(+)-Ivalin

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  • Identifiers

    CAS number
    5938-03-4

    Molecular formula
    C15H20O3

    SMILES
    C[C@]12C[C@H](CC(=C)[C@@H]1C[C@H]3[C@@H](C2)OC(=O)C3=C)O

    Safety labels

  • Odor profile

    Fragrance
    Spicy 37.85%
    Woody 37.41%
    Odorless 33.78%
    Sweet 29.39%
    Mint 29.24%
    Nutty 24.37%
    Tobacco 23.23%
    Herbal 22.2%
    Phenolic 20.97%
    Camphoreous 20.95%

     

    Flavor
    Bitter 83.85%
    Minty 24.47%
    Cedarleaf 21.55%
    Lovage 20.41%
    Basil 19.87%
    Ripe apricot 19.52%
    Fenugreek 19.3%
    Leaves 19.21%
    Red fruit 19.12%
    Alkaline 18.92%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    8.67 (weak base)

    Molecular weight
    248.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    597°C

    Flash point

    • 185.95 ˚C est.

  • Synonyms

    • Ivalin
    • (3aR,4aS,7S,8aR,9aR)-7-hydroxy-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
    • 5938-03-4
    • (3aR,4aS,7S,8aR,9aR)-7-hydroxy-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo(f)(1)benzofuran-2-one
    • (+)-Ivalin
    • RefChem:905469
    • (3aR,4aS,7S,8aR,9aR)-7-hydroxy-8a-methyl-3,5-dimethylene-3a,4,4a,6,7,8,9,9a-octahydrobenzo(f)benzofuran-2-one
    • NSC 85237
    • CHEMBL1644108
    • CHEBI:6077
    • SCHEMBL27903663
    • BDBM50433447
    • Eudesma-4(14),11(13)-dien-12-oic acid, 2,8-dihydroxy-, gamma-lactone
    • C09488
    • Q27107027
    • 5938-03-4

  • Applications

    (+)-Ivalin is a natural terpenoid that is primarily encountered as a fragrance ingredient in the perfumery and cosmetics sectors, with potential use as an odorant additive in household products; it is also viewed as a useful intermediate in organic synthesis, serving as a chiral building block for the preparation of natural product derivatives and other fine chemicals; in research contexts, it may be evaluated as a chiral synthesis platform for enantioselective routes; thus, practical applications typically center on fragrance/cosmetic formulation and its role as a synthetic intermediate, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 99.69
    methanol 289.43
    isopropanol 141.52
    water 0.97
    ethyl acetate 171.84
    n-propanol 109.47
    acetone 286.74
    n-butanol 122.27
    acetonitrile 118.17
    DMF 496.02
    toluene 88.46
    isobutanol 74.29
    1,4-dioxane 485.74
    methyl acetate 148.06
    THF 845.05
    2-butanone 168.09
    n-pentanol 41.19
    sec-butanol 44.98
    n-hexane 0.39
    ethylene glycol 36.9
    NMP 231.58
    cyclohexane 2.02
    DMSO 276.34
    n-butyl acetate 111.46
    n-octanol 28.84
    chloroform 307.52
    n-propyl acetate 86.2
    acetic acid 194.81
    dichloromethane 245.5
    cyclohexanone 256.92
    propylene glycol 50.7
    isopropyl acetate 136.03
    DMAc 220.86
    2-ethoxyethanol 134.29
    isopentanol 107.99
    n-heptane 1.0
    ethyl formate 133.16
    1,2-dichloroethane 131.52
    n-hexanol 69.53
    2-methoxyethanol 420.22
    isobutyl acetate 67.83
    tetrachloromethane 17.7
    n-pentyl acetate 69.79
    transcutol 848.43
    n-heptanol 35.69
    ethylbenzene 19.75
    MIBK 119.19
    2-propoxyethanol 271.51
    tert-butanol 143.07
    MTBE 48.15
    2-butoxyethanol 121.16
    propionic acid 103.56
    o-xylene 35.31
    formic acid 139.01
    diethyl ether 60.02
    m-xylene 69.69
    p-xylene 28.83
    chlorobenzene 105.82
    dimethyl carbonate 119.68
    n-octane 0.63
    formamide 209.04
    cyclopentanone 404.45
    2-pentanone 161.72
    anisole 82.81
    cyclopentyl methyl ether 157.59
    gamma-butyrolactone 474.01
    1-methoxy-2-propanol 336.06
    pyridine 248.92
    3-pentanone 79.89
    furfural 381.37
    n-dodecane 0.95
    diethylene glycol 268.71
    diisopropyl ether 20.05
    tert-amyl alcohol 45.69
    acetylacetone 259.78
    n-hexadecane 1.15
    acetophenone 95.36
    methyl propionate 135.12
    isopentyl acetate 110.2
    trichloroethylene 352.45
    n-nonanol 28.43
    cyclohexanol 82.76
    benzyl alcohol 93.32
    2-ethylhexanol 32.37
    isooctanol 31.95
    dipropyl ether 28.79
    1,2-dichlorobenzene 88.51
    ethyl lactate 67.24
    propylene carbonate 244.86
    n-methylformamide 276.06
    2-pentanol 55.85
    n-pentane 0.79
    1-propoxy-2-propanol 163.72
    1-methoxy-2-propyl acetate 198.92
    2-(2-methoxypropoxy) propanol 126.4
    mesitylene 33.98
    ε-caprolactone 223.44
    p-cymene 19.39
    epichlorohydrin 482.6
    1,1,1-trichloroethane 91.9
    2-aminoethanol 78.77
    morpholine-4-carbaldehyde 397.14
    sulfolane 328.15
    2,2,4-trimethylpentane 0.94
    2-methyltetrahydrofuran 225.97
    n-hexyl acetate 88.15
    isooctane 1.54
    2-(2-butoxyethoxy)ethanol 204.28
    sec-butyl acetate 61.79
    tert-butyl acetate 136.67
    decalin 1.57
    glycerin 121.52
    diglyme 380.55
    acrylic acid 115.8
    isopropyl myristate 33.91
    n-butyric acid 200.79
    acetyl acetate 143.86
    di(2-ethylhexyl) phthalate 49.62
    ethyl propionate 69.53
    nitromethane 358.78
    1,2-diethoxyethane 150.72
    benzonitrile 136.72
    trioctyl phosphate 34.09
    1-bromopropane 36.68
    gamma-valerolactone 543.67
    n-decanol 20.87
    triethyl phosphate 40.77
    4-methyl-2-pentanol 48.49
    propionitrile 96.32
    vinylene carbonate 238.8
    1,1,2-trichlorotrifluoroethane 236.18
    DMS 109.21
    cumene 14.9
    2-octanol 21.92
    2-hexanone 66.89
    octyl acetate 44.35
    limonene 20.98
    1,2-dimethoxyethane 244.0
    ethyl orthosilicate 37.17
    tributyl phosphate 41.77
    diacetone alcohol 181.66
    N,N-dimethylaniline 46.63
    acrylonitrile 158.96
    aniline 135.89
    1,3-propanediol 199.45
    bromobenzene 96.59
    dibromomethane 104.43
    1,1,2,2-tetrachloroethane 243.57
    2-methyl-cyclohexyl acetate 65.41
    tetrabutyl urea 52.83
    diisobutyl methanol 25.79
    2-phenylethanol 106.56
    styrene 25.09
    dioctyl adipate 56.94
    dimethyl sulfate 151.51
    ethyl butyrate 71.64
    methyl lactate 117.99
    butyl lactate 79.53
    diethyl carbonate 55.69
    propanediol butyl ether 126.03
    triethyl orthoformate 58.28
    p-tert-butyltoluene 19.67
    methyl 4-tert-butylbenzoate 93.95
    morpholine 468.51
    tert-butylamine 37.7
    n-dodecanol 14.86
    dimethoxymethane 429.25
    ethylene carbonate 200.75
    cyrene 126.02
    2-ethoxyethyl acetate 146.65
    2-ethylhexyl acetate 74.62
    1,2,4-trichlorobenzene 112.44
    4-methylpyridine 238.7
    dibutyl ether 27.91
    2,6-dimethyl-4-heptanol 25.79
    DEF 130.33
    dimethyl isosorbide 233.79
    tetrachloroethylene 123.29
    eugenol 104.56
    triacetin 117.46
    span 80 96.05
    1,4-butanediol 41.27
    1,1-dichloroethane 124.19
    2-methyl-1-pentanol 40.99
    methyl formate 248.36
    2-methyl-1-butanol 57.19
    n-decane 1.49
    butyronitrile 112.5
    3,7-dimethyl-1-octanol 37.13
    1-chlorooctane 11.36
    1-chlorotetradecane 4.67
    n-nonane 1.08
    undecane 1.17
    tert-butylcyclohexane 1.48
    cyclooctane 0.9
    cyclopentanol 115.22
    tetrahydropyran 224.05
    tert-amyl methyl ether 29.02
    2,5,8-trioxanonane 230.2
    1-hexene 3.21
    2-isopropoxyethanol 95.15
    2,2,2-trifluoroethanol 88.69
    methyl butyrate 92.33

    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