Picrocrocin

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  • Identifiers

    CAS number
    138-55-6

    Molecular formula
    C16H26O7

    SMILES
    CC1=C(C(C[C@@H](C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)(C)C)C=O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 59.08%
    Sweet 27.02%
    Mint 23.54%
    Cooling 22.03%
    Woody 21.25%
    Vanilla 20.8%
    Milky 19.19%
    Spicy 18.89%
    Creamy 17.31%
    Caramellic 16.94%

     

    Flavor
    Bitter 72.77%
    Sweet 24.15%
    Odorless 23.53%
    Sweet-like 23.05%
    Minty 22.35%
    Cedarleaf 21.27%
    Leaves 20.64%
    Fenugreek 20.17%
    Naphthalic 20.0%
    Cauliflower 19.9%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    6.4 (neutral)

    Molecular weight
    330.37 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1231°C

    Flash point

    • 201.88 ˚C est.

  • Synonyms

    • Picrocrocin
    • 138-55-6
    • 1-Cyclohexene-1-carboxaldehyde, 4-(beta-D-glucopyranosyloxy)-2,6,6-trimethyl-, (4R)-
    • ON5B022511
    • (R)-4-(beta-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde
    • CHEBI:53168
    • DTXSID40160450
    • (1R)-4-formyl-3,5,5-trimethylcyclohex-3-en-1-yl beta-D-glucopyranoside
    • (4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde
    • (4R)-2,6,6-trimethyl-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxycyclohexene-1-carbaldehyde
    • RefChem:174190
    • DTXCID0082941
    • Picrocrocine
    • saffron-bitter
    • (R)-2,6,6-trimethyl-4-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohex-1-ene-1-carbaldehyde
    • Saffronbitter
    • Safranbitter
    • UNII-ON5B022511
    • Picrocrocin (Standard)
    • PICROCROCIN [MI]
    • SCHEMBL22180
    • orb1297245
    • HY-N4114R
    • WMHJCSAICLADIN-WYWSWGBSSA-N
    • HY-N4114
    • MSK15440
    • AKOS027326831
    • EBC-615382
    • (4R)-2,6,6-Trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-1-ene-1-carbaldehyde
    • AC-34396
    • AS-79122
    • MP156887
    • CS-0032123
    • NS00094694
    • C17055
    • E80643
    • Q289866
    • (4R)-4-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,6,6-TRIMETHYL-1-CYCLOHEXENE-1-CARBOXALDEHYDE
    • (4R)-4-(b-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde
    • 1-Cyclohexene-1-carboxaldehyde, 4-(|A-D-glucopyranosyloxy)-2,6,6-trimethyl-, (4R)-
    • 1-Cyclohexene-1-carboxaldehyde, 4-(beta-D-glucopyranosyloxy)-2,6,6-trimethyl-, (R)-
    • 1-Cyclohexene-1-carboxaldehyde, 4-(ss-D-glucopyranosyloxy)-2,6,6-trimethyl-, (4R)-
    • (4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-cyclohexene-1-carbaldehyde
    • (4R)-2,6,6-Trimethyl-4-[(2R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde
    • 138-55-6

  • Applications

    Picrocrocin, CAS 138-55-6, is a natural constituent of Crocus sativus (saffron) and a precursor to safranal, responsible for saffron's characteristic bitter taste. In industry, practical applications include: (1) food processing and flavoring, where it contributes saffron flavor and bitterness; (2) fragrance and cosmetics, studied as a precursor to aroma compounds; (3) analytical/quality control, using it as a marker for saffron authenticity and purity; (4) industrial synthesis, serving as a precursor in the production of safranal and related aroma materials; (5) pharmaceutical/natural product research, evaluating saffron-derived formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 14.62
    methanol 77.2
    isopropanol 2.68
    water 6.87
    ethyl acetate 3.43
    n-propanol 6.23
    acetone 3.21
    n-butanol 4.87
    acetonitrile 1.84
    DMF 38.6
    toluene 1.04
    isobutanol 2.5
    1,4-dioxane 7.26
    methyl acetate 2.61
    THF 18.04
    2-butanone 3.06
    n-pentanol 1.97
    sec-butanol 2.15
    n-hexane 0.09
    ethylene glycol 35.77
    NMP 75.1
    cyclohexane 0.25
    DMSO 199.75
    n-butyl acetate 2.21
    n-octanol 2.45
    chloroform 3.05
    n-propyl acetate 1.58
    acetic acid 89.82
    dichloromethane 3.91
    cyclohexanone 11.0
    propylene glycol 20.53
    isopropyl acetate 2.3
    DMAc 51.13
    2-ethoxyethanol 23.64
    isopentanol 3.03
    n-heptane 0.21
    ethyl formate 4.23
    1,2-dichloroethane 3.1
    n-hexanol 3.7
    2-methoxyethanol 83.6
    isobutyl acetate 1.05
    tetrachloromethane 0.58
    n-pentyl acetate 2.58
    transcutol 74.2
    n-heptanol 3.9
    ethylbenzene 0.56
    MIBK 3.49
    2-propoxyethanol 28.31
    tert-butanol 2.76
    MTBE 0.93
    2-butoxyethanol 16.6
    propionic acid 12.77
    o-xylene 1.16
    formic acid 248.01
    diethyl ether 1.58
    m-xylene 1.32
    p-xylene 0.61
    chlorobenzene 1.0
    dimethyl carbonate 7.35
    n-octane 0.12
    formamide 184.52
    cyclopentanone 16.1
    2-pentanone 3.71
    anisole 1.76
    cyclopentyl methyl ether 6.37
    gamma-butyrolactone 32.07
    1-methoxy-2-propanol 34.73
    pyridine 5.05
    3-pentanone 3.05
    furfural 31.02
    n-dodecane 0.07
    diethylene glycol 57.32
    diisopropyl ether 0.52
    tert-amyl alcohol 2.46
    acetylacetone 10.23
    n-hexadecane 0.08
    acetophenone 4.62
    methyl propionate 5.82
    isopentyl acetate 2.64
    trichloroethylene 7.12
    n-nonanol 2.51
    cyclohexanol 4.31
    benzyl alcohol 4.65
    2-ethylhexanol 1.9
    isooctanol 2.8
    dipropyl ether 1.72
    1,2-dichlorobenzene 1.57
    ethyl lactate 6.56
    propylene carbonate 12.42
    n-methylformamide 34.26
    2-pentanol 1.8
    n-pentane 0.13
    1-propoxy-2-propanol 13.53
    1-methoxy-2-propyl acetate 10.57
    2-(2-methoxypropoxy) propanol 16.44
    mesitylene 0.85
    ε-caprolactone 13.9
    p-cymene 1.0
    epichlorohydrin 19.98
    1,1,1-trichloroethane 1.06
    2-aminoethanol 38.11
    morpholine-4-carbaldehyde 58.07
    sulfolane 94.89
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 5.07
    n-hexyl acetate 3.63
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 24.34
    sec-butyl acetate 1.16
    tert-butyl acetate 3.5
    decalin 0.13
    glycerin 79.76
    diglyme 37.25
    acrylic acid 25.46
    isopropyl myristate 1.24
    n-butyric acid 13.03
    acetyl acetate 4.11
    di(2-ethylhexyl) phthalate 3.44
    ethyl propionate 2.04
    nitromethane 55.47
    1,2-diethoxyethane 4.37
    benzonitrile 2.22
    trioctyl phosphate 2.53
    1-bromopropane 0.97
    gamma-valerolactone 45.86
    n-decanol 1.61
    triethyl phosphate 2.93
    4-methyl-2-pentanol 1.52
    propionitrile 1.37
    vinylene carbonate 12.27
    1,1,2-trichlorotrifluoroethane 51.73
    DMS 5.63
    cumene 0.5
    2-octanol 1.62
    2-hexanone 1.66
    octyl acetate 2.02
    limonene 1.52
    1,2-dimethoxyethane 13.75
    ethyl orthosilicate 2.43
    tributyl phosphate 2.33
    diacetone alcohol 14.37
    N,N-dimethylaniline 2.16
    acrylonitrile 3.57
    aniline 3.06
    1,3-propanediol 39.61
    bromobenzene 0.76
    dibromomethane 1.98
    1,1,2,2-tetrachloroethane 5.19
    2-methyl-cyclohexyl acetate 3.37
    tetrabutyl urea 3.92
    diisobutyl methanol 1.29
    2-phenylethanol 5.7
    styrene 0.52
    dioctyl adipate 3.14
    dimethyl sulfate 24.36
    ethyl butyrate 2.37
    methyl lactate 20.2
    butyl lactate 6.86
    diethyl carbonate 1.78
    propanediol butyl ether 18.07
    triethyl orthoformate 2.58
    p-tert-butyltoluene 1.0
    methyl 4-tert-butylbenzoate 10.7
    morpholine 13.33
    tert-butylamine 0.86
    n-dodecanol 1.0
    dimethoxymethane 21.49
    ethylene carbonate 7.92
    cyrene 27.21
    2-ethoxyethyl acetate 6.63
    2-ethylhexyl acetate 1.9
    1,2,4-trichlorobenzene 2.49
    4-methylpyridine 3.34
    dibutyl ether 1.01
    2,6-dimethyl-4-heptanol 1.29
    DEF 10.15
    dimethyl isosorbide 31.09
    tetrachloroethylene 5.31
    eugenol 12.01
    triacetin 9.17
    span 80 13.34
    1,4-butanediol 9.17
    1,1-dichloroethane 0.92
    2-methyl-1-pentanol 1.91
    methyl formate 23.57
    2-methyl-1-butanol 3.02
    n-decane 0.15
    butyronitrile 1.3
    3,7-dimethyl-1-octanol 2.11
    1-chlorooctane 0.66
    1-chlorotetradecane 0.22
    n-nonane 0.13
    undecane 0.1
    tert-butylcyclohexane 0.1
    cyclooctane 0.16
    cyclopentanol 5.14
    tetrahydropyran 3.31
    tert-amyl methyl ether 1.47
    2,5,8-trioxanonane 28.52
    1-hexene 0.26
    2-isopropoxyethanol 9.42
    2,2,2-trifluoroethanol 39.01
    methyl butyrate 2.7

    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