[1S-(1alpha,4alpha,7alpha)]-1,2,3,4,5,6,7,8-octahydro-1,4,9,9-tetramethyl-4,7-methanoazulene

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  • Identifiers

    CAS number
    514-51-2

    Molecular formula
    C15H24

    SMILES
    C[C@H]1CCC2=C1C[C@H]3CC[C@@]2(C3(C)C)C

    Retention indicies (RI)

    • DB5: 1380.0
    • Carbowax: 1488.0

  • Odor profile

    Woody 87.74%
    Dry 51.21%
    Amber 47.54%
    Sweet 44.16%
    Cedar 36.83%
    Balsamic 36.74%
    Sandalwood 34.94%
    Spicy 34.88%
    Musk 30.4%
    Vetiver 29.6%

    Scent© AI

  • Properties

    XLogP3-AA
    4.3

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    276°C

    Flash point est.
    101.63 ˚C

  • Synonyms

    • 514-51-2
    • [1S-(1alpha,4alpha,7alpha)]-1,2,3,4,5,6,7,8-octahydro-1,4,9,9-tetramethyl-4,7-methanoazulene
    • (1R,5S,8R)-1,5,11,11-tetramethyltricyclo[6.2.1.02,6]undec-2(6)-ene
    • Patschulen
    • DTXSID7052153
    • CSKINCSXMLCMAR-RWSFTLGLSA-N
    • HY-N12378
    • (1S,4R,7R)-1,4,9,9-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-4,7-methanoazulene
    • DA-61624
    • CS-0899903
    • Q63392424

  • Applications

    A terpenoid sesquiterpene hydrocarbon from pine resins and wood essential oils, [1S-(1alpha,4alpha,7alpha)]-1,2,3,4,5,6,7,8-octahydro-1,4,9,9-tetramethyl-4,7-methanoazulene (CAS 514-51-2) is used primarily in fragrance and essential-oil applications: dosed at very low levels to impart woody–resinous–amber nuances, to build and round out woody, chypre, fougère, incense accords and household care scents; and, more importantly, as a starting material for making more stable, fixative odorants via oxidation/functionalization to related ketones and oxides (e.g., isolongifolanone/isolongifolenone types) and other woody–amber ingredients; in green chemistry it serves as a renewable terpenoid building block for intermediates, resins and hydrophobic additives in materials; in research it is employed as an analytical reference for essential-oil authentication, as a substrate for selective functionalization and enzyme/microbial biotransformations, and as a marker for tracing natural raw-material provenance; it is also explored as a semiochemical (attractant/repellent) and as a trace flavor modulator in permitted uses subject to local regulations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 122.82
    methanol 88.89
    isopropanol 148.81
    water 0.98
    ethyl acetate 344.93
    n-propanol 150.41
    acetone 378.25
    n-butanol 168.15
    acetonitrile 252.91
    DMF 432.41
    toluene 542.43
    isobutanol 127.44
    1,4-dioxane 667.91
    methyl acetate 321.87
    THF 1028.5
    2-butanone 350.62
    n-pentanol 84.59
    sec-butanol 110.33
    n-hexane 42.36
    ethylene glycol 22.93
    NMP 324.36
    cyclohexane 112.53
    DMSO 161.07
    n-butyl acetate 426.7
    n-octanol 137.0
    chloroform 794.12
    n-propyl acetate 221.04
    acetic acid 80.85
    dichloromethane 635.55
    cyclohexanone 567.16
    propylene glycol 33.8
    isopropyl acetate 332.52
    DMAc 343.78
    2-ethoxyethanol 130.6
    isopentanol 153.8
    n-heptane 78.33
    ethyl formate 189.57
    1,2-dichloroethane 391.53
    n-hexanol 209.82
    2-methoxyethanol 207.37
    isobutyl acetate 209.95
    tetrachloromethane 247.9
    n-pentyl acetate 261.61
    transcutol 428.61
    n-heptanol 142.72
    ethylbenzene 270.28
    MIBK 281.75
    2-propoxyethanol 310.4
    tert-butanol 175.88
    MTBE 287.89
    2-butoxyethanol 208.32
    propionic acid 106.97
    o-xylene 352.64
    formic acid 21.0
    diethyl ether 303.4
    m-xylene 402.59
    p-xylene 402.55
    chlorobenzene 426.22
    dimethyl carbonate 179.02
    n-octane 39.02
    formamide 56.23
    cyclopentanone 698.45
    2-pentanone 337.65
    anisole 394.65
    cyclopentyl methyl ether 447.38
    gamma-butyrolactone 580.27
    1-methoxy-2-propanol 211.86
    pyridine 613.55
    3-pentanone 284.66
    furfural 443.97
    n-dodecane 28.83
    diethylene glycol 149.47
    diisopropyl ether 162.25
    tert-amyl alcohol 125.67
    acetylacetone 475.38
    n-hexadecane 35.53
    acetophenone 328.81
    methyl propionate 273.79
    isopentyl acetate 437.4
    trichloroethylene 678.42
    n-nonanol 140.12
    cyclohexanol 179.51
    benzyl alcohol 197.84
    2-ethylhexanol 169.03
    isooctanol 129.22
    dipropyl ether 313.32
    1,2-dichlorobenzene 421.47
    ethyl lactate 95.28
    propylene carbonate 331.41
    n-methylformamide 160.92
    2-pentanol 117.18
    n-pentane 55.05
    1-propoxy-2-propanol 270.78
    1-methoxy-2-propyl acetate 451.87
    2-(2-methoxypropoxy) propanol 222.34
    mesitylene 293.61
    ε-caprolactone 453.16
    p-cymene 255.86
    epichlorohydrin 531.35
    1,1,1-trichloroethane 534.69
    2-aminoethanol 51.66
    morpholine-4-carbaldehyde 472.3
    sulfolane 413.09
    2,2,4-trimethylpentane 34.43
    2-methyltetrahydrofuran 514.39
    n-hexyl acetate 327.82
    isooctane 40.94
    2-(2-butoxyethoxy)ethanol 248.91
    sec-butyl acetate 196.57
    tert-butyl acetate 379.52
    decalin 70.5
    glycerin 47.45
    diglyme 530.65
    acrylic acid 87.84
    isopropyl myristate 189.4
    n-butyric acid 203.49
    acetyl acetate 318.33
    di(2-ethylhexyl) phthalate 151.4
    ethyl propionate 237.33
    nitromethane 245.73
    1,2-diethoxyethane 346.82
    benzonitrile 354.89
    trioctyl phosphate 116.33
    1-bromopropane 294.08
    gamma-valerolactone 705.0
    n-decanol 106.46
    triethyl phosphate 167.08
    4-methyl-2-pentanol 110.52
    propionitrile 284.76
    vinylene carbonate 361.92
    1,1,2-trichlorotrifluoroethane 230.29
    DMS 312.19
    cumene 200.59
    2-octanol 108.08
    2-hexanone 231.28
    octyl acetate 196.7
    limonene 257.47
    1,2-dimethoxyethane 390.13
    ethyl orthosilicate 169.71
    tributyl phosphate 134.89
    diacetone alcohol 240.54
    N,N-dimethylaniline 275.78
    acrylonitrile 296.76
    aniline 318.21
    1,3-propanediol 106.37
    bromobenzene 551.0
    dibromomethane 424.46
    1,1,2,2-tetrachloroethane 488.72
    2-methyl-cyclohexyl acetate 281.06
    tetrabutyl urea 177.68
    diisobutyl methanol 142.86
    2-phenylethanol 298.16
    styrene 295.32
    dioctyl adipate 211.33
    dimethyl sulfate 203.35
    ethyl butyrate 327.54
    methyl lactate 109.32
    butyl lactate 154.11
    diethyl carbonate 227.82
    propanediol butyl ether 135.9
    triethyl orthoformate 246.97
    p-tert-butyltoluene 268.49
    methyl 4-tert-butylbenzoate 338.31
    morpholine 509.28
    tert-butylamine 149.74
    n-dodecanol 85.05
    dimethoxymethane 436.55
    ethylene carbonate 319.89
    cyrene 180.34
    2-ethoxyethyl acetate 321.99
    2-ethylhexyl acetate 358.85
    1,2,4-trichlorobenzene 432.81
    4-methylpyridine 637.37
    dibutyl ether 220.37
    2,6-dimethyl-4-heptanol 142.86
    DEF 299.04
    dimethyl isosorbide 453.94
    tetrachloroethylene 363.68
    eugenol 267.78
    triacetin 284.2
    span 80 185.24
    1,4-butanediol 38.57
    1,1-dichloroethane 429.95
    2-methyl-1-pentanol 90.03
    methyl formate 147.84
    2-methyl-1-butanol 124.6
    n-decane 50.43
    butyronitrile 284.13
    3,7-dimethyl-1-octanol 152.59
    1-chlorooctane 139.31
    1-chlorotetradecane 67.84
    n-nonane 46.31
    undecane 36.98
    tert-butylcyclohexane 67.31
    cyclooctane 61.27
    cyclopentanol 187.93
    tetrahydropyran 567.28
    tert-amyl methyl ether 193.13
    2,5,8-trioxanonane 352.13
    1-hexene 114.06
    2-isopropoxyethanol 122.83
    2,2,2-trifluoroethanol 62.4
    methyl butyrate 264.81

    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
Patchouli (Indonesia, Sumatra) 2 8014-09-3 Pogostemon cablin Benth. (P. patchouli Pellet), fam. Lamiaceae (Labiatae) 2.64%
Patchouli (Indonesia, Sumatra) 1 8014-09-3 Pogostemon cablin Benth. (P. patchouli Pellet), fam. Lamiaceae (Labiatae) 3.35%
Patchouli (Vietnam) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 3.22%
Spikenard 2 8022-22-8 Nardostachys jatamansi (Roxb.) DC., fam. Valerianaceae 0.7%
Guaiacwood 1 8016-23-7 Bulnesia sarmienti Lorentz ex Griseb, fam. Zygophyllaceae 0.2%
Patchouli (India) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.01%
Patchouli (Indonesia) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 13.0%
Patchouli (Indonesia, Java) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.97%
Patchouli (Indonesia, Sumatra) 3 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 2.64%
Patchouli (West India) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 3.88%
Patchouli (Costa Rica) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 6.66%
Patchouli (China) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 6.91%
Patchouli (Indonesia) 4 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.7%
Patchouli (Taiwan) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.91%
Patchouli (The Philippines) 8014-09-3 Posgostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.63%
Patchouli (Japan) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.51%
Patchouli (Indonesia) 3 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.08%
Pectis elongata Pectis elongata Kunth, fam. Asteraceae (Compositae) 0.01%
Psiadia viscosa Psiadia viscosa (Lam.) A.J. Scott, fam. Asteraceae (Compositae) 4.2%
Tagetes (Egypt) 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.37%
Valeriana javanica root (Indonesia) Valeriana javanica Blume, fam. Valerianaceae 0.3%
Curcuma aromatica (India) 1 petiole Curcuma aromatica Salisb., fam. Zingiberaceae 0.3%
Tagetes filifolia (Peru) Tagetes filifolia Lag., fam. Asteraceae (Compositae) 0.01%
Patchouli (Indonesia) 6 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.3%
Tagetes (Italy) 1b 8016-84-0 Tagetes minuta L. (Marigold), fam. Asteraceae (Compositae) 0.1%
Turmeric (India) 5b leaf 8024-37-1 Curcuma longa L., cv. Roma (C. domestica Val.), fam. Zingiberaceae 0.4%
Patchouli (China) 3a root 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.14%
Patchouli (China) 3b rhizome 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.24%
Patchouli (India) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 16.19%
Patchouli (Indonesia) 5 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 15.59%
Calamus (India) 3 root 8015-79-0 Acorus calamus L., fam. Araceae 0.33%
Salvia desoleana (Italy) 1a CO2-extract Salvia desoleana, fam. Lamiaceae (Labiatae) 0.05%
Salvia desoleana (Italy) 1b hydrodistilled Salvia desoleana, fam. Lamiaceae (Labiatae) 0.05%
Lemongrass (Lagos) 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 0.2%
Phlomis fruticosa (Yugoslavia) Phlomis fruticosa L., fam. Lamiaceae (Labiatae) 1.1%
Osage orange fruit, 1b steamdistilled Maclura pomifera (Raf.) Schneid, fam. Moraceae 1.2%
Hypericum perfoliatum (Greece) Hypericum perfoliatum L., fam. Guttiferae (Hyperiaceae) 0.02%
Patchouli (Indonesia)5 ? Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.92%