cis-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-1-methanol

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  • Identifiers

    CAS number
    54164-91-9

    Molecular formula
    C10H18O2

    SMILES
    C[C@@]1(CC[C@H](C=C1)C(C)(C)O)O

    Retention indicies (RI)

    • Carbowax: 1737.0

  • Odor profile

    Herbal 60.92%
    Floral 57.69%
    Mint 51.54%
    Woody 45.68%
    Camphoreous 43.68%
    Sweet 41.4%
    Fresh 37.52%
    Pine 37.03%
    Balsamic 34.34%
    Earthy 34.19%

    Scent© AI

  • Properties

    XLogP3-AA
    0.9

    Molecular weight
    170.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    243°C

    Flash point est.
    129.28 ˚C

  • Synonyms

    • EINECS 259-007-4
    • 54164-91-9
    • cis-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-1-methanol
    • cis-p-menth-2-ene-1,8-diol
    • SCHEMBL1039303
    • p-Menth-2-en-1,8-diol, cis
    • DTXSID50969113
    • XWFVRMWMBYDDFY-WCBMZHEXSA-N
    • NS00032981
    • 259-007-4

  • Applications

    cis-4-Hydroxy-alpha,alpha,4-trimethylcyclohex-2-ene-1-methanol (CAS 54164-91-9) is a stereodefined monoterpenoid diol used as a versatile building block in organic synthesis to access terpene esters, ethers, carbonates, and urethanes, and as an intermediate toward fragrance/flavor ingredients and bioactive precursors; in research it serves as an analytical reference/standard for GC-MS/LC-MS and NMR, to probe enantiomer/diastereomer separations, terpenoid redox/oxidation kinetics, structure–odor relationships, and microbial or enzymatic biotransformations; its two hydroxyl groups enable straightforward derivatization (e.g., acrylate/epoxy introduction) to make bio-based oligomers/polymers for UV-curable inks/adhesives, coatings, and performance additives; in medicinal and agrochemical discovery the compact terpene scaffold is leveraged for analogue libraries and as a synthetic intermediate, while in fragrance/cosmetics it may be explored or used at trace levels as a terpene note modulator subject to safety and regulatory constraints; actual deployment depends on isomeric purity, toxicological data, and compliance, typically progressing from lab to pilot scale before wider adoption.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 383.2
    methanol 604.16
    isopropanol 247.97
    water 22.26
    ethyl acetate 147.04
    n-propanol 236.79
    acetone 236.85
    n-butanol 215.22
    acetonitrile 188.45
    DMF 416.35
    toluene 34.99
    isobutanol 144.23
    1,4-dioxane 619.39
    methyl acetate 157.5
    THF 727.12
    2-butanone 138.77
    n-pentanol 121.35
    sec-butanol 147.64
    n-hexane 13.02
    ethylene glycol 134.1
    NMP 310.15
    cyclohexane 22.96
    DMSO 272.66
    n-butyl acetate 103.46
    n-octanol 127.37
    chloroform 148.51
    n-propyl acetate 86.17
    acetic acid 282.95
    dichloromethane 132.62
    cyclohexanone 204.11
    propylene glycol 207.05
    isopropyl acetate 99.6
    DMAc 290.29
    2-ethoxyethanol 228.6
    isopentanol 147.28
    n-heptane 19.47
    ethyl formate 129.1
    1,2-dichloroethane 68.48
    n-hexanol 186.92
    2-methoxyethanol 493.94
    isobutyl acetate 67.51
    tetrachloromethane 30.77
    n-pentyl acetate 84.5
    transcutol 722.57
    n-heptanol 111.01
    ethylbenzene 22.39
    MIBK 86.96
    2-propoxyethanol 366.1
    tert-butanol 249.13
    MTBE 128.69
    2-butoxyethanol 205.94
    propionic acid 183.04
    o-xylene 34.32
    formic acid 209.1
    diethyl ether 147.61
    m-xylene 35.27
    p-xylene 34.08
    chlorobenzene 48.99
    dimethyl carbonate 88.9
    n-octane 8.36
    formamide 256.16
    cyclopentanone 275.98
    2-pentanone 123.95
    anisole 88.63
    cyclopentyl methyl ether 197.7
    gamma-butyrolactone 343.45
    1-methoxy-2-propanol 358.6
    pyridine 130.48
    3-pentanone 85.75
    furfural 262.97
    n-dodecane 8.31
    diethylene glycol 321.7
    diisopropyl ether 49.31
    tert-amyl alcohol 152.85
    acetylacetone 165.71
    n-hexadecane 8.85
    acetophenone 76.76
    methyl propionate 135.27
    isopentyl acetate 95.85
    trichloroethylene 112.41
    n-nonanol 107.02
    cyclohexanol 144.44
    benzyl alcohol 78.38
    2-ethylhexanol 93.35
    isooctanol 77.38
    dipropyl ether 108.57
    1,2-dichlorobenzene 47.16
    ethyl lactate 76.63
    propylene carbonate 194.06
    n-methylformamide 258.38
    2-pentanol 114.79
    n-pentane 15.78
    1-propoxy-2-propanol 230.05
    1-methoxy-2-propyl acetate 163.92
    2-(2-methoxypropoxy) propanol 195.5
    mesitylene 28.87
    ε-caprolactone 198.59
    p-cymene 31.53
    epichlorohydrin 266.06
    1,1,1-trichloroethane 64.32
    2-aminoethanol 255.51
    morpholine-4-carbaldehyde 466.08
    sulfolane 288.42
    2,2,4-trimethylpentane 9.91
    2-methyltetrahydrofuran 298.85
    n-hexyl acetate 144.39
    isooctane 8.58
    2-(2-butoxyethoxy)ethanol 295.46
    sec-butyl acetate 60.54
    tert-butyl acetate 114.79
    decalin 11.11
    glycerin 274.84
    diglyme 433.37
    acrylic acid 160.0
    isopropyl myristate 59.94
    n-butyric acid 203.45
    acetyl acetate 115.08
    di(2-ethylhexyl) phthalate 67.33
    ethyl propionate 82.13
    nitromethane 345.35
    1,2-diethoxyethane 182.72
    benzonitrile 86.33
    trioctyl phosphate 56.27
    1-bromopropane 45.11
    gamma-valerolactone 437.69
    n-decanol 78.59
    triethyl phosphate 57.01
    4-methyl-2-pentanol 76.28
    propionitrile 132.21
    vinylene carbonate 173.37
    1,1,2-trichlorotrifluoroethane 205.36
    DMS 100.38
    cumene 22.48
    2-octanol 71.88
    2-hexanone 83.77
    octyl acetate 83.75
    limonene 45.78
    1,2-dimethoxyethane 350.31
    ethyl orthosilicate 58.07
    tributyl phosphate 60.6
    diacetone alcohol 159.13
    N,N-dimethylaniline 63.8
    acrylonitrile 140.37
    aniline 89.84
    1,3-propanediol 291.84
    bromobenzene 37.68
    dibromomethane 73.77
    1,1,2,2-tetrachloroethane 103.64
    2-methyl-cyclohexyl acetate 85.26
    tetrabutyl urea 75.34
    diisobutyl methanol 56.42
    2-phenylethanol 102.89
    styrene 24.5
    dioctyl adipate 90.79
    dimethyl sulfate 109.3
    ethyl butyrate 83.31
    methyl lactate 129.1
    butyl lactate 94.31
    diethyl carbonate 64.85
    propanediol butyl ether 218.15
    triethyl orthoformate 81.83
    p-tert-butyltoluene 34.05
    methyl 4-tert-butylbenzoate 110.28
    morpholine 567.84
    tert-butylamine 148.22
    n-dodecanol 57.85
    dimethoxymethane 318.23
    ethylene carbonate 152.1
    cyrene 156.23
    2-ethoxyethyl acetate 132.73
    2-ethylhexyl acetate 75.62
    1,2,4-trichlorobenzene 65.98
    4-methylpyridine 121.15
    dibutyl ether 93.28
    2,6-dimethyl-4-heptanol 56.42
    DEF 151.68
    dimethyl isosorbide 293.64
    tetrachloroethylene 73.04
    eugenol 114.86
    triacetin 136.43
    span 80 185.78
    1,4-butanediol 106.82
    1,1-dichloroethane 71.48
    2-methyl-1-pentanol 84.97
    methyl formate 205.58
    2-methyl-1-butanol 120.31
    n-decane 14.18
    butyronitrile 138.58
    3,7-dimethyl-1-octanol 91.59
    1-chlorooctane 44.93
    1-chlorotetradecane 19.37
    n-nonane 13.18
    undecane 10.45
    tert-butylcyclohexane 11.91
    cyclooctane 9.76
    cyclopentanol 191.01
    tetrahydropyran 323.98
    tert-amyl methyl ether 90.68
    2,5,8-trioxanonane 316.1
    1-hexene 34.23
    2-isopropoxyethanol 148.01
    2,2,2-trifluoroethanol 116.08
    methyl butyrate 96.32

    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
Origanum husnuca-baserii (Turkey) Origanum husnucan-baserii H. Duman, Z. Aytac et A. Duran, fam. Lamiaceae 0.01%
Laurel leaf (Turkey) 2a hydrodistilled 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.2%
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%
Artemisia barrelieri Artemisia barrelieri Besser, fam. Asteraceae (Compositae) 0.6%
Thymus fedtschenkoi var. handelii (Turkey) Thymus fedtschenkoi var. handelii, fam. Lamiaceae (Labiatae) 0.2%