(1R,6S)-gamma-himachalene

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  • Identifiers

    CAS number
    53111-25-4

    Molecular formula
    C15H24

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

    Retention indicies (RI)

    • DB5: 1476.0

  • Odor profile

    Woody 86.04%
    Spicy 58.92%
    Sweet 49.77%
    Dry 47.41%
    Green 45.32%
    Herbal 44.04%
    Fresh 43.8%
    Terpenic 43.55%
    Citrus 42.5%
    Pine 37.46%

    Scent© AI

  • Properties

    XLogP3-AA
    4.2

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    260°C

    Flash point est.
    112.1 ˚C

  • Synonyms

    • (1R,6S)-gamma-himachalene
    • 53111-25-4
    • gamma-Himachalene, (-)-
    • UNII-2M8UNY276Q
    • 2M8UNY276Q
    • .gamma.-HIMACHALENE
    • 1H-Benzocycloheptene, 2,4a,5,6,7,9a-hexahydro-3,5,5,9-tetramethyl-, (4aS-cis)-
    • (4aR,9aS)-2,5,9,9-tetramethyl-3,4,4a,7,8,9a-hexahydrobenzo[7]annulene
    • (4aS,9aR)-3,5,5,9-tetramethyl-2,4a,5,6,7,9a-hexahydro-1H-benzo[7]annulene himachal-4,10-diene
    • DTXSID00967644
    • y-himachalene
    • (-)-gamma-himachalene
    • .GAMMA.-CIS-HIMACHALENE
    • CHEBI:49228
    • 5-Hydroxy-6-methoxy-8-[(4-amino-1-methylbutyl)amino]quinoline trihydrobromide
    • PUWNTRHCKNHSAT-KBPBESRZSA-N
    • (-)-.GAMMA.-HIMACHALENE
    • .GAMMA.-HIMACHALENE, (-)-
    • LMPR0103480009
    • Q27121546
    • (4aS,9aR)-3,5,5,9-tetramethyl-2,4a,5,6,7,9a-hexahydro-1H-benzo[7]annulene
    • 1H-BENZOCYCLOHEPTENE, 2,4A,5,6,7,9A-HEXAHYDRO-3,5,5,9-TETRAMETHYL-, (4AS,9AR)-

  • Applications

    (1R,6S)-gamma-himachalene is a cedarwood-scented sesquiterpene hydrocarbon used mainly in perfumery to impart woody-balsamic notes to fine fragrances, cosmetics, deodorants, soaps, and household care; in forestry, pest management and materials preservation it contributes to the insect-repellent, anti-termite and antifungal performance of cedarwood oils and is explored in bio-based repellent formulations, wood-surface treatments and packaging additives; in analytics it serves as an aroma reference and (chiral) GC standard for quantitation, authentication of cedarwood oils and stereochemical profiling; in synthesis its rigid bicyclic scaffold and defined absolute configuration provide a convenient chiral-pool starting point for derivatization to new sesquiterpene motifs (e.g., aroma ingredients, bio-based monomers, or leads for bioactivity), and it is also studied as a biogenic/environmental marker for cedar emissions and as an odor-masking/coating note in technical formulations; typical use levels are low due to volatility, flammability and fragrance-industry regulatory limits.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 114.12
    methanol 41.4
    isopropanol 166.8
    water 0.05
    ethyl acetate 376.43
    n-propanol 169.4
    acetone 355.51
    n-butanol 228.46
    acetonitrile 143.73
    DMF 346.01
    toluene 733.58
    isobutanol 180.3
    1,4-dioxane 714.91
    methyl acetate 292.81
    THF 1444.16
    2-butanone 484.5
    n-pentanol 153.69
    sec-butanol 193.76
    n-hexane 224.55
    ethylene glycol 11.33
    NMP 421.66
    cyclohexane 434.39
    DMSO 185.6
    n-butyl acetate 661.66
    n-octanol 275.5
    chloroform 784.0
    n-propyl acetate 276.09
    acetic acid 58.47
    dichloromethane 614.47
    cyclohexanone 852.7
    propylene glycol 31.2
    isopropyl acetate 335.83
    DMAc 364.48
    2-ethoxyethanol 125.58
    isopentanol 230.53
    n-heptane 363.21
    ethyl formate 168.74
    1,2-dichloroethane 476.38
    n-hexanol 472.04
    2-methoxyethanol 160.92
    isobutyl acetate 283.44
    tetrachloromethane 213.15
    n-pentyl acetate 370.75
    transcutol 498.05
    n-heptanol 250.15
    ethylbenzene 369.32
    MIBK 358.56
    2-propoxyethanol 366.95
    tert-butanol 253.31
    MTBE 515.07
    2-butoxyethanol 233.58
    propionic acid 97.52
    o-xylene 424.26
    formic acid 6.17
    diethyl ether 505.49
    m-xylene 527.48
    p-xylene 415.27
    chlorobenzene 475.16
    dimethyl carbonate 137.47
    n-octane 134.24
    formamide 14.44
    cyclopentanone 894.54
    2-pentanone 473.62
    anisole 413.48
    cyclopentyl methyl ether 813.61
    gamma-butyrolactone 615.3
    1-methoxy-2-propanol 206.12
    pyridine 591.88
    3-pentanone 417.38
    furfural 375.71
    n-dodecane 96.83
    diethylene glycol 122.46
    diisopropyl ether 278.45
    tert-amyl alcohol 239.92
    acetylacetone 405.13
    n-hexadecane 113.51
    acetophenone 331.31
    methyl propionate 299.02
    isopentyl acetate 634.51
    trichloroethylene 712.75
    n-nonanol 243.69
    cyclohexanol 366.44
    benzyl alcohol 206.52
    2-ethylhexanol 401.04
    isooctanol 212.27
    dipropyl ether 646.74
    1,2-dichlorobenzene 402.3
    ethyl lactate 108.61
    propylene carbonate 376.62
    n-methylformamide 88.49
    2-pentanol 210.96
    n-pentane 208.27
    1-propoxy-2-propanol 376.98
    1-methoxy-2-propyl acetate 469.86
    2-(2-methoxypropoxy) propanol 264.48
    mesitylene 381.84
    ε-caprolactone 612.65
    p-cymene 363.03
    epichlorohydrin 665.38
    1,1,1-trichloroethane 602.55
    2-aminoethanol 33.42
    morpholine-4-carbaldehyde 435.12
    sulfolane 599.66
    2,2,4-trimethylpentane 104.97
    2-methyltetrahydrofuran 1002.35
    n-hexyl acetate 535.34
    isooctane 108.47
    2-(2-butoxyethoxy)ethanol 312.36
    sec-butyl acetate 256.31
    tert-butyl acetate 400.74
    decalin 195.16
    glycerin 37.28
    diglyme 524.59
    acrylic acid 68.12
    isopropyl myristate 295.23
    n-butyric acid 213.5
    acetyl acetate 217.98
    di(2-ethylhexyl) phthalate 200.38
    ethyl propionate 278.31
    nitromethane 125.46
    1,2-diethoxyethane 463.85
    benzonitrile 325.94
    trioctyl phosphate 180.64
    1-bromopropane 578.03
    gamma-valerolactone 704.26
    n-decanol 198.17
    triethyl phosphate 204.15
    4-methyl-2-pentanol 173.15
    propionitrile 230.27
    vinylene carbonate 306.92
    1,1,2-trichlorotrifluoroethane 227.74
    DMS 306.33
    cumene 270.32
    2-octanol 208.13
    2-hexanone 341.66
    octyl acetate 330.59
    limonene 521.01
    1,2-dimethoxyethane 387.47
    ethyl orthosilicate 205.86
    tributyl phosphate 197.89
    diacetone alcohol 284.44
    N,N-dimethylaniline 300.34
    acrylonitrile 180.46
    aniline 315.67
    1,3-propanediol 73.0
    bromobenzene 620.8
    dibromomethane 563.83
    1,1,2,2-tetrachloroethane 622.8
    2-methyl-cyclohexyl acetate 391.09
    tetrabutyl urea 254.19
    diisobutyl methanol 262.84
    2-phenylethanol 342.59
    styrene 386.21
    dioctyl adipate 301.0
    dimethyl sulfate 170.45
    ethyl butyrate 431.95
    methyl lactate 100.03
    butyl lactate 208.02
    diethyl carbonate 255.56
    propanediol butyl ether 182.7
    triethyl orthoformate 306.25
    p-tert-butyltoluene 369.07
    methyl 4-tert-butylbenzoate 358.11
    morpholine 641.25
    tert-butylamine 234.7
    n-dodecanol 168.09
    dimethoxymethane 342.77
    ethylene carbonate 294.24
    cyrene 225.13
    2-ethoxyethyl acetate 365.23
    2-ethylhexyl acetate 592.1
    1,2,4-trichlorobenzene 431.45
    4-methylpyridine 677.39
    dibutyl ether 477.23
    2,6-dimethyl-4-heptanol 262.84
    DEF 384.81
    dimethyl isosorbide 543.42
    tetrachloroethylene 348.83
    eugenol 254.25
    triacetin 335.78
    span 80 266.61
    1,4-butanediol 35.33
    1,1-dichloroethane 517.54
    2-methyl-1-pentanol 168.3
    methyl formate 86.17
    2-methyl-1-butanol 220.54
    n-decane 156.45
    butyronitrile 316.92
    3,7-dimethyl-1-octanol 279.72
    1-chlorooctane 353.1
    1-chlorotetradecane 165.3
    n-nonane 165.31
    undecane 119.82
    tert-butylcyclohexane 170.18
    cyclooctane 233.22
    cyclopentanol 330.84
    tetrahydropyran 1050.92
    tert-amyl methyl ether 405.36
    2,5,8-trioxanonane 372.77
    1-hexene 386.42
    2-isopropoxyethanol 141.89
    2,2,2-trifluoroethanol 25.43
    methyl butyrate 332.14

    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
Anise seed 3 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.99%
Anise herb 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 3.37%
Artemisia vestita (India) Artemisia vestita Wall. ex Dc., fam. Asteraceae (Compositae) 2.82%
Cedrus atlantica (Morocco) Cedrus atlantica Man., fam. Cupressaceae 10.5%
Abies sachalinensis (Finland) Abies sachalinensis (Fr. Schm.) Mast, fam. Pinaceae 0.4%
Abies mayriana (Finland) Abies mayriana Miy. et Kudo Needle, fam. Pinaceae 0.5%
Litsea pungens (China) Litsea pungens Hemsl., fam. Lauraceae 0.06%
Juniperus rigida (Japan) 2 Juniperus rigida Mig., fam. Cupressaceae 0.05%
Premna serratifolia flower bud Premna serratifolia L. (P.obtusifolia Br.R., P.taitensis Sch.),Verbenaceae 0.05%
Guava fruit (Reunion island) 91770-12-6 Psidium guajava L., fam. Myrtaceae 0.1%
Fitzroya cupressoides Fitzroya cupressoides (Mol.) Johnston, fam. Cupressaceae 1.3%
Ferula stenocarpa Ferula stenocarpa Boiss. & Hausskn., fam. Apiaceae (Umbelliferae) 0.3%
Espeletia batata leaf Espeletia batata Quatrec., fam. Asteraceae (Compositae) 0.9%