Isocaryophyllene

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    118-65-0

    Molecular formula
    C15H24

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

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Retention indicies (RI)

    • DB5: 1406.25
    • Carbowax: 1589.0

  • Odor profile

    Woody 81.1%
    Sweet 60.34%
    Spicy 53.77%
    Dry 45.55%
    Citrus 43.88%
    Terpenic 43.38%
    Herbal 41.75%
    Fresh 41.02%
    Green 39.71%
    Pine 38.36%

    Scent© AI

  • Properties

    XLogP3-AA
    4.4

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point

    • 264 to 266 °F at 14 mmHg (NTP, 1992)

    Flash point est.
    104.24 ˚C

    Flash point expt.

    • 214 °F (NTP, 1992)

    Solubility expt.

    • less than 1 mg/mL at 70 °F (NTP, 1992)
    • Insoluble in water; soluble in oils, ether
    • Soluble (in ethanol)

  • Synonyms

    • Isocaryophyllene
    • 118-65-0
    • (-)-ISOCARYOPHYLLENE
    • Caryophyllene
    • Cis-caryophyllene
    • gamma-caryophyllene
    • NRY8I0KNIR
    • UNII-NRY8I0KNIR
    • Isocaryophyllene (80per cent)
    • 87-44-5
    • (1R,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
    • EINECS 204-267-6
    • CHEBI:5993
    • beta-Caryophyllen
    • DTXSID10881246
    • CARYOPHYLLENE ISOCARYOPHYLLENE
    • Isocaryophyllene (80%)
    • (1R-(1R*,4Z,9S*))-4,11,11-Trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene
    • Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4Z,9S)-
    • g-Caryophyllene
    • E-Caryophyllene
    • EINECS 201-746-1
    • (1R,9S,E)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
    • .gamma.-Caryophyllene
    • (-)-E-Caryophyllene
    • AI3-36121
    • .beta.-cis-Caryophyllene
    • Caryophyllene (VAN)
    • UNII-BHW853AU9H
    • CCRIS 8094
    • 2-Methylene-6,10,10-trimethylbicyclo(7.2.0)undec-5-ene
    • beta-Caryophyllene (natural)
    • -Caryophyllene
    • ss-Caryophyllene
    • Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
    • 4,11,11-Trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene, (1R-(1R*,4E,9S))-
    • Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R-(1R*,4E,9S*))-
    • 4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene #
    • CHEMBL448700
    • DTXCID401474828
    • (-)-Caryophyllene sum of enantiomers
    • LMPR0103120002
    • NCGC00389957-01
    • BS-48823
    • CARYOPHYLLENE ISOCARYOPHYLLENE [MI]
    • CARYOPHYLLENE, ALPHA + BETA MIXT.
    • NS00013291
    • C09691
    • E75762
    • Q27106968
    • (-)-(E)-Caryophyllene;()--caryophyllene;()-trans-Caryophyllene
    • 204-267-6

  • Applications

    Isocaryophyllene (CAS 118-65-0) is a sesquiterpene hydrocarbon occurring in essential oils of black pepper, clove and other botanicals; industrially it is used mainly as a fragrance ingredient delivering woody–warm–slightly spicy notes to fine fragrances, personal care, soaps, detergents, air care and candles; in foods and beverages it can be applied at trace levels as a flavor modifier with spicy/resinous facets where permitted; in applied chemistry it serves as a feedstock for oxidation/epoxidation (e.g., to caryophyllene oxide), hydrogenation and functionalization to produce aroma chemicals, terpene monomers/oligomers, greener resins and synthesis intermediates; in analytics it is used as a reference/marker for profiling essential oils, pepper, hops and cannabis and as a GC‑MS reference standard; in agro/household fields it is being investigated as an insect-repellent/antimicrobial agent; in pharma/cosmetic R&D it is studied for bioactivities (antioxidant, anti-inflammatory, antimicrobial) but this does not replace safety and regulatory assessment; formulation-wise, because it is hydrophobic and oxidation-prone, use suitable solvents/solubilizers, encapsulation or lipid carriers for stability and controlled release, and store sealed away from light, oxygen and heat with optional antioxidants; always comply with IFRA, exposure limits and food regulations in the target market.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 355.65
    methanol 119.85
    isopropanol 469.04
    water 0.08
    ethyl acetate 612.95
    n-propanol 426.86
    acetone 475.64
    n-butanol 564.88
    acetonitrile 253.86
    DMF 289.23
    toluene 782.38
    isobutanol 381.92
    1,4-dioxane 1145.33
    methyl acetate 404.82
    THF 2005.97
    2-butanone 621.0
    n-pentanol 300.62
    sec-butanol 423.61
    n-hexane 224.41
    ethylene glycol 21.09
    NMP 247.11
    cyclohexane 458.82
    DMSO 206.45
    n-butyl acetate 923.45
    n-octanol 343.45
    chloroform 972.19
    n-propyl acetate 349.6
    acetic acid 114.49
    dichloromethane 708.29
    cyclohexanone 775.89
    propylene glycol 69.95
    isopropyl acetate 555.58
    DMAc 291.14
    2-ethoxyethanol 241.4
    isopentanol 509.83
    n-heptane 428.49
    ethyl formate 241.6
    1,2-dichloroethane 480.38
    n-hexanol 847.41
    2-methoxyethanol 385.38
    isobutyl acetate 337.38
    tetrachloromethane 223.04
    n-pentyl acetate 402.69
    transcutol 1218.41
    n-heptanol 334.18
    ethylbenzene 339.78
    MIBK 499.92
    2-propoxyethanol 694.33
    tert-butanol 628.56
    MTBE 940.04
    2-butoxyethanol 383.91
    propionic acid 157.25
    o-xylene 362.78
    formic acid 14.62
    diethyl ether 938.36
    m-xylene 525.93
    p-xylene 383.77
    chlorobenzene 454.92
    dimethyl carbonate 138.8
    n-octane 114.23
    formamide 34.01
    cyclopentanone 782.97
    2-pentanone 642.41
    anisole 449.52
    cyclopentyl methyl ether 933.82
    gamma-butyrolactone 560.54
    1-methoxy-2-propanol 471.19
    pyridine 720.23
    3-pentanone 439.68
    furfural 358.33
    n-dodecane 80.17
    diethylene glycol 237.07
    diisopropyl ether 432.45
    tert-amyl alcohol 452.84
    acetylacetone 489.88
    n-hexadecane 92.07
    acetophenone 326.87
    methyl propionate 384.62
    isopentyl acetate 817.22
    trichloroethylene 706.46
    n-nonanol 314.33
    cyclohexanol 521.43
    benzyl alcohol 253.88
    2-ethylhexanol 558.23
    isooctanol 282.88
    dipropyl ether 1048.29
    1,2-dichlorobenzene 342.1
    ethyl lactate 131.07
    propylene carbonate 384.14
    n-methylformamide 113.83
    2-pentanol 463.48
    n-pentane 261.34
    1-propoxy-2-propanol 718.78
    1-methoxy-2-propyl acetate 717.1
    2-(2-methoxypropoxy) propanol 392.93
    mesitylene 355.55
    ε-caprolactone 583.32
    p-cymene 361.25
    epichlorohydrin 710.68
    1,1,1-trichloroethane 569.28
    2-aminoethanol 80.39
    morpholine-4-carbaldehyde 412.14
    sulfolane 382.65
    2,2,4-trimethylpentane 112.05
    2-methyltetrahydrofuran 1339.35
    n-hexyl acetate 591.09
    isooctane 141.24
    2-(2-butoxyethoxy)ethanol 537.67
    sec-butyl acetate 346.02
    tert-butyl acetate 606.46
    decalin 154.18
    glycerin 77.19
    diglyme 864.05
    acrylic acid 83.82
    isopropyl myristate 298.77
    n-butyric acid 405.55
    acetyl acetate 305.9
    di(2-ethylhexyl) phthalate 207.75
    ethyl propionate 340.08
    nitromethane 177.0
    1,2-diethoxyethane 843.99
    benzonitrile 345.26
    trioctyl phosphate 174.71
    1-bromopropane 658.95
    gamma-valerolactone 707.24
    n-decanol 247.1
    triethyl phosphate 196.44
    4-methyl-2-pentanol 352.91
    propionitrile 382.79
    vinylene carbonate 299.91
    1,1,2-trichlorotrifluoroethane 251.02
    DMS 293.33
    cumene 233.8
    2-octanol 234.32
    2-hexanone 412.15
    octyl acetate 330.22
    limonene 493.18
    1,2-dimethoxyethane 615.09
    ethyl orthosilicate 215.04
    tributyl phosphate 206.42
    diacetone alcohol 428.54
    N,N-dimethylaniline 289.65
    acrylonitrile 259.52
    aniline 451.03
    1,3-propanediol 205.47
    bromobenzene 561.68
    dibromomethane 656.6
    1,1,2,2-tetrachloroethane 586.73
    2-methyl-cyclohexyl acetate 436.97
    tetrabutyl urea 243.45
    diisobutyl methanol 390.72
    2-phenylethanol 430.55
    styrene 363.83
    dioctyl adipate 300.19
    dimethyl sulfate 123.44
    ethyl butyrate 592.58
    methyl lactate 127.86
    butyl lactate 247.58
    diethyl carbonate 312.66
    propanediol butyl ether 299.62
    triethyl orthoformate 415.65
    p-tert-butyltoluene 371.66
    methyl 4-tert-butylbenzoate 337.85
    morpholine 1135.95
    tert-butylamine 547.31
    n-dodecanol 198.32
    dimethoxymethane 504.51
    ethylene carbonate 307.77
    cyrene 235.27
    2-ethoxyethyl acetate 475.65
    2-ethylhexyl acetate 702.6
    1,2,4-trichlorobenzene 377.14
    4-methylpyridine 734.31
    dibutyl ether 616.43
    2,6-dimethyl-4-heptanol 390.72
    DEF 403.31
    dimethyl isosorbide 644.6
    tetrachloroethylene 333.61
    eugenol 265.87
    triacetin 370.22
    span 80 368.29
    1,4-butanediol 64.6
    1,1-dichloroethane 597.16
    2-methyl-1-pentanol 295.59
    methyl formate 93.64
    2-methyl-1-butanol 417.07
    n-decane 138.91
    butyronitrile 536.33
    3,7-dimethyl-1-octanol 393.85
    1-chlorooctane 317.58
    1-chlorotetradecane 141.34
    n-nonane 141.67
    undecane 102.58
    tert-butylcyclohexane 149.78
    cyclooctane 208.09
    cyclopentanol 446.47
    tetrahydropyran 1659.43
    tert-amyl methyl ether 568.17
    2,5,8-trioxanonane 573.08
    1-hexene 477.0
    2-isopropoxyethanol 244.56
    2,2,2-trifluoroethanol 37.13
    methyl butyrate 382.64

    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
Savin 2 8024-00-8 Juniperus sabina L., fam. Cupressaceae 0.02%
Hinoki leaf Chamaecyparis obtusa (Sieb. et Zucc.) Endl., fam. Cupressaceae 1.65%
Hinoki root Chamaecyparis obtusa (Sieb. et Zucc.) Endl., fam. Cupressaceae 0.55%
Hinoki wood Chamaecyparis obtusa (Sieb. et Zucc.) Endl., fam. Cupressaceae 0.12%
Marigold pot 2 70892-20-5 Calendula officinalis L. (Pot Marigold), fam. Asteraceae (Compositae) 0.82%
Thymus capitatus (Portugal) Thymus capitatus (L.) Hoffmanns et Link, fam. Lamiaceae (Labiatae) 0.5%
Jasmine sambac (China) headspace Jasminum sambac (L.) Aiton, fam. Oleaceae 13.67%
Pinus koraiensis (China) Pinus koraiensis Sieb. et Zucc., fam. Pinaceae 2.04%
Neocinnamomum delavayi Neocinnamomum delavayi (L. Lec.) Liou, fam. Lauraceae 6.61%
Acronychia oligophlebia (China) Acronychia oligophlebia Merr., fam. Rutaceae 3.98%
Jasmine rose flower headspace (China) 1 Gardenia jasminoides Ellis, fam. Rubiaceae 0.19%
Chamomile, german (India) 2d root 8002-66-2 Chamomilla recutita (L.) Rausch.(Matricaria chamomilla L.), fam.Asteraceae 0.4%
Sage, dalmatian (Serbia-Montenegro) 1a leaf Salvia officinalis L., fam. Lamiaceae (Labiatae) 0.01%
Sage, dalmatian (Serbia-Montenegro) 1b flower 8016-20-4 Salvia officinalis L., fam. Lamiaceae (Labiatae) 0.01%
Hemidesmus indicus Hemidesmus indicus R.Br., fam. Asclepiadaceae 0.2%
Marihuana (Austria) Cannabis sativa L., fam. Cannabinaceae 0.2%
Cerastium candidissimum (Greece) Cerastium candidissimum Correns, fam. Caryophyllaceae 0.5%
Teucrium salviastrum (Portugal) Teucrium salviastrum Schreber, fam. Lamiaceae (Lagiatae) 0.1%