(3R,6S)-6-ethenyl-2,2,6-trimethyloxan-3-ol

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    39028-58-5

    Molecular formula
    C10H18O2

    SMILES
    C[C@]1(CC[C@H](C(O1)(C)C)O)C=C

    Retention indicies (RI)

    • DB5: 1185.0
    • Carbowax: 1736.83

  • Odor profile

    Floral 73.15%
    Sweet 71.3%
    Fresh 59.29%
    Woody 58.29%
    Herbal 57.0%
    Green 49.78%
    Earthy 47.11%
    Citrus 46.68%
    Mint 44.43%
    Camphoreous 38.07%

    Scent© AI

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    9.22 (weak base)

    Molecular weight
    170.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    228°C

    Flash point est.
    80.74 ˚C

  • Synonyms

    • Linalool oxide pyranoid, trans-(-)-
    • Linalool oxide C
    • 39028-58-5
    • 41720-62-1
    • Linalool oxide IV
    • FEMA No. 4593, trans-(-)-
    • UNII-89JV2MJ158
    • Linalool oxide (trans-pyranoid)
    • 89JV2MJ158
    • Trans-pyran linalool oxide
    • (3R,6S)-6-ethenyl-2,2,6-trimethyloxan-3-ol
    • trans-Linalool 3,7-oxide
    • 2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, (3R,6S)-
    • 7VCV9E83EL
    • Trans-pyranoid linalool oxide
    • 2H-Pyran-3-ol, 6-ethenyltetrahydro-2,2,6-trimethyl-, (3R-trans)-
    • Linalool oxide pyranoid, trans-(+/-)-
    • Cnidiol C
    • (E)-Linalol pyranoxide
    • UNII-7VCV9E83EL
    • PYRANOID LINALOOL OXIDE, TRANS
    • LINALOOL OXIDE 4
    • E-Pyranoid linalool oxide
    • linalool oxide, trans-pyranoid
    • Trans-linalol oxide (pyranoid)
    • SCHEMBL4962408
    • (E)-Linalool oxide (pyranoid)
    • Linalool oxide (pyranoid) trans
    • DTXSID00194519
    • linalool oxide (trans, pyranoid)
    • CHEBI:180233
    • linalool oxide IV (trans, pyranoid)
    • FEMA NO. 4593, TRANS-(+/-)-
    • trans-2,2,6-Trimethyl-6-vinyltetrahydropyran-3-ol
    • TRANS-3-HYDROXY-2,2,6-TRIMETHYL-6-VINYLTETRAHYDROPYRAN
    • TRANS-6-ETHENYLTETRAHYDRO-2,2,6-TRIMETHYLPYRAN-3-OL
    • TRANS-6-VINYLTETRAHYDRO-2,2,6-TRIMETHYL-2H-PYRAN-3-OL
    • 6-Ethenyltetrahydro-2,2,6-trimethyl-(3R,6S)-rel-2H-Pyran-3-ol
    • rel-(3R,6S)-2,2,6-Trimethyl-6-vinyltetrahydro-2H-pyran-3-ol
    • 2H-PYRAN-3-OL, 6-ETHENYLTETRAHYDRO-2,2,6-TRIMETHYL-, TRANS-
    • 2H-PYRAN-3-OL, 6-ETHENYLTETRAHYDRO-2,2,6-TRIMETHYL-, (3R,6S)-REL-

  • Applications

    The enantiopure (3R,6S)-6-ethenyl-2,2,6-trimethyloxan-3-ol (a pyranoid linalool oxide; CAS 39028-58-5) is used widely as a fragrance/flavor ingredient providing rose–floral, tea, lychee, citrus and green notes and boosting diffusion in fine fragrance, cosmetics, personal care and cleaners; as a flavor modulator in beverages, aromatic wines, beer, teas, confectionery and baked goods; as an analytical standard (GC–MS, chiral GC) for identification/quantification of aroma markers in tea, coffee, wine, beer and essential oils, for tracking linalool oxidation and aroma stability; as a sensory reference for panel training and recombination studies; as a chiral building block in organic synthesis and asymmetric catalysis research; and in delivery systems/microencapsulation (e.g., cyclodextrin) to control aroma release in consumer products, used in line with prevailing fragrance and food safety guidelines.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 255.08
    methanol 384.6
    isopropanol 230.64
    water 9.46
    ethyl acetate 169.54
    n-propanol 231.84
    acetone 171.96
    n-butanol 228.93
    acetonitrile 168.4
    DMF 330.26
    toluene 154.62
    isobutanol 204.95
    1,4-dioxane 407.98
    methyl acetate 178.04
    THF 507.43
    2-butanone 195.56
    n-pentanol 156.65
    sec-butanol 227.09
    n-hexane 43.5
    ethylene glycol 106.3
    NMP 331.73
    cyclohexane 62.35
    DMSO 266.65
    n-butyl acetate 174.02
    n-octanol 170.21
    chloroform 510.95
    n-propyl acetate 104.44
    acetic acid 149.46
    dichloromethane 443.22
    cyclohexanone 298.21
    propylene glycol 139.93
    isopropyl acetate 128.13
    DMAc 345.55
    2-ethoxyethanol 211.78
    isopentanol 195.57
    n-heptane 56.97
    ethyl formate 142.51
    1,2-dichloroethane 214.23
    n-hexanol 273.77
    2-methoxyethanol 316.43
    isobutyl acetate 92.23
    tetrachloromethane 137.33
    n-pentyl acetate 136.04
    transcutol 447.61
    n-heptanol 156.45
    ethylbenzene 100.45
    MIBK 134.82
    2-propoxyethanol 349.45
    tert-butanol 304.6
    MTBE 235.3
    2-butoxyethanol 197.93
    propionic acid 160.98
    o-xylene 139.75
    formic acid 91.08
    diethyl ether 195.45
    m-xylene 140.26
    p-xylene 138.61
    chlorobenzene 166.49
    dimethyl carbonate 80.24
    n-octane 27.05
    formamide 88.85
    cyclopentanone 309.28
    2-pentanone 157.62
    anisole 162.8
    cyclopentyl methyl ether 242.78
    gamma-butyrolactone 319.97
    1-methoxy-2-propanol 257.95
    pyridine 186.79
    3-pentanone 146.04
    furfural 299.56
    n-dodecane 24.96
    diethylene glycol 270.06
    diisopropyl ether 91.06
    tert-amyl alcohol 263.57
    acetylacetone 181.26
    n-hexadecane 27.39
    acetophenone 147.47
    methyl propionate 148.83
    isopentyl acetate 172.19
    trichloroethylene 367.75
    n-nonanol 143.68
    cyclohexanol 218.11
    benzyl alcohol 135.98
    2-ethylhexanol 170.46
    isooctanol 121.36
    dipropyl ether 156.6
    1,2-dichlorobenzene 175.45
    ethyl lactate 88.86
    propylene carbonate 212.23
    n-methylformamide 156.71
    2-pentanol 165.46
    n-pentane 50.03
    1-propoxy-2-propanol 237.62
    1-methoxy-2-propyl acetate 187.65
    2-(2-methoxypropoxy) propanol 198.0
    mesitylene 106.08
    ε-caprolactone 280.45
    p-cymene 108.28
    epichlorohydrin 323.63
    1,1,1-trichloroethane 251.19
    2-aminoethanol 170.99
    morpholine-4-carbaldehyde 394.97
    sulfolane 383.0
    2,2,4-trimethylpentane 40.75
    2-methyltetrahydrofuran 340.6
    n-hexyl acetate 205.35
    isooctane 31.5
    2-(2-butoxyethoxy)ethanol 235.23
    sec-butyl acetate 88.92
    tert-butyl acetate 156.7
    decalin 43.97
    glycerin 180.96
    diglyme 390.16
    acrylic acid 134.45
    isopropyl myristate 103.46
    n-butyric acid 184.93
    acetyl acetate 125.64
    di(2-ethylhexyl) phthalate 101.58
    ethyl propionate 108.59
    nitromethane 202.64
    1,2-diethoxyethane 178.57
    benzonitrile 169.89
    trioctyl phosphate 89.68
    1-bromopropane 188.44
    gamma-valerolactone 389.73
    n-decanol 108.94
    triethyl phosphate 92.84
    4-methyl-2-pentanol 118.37
    propionitrile 169.7
    vinylene carbonate 215.53
    1,1,2-trichlorotrifluoroethane 239.49
    DMS 149.84
    cumene 92.03
    2-octanol 118.95
    2-hexanone 128.22
    octyl acetate 125.95
    limonene 136.58
    1,2-dimethoxyethane 324.9
    ethyl orthosilicate 91.64
    tributyl phosphate 97.97
    diacetone alcohol 179.88
    N,N-dimethylaniline 137.62
    acrylonitrile 166.0
    aniline 141.53
    1,3-propanediol 197.04
    bromobenzene 179.93
    dibromomethane 292.56
    1,1,2,2-tetrachloroethane 323.76
    2-methyl-cyclohexyl acetate 142.62
    tetrabutyl urea 116.92
    diisobutyl methanol 108.57
    2-phenylethanol 173.28
    styrene 102.39
    dioctyl adipate 128.24
    dimethyl sulfate 142.67
    ethyl butyrate 134.96
    methyl lactate 111.64
    butyl lactate 122.58
    diethyl carbonate 98.18
    propanediol butyl ether 192.28
    triethyl orthoformate 113.56
    p-tert-butyltoluene 110.01
    methyl 4-tert-butylbenzoate 182.77
    morpholine 371.81
    tert-butylamine 234.57
    n-dodecanol 87.85
    dimethoxymethane 238.82
    ethylene carbonate 181.09
    cyrene 170.53
    2-ethoxyethyl acetate 163.22
    2-ethylhexyl acetate 149.05
    1,2,4-trichlorobenzene 203.22
    4-methylpyridine 229.23
    dibutyl ether 137.66
    2,6-dimethyl-4-heptanol 108.57
    DEF 192.89
    dimethyl isosorbide 302.92
    tetrachloroethylene 228.04
    eugenol 166.81
    triacetin 180.1
    span 80 181.68
    1,4-butanediol 105.65
    1,1-dichloroethane 245.28
    2-methyl-1-pentanol 148.66
    methyl formate 138.24
    2-methyl-1-butanol 198.11
    n-decane 39.51
    butyronitrile 177.66
    3,7-dimethyl-1-octanol 160.9
    1-chlorooctane 111.59
    1-chlorotetradecane 54.29
    n-nonane 39.16
    undecane 30.29
    tert-butylcyclohexane 49.66
    cyclooctane 33.02
    cyclopentanol 229.0
    tetrahydropyran 319.32
    tert-amyl methyl ether 194.42
    2,5,8-trioxanonane 301.61
    1-hexene 100.85
    2-isopropoxyethanol 156.91
    2,2,2-trifluoroethanol 83.32
    methyl butyrate 134.58

    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

Botanical

Name CAS Botanical Proportion
Blackcurrant bud 1 68606-81-5 Ribes nigrum L., fam. Grossulariaceae 0.15%
Tea leaf Camellia sinensis Kuntze, fam. Theaceae 1.3%
Lavender (France) 2a 8000-28-0 Lavandula angustifolia Mill. (L. officinalis Chaix), fam. Lamiaceae 0.13%
Osmanthus absolute 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 0.4%
Hedychium coronarium flower (Japan) Hedychium coronarium Koenig, fam. Zingiberaceae 0.14%
Daphne genkwa Daphne genkwa Sieb. et Zucc., fam. Thymelaeaceae 0.86%
Orange, bitter (China) 72968-50-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.01%
Lavender (France) 6 8000-28-0 Lavandula angustifolia Mill., fam. Lamiaceae (Labiatae) 0.01%
Neroli bigarade (bitter orange flower) China 3 8016-38-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.21%
Osmanthus headspace (flowers) (China) 1 68917-05-5 Osmanthus fragrans (Thunb.) Lour., var. auranticus Makino, fam. Oleaceae 1.43%
Magnolia purpurella (China) 1 Magnolia purpurella Law et Zhou, fam. Magnoliaceae 12.21%
Magnolia purpurella (China) 2 Magnolia purpurella Law et Zhou, fam. Magnoliaceae 1.57%
Osmanthus headspace (flowers) (China) 2 68917-05-5 Osmanthus fragrans (Thunb.) Lour., var. thunbergii Makino, fam. Oleaceae 0.6%
Osmanthus headspace (flowers) (China) 3 68917-05-5 Osmanthus fragrans (Thunb.) Lour., var. latifolius Makino, fam. Oleaceae 1.0%
Bitter orange leaf (Petitgrain) (China) 1 8014-17-3 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.6%
Lavandin (France) (Grosso) 2 8022-15-9 Lavandula x hybrida Rev. (L. x intermedia Emeric ex Loiesleur), Lamiaceae 0.01%
Lavandin (France) (Abrialis) 2 8022-15-9 Lavandula x hybrida Rev. (L. x intermedia Emeric ex Loiseleur), Lamiaceae 0.25%
Spike lavender 8016-78-2 Lavandula latifolia Medikus (L. spica D.C.), fam. Lamiaceae (Labiatae) 0.18%
Lawsonia inermis flower headspace (China) Lawsonia inermis L., fam. Lythraceae 1.15%
Acronychia pedunculata (China) Acronychia pedunculata (L.) Miq., fam. Rutaceae 0.87%
Daphne tangutica flower concrete (China) Daphne tangutica Maxim., fam. Thymelaeaceae 0.28%
Jasmine rose flower headspace (China) 2 Gardenia jasminoides Ellis var. fortuniana Lindl., fam. Rubiaceae 0.93%
Clerodendrum fragrans flower (China) Clerodendrum fragrans Vent., fam. Verbenaceae 1.66%
Lawsonia inermis flower 1a Lawsonia inermis L. (syn. L. alba Lam.), fam. Lythraceae 0.5%
Lawsonia inermis flower 1b Lawsonia inermis L. (syn. L. alba Lam.), fam. Lytraceae 0.2%
Fagraea berteriana flower Fagraea berteriana A. Gray ex Benth., fam. Potaliaceae 0.49%
Lavender (Lithuania) 8000-28-0 Lavandula angustifolia Mill., fam. Lamiaceae (Labiatae) 2.0%
Bois-de-Rose (Brazil) 1c 8015-77-8 Aniba rosaeodora var. amazonica Ducke, fam. Lauraceae 0.26%
Bois-de-Rose (Brazil) 1b 8015-77-8 Abina rosaeodora var. amazonica Ducke, fam. Laureaceae 0.15%
Bois-de-Rose (Brazil) 1a 8015-77-8 Aniba rosaeodora var. amazonica Ducke, fam. Lauraceae 0.02%
Neroli bigarade (bitter orange flower) China 1 8016-38-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.09%
Perilla frutescens (China) 2b leaf 90082-61-4 Perilla frutescens (L.) Brit., fam. Lamiaceae (Labiatae) 0.19%
Alstonia scholaris Alstonia scholaris (L.) R.Br., fam. Apocynaceae 0.7%
Zataria multiflora (Iran) 1b flower Zataria multiflora Boiss., fam. Lamiaceae (Labiatae) 0.49%
Cassie absolute 1b headspace 8023-82-3 Acacia farnesiana (L.) Willd., fam. Mimosaceae (Leguminosae) 0.05%