Versicolactone B

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  • Identifiers

    CAS number
    104613-44-7

    Molecular formula
    C15H22O3

    SMILES
    C/C/1=C/C[C@@H]([C@H]2C[C@@H](CC[C@@H]1O)C(=O)O2)C(=C)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 59.0%
    Mint 56.18%
    Spicy 56.13%
    Herbal 49.58%
    Woody 43.55%
    Coconut 32.48%
    Hay 31.52%
    Coumarinic 31.49%
    Celery 29.17%
    Tobacco 28.96%

     

    Flavor
    Minty 49.71%
    Bitter 48.11%
    Herbal 31.26%
    Spearmint 29.12%
    Mint 28.39%
    Fresh 28.14%
    Spice 27.74%
    Celery 21.89%
    Basil 21.18%
    Peppermint 20.82%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    7.79 (neutral)

    Molecular weight
    250.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    510°C

    Flash point

    • 189.26 ˚C est.

  • Synonyms

    • Versicolactone B
    • 104613-44-7
    • (1R,4S,5Z,8R,9R)-4-hydroxy-5-methyl-8-prop-1-en-2-yl-10-oxabicyclo[7.2.1]dodec-5-en-11-one
    • 10-Oxabicyclo(7.2.1)dodec-5-en-11-one, 4-hydroxy-5-methyl-8-(1-methylethenyl)-, (1R-(1R*,4S*,5E,8R*,9R*))-
    • CHEBI:132826
    • (1R,4S,5Z,8R,9R)-4-hydroxy-5-methyl-8-prop-1-en-2-yl-10-oxabicyclo(7.2.1)dodec-5-en-11-one
    • RefChem:194062
    • (5E)-5-((2R,3R)-2,3-dihydroxybutylidene)furan-2-one
    • (5E)-5-((2R,3S)-2,3-dihydroxybutylidene)furan-2-one
    • 104613-44-7

  • Applications

    Versicolactone B (CAS 104613-44-7) is a natural lactone with potential applications across several industrial sectors as an aroma constituent and synthetic intermediate. Specifically, it may serve as a fragrance ingredient in perfumery and in cosmetics/personal care, be evaluated as a building block or intermediate for organic synthesis in specialty chemical manufacturing, and potentially participate in polymer/plastics chemistries or coating/ink formulations. It may also be considered as a fragrance additive in household cleaning products, with use depending on local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 293.25
    methanol 699.78
    isopropanol 272.31
    water 2.62
    ethyl acetate 222.22
    n-propanol 237.22
    acetone 339.27
    n-butanol 238.29
    acetonitrile 152.48
    DMF 771.42
    toluene 131.82
    isobutanol 177.28
    1,4-dioxane 705.32
    methyl acetate 202.93
    THF 888.39
    2-butanone 252.37
    n-pentanol 149.99
    sec-butanol 171.88
    n-hexane 3.18
    ethylene glycol 80.56
    NMP 456.42
    cyclohexane 10.87
    DMSO 568.05
    n-butyl acetate 173.35
    n-octanol 71.81
    chloroform 674.14
    n-propyl acetate 161.0
    acetic acid 399.79
    dichloromethane 550.56
    cyclohexanone 391.13
    propylene glycol 121.88
    isopropyl acetate 180.2
    DMAc 517.59
    2-ethoxyethanol 301.37
    isopentanol 225.4
    n-heptane 3.74
    ethyl formate 193.53
    1,2-dichloroethane 262.81
    n-hexanol 144.23
    2-methoxyethanol 538.39
    isobutyl acetate 127.13
    tetrachloromethane 53.72
    n-pentyl acetate 126.58
    transcutol 1353.58
    n-heptanol 85.94
    ethylbenzene 63.24
    MIBK 174.43
    2-propoxyethanol 312.24
    tert-butanol 259.89
    MTBE 145.38
    2-butoxyethanol 213.35
    propionic acid 210.59
    o-xylene 84.06
    formic acid 244.07
    diethyl ether 147.95
    m-xylene 113.72
    p-xylene 91.09
    chlorobenzene 165.1
    dimethyl carbonate 143.26
    n-octane 2.26
    formamide 374.04
    cyclopentanone 483.99
    2-pentanone 212.81
    anisole 168.02
    cyclopentyl methyl ether 246.05
    gamma-butyrolactone 542.2
    1-methoxy-2-propanol 426.27
    pyridine 386.89
    3-pentanone 140.01
    furfural 527.19
    n-dodecane 2.94
    diethylene glycol 325.83
    diisopropyl ether 50.0
    tert-amyl alcohol 163.25
    acetylacetone 320.39
    n-hexadecane 3.44
    acetophenone 179.16
    methyl propionate 174.01
    isopentyl acetate 176.41
    trichloroethylene 615.53
    n-nonanol 67.84
    cyclohexanol 185.84
    benzyl alcohol 187.21
    2-ethylhexanol 77.4
    isooctanol 74.25
    dipropyl ether 63.04
    1,2-dichlorobenzene 160.57
    ethyl lactate 113.12
    propylene carbonate 326.03
    n-methylformamide 353.95
    2-pentanol 146.19
    n-pentane 4.31
    1-propoxy-2-propanol 205.7
    1-methoxy-2-propyl acetate 226.34
    2-(2-methoxypropoxy) propanol 211.45
    mesitylene 67.03
    ε-caprolactone 346.67
    p-cymene 42.9
    epichlorohydrin 541.76
    1,1,1-trichloroethane 173.29
    2-aminoethanol 171.05
    morpholine-4-carbaldehyde 608.29
    sulfolane 522.75
    2,2,4-trimethylpentane 5.76
    2-methyltetrahydrofuran 360.07
    n-hexyl acetate 159.01
    isooctane 5.83
    2-(2-butoxyethoxy)ethanol 317.67
    sec-butyl acetate 120.94
    tert-butyl acetate 181.09
    decalin 9.23
    glycerin 223.49
    diglyme 586.71
    acrylic acid 226.25
    isopropyl myristate 63.52
    n-butyric acid 301.25
    acetyl acetate 194.16
    di(2-ethylhexyl) phthalate 88.79
    ethyl propionate 121.91
    nitromethane 549.63
    1,2-diethoxyethane 249.28
    benzonitrile 214.36
    trioctyl phosphate 60.34
    1-bromopropane 95.43
    gamma-valerolactone 693.04
    n-decanol 49.03
    triethyl phosphate 75.14
    4-methyl-2-pentanol 109.76
    propionitrile 134.56
    vinylene carbonate 330.74
    1,1,2-trichlorotrifluoroethane 383.53
    DMS 169.1
    cumene 52.2
    2-octanol 54.19
    2-hexanone 150.41
    octyl acetate 80.19
    limonene 54.55
    1,2-dimethoxyethane 483.97
    ethyl orthosilicate 71.0
    tributyl phosphate 74.21
    diacetone alcohol 233.43
    N,N-dimethylaniline 123.89
    acrylonitrile 196.66
    aniline 208.75
    1,3-propanediol 281.83
    bromobenzene 150.17
    dibromomethane 270.08
    1,1,2,2-tetrachloroethane 448.18
    2-methyl-cyclohexyl acetate 117.26
    tetrabutyl urea 91.21
    diisobutyl methanol 54.3
    2-phenylethanol 163.3
    styrene 78.84
    dioctyl adipate 103.72
    dimethyl sulfate 220.56
    ethyl butyrate 117.67
    methyl lactate 160.3
    butyl lactate 133.81
    diethyl carbonate 94.67
    propanediol butyl ether 235.09
    triethyl orthoformate 99.59
    p-tert-butyltoluene 41.6
    methyl 4-tert-butylbenzoate 159.35
    morpholine 657.53
    tert-butylamine 114.45
    n-dodecanol 35.97
    dimethoxymethane 431.71
    ethylene carbonate 270.18
    cyrene 233.31
    2-ethoxyethyl acetate 218.39
    2-ethylhexyl acetate 130.36
    1,2,4-trichlorobenzene 202.72
    4-methylpyridine 342.8
    dibutyl ether 67.15
    2,6-dimethyl-4-heptanol 54.3
    DEF 246.24
    dimethyl isosorbide 331.88
    tetrachloroethylene 293.77
    eugenol 175.63
    triacetin 209.51
    span 80 172.68
    1,4-butanediol 115.01
    1,1-dichloroethane 222.95
    2-methyl-1-pentanol 148.55
    methyl formate 274.95
    2-methyl-1-butanol 170.0
    n-decane 4.83
    butyronitrile 155.49
    3,7-dimethyl-1-octanol 80.91
    1-chlorooctane 30.27
    1-chlorotetradecane 12.55
    n-nonane 3.65
    undecane 3.59
    tert-butylcyclohexane 7.87
    cyclooctane 4.53
    cyclopentanol 199.05
    tetrahydropyran 403.97
    tert-amyl methyl ether 99.23
    2,5,8-trioxanonane 366.79
    1-hexene 21.51
    2-isopropoxyethanol 201.04
    2,2,2-trifluoroethanol 168.88
    methyl butyrate 164.88

    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