(-)-Germacrene A

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  • Identifiers

    CAS number
    28387-44-2

    Molecular formula
    C15H24

    SMILES
    C/C/1=C\CC/C(=C/C[C@H](CC1)C(=C)C)/C

    Retention indicies (RI)

    • DB5: 1503.71
    • Carbowax: 1737.5

  • Odor profile

    Woody 73.91%
    Citrus 71.36%
    Terpenic 63.25%
    Herbal 63.03%
    Lemon 58.34%
    Spicy 55.75%
    Sweet 51.98%
    Fresh 48.68%
    Pine 47.98%
    Camphoreous 38.92%

    Scent© AI

  • Properties

    XLogP3-AA
    4.7

    pKa est.
    8.8 (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.
    94.97 ˚C

  • Synonyms

    • (-)-Germacrene A
    • germacrene a
    • 28387-44-2
    • Germacra-3,9,11-triene, (E,E)-
    • (E,E)-germacra-3,9,11-triene
    • G3R25T5M9A
    • CHEBI:36515
    • (1E,5E,8S)-1,5-dimethyl-8-prop-1-en-2-ylcyclodeca-1,5-diene
    • (1E,5E,8S)-1,5-dimethyl-8-(1-methylethenyl)-1,5-cyclodecadiene
    • (1E,4E,7betaH)-germacra-1(10),4,11(12)-triene
    • (1E,5E,8S)-8-isopropenyl-1,5-dimethylcyclodeca-1,5-diene
    • [S-(E,E)]-1,5-dimethyl-8-(1-methylethenyl)-1,5-cyclodecadiene
    • 1,5-Cyclodecadiene, 1,5-dimethyl-8-(1-methylethenyl)-, (S-(E,E))-
    • Germacrene
    • 1,5-Cyclodecadiene, 1,5-dimethyl-8-(1-methylethenyl)-, (1E,5E,8S)-
    • (S-(E,E))-1,5-dimethyl-8-(1-methylethenyl)-1,5-cyclodecadiene
    • 1,5-Cyclodecadiene, 1,5-dimethyl-8-(1-methylethenyl)-, [S-(E,E)]-
    • UNII-G3R25T5M9A
    • XMRKUJJDDKYUHV-SDFJSLCBSA-N
    • Q27116866

  • Applications

    (-)-Germacrene A (CAS 28387-44-2) is a natural sesquiterpene used mainly in research and R&D: as a reference standard and GC/GC-MS fingerprint marker for essential oils and plant metabolite profiling; as an intermediate/scaffold for synthesis and semisynthesis of sesquiterpene derivatives (oxidation to acids/epoxides/alcohols) and to model biosynthetic steps leading to sesquiterpene lactones; as a biosynthetic branchpoint exploited in metabolic engineering and crop biotechnology to enhance defense volatiles and aroma formation, supporting breeding and functional genomics; as an ecological cue in insect-behavior assays and plant-organism interaction studies; as a chiral reference for developing enantioselective chromatographic methods and quality control; and in flavor and fragrance R&D as an odor reference and blending component, as well as in studies of thermally induced rearrangements (e.g., to beta-elemene) that inform optimization of analytical, storage, and handling conditions.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 274.36
    methanol 90.14
    isopropanol 274.21
    water 0.01
    ethyl acetate 676.63
    n-propanol 291.48
    acetone 287.41
    n-butanol 387.6
    acetonitrile 150.94
    DMF 131.12
    toluene 911.8
    isobutanol 223.8
    1,4-dioxane 1226.61
    methyl acetate 287.37
    THF 1974.79
    2-butanone 470.12
    n-pentanol 270.67
    sec-butanol 320.65
    n-hexane 445.63
    ethylene glycol 7.3
    NMP 169.45
    cyclohexane 701.79
    DMSO 153.62
    n-butyl acetate 1258.39
    n-octanol 267.41
    chloroform 925.27
    n-propyl acetate 387.05
    acetic acid 75.26
    dichloromethane 774.97
    cyclohexanone 653.47
    propylene glycol 31.61
    isopropyl acetate 518.68
    DMAc 199.57
    2-ethoxyethanol 189.4
    isopentanol 371.19
    n-heptane 750.25
    ethyl formate 152.13
    1,2-dichloroethane 507.09
    n-hexanol 721.61
    2-methoxyethanol 235.69
    isobutyl acetate 318.43
    tetrachloromethane 202.82
    n-pentyl acetate 416.11
    transcutol 1480.43
    n-heptanol 262.73
    ethylbenzene 430.22
    MIBK 404.04
    2-propoxyethanol 534.96
    tert-butanol 445.48
    MTBE 1015.88
    2-butoxyethanol 268.33
    propionic acid 85.8
    o-xylene 380.12
    formic acid 7.38
    diethyl ether 1309.98
    m-xylene 515.56
    p-xylene 418.68
    chlorobenzene 390.34
    dimethyl carbonate 65.73
    n-octane 161.65
    formamide 14.74
    cyclopentanone 516.19
    2-pentanone 531.37
    anisole 482.44
    cyclopentyl methyl ether 916.09
    gamma-butyrolactone 338.3
    1-methoxy-2-propanol 276.95
    pyridine 811.8
    3-pentanone 386.26
    furfural 245.55
    n-dodecane 77.3
    diethylene glycol 121.42
    diisopropyl ether 527.04
    tert-amyl alcohol 401.39
    acetylacetone 376.73
    n-hexadecane 91.59
    acetophenone 282.48
    methyl propionate 274.78
    isopentyl acetate 1065.53
    trichloroethylene 684.74
    n-nonanol 269.41
    cyclohexanol 411.52
    benzyl alcohol 174.11
    2-ethylhexanol 698.11
    isooctanol 233.62
    dipropyl ether 1829.95
    1,2-dichlorobenzene 295.74
    ethyl lactate 78.79
    propylene carbonate 249.94
    n-methylformamide 43.19
    2-pentanol 365.95
    n-pentane 359.7
    1-propoxy-2-propanol 660.29
    1-methoxy-2-propyl acetate 745.02
    2-(2-methoxypropoxy) propanol 373.69
    mesitylene 327.41
    ε-caprolactone 510.61
    p-cymene 411.37
    epichlorohydrin 601.28
    1,1,1-trichloroethane 597.44
    2-aminoethanol 34.07
    morpholine-4-carbaldehyde 284.43
    sulfolane 262.14
    2,2,4-trimethylpentane 132.63
    2-methyltetrahydrofuran 1607.2
    n-hexyl acetate 567.19
    isooctane 143.43
    2-(2-butoxyethoxy)ethanol 473.64
    sec-butyl acetate 362.48
    tert-butyl acetate 616.77
    decalin 228.0
    glycerin 33.14
    diglyme 890.38
    acrylic acid 39.91
    isopropyl myristate 317.22
    n-butyric acid 297.19
    acetyl acetate 274.21
    di(2-ethylhexyl) phthalate 195.97
    ethyl propionate 336.38
    nitromethane 99.14
    1,2-diethoxyethane 1583.29
    benzonitrile 262.53
    trioctyl phosphate 134.24
    1-bromopropane 813.94
    gamma-valerolactone 501.01
    n-decanol 200.48
    triethyl phosphate 216.35
    4-methyl-2-pentanol 245.68
    propionitrile 237.45
    vinylene carbonate 166.61
    1,1,2-trichlorotrifluoroethane 162.52
    DMS 220.91
    cumene 263.7
    2-octanol 197.38
    2-hexanone 438.79
    octyl acetate 327.82
    limonene 715.31
    1,2-dimethoxyethane 692.9
    ethyl orthosilicate 263.85
    tributyl phosphate 174.54
    diacetone alcohol 344.5
    N,N-dimethylaniline 321.02
    acrylonitrile 138.46
    aniline 372.72
    1,3-propanediol 101.24
    bromobenzene 530.69
    dibromomethane 712.43
    1,1,2,2-tetrachloroethane 607.9
    2-methyl-cyclohexyl acetate 495.71
    tetrabutyl urea 229.82
    diisobutyl methanol 404.59
    2-phenylethanol 352.27
    styrene 461.7
    dioctyl adipate 352.44
    dimethyl sulfate 63.68
    ethyl butyrate 833.44
    methyl lactate 61.33
    butyl lactate 172.28
    diethyl carbonate 375.41
    propanediol butyl ether 171.85
    triethyl orthoformate 558.65
    p-tert-butyltoluene 428.74
    methyl 4-tert-butylbenzoate 310.68
    morpholine 1301.01
    tert-butylamine 439.31
    n-dodecanol 162.44
    dimethoxymethane 316.53
    ethylene carbonate 177.78
    cyrene 168.09
    2-ethoxyethyl acetate 476.72
    2-ethylhexyl acetate 959.78
    1,2,4-trichlorobenzene 319.34
    4-methylpyridine 729.69
    dibutyl ether 937.69
    2,6-dimethyl-4-heptanol 404.59
    DEF 382.18
    dimethyl isosorbide 690.22
    tetrachloroethylene 351.82
    eugenol 210.09
    triacetin 312.89
    span 80 346.05
    1,4-butanediol 30.32
    1,1-dichloroethane 542.0
    2-methyl-1-pentanol 297.51
    methyl formate 34.22
    2-methyl-1-butanol 318.92
    n-decane 160.25
    butyronitrile 411.07
    3,7-dimethyl-1-octanol 361.82
    1-chlorooctane 363.03
    1-chlorotetradecane 145.06
    n-nonane 174.64
    undecane 104.21
    tert-butylcyclohexane 204.74
    cyclooctane 309.7
    cyclopentanol 254.98
    tetrahydropyran 2079.16
    tert-amyl methyl ether 707.7
    2,5,8-trioxanonane 603.42
    1-hexene 828.32
    2-isopropoxyethanol 188.87
    2,2,2-trifluoroethanol 13.38
    methyl butyrate 369.45

    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
Caraway herb 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.35%
Eupatorium maximilianii Eupatorium maximilianii (Erva de Sao Joao), fam. Asteraceae (Compositae) 0.52%
Aristolochia gigantea Aristolochia gigantea M.E. Zucc., fam. Aristolochiaceae 1.2%
Abies sachalinensis (Finland) Abies sachalinensis (Fr. Schm.) Mast, fam. Pinaceae 0.1%
Abies mayriana (Finland) Abies mayriana Miy. et Kudo Needle, fam. Pinaceae 0.1%
Juniperus rigida (Japan) 2 Juniperus rigida Mig., fam. Cupressaceae 0.05%
Juniperus rigida (China) Juniperus rigida Mig., fam. Cupressaceae 0.05%
Basil (Turkey) 2a 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.15%
Basil (Turkey) 2b 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.07%
Protium heptaphyllum 1b stem Protium heptaphyllum (Aubl.) March., fam. Burseraceae 0.53%
Eugenia uniflora leaf (Brazil) 1 Eugenia uniflora L. (E. michelii Lam., E. pitanga (Berg), fam. Myrtaceae 1.52%
Aristolochia impudica leaf Aristolochia impudica J. Ortega, fam. Aristolochiaceae 18.4%
Ambrosia microcephala Ambrosia microcephala DC., fam. Asteraceae (Compositae) 0.5%
Aristolochia brevipes Aristolochia brevipes Benth., fam. Aristolochiaceae 0.5%
Basil (Brazil) var. purpurascens 8015-73-4 Ocimum basilicum L. cultivar purpurascens Benth., fam.Lamiaceae (Labiatae) 1.0%
Palmarosa (Bangladesh) 8014-19-5 Cymbopogon martini (Roxb.) Wats, var. martini, fam. Poaceae (Gramineae) 0.05%
Acinos alpinus oil (Greece) Acinos alpinus (L.) Moench., fam. Lamiaceae (Labiatae) 30.0%
Spike lavender (Spain) 5 8016-78-2 Lavandula latifolia Medikus (L. spica D.C.), fam. Lamiaceae (Labiatae) 0.08%
Juniper leaf (Sweden) 8012-91-7 Juniperus communis L., fam. Cupressaceae 0.1%
Hyptis crenata (Brazil) Hyptis crenata Pohl ex Benth, fam. Lamiaceae (Labiatae) 0.05%
Calamintha vardarensis Calamintha vardarensis (Greuter et Burdet) Silic, fam.Lamiaceae (Labiatae) 0.05%
Mikania cordata leaf Mikania cordata (Burm.f.) B.L. Robinson var. cordata, fam. Asteraceae 1.3%
Marsypianthes chamaedrys (Brazil) Marsypianthes chamaedrys (Vahl) Kuntze, fam. Lamiaceae (Labiatae) 3.1%
Aristolochia odoratissima Aristolochia odoratissima L., fam. Aristolochaceae 1.6%
Sweetie peel Citrus paradisi Macfayden x Citrus maxima Merill, fam. Rutaceae 0.03%
Calamus (Bangladesh) root 8015-79-0 Acorus calamus L., fam. Araceae 0.02%
Spearmint (Mexico) 8008-79-5 Mentha spicata L., fam. Lamiaceae (Labiatae) 1.2%
Carapa guianensis Carapa guianensis Aubl., fam. Meliaceae 0.2%
Baccharis uncinella (Brazil) Baccharis uncinella DC., fam. Asteraceae (Compositae) 0.05%
Lippia alba (Uruguay) cultivar Lippia alba (Mill.) N.E. Brown, fam. Verbenaceae 1.3%
Lippia lupulina stalk & leaf (Brazil) Lippia lupulina Cham., fam. Verbenaceae 0.6%
Lippia lupulina flower (Brazil) Lippia lupulina Cham., fam. Verbenaceae 1.2%
Croton jimenezii (Costa Rica) Croton jimenezii Standl. et Valerio, fam. Euphorbiaceae 0.55%
Conyza bonariensis (Brazil) Conyza bonariensis (L.) Cronquist, fam. Asteraceae (Compositae) 0.2%
Myrceugenia miersiana (Brazil) Myrceugenia miersiana (Gardner) D. Legrand et Kausel, fam. Myrtaceae 0.9%
Lime (Mexican, West Indian, Key) (France) 2 leaf 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 2.24%
Orange leaf, sweet (Malaysia) Citrus sinensis (L.) Osbeck, fam. Rutaceae 3.8%