(-)-alpha-Curcumene

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  • Identifiers

    CAS number
    4176-17-4

    Molecular formula
    C15H22

    SMILES
    CC1=CC=C(C=C1)[C@H](C)CCC=C(C)C

    Retention indicies (RI)

    • DB5: 1482.71
    • Carbowax: 1775.71

  • Odor profile

    Herbal 60.79%
    Citrus 50.57%
    Fresh 42.62%
    Woody 42.47%
    Spicy 42.31%
    Floral 42.27%
    Lemon 38.06%
    Green 36.41%
    Terpenic 33.46%
    Balsamic 27.93%

    Scent© AI

  • Properties

    XLogP3-AA
    5.4

    Molecular weight
    202.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    259°C

    Flash point est.
    105.31 ˚C

  • Synonyms

    • (-)-alpha-curcumene
    • l-alpha-Curcumene
    • 4176-17-4
    • (R)-(-)-curcumene
    • (R)-curcumene
    • (R)-(-)-alpha-curcumene
    • 1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]benzene
    • 4-[(1R)-1,5-dimethylhex-4-enyl]-1-methylbenzene
    • Benzene, 1-(1,5-dimethyl-4-hexenyl)-4-methyl-, (R)-
    • CHEBI:10225
    • L-a-Curcumene
    • (R)-ar-Curcumene
    • (-)-a-Curcumene
    • (R)-1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene
    • (R)-(-)-a-Curcumene
    • CHEMBL469717
    • DTXSID50194584
    • C09649
    • Q27108606

  • Applications

    (-)-alpha-Curcumene (CAS 4176-17-4) is an optically active sesquiterpene found in turmeric and other Zingiberaceae oils, applied mainly in fragrance/flavor and research: used as a warm, spicy, woody–resinous note in fine fragrance, personal care, and home care (leveraging enantiomer-specific nuances); contributing to spice flavor profiles when present via source essential oils; serving as a chiral reference for profiling, quantitation, and enantioselective separations (GC, GC–MS, SFC) in quality control, authenticity testing, and standardization of turmeric-related oils; acting as a building block and stereochemical probe in terpene synthesis and in sensory/odor-threshold method development; and being investigated as a plant-derived bioactive (e.g., antimicrobial, insect-repellent/antifeedant) in preclinical studies and eco-friendly crop protection, typically evaluated within essential-oil mixtures or as a chiral model molecule.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 498.71
    methanol 191.4
    isopropanol 388.39
    water 0.02
    ethyl acetate 1734.28
    n-propanol 473.9
    acetone 759.12
    n-butanol 653.71
    acetonitrile 445.42
    DMF 282.14
    toluene 1492.47
    isobutanol 332.33
    1,4-dioxane 2570.18
    methyl acetate 788.7
    THF 2615.46
    2-butanone 1011.12
    n-pentanol 476.28
    sec-butanol 463.69
    n-hexane 1193.69
    ethylene glycol 15.23
    NMP 280.51
    cyclohexane 1168.51
    DMSO 276.33
    n-butyl acetate 2642.16
    n-octanol 312.57
    chloroform 1902.55
    n-propyl acetate 855.33
    acetic acid 139.58
    dichloromethane 1764.58
    cyclohexanone 1190.79
    propylene glycol 52.53
    isopropyl acetate 1094.64
    DMAc 430.99
    2-ethoxyethanol 423.94
    isopentanol 598.69
    n-heptane 1033.42
    ethyl formate 313.92
    1,2-dichloroethane 1382.77
    n-hexanol 1184.87
    2-methoxyethanol 446.56
    isobutyl acetate 634.21
    tetrachloromethane 366.48
    n-pentyl acetate 646.6
    transcutol 2920.22
    n-heptanol 340.22
    ethylbenzene 732.09
    MIBK 745.93
    2-propoxyethanol 1044.24
    tert-butanol 634.87
    MTBE 2184.22
    2-butoxyethanol 417.22
    propionic acid 165.1
    o-xylene 614.66
    formic acid 14.15
    diethyl ether 3418.71
    m-xylene 792.74
    p-xylene 694.08
    chlorobenzene 748.45
    dimethyl carbonate 168.37
    n-octane 240.67
    formamide 32.41
    cyclopentanone 809.27
    2-pentanone 1165.83
    anisole 972.09
    cyclopentyl methyl ether 1532.01
    gamma-butyrolactone 549.34
    1-methoxy-2-propanol 456.04
    pyridine 1357.21
    3-pentanone 984.33
    furfural 411.8
    n-dodecane 108.55
    diethylene glycol 246.51
    diisopropyl ether 1188.69
    tert-amyl alcohol 623.58
    acetylacetone 827.44
    n-hexadecane 129.17
    acetophenone 505.96
    methyl propionate 698.54
    isopentyl acetate 2033.84
    trichloroethylene 1622.88
    n-nonanol 327.69
    cyclohexanol 566.99
    benzyl alcohol 302.04
    2-ethylhexanol 1093.25
    isooctanol 302.38
    dipropyl ether 3919.9
    1,2-dichlorobenzene 570.43
    ethyl lactate 148.67
    propylene carbonate 398.73
    n-methylformamide 96.42
    2-pentanol 580.63
    n-pentane 694.91
    1-propoxy-2-propanol 1094.32
    1-methoxy-2-propyl acetate 1459.89
    2-(2-methoxypropoxy) propanol 542.28
    mesitylene 490.67
    ε-caprolactone 911.24
    p-cymene 527.01
    epichlorohydrin 1163.99
    1,1,1-trichloroethane 1301.28
    2-aminoethanol 61.45
    morpholine-4-carbaldehyde 598.35
    sulfolane 445.71
    2,2,4-trimethylpentane 243.46
    2-methyltetrahydrofuran 2332.04
    n-hexyl acetate 893.96
    isooctane 222.28
    2-(2-butoxyethoxy)ethanol 758.86
    sec-butyl acetate 769.09
    tert-butyl acetate 1218.13
    decalin 413.75
    glycerin 50.4
    diglyme 1616.3
    acrylic acid 81.22
    isopropyl myristate 467.81
    n-butyric acid 521.63
    acetyl acetate 677.64
    di(2-ethylhexyl) phthalate 263.27
    ethyl propionate 796.19
    nitromethane 254.29
    1,2-diethoxyethane 3385.04
    benzonitrile 430.77
    trioctyl phosphate 177.9
    1-bromopropane 1759.84
    gamma-valerolactone 833.36
    n-decanol 248.89
    triethyl phosphate 371.73
    4-methyl-2-pentanol 346.83
    propionitrile 536.04
    vinylene carbonate 306.81
    1,1,2-trichlorotrifluoroethane 335.43
    DMS 464.46
    cumene 440.85
    2-octanol 241.81
    2-hexanone 962.81
    octyl acetate 470.93
    limonene 973.53
    1,2-dimethoxyethane 1483.12
    ethyl orthosilicate 455.63
    tributyl phosphate 248.22
    diacetone alcohol 557.27
    N,N-dimethylaniline 552.75
    acrylonitrile 316.06
    aniline 588.62
    1,3-propanediol 162.68
    bromobenzene 1053.85
    dibromomethane 1476.07
    1,1,2,2-tetrachloroethane 1364.78
    2-methyl-cyclohexyl acetate 853.28
    tetrabutyl urea 303.89
    diisobutyl methanol 523.04
    2-phenylethanol 586.95
    styrene 803.2
    dioctyl adipate 522.98
    dimethyl sulfate 149.02
    ethyl butyrate 1801.47
    methyl lactate 112.98
    butyl lactate 238.96
    diethyl carbonate 770.58
    propanediol butyl ether 222.12
    triethyl orthoformate 1034.46
    p-tert-butyltoluene 533.41
    methyl 4-tert-butylbenzoate 441.25
    morpholine 2253.7
    tert-butylamine 635.11
    n-dodecanol 207.3
    dimethoxymethane 707.58
    ethylene carbonate 331.91
    cyrene 246.46
    2-ethoxyethyl acetate 892.54
    2-ethylhexyl acetate 1847.45
    1,2,4-trichlorobenzene 608.64
    4-methylpyridine 1287.23
    dibutyl ether 1750.69
    2,6-dimethyl-4-heptanol 523.04
    DEF 877.8
    dimethyl isosorbide 994.28
    tetrachloroethylene 754.7
    eugenol 318.37
    triacetin 535.56
    span 80 437.56
    1,4-butanediol 55.21
    1,1-dichloroethane 1197.12
    2-methyl-1-pentanol 542.05
    methyl formate 75.85
    2-methyl-1-butanol 531.91
    n-decane 220.91
    butyronitrile 833.18
    3,7-dimethyl-1-octanol 450.82
    1-chlorooctane 566.81
    1-chlorotetradecane 223.55
    n-nonane 254.59
    undecane 144.83
    tert-butylcyclohexane 363.66
    cyclooctane 520.9
    cyclopentanol 303.29
    tetrahydropyran 3369.03
    tert-amyl methyl ether 1506.56
    2,5,8-trioxanonane 1045.13
    1-hexene 2035.03
    2-isopropoxyethanol 389.03
    2,2,2-trifluoroethanol 26.38
    methyl butyrate 839.52

    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
Amyris 1 8015-65-4 Amyris balsamifera L., fam. Rutaceae 3.1%
Shanqiu Anaphalis margaritacea (L.) Benth.et Hook.(Shanqiu),fam.Asteraceae (Comp.) 2.78%
Anise seed 3 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.05%
Anise herb 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.58%
Anise root 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.37%
Ayou Aydendron barbeyana Mez. (Nectandra globosa Mez.), fam. Lauraceae 5.0%
Bergamot (Italy) 3 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Ginger (Malaysia) 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 1.02%
Carrot seed (France) 1 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.14%
Cedrela odorata Cedrela odorata L., fam. Meliaceae 0.5%
Ginger (Australia) 1 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 5.92%
Curcuma angustifolia 8024-37-1 Curcuma angustifolia (Roxb.) Dalz et Gibs, fam. Zingiberaceae 27.84%
Ginger (India) 3 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 18.87%
Ginger (India) 1 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 8.0%
Ginger (Nigeria) 2 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 4.18%
Ginger (Nigeria) 1 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 3.06%
Ginger (Sri Lanka) 1 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 14.5%
Ginger (Sri Lanka) 2 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 27.1%
Ginger (Sri Lanka) 3 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 5.7%
Ginger (Sri Lanka) 4 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 17.7%
Ginger (Vietnam) 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 3.8%
Hortensis leaf Euodia hortensis forma hortensis, fam. Saxifragaceae (Hydrangea) 0.1%
Hortensis flower Euodia hortensis forma hortensis, fam. Saxifragaceae (Hydrangea) 15.0%
Opoponax 8021-36-1 Commiphora erythraea Engler var. glabrescens Engler, fam. Burseraceae 5.0%
Parsley seed (Egypt) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.02%
Pimento (Allspice) 1 8006-77-7 Pimenta dioica (L.) Merr. (P. officinalis Lindl.), fam. Myrtaceae 0.2%
Pimento (Allspice) (Grenada) 8006-77-7 Pimenta dioica (L.) Merr. (P. officinalis Lindl.), fam. Myrtaceae 0.8%
Pimento (Allspice) (Guatamala) 8006-77-7 Pimenta dioica (L.) Merr. (P. officinalis Lindl.), fam. Myrtaceae 0.09%
Pimento (Allspice) (Honduras) 8006-77-7 Pimenta dioica (L.) Merr. (P. officinalis Lindl.), fam. Myrtaceae 0.13%
Pimento (Allspice) (Mexico) 1 8006-77-7 Pimenta dioica (L.) Merr. (P. officinalis Lindl.), fam. Myrtaceae 0.07%
Pimento (Allspice) (Jamaica) 1 8006-77-7 Pimenta dioica (L.) Merr. (P. officinalis Lindl.), fam. Myrtaceae 0.17%
Pteronia incana 2 Pteronia incana, fam. Asteraceae (Compositae) 2.1%
Sage, spanish (Spain) 3 8016-65-7 Salvia lavandulaefolia Vahl., fam. Lamiaceae (Labiatae) 0.4%
Santolina canescens Santolina rosmarinifolia (L.) ssp. canescens (Lag.) Nyman, fam. Asteraceae 7.4%
Santolina pectina Santolina pectina Lag., fam. Asteraceae (Compositae) 2.6%
Santolina rosmarinifolia Santolina rosmarinifolia L.ssp.rosmarinifolia, fam.Asteraceae (Compositae) 5.8%
Santolina semidentata Santolina semidentata Hoffmanns. & Link, fam. Asteraceae (Compositae) 2.2%
Senecio Senecio glaucus ssp. coronopifolius (Maire Alexander), fam. Asteraceae 1.8%
Sideritis granatensis Sideritis granatensis (Pau) Rivas-Goday, fam. Lamiaceae (Labiatae) 0.9%
Turmeric 1 8024-37-1 Curcuma longa L. (C. domestica Val.), fam. Zingiberaceae 2.0%
Verbena 2 8024-12-2 Lippia citriodora Kunth., fam. Verbenaceae 2.4%
Zdravets Geranium macrorrhizum L., fam. Geraniaceae 0.5%
Populus deltoides Populus deltoides Bartr. (P. deltoides Marsh.), fam. Salicaceae 17.0%
Zingiber cassumunar root (Indonesia) 1 Zingiber cassumunar Roxb., fam. Zingiberaceae 2.4%
Basil (Italy) 2 var. hispidum Ocimum basilicum L. cultivar hispidum (Lam.) Chiov., fam. Lamiaceae 0.35%
Zingiber cassumunar root (Indonesia) 2 Zingiber cassumunar Roxb., fam. Zingiberaceae 1.6%
Sandalwood, indian (India) 2 8006-87-9 Santalum album L., fam. Santalaceae 0.26%
Sandalwood, indian (India) 3 8006-87-9 Santalum album L., fam. Santalaceae 0.5%
Sandalwood, indian (China) 1 8006-87-9 Santalum album L., fam. Santalaceae 0.43%
Ginger (Japan) 2 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 0.2%