Terrein

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  • Identifiers

    CAS number
    582-46-7

    Molecular formula
    C8H10O3

    SMILES
    C/C=C/C1=CC(=O)[C@@H]([C@H]1O)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 51.36%
    Caramellic 48.07%
    Spicy 45.86%
    Burnt 33.65%
    Odorless 23.8%
    Roasted 22.71%
    Nutty 21.61%
    Vanilla 21.54%
    Warm 20.32%
    Phenolic 19.44%

     

    Flavor
    Bitter 53.53%
    Spice 21.05%
    Spicy 20.17%
    Basil 20.09%
    Leaves 19.83%
    Lovage 19.42%
    Fenugreek 19.23%
    Maple syrup 19.13%
    Nitrile 19.1%
    Cotton candy 18.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.6

    pKa est.
    6.9 (neutral)

    Molecular weight
    154.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    312°C

    Flash point

    • 145.57 ˚C est.

  • Synonyms

    • Terrein
    • 582-46-7
    • (+)-TERREIN
    • 3I47HPE16N
    • (4S,5R)-4,5-dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
    • NSC-291308
    • DTXSID101017469
    • 2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1-propenyl)-, (4S-(3(E),4alpha,5beta))-
    • (4S,5R)-4,5-dihydroxy-3-((E)-prop-1-enyl)cyclopent-2-en-1-one
    • RefChem:932745
    • DTXCID401475664
    • (+)Terrein
    • MFCD09752761
    • (4S,5R)-4,5-Dihydroxy-3-((E)-prop-1-en-1-yl)cyclopent-2-enone
    • UNII-3I47HPE16N
    • Terrein (NIST)
    • NSC 291308
    • 2-Cyclopenten-1-one, 4,5-dihydroxy-3-propenyl-
    • CHEMBL506722
    • MEGxm0_000160
    • orb1695088
    • SCHEMBL1884980
    • ACon1_001984
    • MHOOPNKRBMHHEC-HZIBQTDNSA-
    • 2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1-propenyl)-, (4S-(3(E),4.alpha.,5.beta.))-
    • CHEBI:177543
    • GLXC-15930
    • SBB086996
    • AKOS006327725
    • (4S,5R)-4,5-DIHYDROXY-3-[(1E)-PROP-1-EN-1-YL]CYCLOPENT-2-EN-1-ONE
    • NCGC00179945-01
    • DA-58416
    • HY-119808
    • CS-0078056
    • AB-131/42300811
    • 4,5-dihydroxy-3-(1-propenyl)-2-cyclopenten-1-one
    • BRD-K68034638-001-01-1
    • Q27257243
    • 3-((1E)prop-1-enyl)(4S,5R)-4,5-dihydroxycyclopent-2-en-1-one
    • (4S,5R)-4,5-Dihydroxy-3-((E)-prop-1-en-1-yl)cyclopent-2-en-1-one
    • (4S,5R)-4,5-dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one
    • 2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1E)-1-propenyl-, (4S,5R)-
    • 2-CYCLOPENTEN-1-ONE, 4,5-DIHYDROXY-3-(1E)-1-PROPEN-1-YL-, (4S,5R)-
    • InChI=1/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1
    • 582-46-7

  • Applications

    Terrein (CAS 582-46-7) is a natural fungal metabolite of interest primarily in pharmaceutical and organic synthesis contexts; it is regarded as an intermediate or lead scaffold for the preparation of derivative compounds and other terpene-related structures; it has been reported to exhibit antimicrobial activity in scientific studies, making it a subject of ongoing bioactivity research; in addition, terrein is used as a reference scaffold in natural product chemistry and related laboratory investigations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 78.28
    methanol 149.03
    isopropanol 46.91
    water 28.8
    ethyl acetate 22.65
    n-propanol 45.18
    acetone 50.26
    n-butanol 33.01
    acetonitrile 29.91
    DMF 253.79
    toluene 5.55
    isobutanol 30.7
    1,4-dioxane 71.08
    methyl acetate 33.36
    THF 95.05
    2-butanone 31.33
    n-pentanol 29.54
    sec-butanol 34.34
    n-hexane 0.93
    ethylene glycol 132.78
    NMP 189.4
    cyclohexane 2.16
    DMSO 419.1
    n-butyl acetate 17.12
    n-octanol 27.56
    chloroform 29.07
    n-propyl acetate 18.46
    acetic acid 72.64
    dichloromethane 50.67
    cyclohexanone 51.65
    propylene glycol 77.45
    isopropyl acetate 16.65
    DMAc 177.6
    2-ethoxyethanol 92.89
    isopentanol 30.61
    n-heptane 2.85
    ethyl formate 32.04
    1,2-dichloroethane 32.04
    n-hexanol 32.26
    2-methoxyethanol 154.55
    isobutyl acetate 12.88
    tetrachloromethane 6.44
    n-pentyl acetate 17.38
    transcutol 118.28
    n-heptanol 28.46
    ethylbenzene 7.8
    MIBK 23.93
    2-propoxyethanol 76.03
    tert-butanol 61.61
    MTBE 22.93
    2-butoxyethanol 53.63
    propionic acid 44.82
    o-xylene 11.26
    formic acid 102.51
    diethyl ether 13.55
    m-xylene 10.65
    p-xylene 10.29
    chlorobenzene 13.61
    dimethyl carbonate 29.99
    n-octane 1.91
    formamide 141.26
    cyclopentanone 77.17
    2-pentanone 24.02
    anisole 28.54
    cyclopentyl methyl ether 29.87
    gamma-butyrolactone 99.59
    1-methoxy-2-propanol 92.93
    pyridine 30.36
    3-pentanone 17.27
    furfural 93.55
    n-dodecane 2.33
    diethylene glycol 118.16
    diisopropyl ether 7.11
    tert-amyl alcohol 45.95
    acetylacetone 44.04
    n-hexadecane 2.47
    acetophenone 36.92
    methyl propionate 30.64
    isopentyl acetate 19.2
    trichloroethylene 52.6
    n-nonanol 25.29
    cyclohexanol 29.01
    benzyl alcohol 36.29
    2-ethylhexanol 21.32
    isooctanol 24.27
    dipropyl ether 15.34
    1,2-dichlorobenzene 18.96
    ethyl lactate 29.7
    propylene carbonate 56.52
    n-methylformamide 102.41
    2-pentanol 21.02
    n-pentane 1.26
    1-propoxy-2-propanol 50.67
    1-methoxy-2-propyl acetate 35.05
    2-(2-methoxypropoxy) propanol 55.81
    mesitylene 9.7
    ε-caprolactone 48.98
    p-cymene 12.09
    epichlorohydrin 85.5
    1,1,1-trichloroethane 18.06
    2-aminoethanol 112.93
    morpholine-4-carbaldehyde 137.86
    sulfolane 192.42
    2,2,4-trimethylpentane 2.12
    2-methyltetrahydrofuran 43.21
    n-hexyl acetate 26.89
    isooctane 1.93
    2-(2-butoxyethoxy)ethanol 65.84
    sec-butyl acetate 13.25
    tert-butyl acetate 25.79
    decalin 2.8
    glycerin 142.71
    diglyme 106.21
    acrylic acid 53.7
    isopropyl myristate 15.63
    n-butyric acid 39.64
    acetyl acetate 21.07
    di(2-ethylhexyl) phthalate 23.73
    ethyl propionate 18.23
    nitromethane 109.85
    1,2-diethoxyethane 26.22
    benzonitrile 27.66
    trioctyl phosphate 20.28
    1-bromopropane 10.48
    gamma-valerolactone 100.03
    n-decanol 21.17
    triethyl phosphate 18.12
    4-methyl-2-pentanol 17.91
    propionitrile 21.28
    vinylene carbonate 51.2
    1,1,2-trichlorotrifluoroethane 91.99
    DMS 26.97
    cumene 9.33
    2-octanol 17.6
    2-hexanone 19.52
    octyl acetate 21.05
    limonene 15.59
    1,2-dimethoxyethane 88.66
    ethyl orthosilicate 16.58
    tributyl phosphate 17.18
    diacetone alcohol 54.7
    N,N-dimethylaniline 30.53
    acrylonitrile 37.58
    aniline 19.96
    1,3-propanediol 93.14
    bromobenzene 11.14
    dibromomethane 24.14
    1,1,2,2-tetrachloroethane 41.37
    2-methyl-cyclohexyl acetate 25.02
    tetrabutyl urea 28.13
    diisobutyl methanol 17.15
    2-phenylethanol 35.74
    styrene 7.86
    dioctyl adipate 26.92
    dimethyl sulfate 68.55
    ethyl butyrate 18.61
    methyl lactate 49.9
    butyl lactate 24.8
    diethyl carbonate 16.08
    propanediol butyl ether 54.29
    triethyl orthoformate 17.81
    p-tert-butyltoluene 11.96
    methyl 4-tert-butylbenzoate 48.26
    morpholine 74.32
    tert-butylamine 27.64
    n-dodecanol 16.98
    dimethoxymethane 83.72
    ethylene carbonate 38.78
    cyrene 75.23
    2-ethoxyethyl acetate 25.89
    2-ethylhexyl acetate 14.02
    1,2,4-trichlorobenzene 26.6
    4-methylpyridine 26.25
    dibutyl ether 12.97
    2,6-dimethyl-4-heptanol 17.15
    DEF 51.21
    dimethyl isosorbide 81.35
    tetrachloroethylene 27.8
    eugenol 50.94
    triacetin 37.45
    span 80 47.14
    1,4-butanediol 57.34
    1,1-dichloroethane 18.06
    2-methyl-1-pentanol 26.29
    methyl formate 81.04
    2-methyl-1-butanol 27.49
    n-decane 3.01
    butyronitrile 19.57
    3,7-dimethyl-1-octanol 25.0
    1-chlorooctane 11.29
    1-chlorotetradecane 6.03
    n-nonane 2.66
    undecane 2.63
    tert-butylcyclohexane 2.66
    cyclooctane 1.5
    cyclopentanol 41.4
    tetrahydropyran 27.74
    tert-amyl methyl ether 20.54
    2,5,8-trioxanonane 88.94
    1-hexene 3.35
    2-isopropoxyethanol 57.99
    2,2,2-trifluoroethanol 52.28
    methyl butyrate 25.58

    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