(+)-Norpatchoulenol

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  • Identifiers

    CAS number
    41429-52-1

    Molecular formula
    C14H22O

    SMILES
    C[C@@]12CC[C@H]3C[C@@H]1C=CC[C@]2(C3(C)C)O

  • Odor profile

    Woody 66.95%
    Earthy 57.74%
    Camphoreous 51.85%
    Herbal 49.74%
    Sweet 44.08%
    Spicy 41.17%
    Pine 40.7%
    Balsamic 40.48%
    Mint 38.38%
    Green 37.75%

    Scent© AI

  • Properties

    XLogP3-AA
    3.5

    Molecular weight
    206.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    289°C

    Flash point est.
    124.17 ˚C

  • Synonyms

    • (+)-Norpatchoulenol
    • Norpatchoulenol
    • 41429-52-1
    • (1R-(1alpha,4aalpha,6beta,8aalpha))-4a,5,6,7,8,8a-Hexahydro-8a,9,9-trimethyl-1,6-methanonaphthalen-1(2H)-ol
    • 1,6-Methanonaphthalen-1(2H)-ol, 4a,5,6,7,8,8a-hexahydro-8a,9,9-trimethyl-, (1R-(1alpha,4aalpha,6beta,8aalpha))-
    • (1S,3R,7R,8R)-2,2,8-trimethyltricyclo[5.3.1.03,8]undec-5-en-3-ol
    • SCHEMBL4935856
    • DTXSID90961676

  • Applications

    (+)-Norpatchoulenol (CAS 41429-52-1) is a rare chiral sesquiterpenoid alcohol originating from patchouli essential oil and also available synthetically; in perfumery it serves as a woody-earthy odorant and a low-volatility fixative that deepens, naturalizes, and extends accords in woody, amber, leather, and fougère compositions, as well as in soaps, detergents, personal care products, and scented candles; in analytics it is used as a GC-MS/HPLC reference standard to build chemical fingerprints, authenticate origin, and monitor storage/aging effects and chemotype quantification of patchouli oil; in synthesis and academia, the patchoulane scaffold of (+)-norpatchoulenol is exploited as a chiral building block for functionalization to new odorants and as a model for sesquiterpene rearrangement mechanisms, stereochemical studies, and terpene biosynthesis; moreover, its low water solubility and compatibility with common perfume solvents make it useful for evaluating fragrance carriers and controlled-release technologies in polymer matrices, microcapsules, and surfactant systems.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 164.69
    methanol 224.25
    isopropanol 120.91
    water 2.49
    ethyl acetate 162.82
    n-propanol 150.75
    acetone 209.3
    n-butanol 129.51
    acetonitrile 156.36
    DMF 382.13
    toluene 198.5
    isobutanol 93.86
    1,4-dioxane 508.98
    methyl acetate 155.39
    THF 819.52
    2-butanone 170.16
    n-pentanol 63.94
    sec-butanol 72.73
    n-hexane 18.71
    ethylene glycol 32.06
    NMP 186.41
    cyclohexane 33.24
    DMSO 180.26
    n-butyl acetate 131.9
    n-octanol 57.48
    chloroform 391.76
    n-propyl acetate 88.32
    acetic acid 82.84
    dichloromethane 306.95
    cyclohexanone 259.71
    propylene glycol 30.26
    isopropyl acetate 132.69
    DMAc 156.85
    2-ethoxyethanol 118.82
    isopentanol 91.45
    n-heptane 21.49
    ethyl formate 102.33
    1,2-dichloroethane 213.98
    n-hexanol 123.06
    2-methoxyethanol 239.08
    isobutyl acetate 73.5
    tetrachloromethane 106.84
    n-pentyl acetate 98.52
    transcutol 345.49
    n-heptanol 82.55
    ethylbenzene 82.18
    MIBK 124.61
    2-propoxyethanol 239.62
    tert-butanol 123.42
    MTBE 139.37
    2-butoxyethanol 147.39
    propionic acid 80.52
    o-xylene 107.51
    formic acid 50.98
    diethyl ether 212.88
    m-xylene 152.6
    p-xylene 104.13
    chlorobenzene 158.55
    dimethyl carbonate 104.79
    n-octane 10.57
    formamide 100.26
    cyclopentanone 384.59
    2-pentanone 165.83
    anisole 146.57
    cyclopentyl methyl ether 258.91
    gamma-butyrolactone 357.27
    1-methoxy-2-propanol 206.5
    pyridine 283.86
    3-pentanone 132.77
    furfural 260.08
    n-dodecane 7.01
    diethylene glycol 152.29
    diisopropyl ether 77.2
    tert-amyl alcohol 72.43
    acetylacetone 191.34
    n-hexadecane 8.3
    acetophenone 114.99
    methyl propionate 141.88
    isopentyl acetate 117.67
    trichloroethylene 323.36
    n-nonanol 57.95
    cyclohexanol 97.94
    benzyl alcohol 88.88
    2-ethylhexanol 68.75
    isooctanol 64.17
    dipropyl ether 117.89
    1,2-dichlorobenzene 146.28
    ethyl lactate 52.51
    propylene carbonate 151.63
    n-methylformamide 198.79
    2-pentanol 77.62
    n-pentane 26.01
    1-propoxy-2-propanol 164.89
    1-methoxy-2-propyl acetate 179.16
    2-(2-methoxypropoxy) propanol 100.47
    mesitylene 105.0
    ε-caprolactone 192.87
    p-cymene 59.15
    epichlorohydrin 375.06
    1,1,1-trichloroethane 211.44
    2-aminoethanol 71.92
    morpholine-4-carbaldehyde 292.49
    sulfolane 275.2
    2,2,4-trimethylpentane 12.95
    2-methyltetrahydrofuran 275.54
    n-hexyl acetate 119.29
    isooctane 17.17
    2-(2-butoxyethoxy)ethanol 150.18
    sec-butyl acetate 73.03
    tert-butyl acetate 155.45
    decalin 21.48
    glycerin 56.86
    diglyme 285.68
    acrylic acid 70.21
    isopropyl myristate 54.92
    n-butyric acid 121.48
    acetyl acetate 115.88
    di(2-ethylhexyl) phthalate 48.09
    ethyl propionate 96.35
    nitromethane 204.64
    1,2-diethoxyethane 159.74
    benzonitrile 135.26
    trioctyl phosphate 41.58
    1-bromopropane 148.23
    gamma-valerolactone 429.78
    n-decanol 43.09
    triethyl phosphate 56.02
    4-methyl-2-pentanol 61.3
    propionitrile 159.05
    vinylene carbonate 165.25
    1,1,2-trichlorotrifluoroethane 160.89
    DMS 120.18
    cumene 60.87
    2-octanol 49.52
    2-hexanone 91.62
    octyl acetate 61.86
    limonene 66.11
    1,2-dimethoxyethane 255.46
    ethyl orthosilicate 59.1
    tributyl phosphate 44.17
    diacetone alcohol 132.13
    N,N-dimethylaniline 100.74
    acrylonitrile 174.96
    aniline 152.55
    1,3-propanediol 115.64
    bromobenzene 172.53
    dibromomethane 217.91
    1,1,2,2-tetrachloroethane 241.09
    2-methyl-cyclohexyl acetate 83.65
    tetrabutyl urea 56.24
    diisobutyl methanol 56.76
    2-phenylethanol 128.05
    styrene 94.25
    dioctyl adipate 61.56
    dimethyl sulfate 131.69
    ethyl butyrate 97.02
    methyl lactate 72.54
    butyl lactate 74.01
    diethyl carbonate 66.21
    propanediol butyl ether 97.61
    triethyl orthoformate 80.66
    p-tert-butyltoluene 62.55
    methyl 4-tert-butylbenzoate 129.66
    morpholine 444.44
    tert-butylamine 94.51
    n-dodecanol 32.2
    dimethoxymethane 375.49
    ethylene carbonate 144.63
    cyrene 96.31
    2-ethoxyethyl acetate 145.35
    2-ethylhexyl acetate 96.66
    1,2,4-trichlorobenzene 151.2
    4-methylpyridine 251.92
    dibutyl ether 69.13
    2,6-dimethyl-4-heptanol 56.76
    DEF 139.34
    dimethyl isosorbide 192.28
    tetrachloroethylene 185.34
    eugenol 113.38
    triacetin 108.14
    span 80 88.2
    1,4-butanediol 33.39
    1,1-dichloroethane 210.85
    2-methyl-1-pentanol 51.34
    methyl formate 153.99
    2-methyl-1-butanol 77.7
    n-decane 13.25
    butyronitrile 154.15
    3,7-dimethyl-1-octanol 56.35
    1-chlorooctane 43.29
    1-chlorotetradecane 18.04
    n-nonane 11.87
    undecane 9.28
    tert-butylcyclohexane 21.43
    cyclooctane 18.55
    cyclopentanol 118.57
    tetrahydropyran 360.85
    tert-amyl methyl ether 89.14
    2,5,8-trioxanonane 176.74
    1-hexene 52.75
    2-isopropoxyethanol 83.1
    2,2,2-trifluoroethanol 58.19
    methyl butyrate 103.03

    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) 0.48%
Patchouli (Indonesia, Sumatra) 1 8014-09-3 Pogostemon cablin Benth. (P. patchouli Pellet), fam. Lamiaceae (Labiatae) 0.5%
Patchouli (Indonesia) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.5%
Patchouli (India) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.63%
Patchouli (Indonesia) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.0%
Patchouli (Indonesia, Java) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.79%
Patchouli (Indonesia, Sumatra) 3 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.48%
Patchouli (West India) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.53%
Patchouli (Costa Rica) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.68%
Patchouli (Taiwan) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.08%
Patchouli (The Philippines) 8014-09-3 Posgostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.11%
Patchouli (Japan) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.08%
Patchouli (Indonesia) 3 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.58%
Patchouli (Indonesia)5 ? Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.6%