(1S)-2-(Methoxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene

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  • Identifiers

    CAS number
    10300-03-5

    Molecular formula
    C11H18O

    SMILES
    CC1([C@@H]2CC1CC=C2COC)C

    Retention indicies (RI)

    • Carbowax: 1371.0

  • Odor profile

    Woody 84.11%
    Herbal 72.75%
    Sweet 65.12%
    Pine 63.94%
    Camphoreous 60.51%
    Spicy 55.43%
    Fresh 55.43%
    Green 50.52%
    Mint 49.83%
    Cooling 44.67%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    Molecular weight
    166.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    213°C

    Flash point est.
    73.97 ˚C

  • Synonyms

    • 10300-03-5
    • DTXSID40780036
    • (1S)-2-(Methoxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene

  • Applications

    (1S)-2-(Methoxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene is a hydrophobic, chiral pinane-derived building block commonly leveraged as a chiral-pool feedstock in synthesis: the methoxymethyl group acts as a versatile handle/protecting group that can be unveiled or transformed (to alcohols, aldehydes, halides, etc.) to access terpenoid scaffolds, pinane-based ligands, and chiral auxiliaries for asymmetric catalysis; in medicinal and agrochemical discovery, the rigid bicyclic core imparts lipophilicity, steric bulk, and shape selectivity to lead analogs; in fragrance work, the compound or its close transformations (after hydrolysis/oxidation) serves as an intermediate to tune pine–herbal–citrus notes and modulate longevity and diffusion; in materials, it can be converted to monomers/crosslinkers to enhance thermal stability, hardness, and hydrophobicity of resins and coatings; it is also useful as a reference standard and stereochemical probe to study how the (1S) configuration governs activity, odor, and reactivity.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 265.5
    methanol 225.37
    isopropanol 224.28
    water 4.87
    ethyl acetate 215.93
    n-propanol 233.95
    acetone 169.94
    n-butanol 234.09
    acetonitrile 245.0
    DMF 190.03
    toluene 236.94
    isobutanol 170.29
    1,4-dioxane 550.06
    methyl acetate 204.34
    THF 427.1
    2-butanone 178.5
    n-pentanol 112.66
    sec-butanol 156.58
    n-hexane 17.04
    ethylene glycol 96.25
    NMP 125.2
    cyclohexane 68.97
    DMSO 124.85
    n-butyl acetate 183.24
    n-octanol 104.19
    chloroform 825.52
    n-propyl acetate 119.01
    acetic acid 197.42
    dichloromethane 541.62
    cyclohexanone 254.38
    propylene glycol 118.19
    isopropyl acetate 132.92
    DMAc 131.21
    2-ethoxyethanol 183.57
    isopentanol 186.0
    n-heptane 36.39
    ethyl formate 185.64
    1,2-dichloroethane 268.08
    n-hexanol 222.18
    2-methoxyethanol 360.96
    isobutyl acetate 89.64
    tetrachloromethane 189.16
    n-pentyl acetate 104.3
    transcutol 523.37
    n-heptanol 116.99
    ethylbenzene 109.02
    MIBK 114.58
    2-propoxyethanol 318.01
    tert-butanol 227.95
    MTBE 160.01
    2-butoxyethanol 184.68
    propionic acid 155.52
    o-xylene 142.25
    formic acid 103.91
    diethyl ether 177.97
    m-xylene 165.85
    p-xylene 138.41
    chlorobenzene 229.1
    dimethyl carbonate 85.38
    n-octane 15.78
    formamide 141.7
    cyclopentanone 240.43
    2-pentanone 148.89
    anisole 172.3
    cyclopentyl methyl ether 185.27
    gamma-butyrolactone 268.89
    1-methoxy-2-propanol 273.94
    pyridine 377.01
    3-pentanone 115.37
    furfural 312.41
    n-dodecane 14.33
    diethylene glycol 269.49
    diisopropyl ether 67.82
    tert-amyl alcohol 143.08
    acetylacetone 158.43
    n-hexadecane 16.47
    acetophenone 140.99
    methyl propionate 150.03
    isopentyl acetate 166.77
    trichloroethylene 517.94
    n-nonanol 93.32
    cyclohexanol 189.94
    benzyl alcohol 151.83
    2-ethylhexanol 131.33
    isooctanol 93.0
    dipropyl ether 130.65
    1,2-dichlorobenzene 212.63
    ethyl lactate 86.42
    propylene carbonate 203.62
    n-methylformamide 153.6
    2-pentanol 139.07
    n-pentane 33.33
    1-propoxy-2-propanol 238.47
    1-methoxy-2-propyl acetate 209.23
    2-(2-methoxypropoxy) propanol 157.51
    mesitylene 109.05
    ε-caprolactone 234.88
    p-cymene 100.62
    epichlorohydrin 346.89
    1,1,1-trichloroethane 342.29
    2-aminoethanol 172.11
    morpholine-4-carbaldehyde 261.09
    sulfolane 183.5
    2,2,4-trimethylpentane 19.33
    2-methyltetrahydrofuran 277.65
    n-hexyl acetate 145.66
    isooctane 21.0
    2-(2-butoxyethoxy)ethanol 222.79
    sec-butyl acetate 90.2
    tert-butyl acetate 135.58
    decalin 32.22
    glycerin 164.15
    diglyme 370.27
    acrylic acid 143.69
    isopropyl myristate 69.71
    n-butyric acid 249.7
    acetyl acetate 159.56
    di(2-ethylhexyl) phthalate 72.02
    ethyl propionate 113.21
    nitromethane 258.43
    1,2-diethoxyethane 189.3
    benzonitrile 224.02
    trioctyl phosphate 53.98
    1-bromopropane 188.65
    gamma-valerolactone 347.82
    n-decanol 71.5
    triethyl phosphate 75.25
    4-methyl-2-pentanol 101.7
    propionitrile 221.17
    vinylene carbonate 248.58
    1,1,2-trichlorotrifluoroethane 262.96
    DMS 121.85
    cumene 81.8
    2-octanol 70.21
    2-hexanone 102.85
    octyl acetate 81.55
    limonene 112.22
    1,2-dimethoxyethane 253.34
    ethyl orthosilicate 76.64
    tributyl phosphate 59.2
    diacetone alcohol 159.9
    N,N-dimethylaniline 104.06
    acrylonitrile 235.77
    aniline 239.76
    1,3-propanediol 253.14
    bromobenzene 248.67
    dibromomethane 387.52
    1,1,2,2-tetrachloroethane 388.5
    2-methyl-cyclohexyl acetate 121.87
    tetrabutyl urea 65.77
    diisobutyl methanol 90.15
    2-phenylethanol 202.68
    styrene 118.28
    dioctyl adipate 84.97
    dimethyl sulfate 86.11
    ethyl butyrate 140.37
    methyl lactate 114.63
    butyl lactate 97.28
    diethyl carbonate 106.95
    propanediol butyl ether 157.41
    triethyl orthoformate 113.74
    p-tert-butyltoluene 98.46
    methyl 4-tert-butylbenzoate 143.02
    morpholine 506.62
    tert-butylamine 160.83
    n-dodecanol 56.69
    dimethoxymethane 195.88
    ethylene carbonate 211.21
    cyrene 121.56
    2-ethoxyethyl acetate 162.14
    2-ethylhexyl acetate 135.09
    1,2,4-trichlorobenzene 243.77
    4-methylpyridine 303.63
    dibutyl ether 91.42
    2,6-dimethyl-4-heptanol 90.15
    DEF 134.28
    dimethyl isosorbide 227.77
    tetrachloroethylene 289.93
    eugenol 143.58
    triacetin 141.76
    span 80 139.65
    1,4-butanediol 85.8
    1,1-dichloroethane 319.08
    2-methyl-1-pentanol 98.8
    methyl formate 134.61
    2-methyl-1-butanol 154.08
    n-decane 22.5
    butyronitrile 226.61
    3,7-dimethyl-1-octanol 103.9
    1-chlorooctane 72.08
    1-chlorotetradecane 32.93
    n-nonane 20.24
    undecane 17.6
    tert-butylcyclohexane 28.59
    cyclooctane 29.92
    cyclopentanol 176.86
    tetrahydropyran 375.98
    tert-amyl methyl ether 103.75
    2,5,8-trioxanonane 249.66
    1-hexene 52.69
    2-isopropoxyethanol 136.63
    2,2,2-trifluoroethanol 108.49
    methyl butyrate 132.71

    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
Hyssop (France) 1 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 2.7%
Hyssop (USA) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 3.97%
Hyssop (Himalaya) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 2.46%
Hyssop flower 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 2.0%
Hyssop leaf 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 1.2%
Hyssop stem 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 1.1%
Hyssop root 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.5%
Hyssop (Finland) 1 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 1.2%
Hyssop (Finland) 2 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.96%
Hyssop (Finland) 3 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.35%
Hyssop (Finland) 4 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.85%
Hyssop (Bulgaria) 8006-83-5 Hyssopus officinalis L. ssp officinalis, fam. Lamiaceae (Labiatae) 2.0%
Hyssop (Montenegro) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.14%
Hyssop (Spain) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 1.21%
Hyssop (Yugoslavia) 1b form cyaneus 8006-83-5 Hyssopus officinalis L., f. cyaneus Alef., fam. Lamiaceae (Labiatae) 2.7%
Hyssop (Yugoslavia) 1a form albus 8006-83-5 Hyssopus officinalis L., f. albus Alef., fam. Lamiaceae (Labiatae) 2.8%
Hyssop (Yugoslavia) 1c form ruber 8006-83-5 Hyssopus officinalis L., f. ruber Mill., fam. Lamiaceae (Labiatae) 1.3%