Lupeol

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  • Identifiers

    CAS number
    545-47-1

    Molecular formula
    C30H50O

    SMILES
    CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Woody 88.25%
    Sweet 52.57%
    Amber 51.26%
    Dry 49.83%
    Sandalwood 45.73%
    Cedar 43.46%
    Balsamic 37.07%
    Spicy 36.96%
    Musk 35.58%
    Vetiver 34.47%

     

    Flavor
    Woody 73.13%
    Sweet 58.86%
    Pine 45.22%
    Camphor 44.44%
    Dry 42.34%
    Balsam 39.7%
    Wood 39.03%
    Earthy 37.12%
    Fresh 32.89%
    Herbal 31.53%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    9.9

    pKa est.
    7.41 (neutral)

    Molecular weight
    426.7 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    485°C

    Flash point

    • 214.03 ˚C est.

    Solubility expt.

    • Very soluble in ethanol, acetone, chloroform
    • Freely soluble in ether, benzene, petroleum ether, warm alcohol. Practically insoluble in dilute acid and alkalies.

  • Synonyms

    • Lupeol
    • 545-47-1
    • Fagarasterol
    • Clerodol
    • Monogynol B
    • Fagarsterol
    • Lupenol
    • Triterpene lupeol
    • farganasterol
    • beta-Viscol
    • Lup-20(29)-en-3beta-ol
    • Lup-20(29)-en-3-ol, (3-beta)-
    • O268W13H3O
    • NSC-90487
    • (3-beta)-Lup-20(29)-en-3-ol
    • CHEBI:6570
    • Lup-20(29)-en-3-beta-ol
    • DTXSID901025006
    • (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
    • (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta(a)chrysen-9-ol
    • RefChem:41970
    • DTXCID901509232
    • 208-889-9
    • Lup-20(29)-en-3-ol, (3b)-
    • Lup-20(29)-en-3b-ol
    • .beta.-Viscol
    • MFCD00017351
    • NSC90487
    • NSC 90487
    • Lup-20(29)-en-3-ol, (3.beta.)-
    • Lup-20(29)-en-3.beta.-ol
    • (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
    • 20(29)-Lupen-3beta-ol
    • UNII-O268W13H3O
    • HSDB 7687
    • Lupeol (Standard)
    • EINECS 208-889-9
    • (+)-Lupeol
    • Lup-20(29)-en-3-ol, (3beta)-
    • LUPEOL [HSDB]
    • LUPEOL [MI]
    • Lupeol, >=94%
    • Lupeol, analytical standard
    • SCHEMBL148518
    • CHEMBL289191
    • LUPEOL, (+)-
    • orb1304879
    • SCHEMBL3719258
    • HY-N0790R
    • 3beta-lup-20(29)-en-3-ol
    • HY-N0790
    • MSK40145
    • (3beta)-lup-20(29)-en-3-ol
    • BDBM50377927
    • s3614
    • AKOS016008524
    • CCG-268968
    • CS-7563
    • DB12622
    • DS-3391
    • EBC-221024
    • FL16230
    • LMPR0106130001
    • NCGC00168853-06
    • NCGC00168853-07
    • NCI60_042005
    • 3.BETA.-HYDROXYLUP-20(29)-ENE
    • LUP-20(29)-EN-3-.BETA.-OL
    • L0321
    • NS00043298
    • C08628
    • (3-.BETA.)-LUP-20(29)-EN-3-OL
    • 545L471
    • Q409366
    • LUP-20(29)-EN-3-OL, (3-.BETA.)-
    • Clerodol; Fagarasterol; Lupenol; Monogynol B; NSC 90487; |A-Viscol
    • 545-47-1

  • Applications

    Lupeol (CAS 545-47-1) is a natural pentacyclic triterpenoid used as a bioactive ingredient in cosmetics and personal care, commonly pursued for anti-inflammatory and soothing skin effects; it is also investigated as a lead scaffold in pharmaceutical research and used as a starting material for the synthesis of semi-synthetic triterpenoids; lupeol occurs in plant extracts and is present in some nutraceutical or functional-ingredient formulations; it has been studied for antimicrobial activities and has potential pesticidal effects in agriculture; and it serves as an intermediate in the synthesis of related triterpenoids for specialty polymers and coatings.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 7.05
    methanol 2.71
    isopropanol 7.83
    water 0.05
    ethyl acetate 12.96
    n-propanol 10.24
    acetone 11.94
    n-butanol 13.99
    acetonitrile 4.47
    DMF 20.29
    toluene 25.52
    isobutanol 8.65
    1,4-dioxane 28.19
    methyl acetate 6.9
    THF 66.62
    2-butanone 12.51
    n-pentanol 7.89
    sec-butanol 5.1
    n-hexane 0.75
    ethylene glycol 0.68
    NMP 23.38
    cyclohexane 0.96
    DMSO 7.22
    n-butyl acetate 15.2
    n-octanol 8.04
    chloroform 33.35
    n-propyl acetate 9.64
    acetic acid 5.48
    dichloromethane 16.94
    cyclohexanone 24.45
    propylene glycol 1.56
    isopropyl acetate 17.47
    DMAc 23.06
    2-ethoxyethanol 12.63
    isopentanol 13.81
    n-heptane 1.05
    ethyl formate 3.73
    1,2-dichloroethane 10.43
    n-hexanol 10.29
    2-methoxyethanol 15.96
    isobutyl acetate 12.55
    tetrachloromethane 6.82
    n-pentyl acetate 21.88
    transcutol 55.9
    n-heptanol 13.4
    ethylbenzene 9.69
    MIBK 20.03
    2-propoxyethanol 35.26
    tert-butanol 8.98
    MTBE 10.66
    2-butoxyethanol 32.95
    propionic acid 5.06
    o-xylene 11.84
    formic acid 1.36
    diethyl ether 13.18
    m-xylene 19.82
    p-xylene 10.56
    chlorobenzene 18.85
    dimethyl carbonate 8.34
    n-octane 0.37
    formamide 2.39
    cyclopentanone 30.68
    2-pentanone 17.4
    anisole 24.04
    cyclopentyl methyl ether 24.3
    gamma-butyrolactone 24.14
    1-methoxy-2-propanol 25.26
    pyridine 30.18
    3-pentanone 12.5
    furfural 23.32
    n-dodecane 0.16
    diethylene glycol 12.21
    diisopropyl ether 6.52
    tert-amyl alcohol 5.57
    acetylacetone 24.26
    n-hexadecane 0.21
    acetophenone 19.4
    methyl propionate 12.35
    isopentyl acetate 22.89
    trichloroethylene 29.1
    n-nonanol 9.66
    cyclohexanol 8.38
    benzyl alcohol 14.38
    2-ethylhexanol 8.67
    isooctanol 13.05
    dipropyl ether 14.63
    1,2-dichlorobenzene 17.8
    ethyl lactate 6.71
    propylene carbonate 13.8
    n-methylformamide 5.32
    2-pentanol 8.44
    n-pentane 0.97
    1-propoxy-2-propanol 32.14
    1-methoxy-2-propyl acetate 36.25
    2-(2-methoxypropoxy) propanol 25.09
    mesitylene 11.16
    ε-caprolactone 22.14
    p-cymene 9.22
    epichlorohydrin 27.24
    1,1,1-trichloroethane 15.07
    2-aminoethanol 2.91
    morpholine-4-carbaldehyde 34.9
    sulfolane 22.86
    2,2,4-trimethylpentane 0.78
    2-methyltetrahydrofuran 21.18
    n-hexyl acetate 21.51
    isooctane 1.01
    2-(2-butoxyethoxy)ethanol 33.87
    sec-butyl acetate 10.42
    tert-butyl acetate 24.46
    decalin 1.05
    glycerin 3.35
    diglyme 57.7
    acrylic acid 4.33
    isopropyl myristate 8.55
    n-butyric acid 12.82
    acetyl acetate 11.53
    di(2-ethylhexyl) phthalate 13.01
    ethyl propionate 10.85
    nitromethane 9.02
    1,2-diethoxyethane 19.62
    benzonitrile 13.28
    trioctyl phosphate 8.16
    1-bromopropane 7.36
    gamma-valerolactone 50.43
    n-decanol 5.52
    triethyl phosphate 9.78
    4-methyl-2-pentanol 9.27
    propionitrile 7.71
    vinylene carbonate 14.1
    1,1,2-trichlorotrifluoroethane 17.8
    DMS 14.92
    cumene 7.07
    2-octanol 7.36
    2-hexanone 11.1
    octyl acetate 9.85
    limonene 8.71
    1,2-dimethoxyethane 24.52
    ethyl orthosilicate 11.62
    tributyl phosphate 7.27
    diacetone alcohol 21.71
    N,N-dimethylaniline 18.38
    acrylonitrile 7.54
    aniline 18.44
    1,3-propanediol 8.07
    bromobenzene 21.87
    dibromomethane 11.73
    1,1,2,2-tetrachloroethane 22.5
    2-methyl-cyclohexyl acetate 17.38
    tetrabutyl urea 10.68
    diisobutyl methanol 8.59
    2-phenylethanol 21.42
    styrene 10.64
    dioctyl adipate 13.84
    dimethyl sulfate 11.91
    ethyl butyrate 14.28
    methyl lactate 7.79
    butyl lactate 19.13
    diethyl carbonate 8.91
    propanediol butyl ether 19.96
    triethyl orthoformate 16.97
    p-tert-butyltoluene 10.27
    methyl 4-tert-butylbenzoate 34.51
    morpholine 29.53
    tert-butylamine 6.16
    n-dodecanol 3.13
    dimethoxymethane 29.34
    ethylene carbonate 11.42
    cyrene 23.24
    2-ethoxyethyl acetate 31.24
    2-ethylhexyl acetate 17.34
    1,2,4-trichlorobenzene 23.5
    4-methylpyridine 29.08
    dibutyl ether 7.19
    2,6-dimethyl-4-heptanol 8.59
    DEF 15.43
    dimethyl isosorbide 47.93
    tetrachloroethylene 15.73
    eugenol 32.73
    triacetin 23.36
    span 80 21.82
    1,4-butanediol 2.74
    1,1-dichloroethane 11.38
    2-methyl-1-pentanol 8.15
    methyl formate 3.65
    2-methyl-1-butanol 9.79
    n-decane 0.53
    butyronitrile 9.5
    3,7-dimethyl-1-octanol 9.09
    1-chlorooctane 3.6
    1-chlorotetradecane 0.83
    n-nonane 0.44
    undecane 0.27
    tert-butylcyclohexane 1.19
    cyclooctane 0.6
    cyclopentanol 7.86
    tetrahydropyran 22.7
    tert-amyl methyl ether 8.29
    2,5,8-trioxanonane 34.16
    1-hexene 3.04
    2-isopropoxyethanol 12.03
    2,2,2-trifluoroethanol 3.13
    methyl butyrate 11.04

    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