gamma-Bisabolene, (Z)-

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  • Identifiers

    CAS number
    13062-00-5

    Molecular formula
    C15H24

    SMILES
    CC1=CC/C(=C(/C)\CCC=C(C)C)/CC1

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Retention indicies (RI)

    • DB5: 1517.25

  • Odor profile

    Floral 72.99%
    Woody 72.73%
    Sweet 71.22%
    Tropical 57.19%
    Balsamic 56.7%
    Citrus 56.04%
    Fruity 52.07%
    Spicy 48.99%
    Green 45.51%
    Herbal 43.44%

    Scent© AI

  • Properties

    XLogP3-AA
    4.7

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    274°C

    Flash point est.
    103.3 ˚C

    Solubility expt.

    • Insoluble in water; soluble in oils
    • Insoluble (in ethanol)

  • Synonyms

    • (Z)-gamma-bisabolene
    • gamma-Bisabolene
    • Bisabolene
    • cis-gamma-Bisabolene
    • 13062-00-5
    • Limene
    • gamma-Bisabolene, (Z)-
    • gamma-Bisabolene, (4Z)-
    • 495-62-5
    • UNII-E452K502K0
    • (Z)-.gamma.-Bisabolene
    • 4-(1,5-Dimethyl-4-hexenylidene)-1-methylcyclohexene
    • E452K502K0
    • Cyclohexene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-, (4Z)-
    • Cyclohexene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-, (Z)-
    • 2-Heptene, 2-methyl-6-(4-methyl-3-cyclohexen-1-ylidene)-, (Z)-
    • Cyclohexene, 4-(1,5-dimethyl-4-hexen-1-ylidene)-1-methyl-, (4Z)-
    • cis-.gamma.-Bisabolene
    • (4Z)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohexene
    • CHEBI:49238
    • 1-Methyl-4-(1,5-dimethyl-4-hexenylidene)-1-cyclohexene
    • 2-Methyl-6-(4-methyl-3-cyclohexen-1-ylidene)-2-heptene
    • (1Z)-bisabola-1(10),4,7(11)-triene
    • CYCLOHEXENE, 4-(1,5-DIMETHYL-4-HEXENYLIDENE)-1-METHYL-
    • (4Z)-1-Methyl-4-(6-methyl-5-hepten-2-ylidene)cyclohexene
    • (4Z)-4-(1,5-dimethylhex-4-en-1-ylidene)-1-methylcyclohexene
    • (Z)-1-Methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene
    • (1Z)-bisabola-1(10),4,7(11)-triene (4Z)-4-(1,5-dimethylhex-4-en-1-ylidene)-1-methylcyclohexene
    • Bisabolene (natural)
    • gamma-Bisabolen
    • FEMA No. 3331
    • EINECS 207-805-8
    • (Z) gamma-bisabolene
    • 1-Methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene
    • 4-(1,5-Dimethyl-4-hexen-1-ylidene)-1-methylcyclohexene
    • UNII-E6941S3U3Q
    • CHEBI:49237
    • 2-Heptene, 2-methyl-6-(4-methyl-3-cyclohexen-1-ylidene)-
    • DTXSID901037003
    • E6941S3U3Q
    • .GAMMA.-BISABOLENE, (Z)-
    • .GAMMA.-BISABOLENE, (4Z)-
    • bisabola-1(10),4,7(11)-triene
    • AKOS024287123
    • LMPR0103060004
    • B1413
    • NS00012017
    • Q4039091
    • 4-(1,5-dimethylhex-4-en-1-ylidene)-1-methylcyclohexene
    • Cyclohexene, 4-(1,5-dimethyl-4-hexen-1-ylidene)-1-methyl-

  • Applications

    gamma-Bisabolene, (Z)- (CAS 13062-00-5) is a sesquiterpene hydrocarbon with a woody–herbal character found in plant essential oils, thus used in perfumery as a warm, balsamic note and as a modifier to enrich citrus–spicy accords; in food and beverage flavoring it can be employed at very low levels to fine-tune aroma and add roundness to citrus, herbal, or resinous profiles; in laboratories and R&D, (Z)-γ-bisabolene serves as an analytical/reference standard for GC–MS, for studies of geometric/stereochemical isomerism in terpenes, and for investigating oxidative pathways and secondary product formation in aroma matrices and atmospheric chemistry; moreover, bisabolene is a target of microbial biosynthesis as a renewable feedstock that can be hydrogenated to “bisabolane” for diesel/jet fuel applications and used as a building block toward higher-value chemicals, so (Z)-γ-bisabolene is employed as a reference substrate in process optimization, fuel property evaluation (volatility, energy density, stability), and safety/materials-compatibility studies; practical use should account for its volatility, hydrophobicity, and oxidation sensitivity, with storage in cool, dark, oxygen-limited conditions to preserve odor quality.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 98.14
    methanol 40.88
    isopropanol 84.41
    water 0.01
    ethyl acetate 436.43
    n-propanol 103.66
    acetone 122.04
    n-butanol 157.73
    acetonitrile 73.75
    DMF 62.6
    toluene 625.08
    isobutanol 71.9
    1,4-dioxane 751.73
    methyl acetate 172.21
    THF 858.38
    2-butanone 230.04
    n-pentanol 114.57
    sec-butanol 122.3
    n-hexane 430.31
    ethylene glycol 3.66
    NMP 109.14
    cyclohexane 538.88
    DMSO 66.52
    n-butyl acetate 770.58
    n-octanol 115.31
    chloroform 614.17
    n-propyl acetate 238.41
    acetic acid 36.06
    dichloromethane 456.3
    cyclohexanone 366.55
    propylene glycol 13.36
    isopropyl acetate 372.16
    DMAc 150.34
    2-ethoxyethanol 108.49
    isopentanol 160.68
    n-heptane 506.19
    ethyl formate 71.21
    1,2-dichloroethane 330.48
    n-hexanol 334.0
    2-methoxyethanol 113.14
    isobutyl acetate 216.17
    tetrachloromethane 126.27
    n-pentyl acetate 254.34
    transcutol 1119.52
    n-heptanol 126.3
    ethylbenzene 370.04
    MIBK 242.11
    2-propoxyethanol 303.3
    tert-butanol 161.3
    MTBE 642.78
    2-butoxyethanol 149.55
    propionic acid 41.23
    o-xylene 334.55
    formic acid 4.55
    diethyl ether 916.94
    m-xylene 384.8
    p-xylene 341.95
    chlorobenzene 254.92
    dimethyl carbonate 45.51
    n-octane 114.47
    formamide 8.36
    cyclopentanone 246.84
    2-pentanone 281.04
    anisole 406.93
    cyclopentyl methyl ether 591.53
    gamma-butyrolactone 157.15
    1-methoxy-2-propanol 134.44
    pyridine 436.62
    3-pentanone 275.68
    furfural 141.62
    n-dodecane 53.19
    diethylene glycol 73.43
    diisopropyl ether 465.48
    tert-amyl alcohol 188.1
    acetylacetone 240.44
    n-hexadecane 65.24
    acetophenone 221.49
    methyl propionate 183.12
    isopentyl acetate 708.14
    trichloroethylene 495.72
    n-nonanol 132.99
    cyclohexanol 193.91
    benzyl alcohol 106.13
    2-ethylhexanol 379.88
    isooctanol 116.05
    dipropyl ether 1312.23
    1,2-dichlorobenzene 234.6
    ethyl lactate 55.7
    propylene carbonate 124.52
    n-methylformamide 20.0
    2-pentanol 162.44
    n-pentane 255.34
    1-propoxy-2-propanol 379.55
    1-methoxy-2-propyl acetate 585.08
    2-(2-methoxypropoxy) propanol 288.15
    mesitylene 282.2
    ε-caprolactone 323.12
    p-cymene 307.79
    epichlorohydrin 322.12
    1,1,1-trichloroethane 439.13
    2-aminoethanol 14.87
    morpholine-4-carbaldehyde 207.78
    sulfolane 155.92
    2,2,4-trimethylpentane 126.24
    2-methyltetrahydrofuran 765.4
    n-hexyl acetate 364.75
    isooctane 106.78
    2-(2-butoxyethoxy)ethanol 331.4
    sec-butyl acetate 299.06
    tert-butyl acetate 505.39
    decalin 251.3
    glycerin 16.25
    diglyme 677.23
    acrylic acid 22.02
    isopropyl myristate 230.53
    n-butyric acid 132.96
    acetyl acetate 217.69
    di(2-ethylhexyl) phthalate 141.31
    ethyl propionate 260.52
    nitromethane 56.91
    1,2-diethoxyethane 1308.23
    benzonitrile 142.21
    trioctyl phosphate 79.64
    1-bromopropane 487.33
    gamma-valerolactone 277.4
    n-decanol 101.78
    triethyl phosphate 211.11
    4-methyl-2-pentanol 128.41
    propionitrile 117.26
    vinylene carbonate 95.51
    1,1,2-trichlorotrifluoroethane 122.02
    DMS 189.38
    cumene 257.37
    2-octanol 95.49
    2-hexanone 267.59
    octyl acetate 222.86
    limonene 509.98
    1,2-dimethoxyethane 412.46
    ethyl orthosilicate 266.84
    tributyl phosphate 118.88
    diacetone alcohol 209.13
    N,N-dimethylaniline 293.49
    acrylonitrile 68.48
    aniline 206.69
    1,3-propanediol 40.62
    bromobenzene 367.99
    dibromomethane 393.38
    1,1,2,2-tetrachloroethane 500.37
    2-methyl-cyclohexyl acetate 453.72
    tetrabutyl urea 150.96
    diisobutyl methanol 247.25
    2-phenylethanol 226.13
    styrene 352.88
    dioctyl adipate 285.9
    dimethyl sulfate 48.66
    ethyl butyrate 647.49
    methyl lactate 39.6
    butyl lactate 101.4
    diethyl carbonate 324.28
    propanediol butyl ether 84.15
    triethyl orthoformate 510.53
    p-tert-butyltoluene 321.79
    methyl 4-tert-butylbenzoate 267.78
    morpholine 653.05
    tert-butylamine 186.13
    n-dodecanol 86.45
    dimethoxymethane 178.68
    ethylene carbonate 99.56
    cyrene 119.49
    2-ethoxyethyl acetate 346.04
    2-ethylhexyl acetate 720.97
    1,2,4-trichlorobenzene 275.36
    4-methylpyridine 395.22
    dibutyl ether 697.72
    2,6-dimethyl-4-heptanol 247.25
    DEF 249.57
    dimethyl isosorbide 539.16
    tetrachloroethylene 274.58
    eugenol 159.2
    triacetin 254.27
    span 80 217.31
    1,4-butanediol 12.69
    1,1-dichloroethane 299.9
    2-methyl-1-pentanol 160.5
    methyl formate 15.48
    2-methyl-1-butanol 143.68
    n-decane 105.26
    butyronitrile 180.67
    3,7-dimethyl-1-octanol 182.93
    1-chlorooctane 241.78
    1-chlorotetradecane 109.22
    n-nonane 114.38
    undecane 69.85
    tert-butylcyclohexane 222.8
    cyclooctane 280.68
    cyclopentanol 98.98
    tetrahydropyran 1062.78
    tert-amyl methyl ether 571.32
    2,5,8-trioxanonane 502.44
    1-hexene 607.73
    2-isopropoxyethanol 115.7
    2,2,2-trifluoroethanol 8.09
    methyl butyrate 251.65

    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 0.5%
Ginger (India) 1 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 7.0%
Oregano, greek (European) 84012-24-8 Origanum vulgare L. ssp. vulgare, fam. Lamiaceae (Labiatae) 0.1%
Pepper, black 3 8006-82-4 Piper nigrum L., fam. Piperaceae 0.7%
Guava leaf 3 91770-12-6 Psidium guajava L., fam. Myrtaceae 1.49%
Psidium guineense leaf Psidium guineense Sw., fam. Myrtaceae 2.3%
Bergamot (Italy) 4 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Helichrysum italicum 1a 8023-95-8 Helichrysum italicum (Roth) G. Don ssp. italicum, fam. Asteraceae 0.07%
Lime (Mexican, West Indian, Key) 5 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.04%
Rue (Cuba) 8014-29-7 Ruta graveolens L., fam. Rutaceae 0.77%
Stevia achalensis Stevia achalensis Hieronymus, fam. Asteraceae (Compositae) 6.6%
Lime (Mexican, West Indian, Key) (Peru) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.01%
Lime (Mexican, West Indian, Key) (Ivory Coast) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.01%
Lime (Mexican, West Indian, Key) 7 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.01%
Basil (Italy) 4a steamdistillate 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 1.1%
Basil (Italy) 4b CO2-extract 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.01%
Basil (Italy) 4b extract 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 1.26%
Commiphora africana (Benin) Commiphora africana (A. Rich.) Engl. (Heudelotia africana),fam. Burseracea 10.0%
Guava fruit (Reunion island) 91770-12-6 Psidium guajava L., fam. Myrtaceae 0.1%
Balsamite/Costmary (Iran) Chrysanthemum balsamita L., fam. Asteraceae (Compositae) 1.0%
Mikania cordata leaf Mikania cordata (Burm.f.) B.L. Robinson var. cordata, fam. Asteraceae 0.5%
Guava leaf 4 Psidium guajava L., fam. Myrtaceae 0.2%
Ruta chalepensis (Greece) Ruta chalepensis L., fam. Rutaceae 0.05%
Carapa guianensis Carapa guianensis Aubl., fam. Meliaceae 0.2%
Bergamot (Italy, Sicily) 1a Castagnaro 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Bergamot (Italy, Sicily) 1b Fantastico 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Bergamot (Italy, Sicily) 1c Feminello 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Bergamot (Italy, Sicily) 1d PCF 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Bergamot (Italy, Calabria) 8 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Teucrium melissoides (Iran) Teucrium melissoides Boiss. et Hauskn. ex Boiss., fam.Lamiaceae (Labiatae) 7.5%
Elionurus elegans aerial parts Elionurus elegans Kunth (African Pasture Grass), fam. Poaceae (Gramineae) 0.6%
Elionurus elegans roots Elionurus elegans Kunth (African Pasture Grass), fam. Poaceae (Gramineae) 0.2%