Tutin

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  • Identifiers

    CAS number
    2571-22-4

    Molecular formula
    C15H18O6

    SMILES
    CC(=C)[C@@H]1[C@@H]2[C@H]([C@]3([C@@]4(CO4)[C@H]5[C@@H]([C@]3([C@H]1C(=O)O2)O)O5)C)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 63.69%
    Spicy 25.75%
    Woody 22.16%
    Sweet 19.96%
    Cooling 19.51%
    Savory 17.68%
    Burnt 16.66%
    Mint 16.26%
    Roasted 15.2%
    Bitter 14.9%

     

    Flavor
    Bitter 90.23%
    Sweet-like 21.27%
    Cedarleaf 21.12%
    Bland 20.44%
    Lovage 18.49%
    Ripe apricot 18.12%
    Parsley 18.1%
    Basil 18.03%
    Nitrile 17.97%
    Red fruit 17.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    6.29 (neutral)

    Molecular weight
    294.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    641°C

    Flash point

    • 172.3 ˚C est.

  • Synonyms

    • Tutin
    • Tutine
    • Tutu
    • Toot poison
    • (+)-Tutin
    • 2571-22-4
    • DTXSID30180400
    • B69P754702
    • (1S,2R,3S,5R,6R,7R,8S,9R,12R)-2,8-dihydroxy-7-methyl-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one
    • (1S,2R,3S,5R,6R,7R,8S,9R,12R)-2,8-dihydroxy-7-methyl-12-prop-1-en-2-ylspiro(4,10-dioxatetracyclo(7.2.1.02,7.03,5)dodecane-6,2'-oxirane)-11-one
    • RefChem:192599
    • DTXCID00102891
    • (1aS-(1a alpha,1b beta,2 beta,5 beta,6 alpha,6a beta,7 beta,7a alpha,8S*))-hexahydro-1b,6-dihydroxy-6a-methyl-8-(1-methylethenyl)spiro(2,5-methano-7H-oxireno(3,4)cyclopent(1,2-d)oxepin-7,2'-oxiran)-3(2 alpha H)-one
    • 2',8'-dihydroxy-7'-methyl-12'-(prop-1-en-2-yl)-4',10'-dioxaspiro(oxirane-2,6'-tetracyclo(7.2.1.02,7.03,5)dodecane)-11'-one
    • Tutinlosung
    • UNII-B69P754702
    • TUTIN [MI]
    • SCHEMBL290472
    • CHEBI:9783
    • CHEMBL297057
    • TUTIN, (+)-
    • GLXC-17307
    • (1aS-(1aalpha,1bbeta,2beta,5beta,6alpha,6abeta,7beta,7aalpha,8S*))-Hexahydro-1b,6-dihydroxy-6a-methyl-8-(1-methylethenyl)spiro(2,5-methano-7H-oxireno(3,4)cyclopent(1,2-d)oxepin-7,2'-oxiran)-3(2alpha H)-one
    • Spiro(2,5-methano-7H-oxireno(3,4)cyclopent(1,2-d)oxepin-7,2'-oxiran)-3(2ah)-one, 1a-beta,1b,5a,6,6a,7a-beta-hexahydro-1b-alpha,6-beta-dihydroxy-8a-isopropenyl-6a-alpha-methyl-
    • NS00075416
    • C09570
    • Q7856945
    • (1aS,1bR,2S,2'R,5R,6S,6aR,7aR,8R)-1b,6-Dihydroxy-6a-methyl-8-(prop-1-en-2-yl)hexahydrospiro[2,5-methanooxireno[3,4]cyclopenta[1,2-d]oxepine-7,2'-oxiran]-3(2H)-one
    • (1S,2R,3S,5R,6R,7R,8S,9R,12R)-2,8-dihydroxy-12-isopropenyl-7-methyl-spiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one
    • SPIRO(2,5-METHANO-7H-OXIRENO(3,4)CYCLOPENT(1,2-D)OXEPIN-7,2'-OXIRAN)-3(2H)-ONE, HEXAHYDRO-1B,6-DIHYDROXY-6A-METHYL-8-(1-METHYLETHENYL)-, (1AS,1BR,2S,2'R,5R,6S,6AR,7AR,8R)-
    • 2571-22-4

  • Applications

    Tutin (CAS 2571-22-4) is primarily of interest in laboratory settings as a natural product toxin and reference material. In analytical toxicology and method development, it may be used as a reference standard for GC/LC methods and for validating toxin-detection workflows. In natural product chemistry and biosynthetic research, it is studied for structure elucidation, isolation methodologies, and synthetic approaches to related natural products. In academic and industrial research, it serves as a learning material in teaching laboratories and as a benchmark compound for extraction, purification, and spectroscopic characterization. Its use is typically restricted to research contexts and is subject to local regulatory controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.02
    methanol 9.1
    isopropanol 2.45
    water 0.18
    ethyl acetate 9.58
    n-propanol 1.94
    acetone 20.51
    n-butanol 2.4
    acetonitrile 9.65
    DMF 48.07
    toluene 2.7
    isobutanol 1.7
    1,4-dioxane 21.39
    methyl acetate 8.78
    THF 41.95
    2-butanone 10.44
    n-pentanol 1.86
    sec-butanol 1.11
    n-hexane 0.06
    ethylene glycol 4.4
    NMP 36.53
    cyclohexane 0.23
    DMSO 66.02
    n-butyl acetate 6.68
    n-octanol 2.61
    chloroform 11.0
    n-propyl acetate 6.44
    acetic acid 11.04
    dichloromethane 8.41
    cyclohexanone 24.0
    propylene glycol 1.62
    isopropyl acetate 9.8
    DMAc 38.7
    2-ethoxyethanol 12.02
    isopentanol 3.32
    n-heptane 0.14
    ethyl formate 9.14
    1,2-dichloroethane 7.26
    n-hexanol 4.01
    2-methoxyethanol 27.05
    isobutyl acetate 5.26
    tetrachloromethane 1.91
    n-pentyl acetate 6.33
    transcutol 16.99
    n-heptanol 3.73
    ethylbenzene 1.53
    MIBK 10.87
    2-propoxyethanol 22.79
    tert-butanol 4.59
    MTBE 2.06
    2-butoxyethanol 13.2
    propionic acid 4.44
    o-xylene 2.3
    formic acid 15.27
    diethyl ether 2.88
    m-xylene 2.47
    p-xylene 2.7
    chlorobenzene 4.23
    dimethyl carbonate 14.36
    n-octane 0.08
    formamide 26.06
    cyclopentanone 34.37
    2-pentanone 12.01
    anisole 5.3
    cyclopentyl methyl ether 7.84
    gamma-butyrolactone 34.16
    1-methoxy-2-propanol 18.7
    pyridine 13.04
    3-pentanone 8.03
    furfural 33.14
    n-dodecane 0.12
    diethylene glycol 30.12
    diisopropyl ether 1.36
    tert-amyl alcohol 2.09
    acetylacetone 30.84
    n-hexadecane 0.15
    acetophenone 9.87
    methyl propionate 9.87
    isopentyl acetate 7.81
    trichloroethylene 16.74
    n-nonanol 3.23
    cyclohexanol 2.98
    benzyl alcohol 5.92
    2-ethylhexanol 2.77
    isooctanol 3.42
    dipropyl ether 2.66
    1,2-dichlorobenzene 5.26
    ethyl lactate 6.97
    propylene carbonate 15.61
    n-methylformamide 20.82
    2-pentanol 1.38
    n-pentane 0.07
    1-propoxy-2-propanol 11.8
    1-methoxy-2-propyl acetate 15.49
    2-(2-methoxypropoxy) propanol 12.45
    mesitylene 1.82
    ε-caprolactone 15.79
    p-cymene 2.16
    epichlorohydrin 28.81
    1,1,1-trichloroethane 5.62
    2-aminoethanol 4.1
    morpholine-4-carbaldehyde 43.04
    sulfolane 46.74
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 9.01
    n-hexyl acetate 7.23
    isooctane 0.09
    2-(2-butoxyethoxy)ethanol 14.01
    sec-butyl acetate 4.69
    tert-butyl acetate 11.03
    decalin 0.22
    glycerin 9.35
    diglyme 30.72
    acrylic acid 7.01
    isopropyl myristate 3.69
    n-butyric acid 8.42
    acetyl acetate 13.72
    di(2-ethylhexyl) phthalate 5.47
    ethyl propionate 6.81
    nitromethane 39.43
    1,2-diethoxyethane 5.92
    benzonitrile 9.02
    trioctyl phosphate 4.33
    1-bromopropane 1.67
    gamma-valerolactone 48.83
    n-decanol 2.29
    triethyl phosphate 5.51
    4-methyl-2-pentanol 2.19
    propionitrile 6.32
    vinylene carbonate 18.0
    1,1,2-trichlorotrifluoroethane 27.41
    DMS 9.2
    cumene 1.42
    2-octanol 1.87
    2-hexanone 7.6
    octyl acetate 4.61
    limonene 2.4
    1,2-dimethoxyethane 26.53
    ethyl orthosilicate 4.71
    tributyl phosphate 4.19
    diacetone alcohol 16.52
    N,N-dimethylaniline 4.41
    acrylonitrile 12.87
    aniline 4.66
    1,3-propanediol 8.36
    bromobenzene 3.66
    dibromomethane 4.34
    1,1,2,2-tetrachloroethane 11.85
    2-methyl-cyclohexyl acetate 7.84
    tetrabutyl urea 7.63
    diisobutyl methanol 2.43
    2-phenylethanol 9.79
    styrene 1.55
    dioctyl adipate 6.09
    dimethyl sulfate 25.1
    ethyl butyrate 6.1
    methyl lactate 12.61
    butyl lactate 6.98
    diethyl carbonate 5.43
    propanediol butyl ether 7.26
    triethyl orthoformate 5.77
    p-tert-butyltoluene 2.05
    methyl 4-tert-butylbenzoate 12.1
    morpholine 16.95
    tert-butylamine 1.48
    n-dodecanol 1.61
    dimethoxymethane 35.88
    ethylene carbonate 16.02
    cyrene 20.1
    2-ethoxyethyl acetate 10.44
    2-ethylhexyl acetate 5.49
    1,2,4-trichlorobenzene 6.71
    4-methylpyridine 10.51
    dibutyl ether 1.86
    2,6-dimethyl-4-heptanol 2.43
    DEF 13.96
    dimethyl isosorbide 24.4
    tetrachloroethylene 9.48
    eugenol 13.34
    triacetin 9.96
    span 80 8.54
    1,4-butanediol 3.35
    1,1-dichloroethane 4.35
    2-methyl-1-pentanol 2.34
    methyl formate 21.13
    2-methyl-1-butanol 1.84
    n-decane 0.19
    butyronitrile 5.75
    3,7-dimethyl-1-octanol 3.02
    1-chlorooctane 1.01
    1-chlorotetradecane 0.56
    n-nonane 0.12
    undecane 0.15
    tert-butylcyclohexane 0.17
    cyclooctane 0.12
    cyclopentanol 4.41
    tetrahydropyran 7.56
    tert-amyl methyl ether 1.8
    2,5,8-trioxanonane 22.57
    1-hexene 0.3
    2-isopropoxyethanol 8.57
    2,2,2-trifluoroethanol 11.52
    methyl butyrate 8.88

    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