(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione

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  • Identifiers

    CAS number
    121-40-4

    Molecular formula
    C7H6O4

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Caramellic 74.79%
    Burnt 57.97%
    Sweet 49.95%
    Odorless 33.33%
    Roasted 31.34%
    Coffee 26.9%
    Buttery 21.17%
    Nutty 20.5%
    Sharp 20.23%
    Savory 20.08%

     

    Flavor
    Bitter 52.92%
    Maple 28.45%
    Very mild 24.3%
    Fenugreek 22.64%
    Cotton candy 22.25%
    Caramel 22.16%
    Seedy 22.09%
    Extremely sweet 21.98%
    Sugar 21.84%
    Maple syrup 21.43%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.2

    pKa est.
    6.35 (neutral)

    Molecular weight
    154.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    336°C

    Flash point

    • 140.11 ˚C est.

  • Synonyms

    • Terreic acid
    • (-)-Terreic Acid
    • 121-40-4
    • (1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
    • XM2Y0DRJ7D
    • NSC-294734
    • (1R)-3-Hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
    • DTXSID40879070
    • (1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
    • versilin
    • RefChem:188061
    • DTXCID601017088
    • 3-Hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
    • NSC294734
    • 5,6-Epoxy-3-hydroxy-p-toluquinone
    • UNII-XM2Y0DRJ7D
    • NSC 294734
    • (-)-TerreicAcid
    • 2-Hydroxy-3-methyl-1,4-benzoquinone 5,6-epoxide
    • BiomolKI_000073
    • BiomolKI2_000077
    • TERREIC ACID [MI]
    • 7-Oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, stereoisomer
    • SCHEMBL51229
    • CHEMBL1455300
    • CHEBI:156546
    • HMS3267H06
    • HMS3412M22
    • HMS3676M22
    • 7-Oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, (1R)-
    • AKOS006281919
    • CCG-100677
    • SMP2_000322
    • NCGC00025148-02
    • NCGC00025148-03
    • DA-59416
    • NCI60_002449
    • HY-110013
    • CS-0032828
    • (-)-Terreic Acid, Synthetic - CAS 121-40-4
    • (5R),(6S)-EPOXY-3-HYDROXY-P-TOLUQUINONE
    • SR-01000597558
    • SR-01000597558-1
    • Q27293905
    • 7-Oxabicyclo[4.1.0]hept-3-ene-2, 3-hydroxy-4-methyl-, (1R-cis)-
    • 7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-,(1R,6S)-
    • 121-40-4

  • Applications

    The compound (1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione (CAS 121-40-4) is primarily used as an intermediate in organic synthesis. In practice, it serves as a versatile chiral building block for the preparation of more complex pharmaceuticals and agrochemicals. It is also evaluated as a precursor or intermediate in polymer and materials chemistry, including specialty monomers and crosslinking frameworks for coatings or adhesives. In industrial manufacturing and research settings, it supports asymmetric synthesis and catalysis development, and may be used to access stereochemically defined scaffolds for drug discovery or agrochemical programs. Subject to local regulations and formulation limits, the compound may be handled and formulated under typical industrial practices.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.82
    methanol 10.01
    isopropanol 5.11
    water 1.12
    ethyl acetate 7.31
    n-propanol 4.51
    acetone 11.67
    n-butanol 4.35
    acetonitrile 5.2
    DMF 31.87
    toluene 0.78
    isobutanol 3.0
    1,4-dioxane 14.21
    methyl acetate 8.06
    THF 22.6
    2-butanone 8.29
    n-pentanol 4.2
    sec-butanol 3.84
    n-hexane 0.21
    ethylene glycol 9.41
    NMP 21.75
    cyclohexane 0.21
    DMSO 49.61
    n-butyl acetate 4.48
    n-octanol 3.07
    chloroform 2.73
    n-propyl acetate 5.51
    acetic acid 9.64
    dichloromethane 4.11
    cyclohexanone 9.15
    propylene glycol 3.49
    isopropyl acetate 5.88
    DMAc 28.67
    2-ethoxyethanol 25.82
    isopentanol 4.97
    n-heptane 0.4
    ethyl formate 5.53
    1,2-dichloroethane 3.94
    n-hexanol 4.2
    2-methoxyethanol 36.25
    isobutyl acetate 2.63
    tetrachloromethane 0.88
    n-pentyl acetate 4.89
    transcutol 53.94
    n-heptanol 3.72
    ethylbenzene 0.99
    MIBK 8.16
    2-propoxyethanol 19.73
    tert-butanol 8.34
    MTBE 4.63
    2-butoxyethanol 13.35
    propionic acid 5.42
    o-xylene 1.25
    formic acid 17.85
    diethyl ether 6.19
    m-xylene 1.18
    p-xylene 1.31
    chlorobenzene 1.16
    dimethyl carbonate 7.45
    n-octane 0.23
    formamide 38.62
    cyclopentanone 14.04
    2-pentanone 9.56
    anisole 4.89
    cyclopentyl methyl ether 7.19
    gamma-butyrolactone 17.45
    1-methoxy-2-propanol 23.58
    pyridine 5.8
    3-pentanone 6.49
    furfural 18.19
    n-dodecane 0.22
    diethylene glycol 27.88
    diisopropyl ether 2.53
    tert-amyl alcohol 6.41
    acetylacetone 14.27
    n-hexadecane 0.25
    acetophenone 6.85
    methyl propionate 8.57
    isopentyl acetate 4.67
    trichloroethylene 5.88
    n-nonanol 3.38
    cyclohexanol 3.4
    benzyl alcohol 5.25
    2-ethylhexanol 3.13
    isooctanol 3.35
    dipropyl ether 3.91
    1,2-dichlorobenzene 1.84
    ethyl lactate 7.15
    propylene carbonate 6.99
    n-methylformamide 17.14
    2-pentanol 3.85
    n-pentane 0.24
    1-propoxy-2-propanol 12.18
    1-methoxy-2-propyl acetate 10.02
    2-(2-methoxypropoxy) propanol 16.32
    mesitylene 1.1
    ε-caprolactone 9.5
    p-cymene 1.52
    epichlorohydrin 19.34
    1,1,1-trichloroethane 2.2
    2-aminoethanol 8.68
    morpholine-4-carbaldehyde 32.33
    sulfolane 26.88
    2,2,4-trimethylpentane 0.24
    2-methyltetrahydrofuran 9.81
    n-hexyl acetate 6.22
    isooctane 0.24
    2-(2-butoxyethoxy)ethanol 20.56
    sec-butyl acetate 3.98
    tert-butyl acetate 8.49
    decalin 0.27
    glycerin 15.54
    diglyme 39.1
    acrylic acid 6.64
    isopropyl myristate 3.16
    n-butyric acid 6.33
    acetyl acetate 5.6
    di(2-ethylhexyl) phthalate 3.65
    ethyl propionate 5.91
    nitromethane 26.48
    1,2-diethoxyethane 10.85
    benzonitrile 3.55
    trioctyl phosphate 2.87
    1-bromopropane 1.55
    gamma-valerolactone 22.9
    n-decanol 2.53
    triethyl phosphate 4.27
    4-methyl-2-pentanol 3.66
    propionitrile 3.67
    vinylene carbonate 6.13
    1,1,2-trichlorotrifluoroethane 18.69
    DMS 6.66
    cumene 1.15
    2-octanol 2.64
    2-hexanone 6.31
    octyl acetate 3.77
    limonene 2.0
    1,2-dimethoxyethane 31.09
    ethyl orthosilicate 3.95
    tributyl phosphate 3.04
    diacetone alcohol 16.64
    N,N-dimethylaniline 4.53
    acrylonitrile 5.89
    aniline 2.72
    1,3-propanediol 12.82
    bromobenzene 0.82
    dibromomethane 2.13
    1,1,2,2-tetrachloroethane 4.93
    2-methyl-cyclohexyl acetate 5.24
    tetrabutyl urea 5.31
    diisobutyl methanol 2.92
    2-phenylethanol 5.85
    styrene 0.99
    dioctyl adipate 5.0
    dimethyl sulfate 15.72
    ethyl butyrate 5.34
    methyl lactate 10.48
    butyl lactate 6.0
    diethyl carbonate 3.93
    propanediol butyl ether 10.41
    triethyl orthoformate 4.79
    p-tert-butyltoluene 1.43
    methyl 4-tert-butylbenzoate 9.72
    morpholine 15.06
    tert-butylamine 3.55
    n-dodecanol 1.91
    dimethoxymethane 29.5
    ethylene carbonate 5.14
    cyrene 17.03
    2-ethoxyethyl acetate 10.21
    2-ethylhexyl acetate 3.34
    1,2,4-trichlorobenzene 2.47
    4-methylpyridine 4.44
    dibutyl ether 3.37
    2,6-dimethyl-4-heptanol 2.92
    DEF 13.35
    dimethyl isosorbide 23.18
    tetrachloroethylene 4.29
    eugenol 11.76
    triacetin 10.42
    span 80 9.11
    1,4-butanediol 6.82
    1,1-dichloroethane 2.13
    2-methyl-1-pentanol 4.21
    methyl formate 12.96
    2-methyl-1-butanol 3.77
    n-decane 0.35
    butyronitrile 3.51
    3,7-dimethyl-1-octanol 3.31
    1-chlorooctane 1.37
    1-chlorotetradecane 0.69
    n-nonane 0.29
    undecane 0.27
    tert-butylcyclohexane 0.28
    cyclooctane 0.16
    cyclopentanol 4.77
    tetrahydropyran 5.27
    tert-amyl methyl ether 4.93
    2,5,8-trioxanonane 29.11
    1-hexene 0.79
    2-isopropoxyethanol 15.7
    2,2,2-trifluoroethanol 11.78
    methyl butyrate 7.04

    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