(1S,2R,4S)-Neo-dihydrocarveol

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  • Identifiers

    CAS number
    18675-33-7

    Molecular formula
    C10H18O

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

    Retention indicies (RI)

    • DB5: 1226.0

  • Odor profile

    Herbal 84.36%
    Mint 74.26%
    Sweet 67.61%
    Floral 63.47%
    Woody 60.34%
    Fresh 59.86%
    Spicy 58.98%
    Cooling 58.66%
    Camphoreous 58.1%
    Green 57.06%

    Scent© AI

  • Properties

    XLogP3-AA
    3.0

    Molecular weight
    154.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    224°C

    Flash point est.
    86.36 ˚C

  • Synonyms

    • (1S,2R,4S)-Neo-dihydrocarveol
    • (-)-neodihydrocarveol
    • 22567-22-2
    • (1R,2S,5S)-2-methyl-5-prop-1-en-2-ylcyclohexan-1-ol
    • (1S,2R,4S)-neodihydrocarveol
    • (1S,2R,4S)-p-menth-8-en-2-ol
    • (1R,2S,5S)-2-Methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol
    • 18675-33-7
    • CHEBI:158
    • SCHEMBL15012431
    • DTXSID10332061
    • DIHYDROCARVEOL(TRANS-AXIAL)
    • LMPR0102090040
    • (1R,2S,5S)-5-isopropenyl-2-methylcyclohexanol
    • EN300-1196632
    • Q27105266
    • (1R,2S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexanol

  • Applications

    (1S,2R,4S)-Neo-dihydrocarveol (CAS 18675-33-7) is a chiral, bio-based monoterpenoid alcohol used as a chiral-pool building block in advanced synthesis (an intermediate for stereoselective routes to p-menthane frameworks and minty/herbal fragrance–flavor components such as fragrant esters and pro-fragrances), a precursor/entry point toward menthol and related terpenes, a model substrate to probe enantioselective catalysis and biocatalysis (lipase resolutions, controlled oxidations/esterifications, dynamic kinetic resolution), an enantiomeric reference for gas chromatography and GC–MS on cyclodextrin phases and chiroptical studies, and a source of monoterpenoid esters/carbamates/ureas for use as bio-based solvents and functional additives in materials; owing to its origin from natural carvone/carveol, it is favored in green-chemistry workflows and education to illustrate asymmetric synthesis, enantiomer separation, and optical-purity assessment.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1330.85
    methanol 789.65
    isopropanol 1424.65
    water 1.31
    ethyl acetate 539.45
    n-propanol 1149.48
    acetone 435.94
    n-butanol 1017.57
    acetonitrile 616.1
    DMF 284.73
    toluene 281.11
    isobutanol 713.03
    1,4-dioxane 1350.16
    methyl acetate 422.56
    THF 1392.92
    2-butanone 519.88
    n-pentanol 497.63
    sec-butanol 800.93
    n-hexane 47.41
    ethylene glycol 106.73
    NMP 137.82
    cyclohexane 105.62
    DMSO 316.02
    n-butyl acetate 603.75
    n-octanol 282.62
    chloroform 1206.71
    n-propyl acetate 268.28
    acetic acid 412.45
    dichloromethane 800.02
    cyclohexanone 474.38
    propylene glycol 248.17
    isopropyl acetate 310.2
    DMAc 219.52
    2-ethoxyethanol 484.34
    isopentanol 732.13
    n-heptane 80.18
    ethyl formate 363.42
    1,2-dichloroethane 394.9
    n-hexanol 924.75
    2-methoxyethanol 905.51
    isobutyl acetate 180.49
    tetrachloromethane 201.54
    n-pentyl acetate 247.36
    transcutol 1349.23
    n-heptanol 332.87
    ethylbenzene 123.92
    MIBK 250.77
    2-propoxyethanol 893.47
    tert-butanol 1328.64
    MTBE 667.4
    2-butoxyethanol 443.93
    propionic acid 365.72
    o-xylene 142.95
    formic acid 110.42
    diethyl ether 650.54
    m-xylene 178.8
    p-xylene 153.4
    chlorobenzene 256.16
    dimethyl carbonate 67.92
    n-octane 27.77
    formamide 154.62
    cyclopentanone 432.96
    2-pentanone 409.75
    anisole 244.02
    cyclopentyl methyl ether 383.48
    gamma-butyrolactone 437.08
    1-methoxy-2-propanol 758.12
    pyridine 701.82
    3-pentanone 209.68
    furfural 426.4
    n-dodecane 20.37
    diethylene glycol 446.86
    diisopropyl ether 164.04
    tert-amyl alcohol 644.89
    acetylacetone 273.52
    n-hexadecane 23.12
    acetophenone 167.67
    methyl propionate 257.43
    isopentyl acetate 482.38
    trichloroethylene 675.15
    n-nonanol 234.11
    cyclohexanol 484.3
    benzyl alcohol 229.76
    2-ethylhexanol 410.61
    isooctanol 249.1
    dipropyl ether 442.89
    1,2-dichlorobenzene 183.03
    ethyl lactate 105.61
    propylene carbonate 286.67
    n-methylformamide 247.97
    2-pentanol 577.34
    n-pentane 70.45
    1-propoxy-2-propanol 725.37
    1-methoxy-2-propyl acetate 359.28
    2-(2-methoxypropoxy) propanol 289.41
    mesitylene 106.49
    ε-caprolactone 417.51
    p-cymene 126.39
    epichlorohydrin 647.21
    1,1,1-trichloroethane 446.86
    2-aminoethanol 371.41
    morpholine-4-carbaldehyde 393.24
    sulfolane 247.95
    2,2,4-trimethylpentane 34.2
    2-methyltetrahydrofuran 837.01
    n-hexyl acetate 316.24
    isooctane 41.18
    2-(2-butoxyethoxy)ethanol 451.92
    sec-butyl acetate 187.21
    tert-butyl acetate 282.98
    decalin 37.75
    glycerin 243.37
    diglyme 730.54
    acrylic acid 205.45
    isopropyl myristate 120.24
    n-butyric acid 737.23
    acetyl acetate 217.82
    di(2-ethylhexyl) phthalate 110.39
    ethyl propionate 185.78
    nitromethane 417.37
    1,2-diethoxyethane 557.51
    benzonitrile 331.26
    trioctyl phosphate 83.48
    1-bromopropane 407.63
    gamma-valerolactone 643.42
    n-decanol 166.47
    triethyl phosphate 96.9
    4-methyl-2-pentanol 312.78
    propionitrile 578.58
    vinylene carbonate 269.75
    1,1,2-trichlorotrifluoroethane 310.56
    DMS 132.1
    cumene 91.35
    2-octanol 203.74
    2-hexanone 280.22
    octyl acetate 145.25
    limonene 176.72
    1,2-dimethoxyethane 699.8
    ethyl orthosilicate 109.61
    tributyl phosphate 94.22
    diacetone alcohol 325.68
    N,N-dimethylaniline 139.15
    acrylonitrile 456.56
    aniline 370.18
    1,3-propanediol 710.07
    bromobenzene 258.31
    dibromomethane 593.24
    1,1,2,2-tetrachloroethane 508.58
    2-methyl-cyclohexyl acetate 197.09
    tetrabutyl urea 108.96
    diisobutyl methanol 231.17
    2-phenylethanol 328.27
    styrene 146.75
    dioctyl adipate 137.07
    dimethyl sulfate 65.95
    ethyl butyrate 319.67
    methyl lactate 129.06
    butyl lactate 175.95
    diethyl carbonate 170.02
    propanediol butyl ether 345.32
    triethyl orthoformate 213.23
    p-tert-butyltoluene 129.19
    methyl 4-tert-butylbenzoate 187.85
    morpholine 1511.59
    tert-butylamine 819.31
    n-dodecanol 123.71
    dimethoxymethane 352.31
    ethylene carbonate 256.95
    cyrene 154.78
    2-ethoxyethyl acetate 299.3
    2-ethylhexyl acetate 330.32
    1,2,4-trichlorobenzene 203.45
    4-methylpyridine 566.76
    dibutyl ether 271.96
    2,6-dimethyl-4-heptanol 231.17
    DEF 268.85
    dimethyl isosorbide 361.58
    tetrachloroethylene 335.48
    eugenol 184.77
    triacetin 199.24
    span 80 280.22
    1,4-butanediol 177.34
    1,1-dichloroethane 618.33
    2-methyl-1-pentanol 352.48
    methyl formate 147.98
    2-methyl-1-butanol 540.2
    n-decane 37.72
    butyronitrile 754.42
    3,7-dimethyl-1-octanol 272.67
    1-chlorooctane 134.91
    1-chlorotetradecane 47.18
    n-nonane 35.64
    undecane 26.46
    tert-butylcyclohexane 41.92
    cyclooctane 32.98
    cyclopentanol 470.51
    tetrahydropyran 1230.83
    tert-amyl methyl ether 302.18
    2,5,8-trioxanonane 441.16
    1-hexene 205.84
    2-isopropoxyethanol 337.09
    2,2,2-trifluoroethanol 91.95
    methyl butyrate 259.99

    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
Caraway seed 1 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.01%
Indian dill Anethum sowa Roxb., fam. Apiaceae (Umbelliferae) 0.05%
Mentha aquatica x viridis (Italy) Mentha aquatica x viridis F. Schultz, fam. Lamiaceae (Labiatae) 0.79%
Mentha longifolia var. crispa (Italy) 90063-99-3 Mentha longifolia (L.) var. crispa Ten., fam. Lamiaceae (Labiatae) 0.12%
Spearmint (Italy) 8008-79-5 Mentha spicata L., fam. Lamiaceae (Labiatae) 3.93%
Spearmint, scotch (Italy) Mentha gracilis Sole, fam. Lamiaceae (Labiatae) 1.62%
Caraway seed (The Netherlands) 2 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.29%
Cleonia lusitanica (Spain) Cleonia lusitanica (L.) L., (Prunella lusitanica L.), fam. Lamiaceae 0.68%
Sphaeranthus cyathuloides (Kenya) Sphaeranthus cyathuloides O. Hoffm., fam. Asteraceae (Compositae) 1.34%
Origanum husnuca-baserii (Turkey) Origanum husnucan-baserii H. Duman, Z. Aytac et A. Duran, fam. Lamiaceae 0.01%