Caryophyllenol II

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  • Identifiers

    CAS number
    32214-89-4

    Molecular formula
    C15H24O

    SMILES
    C/C/1=C\C[C@@H]2[C@H](CC2(C)C)C(=C)CC[C@H]1O

    Retention indicies (RI)

    • DB5: 1663.0
    • Carbowax: 2300.33

  • Odor profile

    Woody 80.84%
    Sweet 56.68%
    Spicy 47.56%
    Camphoreous 44.03%
    Cedar 42.59%
    Dry 42.57%
    Amber 41.65%
    Herbal 41.18%
    Balsamic 36.4%
    Earthy 35.84%

    Scent© AI

  • Properties

    XLogP3-AA
    3.1

    Molecular weight
    220.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    330°C

    Flash point est.
    130.79 ˚C

  • Synonyms

    • Caryophyllenol II
    • .alpha.-Caryophyllenol
    • 32214-89-4
    • DTXSID40885530
    • V09T2VX540
    • Bicyclo(7.2.0)undec-3-en-5-ol, 4,11,11-trimethyl-8-methylene-, (1R,3E,5R,9S)-
    • Bicyclo[7.2.0]undec-3-en-5-ol, 4,11,11-trimethyl-8-methylene-, (1R,3E,5R,9S)-
    • (1R,3E,5R,9S)-4,11,11-TRIMETHYL-8-METHYLENEBICYCLO(7.2.0)UNDEC-3-EN-5-OL
    • (1R,3E,5R,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-3-en-5-ol
    • UNII-V09T2VX540
    • EINECS 250-959-6
    • (3Z)-4,11,11-trimethyl-8-methylidenebicyclo(7.2.0)undec-3-en-5-ol
    • (3Z)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-3-en-5-ol
    • Caryophyllenol-II
    • (1R,3E,5R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-3-en-5-ol
    • (1R,3E,5R,9S)-4,11,11-trimethyl-8-methylidenebicyclo(7.2.0)undec-3-en-5-ol
    • I+--Caryophyllenol
    • DWUYGFWOANEJRE-ZHBPPSIXSA-N
    • DTXCID001024899
    • Q27291374
    • 250-959-6

  • Applications

    Caryophyllenol II (CAS 32214-89-4) is a caryophyllane-type sesquiterpenol occurring at trace levels in certain spice and medicinal essential oils; in practice, it is used mainly as a research reference standard for GC–MS/LC–MS, a chemotaxonomic and quality-control marker for botanicals/essential oils, and as an intermediate/building block for semi-synthesis of caryophyllane derivatives (e.g., related alcohols, epoxides, and oxides); in fragrance–flavor technology, it is investigated to impart or modulate woody, warm-spicy, and balsamic nuances and to fine-tune terpene backbones in perfume or food-flavor formulations; in pharmacology and chemical biology, Caryophyllenol II serves as a model compound to study metabolism, stability, and oxidative/stereochemical rearrangements of the caryophyllane scaffold, and as a scaffold in in vitro screening for potential activities (such as anti-inflammatory, antimicrobial, antioxidant, or insect-modulating) to guide drug discovery and crop-protection leads; additionally, it supports analytical method development (calibration, spike-in, spectral-library matching), assessment of purity/isomer ratio effects on aroma and bioactivity, and studies on encapsulation or delivery to enhance formulation stability; practical use should comply with local regulations for fragrance, food-additive, and chemical handling, as this compound is not an approved drug and is typically intended for research purposes.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 825.9
    methanol 417.76
    isopropanol 1005.38
    water 0.57
    ethyl acetate 645.82
    n-propanol 848.61
    acetone 615.93
    n-butanol 821.57
    acetonitrile 438.82
    DMF 501.01
    toluene 511.52
    isobutanol 620.08
    1,4-dioxane 1150.75
    methyl acetate 521.76
    THF 1859.1
    2-butanone 717.55
    n-pentanol 365.51
    sec-butanol 658.73
    n-hexane 46.73
    ethylene glycol 68.6
    NMP 214.41
    cyclohexane 97.93
    DMSO 343.6
    n-butyl acetate 529.16
    n-octanol 241.34
    chloroform 1115.34
    n-propyl acetate 349.75
    acetic acid 221.28
    dichloromethane 704.65
    cyclohexanone 558.1
    propylene glycol 198.12
    isopropyl acetate 475.72
    DMAc 378.5
    2-ethoxyethanol 443.68
    isopentanol 689.21
    n-heptane 51.96
    ethyl formate 325.02
    1,2-dichloroethane 445.68
    n-hexanol 606.72
    2-methoxyethanol 850.76
    isobutyl acetate 273.59
    tetrachloromethane 192.55
    n-pentyl acetate 300.78
    transcutol 1743.68
    n-heptanol 267.77
    ethylbenzene 211.65
    MIBK 433.16
    2-propoxyethanol 758.62
    tert-butanol 898.45
    MTBE 891.79
    2-butoxyethanol 444.91
    propionic acid 261.76
    o-xylene 226.17
    formic acid 63.04
    diethyl ether 869.92
    m-xylene 345.55
    p-xylene 247.26
    chlorobenzene 346.55
    dimethyl carbonate 164.22
    n-octane 19.92
    formamide 133.39
    cyclopentanone 680.47
    2-pentanone 613.3
    anisole 389.12
    cyclopentyl methyl ether 605.04
    gamma-butyrolactone 579.97
    1-methoxy-2-propanol 875.22
    pyridine 687.76
    3-pentanone 351.57
    furfural 447.51
    n-dodecane 14.48
    diethylene glycol 392.33
    diisopropyl ether 261.02
    tert-amyl alcohol 584.64
    acetylacetone 448.91
    n-hexadecane 17.12
    acetophenone 272.95
    methyl propionate 417.05
    isopentyl acetate 504.07
    trichloroethylene 760.39
    n-nonanol 209.28
    cyclohexanol 436.46
    benzyl alcohol 276.92
    2-ethylhexanol 302.89
    isooctanol 228.0
    dipropyl ether 422.23
    1,2-dichlorobenzene 270.95
    ethyl lactate 167.12
    propylene carbonate 340.49
    n-methylformamide 280.14
    2-pentanol 569.89
    n-pentane 79.57
    1-propoxy-2-propanol 645.92
    1-methoxy-2-propyl acetate 531.47
    2-(2-methoxypropoxy) propanol 367.42
    mesitylene 200.66
    ε-caprolactone 480.72
    p-cymene 155.34
    epichlorohydrin 810.89
    1,1,1-trichloroethane 462.4
    2-aminoethanol 244.77
    morpholine-4-carbaldehyde 451.06
    sulfolane 369.24
    2,2,4-trimethylpentane 41.88
    2-methyltetrahydrofuran 1045.09
    n-hexyl acetate 405.91
    isooctane 53.62
    2-(2-butoxyethoxy)ethanol 544.18
    sec-butyl acetate 291.31
    tert-butyl acetate 475.64
    decalin 43.39
    glycerin 210.06
    diglyme 872.45
    acrylic acid 157.66
    isopropyl myristate 155.3
    n-butyric acid 538.07
    acetyl acetate 281.41
    di(2-ethylhexyl) phthalate 141.93
    ethyl propionate 299.58
    nitromethane 339.42
    1,2-diethoxyethane 637.11
    benzonitrile 334.75
    trioctyl phosphate 109.49
    1-bromopropane 422.1
    gamma-valerolactone 744.41
    n-decanol 150.74
    triethyl phosphate 123.66
    4-methyl-2-pentanol 367.01
    propionitrile 535.18
    vinylene carbonate 323.96
    1,1,2-trichlorotrifluoroethane 385.79
    DMS 226.51
    cumene 149.81
    2-octanol 184.85
    2-hexanone 347.88
    octyl acetate 187.98
    limonene 189.17
    1,2-dimethoxyethane 770.3
    ethyl orthosilicate 133.03
    tributyl phosphate 126.7
    diacetone alcohol 469.77
    N,N-dimethylaniline 223.54
    acrylonitrile 426.47
    aniline 451.76
    1,3-propanediol 484.79
    bromobenzene 368.28
    dibromomethane 531.95
    1,1,2,2-tetrachloroethane 605.56
    2-methyl-cyclohexyl acetate 246.83
    tetrabutyl urea 141.69
    diisobutyl methanol 218.07
    2-phenylethanol 372.91
    styrene 239.77
    dioctyl adipate 180.53
    dimethyl sulfate 152.67
    ethyl butyrate 342.29
    methyl lactate 206.27
    butyl lactate 242.2
    diethyl carbonate 195.79
    propanediol butyl ether 403.46
    triethyl orthoformate 237.5
    p-tert-butyltoluene 167.76
    methyl 4-tert-butylbenzoate 267.26
    morpholine 1305.07
    tert-butylamine 646.22
    n-dodecanol 110.65
    dimethoxymethane 636.43
    ethylene carbonate 302.27
    cyrene 228.23
    2-ethoxyethyl acetate 400.44
    2-ethylhexyl acetate 351.87
    1,2,4-trichlorobenzene 304.34
    4-methylpyridine 660.91
    dibutyl ether 283.85
    2,6-dimethyl-4-heptanol 218.07
    DEF 392.63
    dimethyl isosorbide 481.44
    tetrachloroethylene 353.41
    eugenol 258.13
    triacetin 303.87
    span 80 304.39
    1,4-butanediol 135.91
    1,1-dichloroethane 603.8
    2-methyl-1-pentanol 317.13
    methyl formate 190.49
    2-methyl-1-butanol 537.44
    n-decane 28.87
    butyronitrile 618.13
    3,7-dimethyl-1-octanol 279.7
    1-chlorooctane 126.61
    1-chlorotetradecane 44.27
    n-nonane 27.14
    undecane 19.48
    tert-butylcyclohexane 48.14
    cyclooctane 38.98
    cyclopentanol 423.73
    tetrahydropyran 1282.81
    tert-amyl methyl ether 453.74
    2,5,8-trioxanonane 529.7
    1-hexene 205.09
    2-isopropoxyethanol 358.9
    2,2,2-trifluoroethanol 82.42
    methyl butyrate 355.32

    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
Lavandula multifida Lavandula multifida L., fam. Lamiaceae (Labiatae) 0.7%
Rosa rugosa (China) 1 Rosa rugosa Thunb. (hybrids), fam. Rosaceae 0.4%
Salvia aramiensis (Turkey) Salvia aramiensis Rech. fil., fam. Lamiaceae (Labiatae) 0.25%
Nepeta betonicifolia (Turkey) Nepeta betonicifolia C.A. Meyer, fam. Lamiaceae (Labiatae) 5.1%
Yarrow (Estonia) 1a flower 84082-83-7 Achillea millefolium L., fam. Asteraceae (Compositae) 0.1%
Yarrow (Estonia) 1b leaf 84082-83-7 Achillea millefolium L., fam. Asteraceae (Compositae) 0.25%
Yarrow (Estonia) 1c stem 84082-83-7 Achillea millefolium L., fam. Asteraceae (Compositae) 0.05%
Laurel leaf (Turkey) 2a hydrodistilled 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.1%
Laurel leaf (Turkey) 2b steamdistilled 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.1%
Laurel leaf (Turkey) 2c CO2-extracted 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.1%
Myrtle leaf (Turkey) 2 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.2%
Ferula elaeochytris fruit Ferula elaeochytris Korovin, fam. Apiaceae (Umbelliferae) 0.2%
Seafennel (Turkey) 2 89997-98-8 Crithmum maritimum L., fam. Apiaceae (Umbelliferae) 0.01%
Cinnamomum tamala leaf (Pakistan) Cinnamomum tamala (Ham.) Nees et Eberm., fam. Lauraceae 0.4%