(1aR,4aR,7aR,7bR)-1a,2,3,4,4a,5,7a,7b-Octahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop(e)azulene

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  • Identifiers

    CAS number
    53526-64-0

    Molecular formula
    C15H22

    SMILES
    CC1=CC[C@@H]2[C@@H]1[C@H]3[C@H](C3(C)C)CCC2=C

  • Odor profile

    Woody 81.95%
    Herbal 49.6%
    Spicy 48.05%
    Fresh 44.42%
    Sweet 44.11%
    Green 37.33%
    Cedar 36.44%
    Dry 35.47%
    Oily 35.38%
    Citrus 34.44%

    Scent© AI

  • Properties

    XLogP3-AA
    3.7

    Molecular weight
    202.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    280°C

    Flash point est.
    73.17 ˚C

  • Synonyms

    • beta-Spathulene
    • 53526-64-0
    • (1aR,4aR,7aR,7bR)-1a,2,3,4,4a,5,7a,7b-Octahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop[e]azulene
    • Spathulene, beta-
    • (1aR,4aR,7aR,7bR)-1a,2,3,4,4a,5,7a,7b-Octahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop(e)azulene
    • TB6UA4EHU7
    • DTXSID601115098
    • 1H-Cycloprop[e]azulene, 1a,2,3,4,4a,5,7a,7b-octahydro-1,1,7-trimethyl-4-methylene-, (1aR,4aR,7aR,7bR)-
    • 1H-Cycloprop[e]azulene, 1a,2,3,4,4a,5,7a,7b-octahydro-1,1,7-trimethyl-4-methylene-, [1aR-(1aalpha,4aalpha,7abeta,7balpha)]-

  • Applications

    A sesquiterpene hydrocarbon with a cycloprop[e]azulene scaffold, this compound occurs in conifer-derived essential oils (e.g., cedarwood, turpentine) and is used mainly in perfumery for woody, resinous, pine-like notes that enhance diffusion and longevity in fine fragrance, soaps, cleaners, and deodorizing products; in flavor it can be dosed at trace levels to impart a forest/woody nuance; in synthesis it serves as a renewable starting material for oxygenated sesquiterpene derivatives (epoxides, alcohols, aldehydes such as longifolenal/longifolenone) used as aroma ingredients and chiral building blocks; analytically it is employed as a GC–MS reference/marker to support identification and authenticity control of essential oils, aromatic woods, and resins; in biological and agrochemical research it is studied as a constituent contributing to antimicrobial or insect-behavior effects of oils, and in materials science it is explored as a bio-based hydrocarbon feedstock for resins/adhesives and hydrophobic coatings, with practical uses subject to regulatory and safety evaluation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 280.6
    methanol 126.75
    isopropanol 420.73
    water 0.24
    ethyl acetate 521.45
    n-propanol 360.14
    acetone 622.89
    n-butanol 400.47
    acetonitrile 248.26
    DMF 507.38
    toluene 658.46
    isobutanol 344.4
    1,4-dioxane 1067.35
    methyl acetate 442.53
    THF 2034.72
    2-butanone 641.21
    n-pentanol 230.0
    sec-butanol 345.82
    n-hexane 102.04
    ethylene glycol 39.7
    NMP 339.36
    cyclohexane 227.96
    DMSO 272.69
    n-butyl acetate 520.66
    n-octanol 257.17
    chloroform 874.38
    n-propyl acetate 318.42
    acetic acid 115.61
    dichloromethane 679.18
    cyclohexanone 778.22
    propylene glycol 90.47
    isopropyl acetate 490.74
    DMAc 416.39
    2-ethoxyethanol 268.93
    isopentanol 380.02
    n-heptane 145.0
    ethyl formate 254.5
    1,2-dichloroethane 500.05
    n-hexanol 461.37
    2-methoxyethanol 410.45
    isobutyl acetate 312.42
    tetrachloromethane 213.78
    n-pentyl acetate 347.81
    transcutol 699.5
    n-heptanol 242.37
    ethylbenzene 302.36
    MIBK 500.48
    2-propoxyethanol 561.42
    tert-butanol 471.14
    MTBE 722.93
    2-butoxyethanol 338.54
    propionic acid 167.59
    o-xylene 345.28
    formic acid 20.14
    diethyl ether 658.87
    m-xylene 461.55
    p-xylene 354.64
    chlorobenzene 444.39
    dimethyl carbonate 208.42
    n-octane 70.77
    formamide 46.51
    cyclopentanone 1004.68
    2-pentanone 605.47
    anisole 460.52
    cyclopentyl methyl ether 774.23
    gamma-butyrolactone 717.84
    1-methoxy-2-propanol 438.96
    pyridine 698.71
    3-pentanone 460.52
    furfural 453.86
    n-dodecane 56.0
    diethylene glycol 276.82
    diisopropyl ether 311.24
    tert-amyl alcohol 344.21
    acetylacetone 612.52
    n-hexadecane 65.97
    acetophenone 347.62
    methyl propionate 395.53
    isopentyl acetate 577.27
    trichloroethylene 741.88
    n-nonanol 242.24
    cyclohexanol 394.67
    benzyl alcohol 286.4
    2-ethylhexanol 297.07
    isooctanol 213.55
    dipropyl ether 477.43
    1,2-dichlorobenzene 370.81
    ethyl lactate 157.89
    propylene carbonate 393.56
    n-methylformamide 176.64
    2-pentanol 328.99
    n-pentane 136.49
    1-propoxy-2-propanol 486.38
    1-methoxy-2-propyl acetate 607.15
    2-(2-methoxypropoxy) propanol 315.42
    mesitylene 308.56
    ε-caprolactone 577.94
    p-cymene 248.02
    epichlorohydrin 840.31
    1,1,1-trichloroethane 567.82
    2-aminoethanol 98.99
    morpholine-4-carbaldehyde 518.56
    sulfolane 535.71
    2,2,4-trimethylpentane 72.6
    2-methyltetrahydrofuran 1074.35
    n-hexyl acetate 486.74
    isooctane 88.03
    2-(2-butoxyethoxy)ethanol 409.9
    sec-butyl acetate 291.34
    tert-butyl acetate 529.13
    decalin 102.9
    glycerin 99.63
    diglyme 698.18
    acrylic acid 117.96
    isopropyl myristate 242.28
    n-butyric acid 315.19
    acetyl acetate 336.57
    di(2-ethylhexyl) phthalate 183.46
    ethyl propionate 323.33
    nitromethane 232.98
    1,2-diethoxyethane 488.46
    benzonitrile 366.61
    trioctyl phosphate 155.77
    1-bromopropane 502.98
    gamma-valerolactone 835.49
    n-decanol 187.75
    triethyl phosphate 184.7
    4-methyl-2-pentanol 264.34
    propionitrile 363.01
    vinylene carbonate 350.51
    1,1,2-trichlorotrifluoroethane 329.53
    DMS 335.76
    cumene 212.68
    2-octanol 197.11
    2-hexanone 386.94
    octyl acetate 268.65
    limonene 311.46
    1,2-dimethoxyethane 614.64
    ethyl orthosilicate 188.55
    tributyl phosphate 173.1
    diacetone alcohol 401.82
    N,N-dimethylaniline 274.02
    acrylonitrile 309.63
    aniline 400.0
    1,3-propanediol 202.68
    bromobenzene 532.02
    dibromomethane 555.3
    1,1,2,2-tetrachloroethane 607.05
    2-methyl-cyclohexyl acetate 326.62
    tetrabutyl urea 206.76
    diisobutyl methanol 240.91
    2-phenylethanol 397.11
    styrene 327.89
    dioctyl adipate 252.14
    dimethyl sulfate 212.55
    ethyl butyrate 385.68
    methyl lactate 170.94
    butyl lactate 234.41
    diethyl carbonate 240.6
    propanediol butyl ether 273.32
    triethyl orthoformate 294.08
    p-tert-butyltoluene 264.47
    methyl 4-tert-butylbenzoate 327.34
    morpholine 943.62
    tert-butylamine 349.9
    n-dodecanol 149.45
    dimethoxymethane 601.76
    ethylene carbonate 341.8
    cyrene 256.05
    2-ethoxyethyl acetate 422.65
    2-ethylhexyl acetate 450.88
    1,2,4-trichlorobenzene 396.93
    4-methylpyridine 717.24
    dibutyl ether 357.67
    2,6-dimethyl-4-heptanol 240.91
    DEF 434.86
    dimethyl isosorbide 520.27
    tetrachloroethylene 384.08
    eugenol 261.41
    triacetin 358.31
    span 80 278.59
    1,4-butanediol 95.06
    1,1-dichloroethane 606.97
    2-methyl-1-pentanol 223.89
    methyl formate 159.59
    2-methyl-1-butanol 316.66
    n-decane 92.24
    butyronitrile 430.66
    3,7-dimethyl-1-octanol 273.75
    1-chlorooctane 228.64
    1-chlorotetradecane 108.39
    n-nonane 90.97
    undecane 70.99
    tert-butylcyclohexane 99.07
    cyclooctane 112.2
    cyclopentanol 425.74
    tetrahydropyran 1179.78
    tert-amyl methyl ether 423.73
    2,5,8-trioxanonane 462.39
    1-hexene 239.24
    2-isopropoxyethanol 255.5
    2,2,2-trifluoroethanol 60.87
    methyl butyrate 369.86

    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
Cedrus atlantica (Morocco) Cedrus atlantica Man., fam. Cupressaceae 0.02%
Eucalyptus globulus (Spain) 2a old leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.1%
Eucalyptus globulus (Yugoslavia) 1a leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.45%