Theaspirane

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  • Identifiers

    CAS number
    36431-72-8

    Molecular formula
    C13H22O

    SMILES
    CC1CCC2(O1)C(=CCCC2(C)C)C

    Retention indicies (RI)

    • Carbowax: 1496.0

  • Odor profile

    Fragrance
    Green 78.7%
    Woody 76.27%
    Fruity 72.94%
    Herbal 71.72%
    Sweet 60.07%
    Mint 57.63%
    Fresh 56.13%
    Camphoreous 55.15%
    Spicy 50.43%
    Cooling 47.49%

     

    Flavor
    Woody 67.11%
    Green 63.2%
    Herbal 58.22%
    Earthy 52.6%
    Spicy 50.79%
    Camphor 39.56%
    Tobacco 35.17%
    Musty 33.1%
    Earth 32.08%
    Wood 31.05%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    9.72 (weak base)

    Molecular weight
    194.31 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point

    • 68.00 to 72.00 °C. @ 3.00 mm Hg

    Flash point

    • 83.23 ˚C est.

    Solubility expt.

    • Insoluble in water, soluble in fats
    • soluble (in ethanol)

  • Synonyms

    • Theaspirane
    • 2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene
    • 36431-72-8
    • 1-Oxaspiro[4.5]dec-6-ene, 2,6,10,10-tetramethyl-
    • 169102-88-9
    • (+/-)-Theaspirane
    • theaspirane Is I
    • cis-Theaspirane
    • Theaspirane A
    • Theaspirane B
    • theaspirane, I
    • theaspirane, II
    • 2,6,6,10-tetramethyl-1-oxaspiro[4.5]dec-9-ene
    • theaspirane Is II
    • FEMA No. 3774
    • DTXSID3047055
    • CHEBI:89598
    • 2,6,10,10-Tetramethyl-1-oxaspiro(4.5)dec-6-ene
    • EINECS 253-031-9
    • 1-Oxaspiro-2,6,10,10-tetramethyl(4.5)dec-6-ene
    • DTXCID1027055
    • FEMA 3774
    • 7371A7GT6E
    • 1-Oxaspiro(4.5)dec-6-ene, 2,6,10,10-tetramethyl-
    • 2,6,6,10-tetramethyl-1-oxaspiro(4.5)dec-9-ene
    • 1-Oxaspiro-(4,5)-2,6,10,10-tetramethyl-6-decene
    • 1-Oxaspiro-[4,5]-2,6,10,10-tetramethyl-6-decene
    • 1-oxaspiro-2,6,10,10-tetramethyl[4.5]dec-6-ene
    • UNII-7371A7GT6E
    • MFCD00085214
    • Theaspirane (Isomer 1)
    • Theaspirane (Isomer 2)
    • THEASPIRANE [FHFI]
    • 6,9-Epoxy-4-megastigmene
    • SCHEMBL140967
    • CHEMBL3185445
    • Tox21_302289
    • AKOS015902001
    • CS-W010641
    • DS-3982
    • NCGC00256059-01
    • CAS-36431-72-8
    • DB-003238
    • NS00013236
    • 2,6,10,10-tetramethyl-oxa-spiro-dec-6-ene
    • (+/-)-Theaspirane, technical, >=90% (GC)
    • D70274
    • 1-Oxaspiro4.5dec-6-ene, 2,6,10,10-tetramethyl-
    • 2,6,10,10-Tetramethyl-1-oxa-spiro[4.5]dec-6-ene
    • Q27161796
    • 2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene, 9CI
    • 2,6,10,10-Tetramethyl-1-oxaspiro[4.5]dec-6-ene, mixture of isomers
    • 253-031-9

  • Applications

    Theaspirane (CAS 36431-72-8) is a colorless bicyclic monoterpenoid occurring naturally in tea leaves, raspberries, ripe mangoes and many aromatic plants, and is prized by the flavor-and-fragrance industry for its sweet, green, peach-like note; beverage formulators add it to ready-to-drink teas, fruit beers and soft drinks to build aromatic complexity, while confectionery and dairy technologists use it to refine the flavor profile of gummies, ice creams and yogurts; the tobacco sector incorporates it into shisha molasses and cigars to impart greater depth and freshness; beyond direct flavoring, theaspirane serves as a biosensory marker for assessing tea quality and as a versatile scaffold for the synthesis of novel terpenoid derivatives in medicinal-chemistry research.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 454.74
    methanol 492.3
    isopropanol 440.48
    water 4.77
    ethyl acetate 780.97
    n-propanol 556.99
    acetone 701.79
    n-butanol 586.93
    acetonitrile 709.24
    DMF 850.58
    toluene 1225.82
    isobutanol 515.51
    1,4-dioxane 1126.87
    methyl acetate 656.09
    THF 1655.18
    2-butanone 763.76
    n-pentanol 417.6
    sec-butanol 497.76
    n-hexane 273.08
    ethylene glycol 117.29
    NMP 984.35
    cyclohexane 471.98
    DMSO 468.59
    n-butyl acetate 796.38
    n-octanol 545.26
    chloroform 2952.39
    n-propyl acetate 532.63
    acetic acid 352.53
    dichloromethane 2487.16
    cyclohexanone 1362.53
    propylene glycol 157.23
    isopropyl acetate 635.88
    DMAc 780.78
    2-ethoxyethanol 477.49
    isopentanol 559.8
    n-heptane 311.08
    ethyl formate 491.31
    1,2-dichloroethane 1231.3
    n-hexanol 728.05
    2-methoxyethanol 660.2
    isobutyl acetate 453.23
    tetrachloromethane 899.38
    n-pentyl acetate 643.78
    transcutol 1018.07
    n-heptanol 476.18
    ethylbenzene 697.51
    MIBK 628.4
    2-propoxyethanol 819.18
    tert-butanol 527.17
    MTBE 735.11
    2-butoxyethanol 562.61
    propionic acid 402.62
    o-xylene 818.02
    formic acid 121.81
    diethyl ether 844.82
    m-xylene 968.56
    p-xylene 815.01
    chlorobenzene 1203.53
    dimethyl carbonate 357.68
    n-octane 144.09
    formamide 174.19
    cyclopentanone 1329.07
    2-pentanone 780.25
    anisole 881.0
    cyclopentyl methyl ether 1146.03
    gamma-butyrolactone 1256.99
    1-methoxy-2-propanol 564.53
    pyridine 1137.19
    3-pentanone 731.4
    furfural 1087.17
    n-dodecane 122.32
    diethylene glycol 431.54
    diisopropyl ether 442.17
    tert-amyl alcohol 497.35
    acetylacetone 805.42
    n-hexadecane 139.73
    acetophenone 755.64
    methyl propionate 646.31
    isopentyl acetate 765.33
    trichloroethylene 2155.59
    n-nonanol 453.96
    cyclohexanol 742.96
    benzyl alcohol 548.11
    2-ethylhexanol 569.82
    isooctanol 411.1
    dipropyl ether 701.01
    1,2-dichlorobenzene 1222.89
    ethyl lactate 282.24
    propylene carbonate 845.2
    n-methylformamide 414.11
    2-pentanol 465.0
    n-pentane 294.72
    1-propoxy-2-propanol 619.51
    1-methoxy-2-propyl acetate 707.65
    2-(2-methoxypropoxy) propanol 490.45
    mesitylene 702.49
    ε-caprolactone 1113.39
    p-cymene 558.97
    epichlorohydrin 1310.85
    1,1,1-trichloroethane 1540.48
    2-aminoethanol 232.96
    morpholine-4-carbaldehyde 1078.88
    sulfolane 1217.04
    2,2,4-trimethylpentane 184.85
    2-methyltetrahydrofuran 1261.94
    n-hexyl acetate 918.38
    isooctane 167.2
    2-(2-butoxyethoxy)ethanol 575.47
    sec-butyl acetate 462.58
    tert-butyl acetate 646.16
    decalin 275.98
    glycerin 213.19
    diglyme 1075.71
    acrylic acid 345.41
    isopropyl myristate 428.91
    n-butyric acid 603.82
    acetyl acetate 578.68
    di(2-ethylhexyl) phthalate 347.45
    ethyl propionate 582.88
    nitromethane 612.34
    1,2-diethoxyethane 598.8
    benzonitrile 956.0
    trioctyl phosphate 276.95
    1-bromopropane 1054.49
    gamma-valerolactone 1446.73
    n-decanol 328.51
    triethyl phosphate 338.07
    4-methyl-2-pentanol 356.71
    propionitrile 740.85
    vinylene carbonate 871.96
    1,1,2-trichlorotrifluoroethane 773.79
    DMS 628.42
    cumene 528.93
    2-octanol 395.17
    2-hexanone 576.4
    octyl acetate 503.34
    limonene 660.97
    1,2-dimethoxyethane 876.05
    ethyl orthosilicate 331.42
    tributyl phosphate 320.92
    diacetone alcohol 528.56
    N,N-dimethylaniline 654.7
    acrylonitrile 750.15
    aniline 749.91
    1,3-propanediol 357.35
    bromobenzene 1546.62
    dibromomethane 1859.88
    1,1,2,2-tetrachloroethane 1733.43
    2-methyl-cyclohexyl acetate 576.99
    tetrabutyl urea 402.07
    diisobutyl methanol 343.8
    2-phenylethanol 693.2
    styrene 759.69
    dioctyl adipate 480.26
    dimethyl sulfate 467.42
    ethyl butyrate 663.4
    methyl lactate 297.32
    butyl lactate 404.14
    diethyl carbonate 449.5
    propanediol butyl ether 425.04
    triethyl orthoformate 467.07
    p-tert-butyltoluene 535.31
    methyl 4-tert-butylbenzoate 702.27
    morpholine 1055.88
    tert-butylamine 491.97
    n-dodecanol 255.34
    dimethoxymethane 788.77
    ethylene carbonate 727.04
    cyrene 449.63
    2-ethoxyethyl acetate 655.44
    2-ethylhexyl acetate 703.33
    1,2,4-trichlorobenzene 1206.78
    4-methylpyridine 1349.59
    dibutyl ether 593.85
    2,6-dimethyl-4-heptanol 343.8
    DEF 767.14
    dimethyl isosorbide 844.08
    tetrachloroethylene 1317.6
    eugenol 574.17
    triacetin 676.81
    span 80 456.31
    1,4-butanediol 188.82
    1,1-dichloroethane 1344.85
    2-methyl-1-pentanol 428.04
    methyl formate 380.48
    2-methyl-1-butanol 562.48
    n-decane 197.13
    butyronitrile 803.11
    3,7-dimethyl-1-octanol 481.0
    1-chlorooctane 533.1
    1-chlorotetradecane 232.2
    n-nonane 203.77
    undecane 149.35
    tert-butylcyclohexane 255.69
    cyclooctane 270.93
    cyclopentanol 708.64
    tetrahydropyran 1260.46
    tert-amyl methyl ether 631.5
    2,5,8-trioxanonane 716.91
    1-hexene 514.9
    2-isopropoxyethanol 395.74
    2,2,2-trifluoroethanol 195.15
    methyl butyrate 661.7

    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
Osmanthus concrete 1 (China) 68917-05-5 Osmanthus fragrans, variety Thunbergii (Mak.), fam. Oleaceae 1.2%
Osmanthus concrete 2 (China) 68917-05-5 Osmanthus fragrans, variety Latifolius Mak., fam. Oleaceae 0.9%
Osmanthus concrete 3 (China) 68917-05-5 Osmanthus fragrans, variety Aurantiacus (Mak.), fam. Oleaceae 0.6%
Vassoura (Brazil) 3 Baccharis dracunculifolia DC., fam. Asteraceae (Compositae) 0.05%