Labd-14-ene, 8,13-epoxy-, (13R)-

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  • Identifiers

    CAS number
    596-84-9

    Molecular formula
    C20H34O

    SMILES
    C[C@@]1(CC[C@H]2[C@@]3(CCCC([C@H]3CC[C@@]2(O1)C)(C)C)C)C=C

    Retention indicies (RI)

    • DB5: 1990.57
    • Carbowax: 2341.0

  • Odor profile

    Fragrance
    Woody 84.13%
    Amber 57.48%
    Dry 51.07%
    Sweet 50.77%
    Cedar 48.35%
    Musk 41.94%
    Spicy 41.62%
    Tobacco 40.71%
    Camphoreous 36.28%
    Pine 35.06%

     

    Flavor
    Sweet 64.91%
    Woody 54.04%
    Pine 41.78%
    Dry 40.67%
    Camphor 39.74%
    Herbal 32.25%
    Fresh 29.61%
    Wood 29.09%
    Earthy 27.8%
    Mint 26.31%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    5.9

    pKa est.
    8.42 (weak base)

    Molecular weight
    290.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    346°C

    Flash point

    • 159.67 ˚C est.

  • Synonyms

    • Labd-14-ene, 8,13-epoxy-, (13R)-
    • 596-84-9
    • (+)-Manoyl oxide
    • Manoyl oxide
    • (3R,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromene
    • ent-13-epi-manoyl oxide
    • 1H-Naphtho(2,1-b)pyran, 3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-, (3R-(3alpha,4abeta,6aalpha,10abeta,10balpha))-
    • 3-Ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-1H-naphtho(2,1-b)pyran (3R-(3alpha,4abeta,6aalpha,10abeta,10balpha))-
    • 3-Ethenyl-3,4a,7,7,10a-pentamethyldodecahydro-1H-naphtho[2,1-b]pyran
    • (13R)-ent-8,13-epoxylabd-14-ene
    • (-)-ent-13-epi-Manoyl oxide
    • DTXSID40975006
    • CHEBI:138224
    • (13R)-epi-8,13-epoxylabd-14-ene
    • C21714
    • (3R,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyldodecahydro-1H-naphtho[2,1-b]pyran
    • 1H-NAPHTHO(2,1-B)PYRAN, 3-ETHENYLDODECAHYDRO-3,4A,7,7,10A-PENTAMETHYL-, [3R-(3A,4A,B.,6A,A,10A,B,10B,A)]
    • 1H-Naphtho[2,1-b]pyran, 3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-, (3R,4aS,6aR,10aR,10bS)-
    • 27642-41-7

  • Applications

    Labd-14-ene, 8,13-epoxy-, (13R)- (CAS 596-84-9) is a labdane-type diterpene oxide with an epoxy group. In practice, it is viewed as a synthetic intermediate and core scaffold for diterpene fragrance compounds, and may be used as an intermediate for fragrance ingredients and scent fixatives in perfumery and cosmetics. Its epoxy functionality enables it to serve as a precursor for epoxy-containing monomers or linkages in polymers, coatings, and adhesives. It is also considered a useful chiral building block for the development of fine chemicals in pharmaceuticals or agrochemicals, and may be evaluated for specialized formulation chemistries under local regulations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 339.52
    methanol 215.44
    isopropanol 365.71
    water 0.97
    ethyl acetate 733.97
    n-propanol 457.87
    acetone 595.2
    n-butanol 498.01
    acetonitrile 388.85
    DMF 714.86
    toluene 1232.11
    isobutanol 460.87
    1,4-dioxane 1403.52
    methyl acetate 558.29
    THF 2256.8
    2-butanone 617.03
    n-pentanol 287.2
    sec-butanol 351.61
    n-hexane 161.97
    ethylene glycol 34.76
    NMP 968.3
    cyclohexane 487.77
    DMSO 299.34
    n-butyl acetate 776.6
    n-octanol 303.86
    chloroform 1671.4
    n-propyl acetate 454.15
    acetic acid 287.66
    dichloromethane 1318.5
    cyclohexanone 1344.2
    propylene glycol 71.23
    isopropyl acetate 641.65
    DMAc 699.62
    2-ethoxyethanol 277.08
    isopentanol 502.05
    n-heptane 200.3
    ethyl formate 343.46
    1,2-dichloroethane 800.02
    n-hexanol 645.9
    2-methoxyethanol 419.47
    isobutyl acetate 436.06
    tetrachloromethane 349.96
    n-pentyl acetate 645.66
    transcutol 1273.0
    n-heptanol 336.37
    ethylbenzene 418.0
    MIBK 554.0
    2-propoxyethanol 743.11
    tert-butanol 390.01
    MTBE 712.49
    2-butoxyethanol 461.8
    propionic acid 310.27
    o-xylene 571.97
    formic acid 63.52
    diethyl ether 915.22
    m-xylene 806.36
    p-xylene 512.06
    chlorobenzene 909.54
    dimethyl carbonate 311.44
    n-octane 64.76
    formamide 90.09
    cyclopentanone 1282.83
    2-pentanone 672.38
    anisole 505.24
    cyclopentyl methyl ether 1322.54
    gamma-butyrolactone 1289.59
    1-methoxy-2-propanol 484.4
    pyridine 1118.47
    3-pentanone 607.42
    furfural 855.85
    n-dodecane 42.69
    diethylene glycol 310.09
    diisopropyl ether 436.88
    tert-amyl alcohol 330.41
    acetylacetone 672.44
    n-hexadecane 51.61
    acetophenone 441.72
    methyl propionate 608.06
    isopentyl acetate 791.48
    trichloroethylene 1370.0
    n-nonanol 285.26
    cyclohexanol 676.83
    benzyl alcohol 352.24
    2-ethylhexanol 430.22
    isooctanol 300.55
    dipropyl ether 651.41
    1,2-dichlorobenzene 697.13
    ethyl lactate 202.43
    propylene carbonate 760.97
    n-methylformamide 292.45
    2-pentanol 382.13
    n-pentane 214.53
    1-propoxy-2-propanol 630.38
    1-methoxy-2-propyl acetate 775.09
    2-(2-methoxypropoxy) propanol 404.16
    mesitylene 504.1
    ε-caprolactone 1136.56
    p-cymene 335.16
    epichlorohydrin 1190.87
    1,1,1-trichloroethane 880.07
    2-aminoethanol 117.7
    morpholine-4-carbaldehyde 982.63
    sulfolane 921.08
    2,2,4-trimethylpentane 106.26
    2-methyltetrahydrofuran 1542.88
    n-hexyl acetate 814.59
    isooctane 102.0
    2-(2-butoxyethoxy)ethanol 527.15
    sec-butyl acetate 400.05
    tert-butyl acetate 681.56
    decalin 170.03
    glycerin 102.73
    diglyme 953.71
    acrylic acid 227.59
    isopropyl myristate 304.32
    n-butyric acid 569.63
    acetyl acetate 512.56
    di(2-ethylhexyl) phthalate 263.68
    ethyl propionate 437.48
    nitromethane 439.18
    1,2-diethoxyethane 715.56
    benzonitrile 596.18
    trioctyl phosphate 209.17
    1-bromopropane 735.09
    gamma-valerolactone 1484.27
    n-decanol 199.39
    triethyl phosphate 251.91
    4-methyl-2-pentanol 299.22
    propionitrile 459.44
    vinylene carbonate 704.68
    1,1,2-trichlorotrifluoroethane 539.69
    DMS 517.43
    cumene 289.52
    2-octanol 241.18
    2-hexanone 434.62
    octyl acetate 363.64
    limonene 477.64
    1,2-dimethoxyethane 626.59
    ethyl orthosilicate 262.85
    tributyl phosphate 245.59
    diacetone alcohol 460.54
    N,N-dimethylaniline 374.3
    acrylonitrile 414.8
    aniline 675.97
    1,3-propanediol 229.52
    bromobenzene 1078.94
    dibromomethane 1022.44
    1,1,2,2-tetrachloroethane 1120.56
    2-methyl-cyclohexyl acetate 492.23
    tetrabutyl urea 283.72
    diisobutyl methanol 268.74
    2-phenylethanol 510.16
    styrene 475.14
    dioctyl adipate 360.58
    dimethyl sulfate 342.42
    ethyl butyrate 495.55
    methyl lactate 230.68
    butyl lactate 378.8
    diethyl carbonate 339.54
    propanediol butyl ether 345.94
    triethyl orthoformate 422.63
    p-tert-butyltoluene 329.0
    methyl 4-tert-butylbenzoate 506.69
    morpholine 1364.86
    tert-butylamine 368.16
    n-dodecanol 147.72
    dimethoxymethane 757.9
    ethylene carbonate 677.3
    cyrene 360.36
    2-ethoxyethyl acetate 761.26
    2-ethylhexyl acetate 704.85
    1,2,4-trichlorobenzene 767.36
    4-methylpyridine 1248.17
    dibutyl ether 454.08
    2,6-dimethyl-4-heptanol 268.74
    DEF 665.76
    dimethyl isosorbide 759.8
    tetrachloroethylene 716.69
    eugenol 381.04
    triacetin 569.1
    span 80 401.26
    1,4-butanediol 85.02
    1,1-dichloroethane 864.63
    2-methyl-1-pentanol 324.5
    methyl formate 243.25
    2-methyl-1-butanol 473.83
    n-decane 88.03
    butyronitrile 535.17
    3,7-dimethyl-1-octanol 318.31
    1-chlorooctane 298.38
    1-chlorotetradecane 115.38
    n-nonane 87.87
    undecane 58.17
    tert-butylcyclohexane 136.91
    cyclooctane 199.19
    cyclopentanol 586.88
    tetrahydropyran 1774.38
    tert-amyl methyl ether 528.01
    2,5,8-trioxanonane 586.34
    1-hexene 342.4
    2-isopropoxyethanol 274.74
    2,2,2-trifluoroethanol 134.73
    methyl butyrate 495.21

    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
Cypress 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 0.4%
Pinus strobus 1 Pinus strobus L. (White Pine), fam. Pinaceae 0.2%
Juniperus martinezii Juniperus martinezii Perez de la Rosa, fam. Cupressaceae 0.9%
Juniperus flaccida var. flaccida Juniperus flaccida Schlecht, var. flaccida, fam. Cupressaceae 6.6%
Cypress (Algeria) 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 0.16%
Vitex agnus-castus leaf (Italy) Vitex agnus-castus L., fam. Verbenaceae 0.2%
Vitex agnus-castus fruit (Italy) Vitex agnus-castus L., fam. Verbenaceae 0.01%
Vitex agnus-castus inflorescence (Italy) Vitex agnus-castus L., fam. Verbenaceae 0.1%
Xylopia aethiopica fruit (Benin) 2 Xylopia aethiopica (Dunal) A. Richard, fam. Annonaceae 0.05%
Xylopia aethiopica leaf (Benin) Xylopia aethiopica (Dunal) A. Richard, fam. Annonaceae 0.05%
Clary sage (Spain) 8016-63-5 Salvia sclarea L., fam. Lamiaceae (Labiatae) 1.15%
Keora (India) 4 Pandanus odoratissimus L. (P. fascicularis Lam.), fam. Pandanaceae 0.09%
Teucrium divaricatum (Greece) Teucrium divaricatum Heldr. ssp. divaricatum, fam. Lamiaceae (Labiatae) 0.25%
Cypress, Leyland (Poland) Cupressocyparis leylandii (Dall. et Jacks.) Dall., fam. Cupressaceae 0.4%
Clary sage (Hungary) 1a 8016-63-5 Salvia sclarea L., fam. Lamiaceae (Labiatae) 2.8%
Clary sage (Hungary) 1b 8016-63-5 Salvia sclarea L., fam. Lamiaceae (Labiatae) 3.6%
Cupressus macrocarpa leaf (Argentina) Cupressus macrocarpa Hartw., fam. Cupressaceae 0.05%
Nepeta persica (Iran) Nepeta persica Boiss, fam. Lamiaceae (Labiatae) 1.2%
Guarea macrophylla ssp. tuberculata leaf Guarea macrophylla Vahl. ssp. tuberculata Vellozo, fam. Meliaceae 8.2%
Pinus sylvestris (Greece) 8023-99-2 Pinus sylvestris L. (Scotch pine), fam. Pinaceae 30.2%
Pinus nigra ssp. laricio (Corsica) 1a Pinus nigra ssp. laricio (Poir.) Maire, fam. Pinaceae 1.9%
Pinus nigra ssp. laricio (Corsica) 1b Pinus nigra ssp. laricio (Poir.) Maire, fam. Pinaceae 22.6%
Lime (Mexican, West Indian, Key) (France) 1 leaf 8008-26-2 Citrus aurantifolia (Christm.) Swingle, cultivar Mexican, fam. Rutaceae 0.7%
Baga fruit Annona glabra L., fam. Annonaceae 0.01%
Libanothamus lucidus leaf (Venezuela) Libanothomus lucidus (Aristeg) Cuatr., fam. Asteraceae (Compositae) 0.2%
Guarea macrophylla ssp. tuberculata stem bark Guerea macrophylla Vahl. ssp. tuberculata Vellozo, fam. Meilaceae 0.3%
Elaeoselinum gummiferum Elaeoselinum gummiferum (Desf.) Tutin, fam. Apiaceae (Umbelliferae) 0.01%
Cypress (Croatia) 2 8013-86-3 Cupressus sempervirens L. (C. fastigiata DC), fam. Cupressaceae 1.5%