Barlerin

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  • Identifiers

    CAS number
    57420-46-9

    Molecular formula
    C19H28O12

    SMILES
    CC(=O)O[C@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Odorless 73.39%
    Sweet 25.12%
    Milky 20.68%
    Cooling 18.93%
    Mint 17.97%
    Vanilla 16.91%
    Creamy 16.31%
    Lactonic 15.43%
    Clean 15.29%
    Caramellic 15.12%

     

    Flavor
    Bitter 79.65%
    Odorless 30.2%
    Sweet-like 26.79%
    Bland 26.6%
    Fatty 26.52%
    Cedarleaf 21.47%
    Very mild 21.41%
    Toffee 20.3%
    Cotton candy 20.1%
    Old wood 20.02%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.0

    pKa est.
    5.02 (weak acid)

    Molecular weight
    448.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1704°C

    Flash point

    • 222.24 ˚C est.

  • Synonyms

    • 57420-46-9
    • Barlerin
    • 8-O-Acetyl shanzhiside methyl ester
    • Ac-Shanz-ME
    • methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
    • DTXSID80206008
    • methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-hydroxy-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta(c)pyran-4-carboxylate
    • RefChem:916719
    • DTXCID40128499
    • 8-O-Acetylshanzhiside methyl ester
    • 5beta-Dihydro Finasteride
    • MFCD15071141
    • Cyclopenta[c]pyran-4-carboxylic acid,7-(acetyloxy)-1-(b-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5-hydroxy-7-methyl-, methyl ester, (1S,4aS,5R,7S,7aS)-
    • 172922-52-0
    • Umbroside
    • 8-O-acetyl shanzhiside methylester
    • methyl (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-1-(beta-D-glucopyranosyloxy)-5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
    • 8-Acetylshanzhiside methyl ester
    • Barlerin (Standard)
    • 5b-Dihydro Finasteride
    • CHEMBL463751
    • orb1301281
    • SCHEMBL3244727
    • 8-O-Acetylshanzhisidemethylester
    • HY-N0758R
    • 8-acetyl-shanzhiside methyl ester
    • 8-O-acetylshanzhiside methylester
    • HY-N0758
    • s9244
    • AKOS030573654
    • CCG-269219
    • CS-6504
    • EBC-615586
    • AC-34946
    • AS-76883
    • methyl (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-5-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate
    • Methyl (1S,4aS,5R,7S,7aS)-7-acetoxy-5-hydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
    • methyl (1S,4aS,5R,7S,7aS)-7-acetoxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
    • F17723
    • 420A469
    • (4aR,4bS,6aS,7S,9aS,9bS,11aS)-N-(1,1-Dimethylethyl)hexadecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxamide; (5ss,17ss)-N-(1,1-dimethylethyl)-3-oxo-4-azaandrostane-17-carboxamide; [4aR-(4aa,4bss,6aa,7a,9ass,9ba,11aa)]-N-(1,1-Dimethylethyl)hexadecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxamide
    • Cyclopenta(c)pyran-4-carboxylic acid, 7-(acetyloxy)-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5-hydroxy-7-methyl-, methyl ester, (1S-(1alpha,4aalpha,5alpha,7alpha,7aalpha))-
    • InChI=1/C19H28O12/c1-7(21)31-19(2)4-9(22)11-8(16(26)27-3)6-28-17(12(11)19)30-18-15(25)14(24)13(23)10(5-20)29-18/h6,9-15,17-18,20,22-25H,4-5H2,1-3H3/t9-,10-,11+,12-,13-,14+,15-,17+,18+,19+/m1/s
    • 57420-46-9

  • Applications

    Barlerin (CAS 57420-46-9) is used as a fragrance ingredient with practical applications across perfumery and consumer products. It may serve as an odorant in fragrances, cosmetics and personal care products, and can function as a fixative to help extend scent in those formulations. It is often evaluated as an intermediate in the synthesis of fragrance compounds in industrial manufacturing. Additionally, it can be considered as a fragrance additive in coatings, inks and polymer formulations, as well as in household cleaning products.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 19.35
    methanol 183.95
    isopropanol 4.0
    water 10.76
    ethyl acetate 6.59
    n-propanol 10.49
    acetone 19.38
    n-butanol 5.29
    acetonitrile 9.86
    DMF 338.5
    toluene 0.79
    isobutanol 3.28
    1,4-dioxane 19.06
    methyl acetate 10.04
    THF 30.13
    2-butanone 10.66
    n-pentanol 2.68
    sec-butanol 2.96
    n-hexane 0.07
    ethylene glycol 66.5
    NMP 306.36
    cyclohexane 0.14
    DMSO 355.56
    n-butyl acetate 1.84
    n-octanol 1.97
    chloroform 3.97
    n-propyl acetate 2.99
    acetic acid 164.75
    dichloromethane 7.36
    cyclohexanone 17.89
    propylene glycol 41.9
    isopropyl acetate 2.51
    DMAc 208.73
    2-ethoxyethanol 52.88
    isopentanol 2.4
    n-heptane 0.11
    ethyl formate 13.87
    1,2-dichloroethane 5.16
    n-hexanol 1.62
    2-methoxyethanol 167.75
    isobutyl acetate 1.17
    tetrachloromethane 0.55
    n-pentyl acetate 2.41
    transcutol 52.47
    n-heptanol 2.14
    ethylbenzene 0.41
    MIBK 2.79
    2-propoxyethanol 33.83
    tert-butanol 1.96
    MTBE 0.79
    2-butoxyethanol 18.08
    propionic acid 26.34
    o-xylene 0.63
    formic acid 635.11
    diethyl ether 2.69
    m-xylene 0.56
    p-xylene 0.44
    chlorobenzene 0.91
    dimethyl carbonate 24.07
    n-octane 0.08
    formamide 447.83
    cyclopentanone 39.01
    2-pentanone 7.22
    anisole 2.23
    cyclopentyl methyl ether 5.43
    gamma-butyrolactone 84.06
    1-methoxy-2-propanol 62.06
    pyridine 13.4
    3-pentanone 5.91
    furfural 74.72
    n-dodecane 0.06
    diethylene glycol 75.7
    diisopropyl ether 0.37
    tert-amyl alcohol 1.87
    acetylacetone 17.67
    n-hexadecane 0.06
    acetophenone 5.02
    methyl propionate 16.48
    isopentyl acetate 1.45
    trichloroethylene 10.58
    n-nonanol 1.91
    cyclohexanol 2.92
    benzyl alcohol 5.02
    2-ethylhexanol 0.85
    isooctanol 1.39
    dipropyl ether 1.75
    1,2-dichlorobenzene 1.16
    ethyl lactate 9.52
    propylene carbonate 20.03
    n-methylformamide 220.58
    2-pentanol 1.6
    n-pentane 0.1
    1-propoxy-2-propanol 13.24
    1-methoxy-2-propyl acetate 8.05
    2-(2-methoxypropoxy) propanol 14.98
    mesitylene 0.32
    ε-caprolactone 20.82
    p-cymene 0.35
    epichlorohydrin 43.27
    1,1,1-trichloroethane 1.1
    2-aminoethanol 65.2
    morpholine-4-carbaldehyde 178.42
    sulfolane 151.44
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 6.81
    n-hexyl acetate 2.94
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 21.45
    sec-butyl acetate 1.29
    tert-butyl acetate 2.11
    decalin 0.06
    glycerin 149.7
    diglyme 41.68
    acrylic acid 54.98
    isopropyl myristate 0.83
    n-butyric acid 16.8
    acetyl acetate 5.89
    di(2-ethylhexyl) phthalate 2.42
    ethyl propionate 3.62
    nitromethane 221.08
    1,2-diethoxyethane 4.64
    benzonitrile 3.19
    trioctyl phosphate 1.85
    1-bromopropane 1.18
    gamma-valerolactone 135.48
    n-decanol 1.22
    triethyl phosphate 2.22
    4-methyl-2-pentanol 0.78
    propionitrile 5.15
    vinylene carbonate 25.93
    1,1,2-trichlorotrifluoroethane 86.48
    DMS 5.55
    cumene 0.26
    2-octanol 1.01
    2-hexanone 2.81
    octyl acetate 1.69
    limonene 0.52
    1,2-dimethoxyethane 35.91
    ethyl orthosilicate 1.73
    tributyl phosphate 1.7
    diacetone alcohol 10.48
    N,N-dimethylaniline 1.93
    acrylonitrile 15.56
    aniline 3.04
    1,3-propanediol 45.83
    bromobenzene 0.59
    dibromomethane 2.65
    1,1,2,2-tetrachloroethane 6.44
    2-methyl-cyclohexyl acetate 2.01
    tetrabutyl urea 3.65
    diisobutyl methanol 0.52
    2-phenylethanol 3.37
    styrene 0.45
    dioctyl adipate 2.46
    dimethyl sulfate 57.66
    ethyl butyrate 2.45
    methyl lactate 43.74
    butyl lactate 5.95
    diethyl carbonate 1.79
    propanediol butyl ether 19.07
    triethyl orthoformate 2.29
    p-tert-butyltoluene 0.29
    methyl 4-tert-butylbenzoate 6.32
    morpholine 32.11
    tert-butylamine 0.5
    n-dodecanol 0.78
    dimethoxymethane 85.54
    ethylene carbonate 15.49
    cyrene 39.03
    2-ethoxyethyl acetate 7.01
    2-ethylhexyl acetate 1.1
    1,2,4-trichlorobenzene 1.74
    4-methylpyridine 7.09
    dibutyl ether 0.98
    2,6-dimethyl-4-heptanol 0.52
    DEF 23.27
    dimethyl isosorbide 24.35
    tetrachloroethylene 5.14
    eugenol 9.8
    triacetin 8.15
    span 80 10.9
    1,4-butanediol 16.02
    1,1-dichloroethane 1.57
    2-methyl-1-pentanol 1.54
    methyl formate 136.13
    2-methyl-1-butanol 2.73
    n-decane 0.12
    butyronitrile 3.4
    3,7-dimethyl-1-octanol 1.12
    1-chlorooctane 0.45
    1-chlorotetradecane 0.16
    n-nonane 0.11
    undecane 0.08
    tert-butylcyclohexane 0.04
    cyclooctane 0.08
    cyclopentanol 5.42
    tetrahydropyran 5.32
    tert-amyl methyl ether 1.29
    2,5,8-trioxanonane 28.82
    1-hexene 0.26
    2-isopropoxyethanol 14.9
    2,2,2-trifluoroethanol 75.13
    methyl butyrate 5.52

    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