15H24

    SMILES
    CC1=C[C@H]2[C@@H](CC1)C(=C)CCCC2(C)C

    Retention indicies (RI)

    • DB5: 1448.4
    • Carbowax: 1625.0

  • Odor profile

    Woody 79.82%
    Spicy 55.44%
    Sweet 51.65%
    Dry 44.42%
    Herbal 43.8%
    Citrus 42.51%
    Terpenic 41.61%
    Fresh 41.24%
    Green 40.53%
    Pine 36.49%

    Scent© AI

  • Properties

    XLogP3-AA
    4.5

    pKa est.
    9.49 (weak base)

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    268°C

    Flash point est.
    106.0 ˚C

  • Synonyms

    • (-)-alpha-Himachalene
    • alpha-Himachalene
    • 3853-83-6
    • alpha-cis-Himachalene
    • alpha-Himachalene, (-)-
    • UNII-1DB5J66V5P
    • 1DB5J66V5P
    • CHEBI:49218
    • (-)-2,7(14)-himachaladiene
    • (4aS,9aR)-3,5,5-trimethyl-9-methylidene-2,4a,6,7,8,9a-hexahydro-1H-benzo[7]annulene
    • 1H-Benzocycloheptene, 2,4a,5,6,7,8,9,9a-octahydro-3,5,5-trimethyl-9-methylene-, (4aS,9ar)-
    • 1H-Benzocycloheptene, 2,4a,5,6,7,8,9,9a-octahydro-3,5,5-trimethyl-9-methylene-, (4aS-cis)-
    • himachal-4,11-diene
    • (1R,6S)-alpha-himachalene
    • .ALPHA.-CIS-HIMACHALENE
    • CHEMBL3120652
    • DTXSID30191859
    • (-)-.ALPHA.-HIMACHALENE
    • .ALPHA.-HIMACHALENE, (-)-
    • LMPR0103480001
    • Q27121538
    • (4aS,9aR)-3,5,5-trimethyl-9-methylene-2,4a,5,6,7,8,9,9a-octahydro-1H-benzo[7]annulene
    • (4aS,9aR)-3,5,5-trimethyl-9-methylidene-2,4a,5,6,7,8,9,9a-octahydro-1H-benzo[7]annulene

  • Applications

    (-)-alpha-Himachalene (CAS 3853-83-6) is a sesquiterpene hydrocarbon characteristic of cedarwood oils, used mainly in perfumery and research: it imparts dry, warm woody “cedar” facets, serves as a modifier to add depth and tenacity to woody, leather, and amber bases, and acts as a convenient precursor in fragrance chemistry via epoxidation, hydroboration–oxidation, and related functionalizations to access odor-active sesquiterpene alcohols/ketones; in the lab, this enantiomer is employed as a chiral building block for asymmetric synthesis, as a GC–MS/GC×GC and chiral-GC reference standard to identify/quantify himachalenes and authenticate cedarwood oils (chemotaxonomy), and as a model substrate for atmospheric oxidation studies (O3, •OH) and secondary organic aerosol formation; it has also been investigated as a potential contributor to the antimicrobial, insect-repellent/insecticidal and termiticidal effects of cedarwood oils, although compound-specific evidence remains limited; operationally it is a volatile, flammable hydrocarbon that may irritate skin/eyes—assess IFRA/REACH compliance and store tightly closed, protected from light/oxygen.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 329.09
    methanol 125.35
    isopropanol 508.3
    water 0.06
    ethyl acetate 737.52
    n-propanol 448.35
    acetone 744.8
    n-butanol 567.44
    acetonitrile 324.55
    DMF 708.42
    toluene 1179.77
    isobutanol 451.53
    1,4-dioxane 1373.87
    methyl acetate 564.39
    THF 2927.68
    2-butanone 940.87
    n-pentanol 327.83
    sec-butanol 489.7
    n-hexane 337.16
    ethylene glycol 25.09
    NMP 616.1
    cyclohexane 681.73
    DMSO 379.26
    n-butyl acetate 1200.75
    n-octanol 459.87
    chloroform 1417.07
    n-propyl acetate 469.13
    acetic acid 125.29
    dichloromethane 1199.68
    cyclohexanone 1491.93
    propylene glycol 71.96
    isopropyl acetate 660.61
    DMAc 582.28
    2-ethoxyethanol 252.94
    isopentanol 540.57
    n-heptane 581.66
    ethyl formate 361.8
    1,2-dichloroethane 889.37
    n-hexanol 944.04
    2-methoxyethanol 376.97
    isobutyl acetate 451.06
    tetrachloromethane 362.97
    n-pentyl acetate 597.27
    transcutol 1054.74
    n-heptanol 448.67
    ethylbenzene 528.95
    MIBK 691.85
    2-propoxyethanol 732.06
    tert-butanol 699.58
    MTBE 1151.09
    2-butoxyethanol 425.63
    propionic acid 198.55
    o-xylene 620.02
    formic acid 13.97
    diethyl ether 1089.69
    m-xylene 827.8
    p-xylene 589.84
    chlorobenzene 772.26
    dimethyl carbonate 239.53
    n-octane 183.65
    formamide 33.08
    cyclopentanone 1603.76
    2-pentanone 945.79
    anisole 645.58
    cyclopentyl methyl ether 1457.24
    gamma-butyrolactone 1093.33
    1-methoxy-2-propanol 471.63
    pyridine 1064.55
    3-pentanone 700.5
    furfural 651.43
    n-dodecane 125.1
    diethylene glycol 250.97
    diisopropyl ether 523.17
    tert-amyl alcohol 533.67
    acetylacetone 742.83
    n-hexadecane 148.84
    acetophenone 480.44
    methyl propionate 559.33
    isopentyl acetate 1113.15
    trichloroethylene 1272.71
    n-nonanol 391.81
    cyclohexanol 738.19
    benzyl alcohol 342.9
    2-ethylhexanol 691.44
    isooctanol 372.14
    dipropyl ether 1174.71
    1,2-dichlorobenzene 610.01
    ethyl lactate 180.16
    propylene carbonate 658.22
    n-methylformamide 198.62
    2-pentanol 506.86
    n-pentane 373.23
    1-propoxy-2-propanol 753.31
    1-methoxy-2-propyl acetate 826.05
    2-(2-methoxypropoxy) propanol 428.89
    mesitylene 571.18
    ε-caprolactone 1043.77
    p-cymene 527.75
    epichlorohydrin 1284.69
    1,1,1-trichloroethane 1014.55
    2-aminoethanol 78.52
    morpholine-4-carbaldehyde 742.55
    sulfolane 945.94
    2,2,4-trimethylpentane 163.27
    2-methyltetrahydrofuran 1945.76
    n-hexyl acetate 839.21
    isooctane 186.78
    2-(2-butoxyethoxy)ethanol 554.57
    sec-butyl acetate 409.5
    tert-butyl acetate 741.07
    decalin 246.5
    glycerin 80.9
    diglyme 941.96
    acrylic acid 125.56
    isopropyl myristate 427.95
    n-butyric acid 481.21
    acetyl acetate 378.22
    di(2-ethylhexyl) phthalate 293.53
    ethyl propionate 453.03
    nitromethane 259.79
    1,2-diethoxyethane 858.94
    benzonitrile 560.73
    trioctyl phosphate 265.71
    1-bromopropane 1078.42
    gamma-valerolactone 1266.42
    n-decanol 311.82
    triethyl phosphate 285.79
    4-methyl-2-pentanol 364.71
    propionitrile 516.89
    vinylene carbonate 529.91
    1,1,2-trichlorotrifluoroethane 404.52
    DMS 465.75
    cumene 360.55
    2-octanol 346.83
    2-hexanone 580.19
    octyl acetate 485.19
    limonene 785.42
    1,2-dimethoxyethane 745.47
    ethyl orthosilicate 293.65
    tributyl phosphate 296.36
    diacetone alcohol 530.5
    N,N-dimethylaniline 429.42
    acrylonitrile 390.06
    aniline 587.75
    1,3-propanediol 183.47
    bromobenzene 977.42
    dibromomethane 1055.55
    1,1,2,2-tetrachloroethane 1043.84
    2-methyl-cyclohexyl acetate 559.75
    tetrabutyl urea 375.27
    diisobutyl methanol 449.64
    2-phenylethanol 560.95
    styrene 565.69
    dioctyl adipate 439.63
    dimethyl sulfate 273.24
    ethyl butyrate 720.4
    methyl lactate 182.96
    butyl lactate 339.02
    diethyl carbonate 404.63
    propanediol butyl ether 343.07
    triethyl orthoformate 485.14
    p-tert-butyltoluene 541.98
    methyl 4-tert-butylbenzoate 527.6
    morpholine 1281.33
    tert-butylamine 617.87
    n-dodecanol 258.78
    dimethoxymethane 723.98
    ethylene carbonate 524.76
    cyrene 338.6
    2-ethoxyethyl acetate 608.96
    2-ethylhexyl acetate 957.64
    1,2,4-trichlorobenzene 637.24
    4-methylpyridine 1168.41
    dibutyl ether 812.98
    2,6-dimethyl-4-heptanol 449.64
    DEF 710.78
    dimethyl isosorbide 867.0
    tetrachloroethylene 589.42
    eugenol 382.36
    triacetin 504.38
    span 80 441.98
    1,4-butanediol 72.73
    1,1-dichloroethane 1014.24
    2-methyl-1-pentanol 335.19
    methyl formate 181.62
    2-methyl-1-butanol 483.86
    n-decane 209.35
    butyronitrile 740.22
    3,7-dimethyl-1-octanol 473.95
    1-chlorooctane 518.16
    1-chlorotetradecane 222.42
    n-nonane 220.91
    undecane 158.75
    tert-butylcyclohexane 228.72
    cyclooctane 337.89
    cyclopentanol 706.03
    tetrahydropyran 2075.88
    tert-amyl methyl ether 754.42
    2,5,8-trioxanonane 623.44
    1-hexene 664.55
    2-isopropoxyethanol 274.02
    2,2,2-trifluoroethanol 47.99
    methyl butyrate 564.73

    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
Artemisia vestita (India) Artemisia vestita Wall. ex Dc., fam. Asteraceae (Compositae) 2.82%
Wormwood (Mugwort) (India) 8008-93-3 Artemisia absinthium L., fam. Asteraceae (Compositae) 6.94%
Pistacia lentiscus fruit 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.01%
Cedrus atlantica (Morocco) Cedrus atlantica Man., fam. Cupressaceae 15.5%
Annual wormwood (France) 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.1%
Cassia, bark (China) 2 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.01%
Rhubarb root Rheum palmatum L., fam. Polygonaceae 0.2%
Tarragon (Cuba) 8016-88-4 Artemisia dracunculus L., fam. Asteraceae (Compositae) 1.59%
Rosa rugosa (China) 1 Rosa rugosa Thunb. (hybrids), fam. Rosaceae 0.5%
Eremocharis triradiata Eremocharis triradiata (Wolff.) Johnston, fam. Apiaceae (Umbelliferae) 0.01%
Eugenia ovalifolia leaf Eugenia ovalifolia Camb., fam. Myrtaceae 0.2%
Hyptis crenata (Brazil) Hyptis crenata Pohl ex Benth, fam. Lamiaceae (Labiatae) 0.5%
Ferula stenocarpa Ferula stenocarpa Boiss. & Hausskn., fam. Apiaceae (Umbelliferae) 0.3%
Abies alba needle (Montenegro) 8021-27-0 Abies alba Mill., fam. Pinaceae 0.05%
St. John's wort (Yugoslavia) 84082-80-4 Hypericum perforatum L., fam. Guttiferae (Hypericaceae) 0.4%
Salvia desoleana (Italy) 1a CO2-extract Salvia desoleana, fam. Lamiaceae (Labiatae) 0.7%
Salvia desoleana (Italy) 1b hydrodistilled Salvia desoleana, fam. Lamiaceae (Labiatae) 0.1%
Pistacia lentiscus (Italy) 1b CO2-extract 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 4.53%
Lippia lupulina stalk & leaf (Brazil) Lippia lupulina Cham., fam. Verbenaceae 0.1%