Sclareolide

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  • Identifiers

    CAS number
    564-20-5

    Molecular formula
    C16H26O2

    SMILES
    C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CC(=O)O3)C)(C)C

  • Odor profile

    Fragrance
    Woody 85.9%
    Amber 65.18%
    Dry 60.04%
    Cedar 56.66%
    Musk 56.21%
    Tobacco 45.95%
    Spicy 41.05%
    Animal 36.9%
    Powdery 36.34%
    Vetiver 34.68%

     

    Flavor
    Camphor 47.21%
    Woody 43.85%
    Sweet 38.27%
    Pine 36.6%
    Herbal 35.84%
    Dry 32.22%
    Minty 29.7%
    Earthy 28.65%
    Fresh 28.27%
    Old paper 24.72%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    4.3

    pKa est.
    8.28 (weak base)

    Molecular weight
    250.38 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    374°C

    Flash point

    • 162.14 ˚C est.

    Solubility expt.

    • Insoluble in water and oils; soluble in acetone and toluene
    • slightly soluble (in ethanol)

  • Synonyms

    • Sclareolide
    • 564-20-5
    • (3aR)-(+)-Sclareolide
    • Norambreinolide
    • (+)-sclareolide
    • 12-Norambreinolide
    • CLAREOLIDE
    • Norambreinolide, (+)-
    • (3aR,5aS,9aS,9bR)-Decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one
    • DTXSID8047686
    • Decahydrotetramethylnaphthofuranone
    • 37W4O0O6E6
    • (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-one
    • EINECS 209-269-0
    • SCLAREOLIDE [FHFI]
    • MLS001173371
    • (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzofuran-2-one
    • DTXCID6027686
    • FEMA NO. 3794
    • SMR000538921
    • Naphtho(2,1-b)furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)-
    • 3a,4,5,5aalpha,6,7,8,9,9a,9balpha-decahydro-3abeta,6,6,9abeta-tetramethylnaphtho(2,1-b)furan-2(1H)-one
    • Naphtho(2,1-b)furan-2(1H)-one, 3a,4,5,5aalpha,6,7,8,9,9a,9balpha-decahydro-3abeta,6,6,9abeta-tetramethyl-
    • Naphtho(2,1-b)furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-, (3aR-(3aalpha,5abeta,9aalpha,9bbeta))-
    • MFCD00134168
    • Naphtho[2,1-b]furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)-
    • UNII-37W4O0O6E6
    • (3aR)-(+)-Sclareolide; (+)-12-Norambreinolide; Decahydrotetramethylnaphthofuranone
    • Naphtho[2,1-b]furan-2(1H)-one, decahydro-3a,6,6,9a-tetramethyl-, [3ar-(3a.alpha.,5a.beta.,9a.alpha.,9b.beta.)]-
    • CLARY SAGE LACTONE
    • SCLAREOLIDE [INCI]
    • (3a,R)-(+)-Sclareolide
    • SCHEMBL83395
    • Sclareolide (Norambreinolide)
    • CHEMBL304461
    • cid_929262
    • BDBM75178
    • CHEBI:156168
    • HMS2860M07
    • (3aR)-(+)-Sclareolide, 97%
    • HY-N0129
    • Tox21_302544
    • s2355
    • AKOS015901397
    • CCG-208493
    • DS-7369
    • FS34059
    • NCGC00163620-01
    • NCGC00163620-03
    • NCGC00256856-01
    • CAS-564-20-5
    • (3aR)-(+)-Sclareolide, analytical standard
    • CS-0007855
    • S0847
    • (3aR)-(+)-Sclareolide, natural, 97%, FG
    • H10516
    • SR-01000812893
    • SR-01000812893-3
    • BRD-K72925150-001-10-3
    • BRD-K72925150-001-11-1
    • (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e][1]benzouran-2-one
    • (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[e]benzofuran-2-one
    • (3AR-(3aalpha,5abeta,9aalpha,9bbeta))decahydro-3a,6,6,9a-tetramethylnaphth(2,1-b)furan-2(1H)-one

  • Applications

    (3aR)-(+)-Sclareolide (CAS 564-20-5) is a diterpene lactone derived from clary sage that is prized in fragrance manufacture for its strong amber-woody fixative power, widely employed as a semi-synthetic precursor to high-value Ambrox/Ambroxan, as a flavor enhancer in foods, an odor booster in cosmetics, candles, detergents and deodorants, offering excellent oxidative stability, durable physicochemical properties and good solubility in alcohols and oils, judged safe under IFRA guidelines; it is also being investigated pre-clinically for cyclic-AMP mediated weight-management potential and serves as a versatile scaffold for the synthesis of other bioactive diterpenes.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 165.35
    methanol 230.98
    isopropanol 150.13
    water 2.56
    ethyl acetate 486.06
    n-propanol 212.06
    acetone 602.22
    n-butanol 171.5
    acetonitrile 563.31
    DMF 796.12
    toluene 875.8
    isobutanol 164.84
    1,4-dioxane 926.17
    methyl acetate 521.29
    THF 1588.83
    2-butanone 547.34
    n-pentanol 83.55
    sec-butanol 121.56
    n-hexane 14.01
    ethylene glycol 55.64
    NMP 1056.08
    cyclohexane 73.53
    DMSO 440.83
    n-butyl acetate 308.11
    n-octanol 74.9
    chloroform 1981.8
    n-propyl acetate 242.88
    acetic acid 305.01
    dichloromethane 1540.73
    cyclohexanone 992.47
    propylene glycol 66.01
    isopropyl acetate 344.51
    DMAc 582.07
    2-ethoxyethanol 137.83
    isopentanol 151.85
    n-heptane 13.23
    ethyl formate 318.75
    1,2-dichloroethane 857.79
    n-hexanol 172.75
    2-methoxyethanol 319.67
    isobutyl acetate 191.24
    tetrachloromethane 240.94
    n-pentyl acetate 224.0
    transcutol 608.16
    n-heptanol 87.72
    ethylbenzene 233.1
    MIBK 272.76
    2-propoxyethanol 345.16
    tert-butanol 146.87
    MTBE 169.01
    2-butoxyethanol 184.34
    propionic acid 291.06
    o-xylene 346.35
    formic acid 147.11
    diethyl ether 254.64
    m-xylene 468.31
    p-xylene 289.44
    chlorobenzene 972.95
    dimethyl carbonate 320.56
    n-octane 5.29
    formamide 235.9
    cyclopentanone 1272.49
    2-pentanone 405.49
    anisole 395.93
    cyclopentyl methyl ether 569.32
    gamma-butyrolactone 1510.05
    1-methoxy-2-propanol 264.01
    pyridine 1261.05
    3-pentanone 371.29
    furfural 1129.69
    n-dodecane 4.91
    diethylene glycol 236.08
    diisopropyl ether 95.95
    tert-amyl alcohol 104.5
    acetylacetone 590.83
    n-hexadecane 6.29
    acetophenone 393.28
    methyl propionate 457.86
    isopentyl acetate 286.9
    trichloroethylene 1828.92
    n-nonanol 69.57
    cyclohexanol 266.35
    benzyl alcohol 292.7
    2-ethylhexanol 101.31
    isooctanol 74.11
    dipropyl ether 124.38
    1,2-dichlorobenzene 728.11
    ethyl lactate 135.37
    propylene carbonate 730.32
    n-methylformamide 500.01
    2-pentanol 104.25
    n-pentane 20.3
    1-propoxy-2-propanol 223.22
    1-methoxy-2-propyl acetate 409.44
    2-(2-methoxypropoxy) propanol 183.45
    mesitylene 231.84
    ε-caprolactone 815.74
    p-cymene 118.7
    epichlorohydrin 1284.85
    1,1,1-trichloroethane 830.6
    2-aminoethanol 112.19
    morpholine-4-carbaldehyde 917.61
    sulfolane 1113.19
    2,2,4-trimethylpentane 12.62
    2-methyltetrahydrofuran 788.69
    n-hexyl acetate 293.17
    isooctane 11.69
    2-(2-butoxyethoxy)ethanol 218.67
    sec-butyl acetate 191.56
    tert-butyl acetate 306.66
    decalin 32.66
    glycerin 119.23
    diglyme 472.49
    acrylic acid 311.78
    isopropyl myristate 95.66
    n-butyric acid 334.28
    acetyl acetate 431.23
    di(2-ethylhexyl) phthalate 120.69
    ethyl propionate 243.39
    nitromethane 821.08
    1,2-diethoxyethane 217.79
    benzonitrile 609.92
    trioctyl phosphate 79.54
    1-bromopropane 404.78
    gamma-valerolactone 1439.6
    n-decanol 47.45
    triethyl phosphate 115.11
    4-methyl-2-pentanol 80.4
    propionitrile 450.32
    vinylene carbonate 795.5
    1,1,2-trichlorotrifluoroethane 612.82
    DMS 388.02
    cumene 131.47
    2-octanol 57.03
    2-hexanone 215.02
    octyl acetate 124.69
    limonene 142.64
    1,2-dimethoxyethane 320.78
    ethyl orthosilicate 104.02
    tributyl phosphate 100.42
    diacetone alcohol 252.96
    N,N-dimethylaniline 236.68
    acrylonitrile 636.08
    aniline 638.57
    1,3-propanediol 154.54
    bromobenzene 1093.73
    dibromomethane 951.7
    1,1,2,2-tetrachloroethane 1185.87
    2-methyl-cyclohexyl acetate 204.98
    tetrabutyl urea 125.69
    diisobutyl methanol 61.15
    2-phenylethanol 316.53
    styrene 322.95
    dioctyl adipate 146.73
    dimethyl sulfate 457.97
    ethyl butyrate 199.15
    methyl lactate 214.12
    butyl lactate 175.63
    diethyl carbonate 163.88
    propanediol butyl ether 157.51
    triethyl orthoformate 148.7
    p-tert-butyltoluene 112.1
    methyl 4-tert-butylbenzoate 268.14
    morpholine 856.74
    tert-butylamine 93.2
    n-dodecanol 34.51
    dimethoxymethane 526.94
    ethylene carbonate 653.03
    cyrene 245.51
    2-ethoxyethyl acetate 354.84
    2-ethylhexyl acetate 237.91
    1,2,4-trichlorobenzene 848.87
    4-methylpyridine 1172.27
    dibutyl ether 86.87
    2,6-dimethyl-4-heptanol 61.15
    DEF 382.09
    dimethyl isosorbide 429.43
    tetrachloroethylene 745.0
    eugenol 253.79
    triacetin 310.48
    span 80 166.88
    1,4-butanediol 52.25
    1,1-dichloroethane 803.57
    2-methyl-1-pentanol 87.5
    methyl formate 449.68
    2-methyl-1-butanol 136.78
    n-decane 9.1
    butyronitrile 362.77
    3,7-dimethyl-1-octanol 81.69
    1-chlorooctane 63.98
    1-chlorotetradecane 22.93
    n-nonane 7.8
    undecane 6.5
    tert-butylcyclohexane 22.31
    cyclooctane 24.85
    cyclopentanol 326.61
    tetrahydropyran 822.49
    tert-amyl methyl ether 125.06
    2,5,8-trioxanonane 282.62
    1-hexene 61.74
    2-isopropoxyethanol 114.56
    2,2,2-trifluoroethanol 204.91
    methyl butyrate 285.45

    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