Cafestol

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  • Identifiers

    CAS number
    469-83-0

    Molecular formula
    C20H28O3

    SMILES
    C[C@@]12CCC3=C([C@H]1CC[C@]45[C@H]2CC[C@H](C4)[C@](C5)(CO)O)C=CO3

    Safety labels

  • Odor profile

    Fragrance
    Woody 45.82%
    Animal 36.86%
    Amber 35.77%
    Musk 33.95%
    Balsamic 33.81%
    Sweet 32.38%
    Floral 30.72%
    Dry 29.62%
    Clean 27.44%
    Sandalwood 27.3%

     

    Flavor
    Bitter 41.49%
    Earthy 39.95%
    Sweet 31.88%
    Fatty 28.83%
    Fruity 26.38%
    Spicy 25.2%
    Musty 24.87%
    Soil 24.41%
    Fruit 24.38%
    Beet 24.24%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.3

    pKa est.
    7.58 (neutral)

    Molecular weight
    316.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    432°C

    Flash point

    • 229.95 ˚C est.

  • Synonyms

    • cafestol
    • 469-83-0
    • cafesterol
    • CCRIS 1518
    • AC465T6Q6W
    • DTXSID3040986
    • CHEBI:3291
    • (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-ol
    • 5a,8-Methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-7-hydroxy-10b-methyl-, (3bS-(3balpha,5abeta,7beta,8beta,10aalpha,10bbeta))-
    • (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo(14.2.1.01,13.04,12.05,9)nonadeca-5(9),6-dien-17-ol
    • RefChem:122657
    • DTXCID1020986
    • MFCD01075769
    • Cafestol (>85%)
    • UNII-AC465T6Q6W
    • (3bS,5aS,7R,8R,10aR,10bS)-7-(hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol
    • SR-05000002204
    • Cafestol?
    • (-)-cafestol
    • Cafestol (Standard)
    • CAFESTOL [MI]
    • SCHEMBL93865
    • orb1301547
    • CHEMBL1407645
    • HY-N6257R
    • AAA46983
    • HY-N6257
    • AKOS032949533
    • CCG-208556
    • EBC-511312
    • 5a,8-Methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol, 3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-7-hydroxy-10b-methyl-, (3bS,5aS,7R,8R,10aR,10bS)-
    • MS-24668
    • CS-0032793
    • C09066
    • E80644
    • Q423829
    • SR-05000002204-2
    • SR-05000002204-3
    • BRD-K46741531-001-02-4
    • (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0(1,13).0(4,12).0(5,9)]nonadeca-5(9),6-dien-17-ol
    • (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6-dien-17-ol
    • (3bS,5aS,7R,10aR,10bS)-7-(Hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol
    • 5A,8-METHANO-5AH-CYCLOHEPTA(5,6)NAPHTHO(2,1-B)FURAN-7-METHANOL, 3B,4,5,6,7,8,9,10,10A,10B,11,12-DODECAHYDRO-7-HYDROXY-10B-METHYL-, (3BS-(3B.ALPHA.,5A.BETA.,7.BETA.,8.BETA.,10A.ALPHA.,10B.BETA.))-
    • 469-83-0

  • Applications

    Cafestol (CAS 469-83-0) is a natural diterpene present in coffee oil, primarily recognized as a component of coffee oil and as a subject of study in natural product chemistry and analytical science. In practice, Cafestol is often used as a reference standard in analyses of coffee oil constituents and coffee flavor components (GC-MS/HPLC), supporting characterization of properties, provenance, and diterpenoid abundance in coffee-derived products. It is also regarded as a scaffold for synthetic and early-stage diterpene chemistry in natural product research. Additionally, Cafestol is of interest in fragrance and cosmetics research to understand the contribution of diterpenoids to coffee aroma, and may be evaluated for experimental applications in cosmetic and personal care formulation.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 61.88
    methanol 114.12
    isopropanol 48.73
    water 0.56
    ethyl acetate 61.01
    n-propanol 57.74
    acetone 123.72
    n-butanol 69.18
    acetonitrile 40.07
    DMF 132.86
    toluene 62.33
    isobutanol 31.08
    1,4-dioxane 173.35
    methyl acetate 35.69
    THF 463.66
    2-butanone 51.53
    n-pentanol 11.66
    sec-butanol 8.2
    n-hexane 0.29
    ethylene glycol 16.03
    NMP 32.51
    cyclohexane 1.8
    DMSO 95.35
    n-butyl acetate 33.48
    n-octanol 7.89
    chloroform 178.03
    n-propyl acetate 24.45
    acetic acid 40.94
    dichloromethane 118.57
    cyclohexanone 101.64
    propylene glycol 9.29
    isopropyl acetate 60.25
    DMAc 59.59
    2-ethoxyethanol 57.59
    isopentanol 47.95
    n-heptane 0.62
    ethyl formate 36.9
    1,2-dichloroethane 66.12
    n-hexanol 22.29
    2-methoxyethanol 217.46
    isobutyl acetate 26.35
    tetrachloromethane 14.8
    n-pentyl acetate 29.74
    transcutol 218.12
    n-heptanol 16.38
    ethylbenzene 10.83
    MIBK 59.45
    2-propoxyethanol 111.62
    tert-butanol 36.23
    MTBE 23.14
    2-butoxyethanol 60.92
    propionic acid 20.36
    o-xylene 20.55
    formic acid 31.67
    diethyl ether 42.41
    m-xylene 33.5
    p-xylene 13.08
    chlorobenzene 58.57
    dimethyl carbonate 50.07
    n-octane 0.38
    formamide 58.8
    cyclopentanone 150.2
    2-pentanone 78.14
    anisole 42.27
    cyclopentyl methyl ether 70.73
    gamma-butyrolactone 123.22
    1-methoxy-2-propanol 148.93
    pyridine 124.36
    3-pentanone 38.32
    furfural 124.52
    n-dodecane 0.39
    diethylene glycol 100.6
    diisopropyl ether 10.21
    tert-amyl alcohol 8.38
    acetylacetone 121.76
    n-hexadecane 0.49
    acetophenone 38.61
    methyl propionate 49.99
    isopentyl acetate 41.74
    trichloroethylene 155.93
    n-nonanol 9.73
    cyclohexanol 25.32
    benzyl alcohol 38.86
    2-ethylhexanol 11.58
    isooctanol 14.28
    dipropyl ether 14.79
    1,2-dichlorobenzene 43.31
    ethyl lactate 22.9
    propylene carbonate 53.44
    n-methylformamide 89.28
    2-pentanol 15.48
    n-pentane 0.75
    1-propoxy-2-propanol 57.62
    1-methoxy-2-propyl acetate 86.21
    2-(2-methoxypropoxy) propanol 45.4
    mesitylene 16.06
    ε-caprolactone 62.74
    p-cymene 9.34
    epichlorohydrin 182.48
    1,1,1-trichloroethane 45.78
    2-aminoethanol 30.84
    morpholine-4-carbaldehyde 102.14
    sulfolane 92.34
    2,2,4-trimethylpentane 0.44
    2-methyltetrahydrofuran 61.55
    n-hexyl acetate 26.72
    isooctane 0.82
    2-(2-butoxyethoxy)ethanol 69.39
    sec-butyl acetate 21.16
    tert-butyl acetate 61.93
    decalin 0.88
    glycerin 37.11
    diglyme 145.64
    acrylic acid 25.86
    isopropyl myristate 12.17
    n-butyric acid 70.38
    acetyl acetate 51.85
    di(2-ethylhexyl) phthalate 18.78
    ethyl propionate 26.21
    nitromethane 103.21
    1,2-diethoxyethane 44.58
    benzonitrile 48.6
    trioctyl phosphate 12.76
    1-bromopropane 20.57
    gamma-valerolactone 222.98
    n-decanol 6.66
    triethyl phosphate 16.31
    4-methyl-2-pentanol 17.46
    propionitrile 49.93
    vinylene carbonate 70.74
    1,1,2-trichlorotrifluoroethane 91.83
    DMS 38.41
    cumene 7.39
    2-octanol 6.8
    2-hexanone 19.29
    octyl acetate 14.38
    limonene 9.16
    1,2-dimethoxyethane 104.74
    ethyl orthosilicate 16.16
    tributyl phosphate 12.67
    diacetone alcohol 61.21
    N,N-dimethylaniline 20.66
    acrylonitrile 74.24
    aniline 73.55
    1,3-propanediol 101.53
    bromobenzene 55.67
    dibromomethane 56.98
    1,1,2,2-tetrachloroethane 99.53
    2-methyl-cyclohexyl acetate 24.94
    tetrabutyl urea 17.23
    diisobutyl methanol 9.72
    2-phenylethanol 48.09
    styrene 14.75
    dioctyl adipate 20.23
    dimethyl sulfate 55.78
    ethyl butyrate 26.63
    methyl lactate 38.97
    butyl lactate 31.58
    diethyl carbonate 20.21
    propanediol butyl ether 35.18
    triethyl orthoformate 25.17
    p-tert-butyltoluene 9.66
    methyl 4-tert-butylbenzoate 45.67
    morpholine 154.05
    tert-butylamine 12.85
    n-dodecanol 4.55
    dimethoxymethane 275.63
    ethylene carbonate 65.37
    cyrene 47.15
    2-ethoxyethyl acetate 61.46
    2-ethylhexyl acetate 26.99
    1,2,4-trichlorobenzene 50.15
    4-methylpyridine 97.07
    dibutyl ether 8.5
    2,6-dimethyl-4-heptanol 9.72
    DEF 40.09
    dimethyl isosorbide 82.83
    tetrachloroethylene 70.44
    eugenol 51.03
    triacetin 43.09
    span 80 31.7
    1,4-butanediol 14.5
    1,1-dichloroethane 53.74
    2-methyl-1-pentanol 10.49
    methyl formate 68.11
    2-methyl-1-butanol 21.41
    n-decane 0.73
    butyronitrile 51.32
    3,7-dimethyl-1-octanol 10.48
    1-chlorooctane 3.88
    1-chlorotetradecane 1.57
    n-nonane 0.54
    undecane 0.52
    tert-butylcyclohexane 0.74
    cyclooctane 0.81
    cyclopentanol 24.99
    tetrahydropyran 99.88
    tert-amyl methyl ether 10.1
    2,5,8-trioxanonane 86.34
    1-hexene 1.72
    2-isopropoxyethanol 34.96
    2,2,2-trifluoroethanol 25.71
    methyl butyrate 29.59

    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