alpha-Bergamotene, (E)-(-)-

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  • Identifiers

    CAS number
    17829-53-7

    Molecular formula
    C15H24

    SMILES
    CC1=CC[C@H]2C[C@@H]1[C@]2(C)CCC=C(C)C

    Retention indicies (RI)

    • DB5: 1424.5
    • Carbowax: 1566.33

  • Odor profile

    Woody 80.81%
    Sweet 57.03%
    Balsamic 45.06%
    Spicy 42.51%
    Herbal 41.76%
    Fresh 40.09%
    Citrus 39.38%
    Terpenic 37.05%
    Green 36.57%
    Oily 34.56%

    Scent© AI

  • Properties

    XLogP3-AA
    4.8

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    262°C

    Flash point est.
    92.12 ˚C

  • Synonyms

    • trans-alpha-Bergamotene
    • 13474-59-4
    • (-)-exo-alpha-bergamotene
    • (+/-)-trans-alpha-Bergamotene
    • alpha-Bergamotene, (E)-(-)-
    • (-)-trans-alpha-bergamotene
    • UNII-599TK2712C
    • (1S,5S,6R)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene
    • 599TK2712C
    • (E)-(-)-alpha-bergamotene
    • 2-Norpinene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)-, trans-(-)
    • DTXSID901017570
    • (1S,5S,6R)-2,6-dimethyl-6-(4-methylpent-3-enyl)bicyclo[3.1.1]hept-2-ene
    • 17829-53-7
    • (E)-alpha-bergamotene
    • alpha-trans-Bergamotene
    • cis-.alpha.-Bergamotene
    • .alpha.-trans-Bergamotene
    • exo-alpha-bergamotene
    • trans-.alpha.-Bergamotene
    • alphaBERGAMOTENE, TRANS-
    • bergamotene (Z,.alpha.,cis)
    • FEMA NO. 4960
    • (-)-alphalpha-trans-Bergamotene
    • CHEBI:62756
    • (-)-I+/-lpha-trans-Bergamotene
    • .alpha.-trans-.beta.-Bergamotene
    • DTXCID301475754
    • .ALPHA.BERGAMOTENE, TRANS-
    • alpha-BERGAMOTENE, (-)-TRANS-
    • (-)-EXO-.ALPHA.-BERGAMOTENE
    • (1S,5S,6R)-4,6-dimethyl-6-(4-methylpent-3-enyl)bicyclo[3.1.1]hept-3-ene
    • (-)-TRANS-.ALPHA.-BERGAMOTENE
    • .ALPHA.-BERGAMOTENE, (-)-TRANS-
    • .ALPHA.-BERGAMOTENE, (E)-(-)-
    • C20811
    • Q27132147
    • BICYCLO(3.1.1)HEPT-2-ENE, 2,6-DIMETHYL-6-(4-METHYL-3-PENTEN-1-YL)-, (1S,5S,6R)-
    • BICYCLO(3.1.1)HEPT-2-ENE, 2,6-DIMETHYL-6-(4-METHYL-3-PENTENYL)-, (1S-(1.ALPHA.,5.ALPHA.,6.ALPHA.))-
    • BICYCLO(3.1.1)HEPT-2-ENE, 2,6-DIMETHYL-6-(4-METHYL-3-PENTENYL)-, (1S-(1alpha,5alpha,6alpha))-

  • Applications

    (E)-(-)-alpha-Bergamotene (CAS 17829-53-7) is a naturally occurring sesquiterpene with broad applications: in fragrance-flavor work (imparting citrusy, woody-peppery, herbal nuances to fine fragrance, flavors, beverages, and personal/home care), in analytical science (as a high-purity reference and stereochemical marker for GC-MS/GCxGC and chiral GC to resolve enantiomers, for authenticity testing and aroma fingerprinting of bergamot, hops, tobacco, and other botanical matrices), and in chemical ecology-agriculture (as a semiochemical VOC to study and leverage insect attraction/repellence, natural-enemy recruitment, and pollinator interactions, informing eco-friendly lures and IPM strategies); it is also used as a model molecule/precursor in organic synthesis and terpenoid biosynthetic engineering to probe terpene synthases, optimize MVA/MEP pathways, and program plant scent; these uses require tight control of stereochemical purity, oxidative stability, and storage conditions (inert atmosphere, cool, dark), and are typically positioned for R&D, quality standards, and product development.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 328.7
    methanol 131.52
    isopropanol 313.28
    water 0.12
    ethyl acetate 820.28
    n-propanol 362.96
    acetone 459.44
    n-butanol 479.62
    acetonitrile 238.77
    DMF 228.54
    toluene 1014.3
    isobutanol 285.71
    1,4-dioxane 1443.35
    methyl acetate 460.08
    THF 1680.6
    2-butanone 570.45
    n-pentanol 232.84
    sec-butanol 306.01
    n-hexane 314.47
    ethylene glycol 17.22
    NMP 228.96
    cyclohexane 632.0
    DMSO 130.39
    n-butyl acetate 999.05
    n-octanol 218.7
    chloroform 1099.68
    n-propyl acetate 372.03
    acetic acid 117.47
    dichloromethane 821.42
    cyclohexanone 700.51
    propylene glycol 43.97
    isopropyl acetate 644.66
    DMAc 298.98
    2-ethoxyethanol 241.45
    isopentanol 440.82
    n-heptane 346.64
    ethyl formate 206.58
    1,2-dichloroethane 645.99
    n-hexanol 695.08
    2-methoxyethanol 361.08
    isobutyl acetate 328.99
    tetrachloromethane 264.44
    n-pentyl acetate 358.35
    transcutol 1624.3
    n-heptanol 240.33
    ethylbenzene 360.19
    MIBK 500.63
    2-propoxyethanol 720.0
    tert-butanol 416.13
    MTBE 1100.61
    2-butoxyethanol 322.17
    propionic acid 135.03
    o-xylene 439.32
    formic acid 21.73
    diethyl ether 1523.01
    m-xylene 621.01
    p-xylene 414.17
    chlorobenzene 551.1
    dimethyl carbonate 173.26
    n-octane 101.81
    formamide 42.23
    cyclopentanone 596.51
    2-pentanone 646.24
    anisole 505.8
    cyclopentyl methyl ether 1006.19
    gamma-butyrolactone 459.28
    1-methoxy-2-propanol 388.58
    pyridine 841.22
    3-pentanone 548.03
    furfural 365.32
    n-dodecane 59.55
    diethylene glycol 244.72
    diisopropyl ether 656.4
    tert-amyl alcohol 345.02
    acetylacetone 536.45
    n-hexadecane 70.56
    acetophenone 321.13
    methyl propionate 457.01
    isopentyl acetate 899.12
    trichloroethylene 907.99
    n-nonanol 225.69
    cyclohexanol 433.12
    benzyl alcohol 212.35
    2-ethylhexanol 493.19
    isooctanol 212.06
    dipropyl ether 1160.94
    1,2-dichlorobenzene 437.51
    ethyl lactate 118.45
    propylene carbonate 321.19
    n-methylformamide 91.47
    2-pentanol 393.2
    n-pentane 357.3
    1-propoxy-2-propanol 635.31
    1-methoxy-2-propyl acetate 893.86
    2-(2-methoxypropoxy) propanol 407.39
    mesitylene 416.48
    ε-caprolactone 594.06
    p-cymene 325.03
    epichlorohydrin 700.13
    1,1,1-trichloroethane 661.94
    2-aminoethanol 66.19
    morpholine-4-carbaldehyde 462.71
    sulfolane 304.39
    2,2,4-trimethylpentane 147.52
    2-methyltetrahydrofuran 1299.58
    n-hexyl acetate 521.26
    isooctane 167.15
    2-(2-butoxyethoxy)ethanol 531.64
    sec-butyl acetate 389.78
    tert-butyl acetate 718.81
    decalin 198.0
    glycerin 55.06
    diglyme 936.99
    acrylic acid 77.33
    isopropyl myristate 269.34
    n-butyric acid 366.11
    acetyl acetate 424.32
    di(2-ethylhexyl) phthalate 186.11
    ethyl propionate 386.41
    nitromethane 175.77
    1,2-diethoxyethane 1280.1
    benzonitrile 305.46
    trioctyl phosphate 131.51
    1-bromopropane 737.43
    gamma-valerolactone 679.04
    n-decanol 172.09
    triethyl phosphate 232.82
    4-methyl-2-pentanol 309.64
    propionitrile 333.75
    vinylene carbonate 300.36
    1,1,2-trichlorotrifluoroethane 250.49
    DMS 359.23
    cumene 257.41
    2-octanol 163.09
    2-hexanone 362.36
    octyl acetate 280.61
    limonene 468.0
    1,2-dimethoxyethane 618.64
    ethyl orthosilicate 271.17
    tributyl phosphate 168.7
    diacetone alcohol 395.44
    N,N-dimethylaniline 319.74
    acrylonitrile 222.61
    aniline 497.33
    1,3-propanediol 163.63
    bromobenzene 694.01
    dibromomethane 704.28
    1,1,2,2-tetrachloroethane 729.07
    2-methyl-cyclohexyl acetate 448.34
    tetrabutyl urea 187.88
    diisobutyl methanol 330.08
    2-phenylethanol 398.7
    styrene 398.14
    dioctyl adipate 280.32
    dimethyl sulfate 137.47
    ethyl butyrate 613.89
    methyl lactate 117.26
    butyl lactate 194.59
    diethyl carbonate 355.83
    propanediol butyl ether 196.43
    triethyl orthoformate 496.66
    p-tert-butyltoluene 347.7
    methyl 4-tert-butylbenzoate 344.68
    morpholine 1293.02
    tert-butylamine 412.1
    n-dodecanol 137.39
    dimethoxymethane 580.48
    ethylene carbonate 307.96
    cyrene 187.32
    2-ethoxyethyl acetate 543.29
    2-ethylhexyl acetate 791.06
    1,2,4-trichlorobenzene 456.15
    4-methylpyridine 800.72
    dibutyl ether 623.06
    2,6-dimethyl-4-heptanol 330.08
    DEF 468.95
    dimethyl isosorbide 632.58
    tetrachloroethylene 476.29
    eugenol 244.49
    triacetin 387.18
    span 80 302.93
    1,4-butanediol 45.53
    1,1-dichloroethane 656.73
    2-methyl-1-pentanol 243.88
    methyl formate 70.96
    2-methyl-1-butanol 374.71
    n-decane 110.43
    butyronitrile 455.1
    3,7-dimethyl-1-octanol 301.16
    1-chlorooctane 261.94
    1-chlorotetradecane 123.46
    n-nonane 112.53
    undecane 78.3
    tert-butylcyclohexane 185.86
    cyclooctane 289.76
    cyclopentanol 285.32
    tetrahydropyran 1838.86
    tert-amyl methyl ether 714.36
    2,5,8-trioxanonane 608.08
    1-hexene 525.92
    2-isopropoxyethanol 239.14
    2,2,2-trifluoroethanol 42.53
    methyl butyrate 364.64

    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
Star anise (China) 1 8007-70-3 Illicium verum Hooker fil., fam. Magnoliaceae (Illiciaceae) 0.1%
Star anise (Vietnam) 1 8007-70-3 Illicium verum Hooker fil., fam. Magnoliaceae (Illiciaceae) 0.1%
Basil (Nigeria) 2 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.01%
Bergamot (Italy) 1 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Lemon (Spain) 7 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.03%
Carrot seed (France) 1 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.47%
Cedarwood, Mulanje Widdringtonia whytei Rendle, fam. Cupressaceae 0.2%
Clary sage 1 8016-63-5 Salvia sclarea L., fam. Lamiaceae (Labiatae) 0.3%
Helichrysum italicum (Yugoslavia) 8023-95-8 Helichrysum italicum (Roth) G. Don (H. angustifolium D.C.), fam.Asteraceae 1.3%
Lemon (Italy-Sicily) 7 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.03%
Lemon (Israel) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.03%
Opoponax 8021-36-1 Commiphora erythraea Engler var. glabrescens Engler, fam. Burseraceae 5.0%
Sage, spanish (Spain) 3 8016-65-7 Salvia lavandulaefolia Vahl., fam. Lamiaceae (Labiatae) 0.1%
Lemon (USA-California) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.03%
Lemon (Italy-Sicily) 8 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.03%
Pistacia lentiscus (Spain) 1a leaf 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.05%
Carrot seed (France) 4 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.1%
Orange, sweet (China) 2 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.01%
Carrot seed (France) 3 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.29%
Erigeron canadensis Erigeron canadensis L. (Conyza canadensis (L.) Cronquist), fam. Asteraceae 9.9%
Ocimum gratissimum (Nigeria) leaf Ocimum gratissimum L., fam. Lamiaceae (Labiatae) 0.43%
Ocimum gratissimum (Nigeria) stem Ocimum gratissimum L., fam. Lamiaceae (Labiatae) 1.06%
Pepper, black 3 8006-82-4 Piper nigrum L., fam. Piperaceae 0.7%
Orthodon calveriei (Vietnam) Orthodon calveriei Level. (Mosla calveriei), fam. Lamiaceae (Labiatae) 11.1%
Coleus aromaticus (Mauritius) Coleus aromaticus Benth. (wild oregano), fam. Lamiaceae (Labiatae) 1.5%
Phoebe 1 Phoebe porosa Mez. (syn. Oreodaphne porosa Nees et Mart.), fam. Lauraceae 0.36%
Phoebe 2 Phoebe porsa Mez. (syn. Oreodaphne prosa Nees & Mart.), fam. Lauraceae 1.0%
Guava leaf 3 91770-12-6 Psidium guajava L., fam. Myrtaceae 0.48%
Zingiber zerumbet (Vietnam) 2a stem Zingiber zerumbet (L.) Sm., fam. Zingiberaceae 0.7%
Zingiber zerumbet (Vietnam) 2b leaf Zingiber zerumbet (L.) Sm., fam. Zingiberaceae 1.4%
Zingiber zerumbet (Vietnam) 2c flower Zingiber zerumbet (L.) Sm., fam. Zingiberaceae 1.4%
Polygonum odoratum Polygonum odoratum L., fam. Polygonaceae 0.9%
Lippia multiflora leaf (Benin) Lippia multiflora Moldenke (syn.L.adoensis & L.grandiflora) fam.Verbenacea 0.1%
Ravensara anisata (Madagascar) Ravensara anisata Danguy, fam. Lauraceae 2.12%
Camphor (Cote d'Ivoire), 1b stem 8008-51-3 Cinnamomum camphora (L.) Nees et Ebermaier, fam. Lauraceae 0.4%
Camphor (Cote d'Ivoire), 1c bark 8008-51-3 Cinnamomum camphora (L.) Nees et Ebermaier, fam. Lauraceae 2.4%
Orange leaf, sweet (Italy) 1 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.01%
Orange leaf, sweet (Italy) 2a Valencia Late Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.01%
Orange leaf, sweet (Italy) 2b Biondo Comune Citrus sinensis (L.) Osbeck, cultivar Biondo Comune, fam. Rutaceae 0.01%
Orange leaf, sweet (Italy) 2c Moro Citrus sinensis (L.) Osbeck, cultivar Moro, fam. Rutaceae 0.01%
Bergamot (Italy) 4 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.03%
Sage, spanish (Spain) 13 8016-65-7 Salvia lavandulaefolia Vahl., fam. Lamiaceae (Labiatae) 0.05%
Sage, spanish (Spain) 14 8016-65-7 Salvia lavandulaefolia Vahl., fam. Lamiaceae (Labiatae) 0.01%
Helichrysum italicum 1a 8023-95-8 Helichrysum italicum (Roth) G. Don ssp. italicum, fam. Asteraceae 0.87%
Lime (Mexican, West Indian, Key) 5 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.06%
Lime (Mexican, West Indian, Key) (Peru) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.06%
Lime (Mexican, West Indian, Key) (Ivory Coast) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.04%
Teucrium flavum (Greece) 1b leaf Teucrium flavum L. ssp. hellenicum Rech. fil., fam. Lamiaceae (Labiatae) 0.2%
Teucrium flavum (Greece) 1a flower Teucrium flavum L. ssp. hellenicum Rech. fil., fam. Lamiaceae (Labiatae) 0.3%
Bergamot (Turkey) 2 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%