Delta-Guaiene

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  • Identifiers

    CAS number
    3691-11-0

    Molecular formula
    C15H24

    SMILES
    C[C@H]1CCC2=C(CC[C@H](C[C@@H]12)C(=C)C)C

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Retention indicies (RI)

    • DB5: 1503.33
    • Carbowax: 1664.0

  • Odor profile

    Woody 78.82%
    Sweet 63.04%
    Spicy 52.14%
    Herbal 51.66%
    Citrus 50.97%
    Terpenic 49.76%
    Fresh 45.0%
    Balsamic 41.95%
    Pine 39.91%
    Oily 37.39%

    Scent© AI

  • Properties

    XLogP3-AA
    4.6

    pKa est.
    9.63 (weak base)

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    279°C

    Flash point est.
    77.47 ˚C

  • Synonyms

    • delta-Guaiene
    • 3691-11-0
    • alpha-Bulnesene
    • (+)-alpha-bulnesene
    • .delta.-Guaiene
    • .alpha.-Bulnesene
    • 2U8L6FYE8U
    • (3S,3aS,5R)-3,8-dimethyl-5-prop-1-en-2-yl-1,2,3,3a,4,5,6,7-octahydroazulene
    • .DELTA.-BULNESENE
    • Guaia-1(10),11-diene
    • (3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene
    • CHEBI:63447
    • DTXSID30190387
    • Alpha-Bulnesene (>90%)
    • a-Bulnesene
    • (3R,3AS,5S)-3,8-DIMETHYL-5-PROP-1-EN-2-YL-1,2,3,3A,4,5,6,7-OCTAHYDROAZULENE
    • Azulene, 1,2,3,5,6,7,8,8a-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,7R,8aS)-
    • Azulene, 1,2,3,5,6,7,8,8a-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S-(1alpha,4alpha,7alpha))-
    • (+)-a-Bulnesene
    • DELTA-BULNESENE
    • UNII-2U8L6FYE8U
    • DTXCID40112878
    • 5-Isopropenyl-3,8-dimethyl-1,2,3,3a,4,5,6,7-octahydroazulene-, [1S-(1.alpha.,7.alpha.,8a.beta.)]-
    • HY-N12995
    • CS-1100256
    • NS00114008
    • C20174
    • Q27132629
    • (1S,7R,8aS)-1,2,3,5,6,7,8,8a-Octahydro-1,4-dimethyl-7-(1-methylethenyl)azulene; 1,2,3,5,6,7,8,8a-Octahydro-1,4-dimethyl-7-(1-methylethenyl)-[1S-(1alpha,7alpha,8abeta)]-azulene; alpha-Bulnesene
    • 5-Isopropenyl-3,8-dimethyl-1,2,3,3a,4,5,6,7-octahydroazulene-, (1S-(1alpha,7alpha,8abeta))-
    • 885-851-3
    • Azulene, 1,2,3,5,6,7,8,8a-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S-(1alpha,7alpha,8abeta))-

  • Applications

    Delta-Guaiene (CAS 3691-11-0) is a sesquiterpene hydrocarbon with woody, smoky, balsamic facets commonly occurring in agarwood and patchouli oils; in fragrance practice it serves as a base-note ingredient and fixative for fine fragrances, soaps, candles and incense, enabling woody, oriental, chypre and agarwood–patchouli reconstructions; in flavor work it may be used at trace levels to impart warm woody nuances to tobacco, beverages or smoked/roasted profiles; in analytics and QC it functions as a natural marker and GC–MS reference standard for authentication, quantification and quality control of agarwood/patchouli oils, and for studying aroma development during aging; in biological and biochemical research it is used to probe sesquiterpene biosynthesis in Aquilaria/Pogostemon, volatile-mediated ecology and odor chemistry, and as a starting point to prepare oxygenated derivatives (e.g., guaienol) for complex woody accords; in vitro antimicrobial and antioxidant activities have been reported but are not intended for medical use.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 681.78
    methanol 308.88
    isopropanol 792.84
    water 0.13
    ethyl acetate 1318.27
    n-propanol 758.01
    acetone 912.36
    n-butanol 897.27
    acetonitrile 734.6
    DMF 561.18
    toluene 1613.09
    isobutanol 590.97
    1,4-dioxane 2706.12
    methyl acetate 821.34
    THF 3792.95
    2-butanone 1058.31
    n-pentanol 515.11
    sec-butanol 617.07
    n-hexane 264.55
    ethylene glycol 29.15
    NMP 459.05
    cyclohexane 693.24
    DMSO 404.98
    n-butyl acetate 2135.15
    n-octanol 415.79
    chloroform 2782.23
    n-propyl acetate 736.56
    acetic acid 243.95
    dichloromethane 2580.56
    cyclohexanone 1566.01
    propylene glycol 77.93
    isopropyl acetate 992.52
    DMAc 471.32
    2-ethoxyethanol 397.36
    isopentanol 769.47
    n-heptane 547.01
    ethyl formate 592.85
    1,2-dichloroethane 1315.14
    n-hexanol 1203.22
    2-methoxyethanol 622.88
    isobutyl acetate 622.68
    tetrachloromethane 598.71
    n-pentyl acetate 773.1
    transcutol 1969.51
    n-heptanol 419.39
    ethylbenzene 600.18
    MIBK 765.73
    2-propoxyethanol 1080.39
    tert-butanol 933.85
    MTBE 1486.61
    2-butoxyethanol 519.38
    propionic acid 282.78
    o-xylene 643.35
    formic acid 30.88
    diethyl ether 1723.46
    m-xylene 893.16
    p-xylene 731.15
    chlorobenzene 1095.9
    dimethyl carbonate 230.11
    n-octane 141.97
    formamide 72.49
    cyclopentanone 1532.38
    2-pentanone 1065.94
    anisole 820.14
    cyclopentyl methyl ether 1383.85
    gamma-butyrolactone 1182.11
    1-methoxy-2-propanol 641.56
    pyridine 2051.46
    3-pentanone 715.22
    furfural 785.69
    n-dodecane 88.72
    diethylene glycol 344.51
    diisopropyl ether 598.71
    tert-amyl alcohol 592.09
    acetylacetone 932.17
    n-hexadecane 105.4
    acetophenone 585.02
    methyl propionate 633.61
    isopentyl acetate 1684.84
    trichloroethylene 1983.6
    n-nonanol 388.97
    cyclohexanol 789.02
    benzyl alcohol 440.55
    2-ethylhexanol 841.33
    isooctanol 378.31
    dipropyl ether 1797.7
    1,2-dichlorobenzene 774.93
    ethyl lactate 178.37
    propylene carbonate 750.36
    n-methylformamide 247.56
    2-pentanol 594.44
    n-pentane 308.54
    1-propoxy-2-propanol 998.27
    1-methoxy-2-propyl acetate 1142.77
    2-(2-methoxypropoxy) propanol 495.11
    mesitylene 527.31
    ε-caprolactone 1126.92
    p-cymene 583.03
    epichlorohydrin 1442.63
    1,1,1-trichloroethane 1441.72
    2-aminoethanol 108.88
    morpholine-4-carbaldehyde 730.25
    sulfolane 674.62
    2,2,4-trimethylpentane 119.89
    2-methyltetrahydrofuran 2450.24
    n-hexyl acetate 900.14
    isooctane 145.51
    2-(2-butoxyethoxy)ethanol 720.54
    sec-butyl acetate 586.0
    tert-butyl acetate 977.52
    decalin 207.0
    glycerin 87.58
    diglyme 1503.52
    acrylic acid 164.31
    isopropyl myristate 417.31
    n-butyric acid 829.57
    acetyl acetate 713.09
    di(2-ethylhexyl) phthalate 301.38
    ethyl propionate 605.87
    nitromethane 435.96
    1,2-diethoxyethane 1776.27
    benzonitrile 859.78
    trioctyl phosphate 226.36
    1-bromopropane 1413.85
    gamma-valerolactone 1356.3
    n-decanol 291.56
    triethyl phosphate 318.04
    4-methyl-2-pentanol 417.54
    propionitrile 917.34
    vinylene carbonate 674.39
    1,1,2-trichlorotrifluoroethane 439.8
    DMS 472.8
    cumene 367.54
    2-octanol 308.09
    2-hexanone 723.56
    octyl acetate 464.39
    limonene 787.21
    1,2-dimethoxyethane 1350.78
    ethyl orthosilicate 357.31
    tributyl phosphate 282.66
    diacetone alcohol 569.95
    N,N-dimethylaniline 472.82
    acrylonitrile 686.42
    aniline 852.62
    1,3-propanediol 314.85
    bromobenzene 1332.28
    dibromomethane 1879.36
    1,1,2,2-tetrachloroethane 1348.86
    2-methyl-cyclohexyl acetate 710.5
    tetrabutyl urea 359.54
    diisobutyl methanol 521.28
    2-phenylethanol 735.09
    styrene 708.37
    dioctyl adipate 458.04
    dimethyl sulfate 202.15
    ethyl butyrate 1206.62
    methyl lactate 163.11
    butyl lactate 359.48
    diethyl carbonate 621.38
    propanediol butyl ether 346.31
    triethyl orthoformate 742.8
    p-tert-butyltoluene 558.0
    methyl 4-tert-butylbenzoate 498.18
    morpholine 2512.25
    tert-butylamine 795.89
    n-dodecanol 227.98
    dimethoxymethane 847.87
    ethylene carbonate 664.75
    cyrene 326.34
    2-ethoxyethyl acetate 879.76
    2-ethylhexyl acetate 1346.98
    1,2,4-trichlorobenzene 798.33
    4-methylpyridine 1846.62
    dibutyl ether 1024.73
    2,6-dimethyl-4-heptanol 521.28
    DEF 751.19
    dimethyl isosorbide 975.05
    tetrachloroethylene 908.72
    eugenol 384.06
    triacetin 516.7
    span 80 488.14
    1,4-butanediol 99.03
    1,1-dichloroethane 1497.55
    2-methyl-1-pentanol 460.56
    methyl formate 205.57
    2-methyl-1-butanol 588.1
    n-decane 161.16
    butyronitrile 1262.33
    3,7-dimethyl-1-octanol 479.82
    1-chlorooctane 443.71
    1-chlorotetradecane 176.3
    n-nonane 165.04
    undecane 112.9
    tert-butylcyclohexane 184.39
    cyclooctane 244.79
    cyclopentanol 680.84
    tetrahydropyran 3480.56
    tert-amyl methyl ether 753.06
    2,5,8-trioxanonane 905.72
    1-hexene 719.64
    2-isopropoxyethanol 357.41
    2,2,2-trifluoroethanol 73.67
    methyl butyrate 737.06

    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
Eucalyptus cloeziana leaf (Chemotype 1) Eucalyptus cloeziana F. Muell., fam. Myrtaeceae 0.07%
Patchouli (Indonesia, Sumatra) 2 8014-09-3 Pogostemon cablin Benth. (P. patchouli Pellet), fam. Lamiaceae (Labiatae) 14.73%
Patchouli (Indonesia, Sumatra) 1 8014-09-3 Pogostemon cablin Benth. (P. patchouli Pellet), fam. Lamiaceae (Labiatae) 15.75%
Patchouli (Vietnam) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 14.67%
Guaiacwood 1 8016-23-7 Bulnesia sarmienti Lorentz ex Griseb, fam. Zygophyllaceae 4.5%
Patchouli (Indonesia) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 25.0%
Tea Tree (Australia) 7 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.01%
Patchouli (India) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 14.85%
Patchouli (Indonesia) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 2.0%
Patchouli (Indonesia, Java) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 16.65%
Patchouli (Indonesia, Sumatra) 3 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 14.73%
Patchouli (West India) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 19.67%
Patchouli (Costa Rica) 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 14.44%
Idiospermum australiense Idiospermum australiense (Diels) S.T. Blake, fam. Idiospermaceae 0.01%
Agarwood 2 Aquilaria agallocha Roxb., fam. Thymelaeaceae 0.1%
Agarwood smoke 1 Aquilaria agallocha Roxb., fam. Thymelaeaceae 0.33%
Litchi pulp (China) Lichi sinensis Sonn., fam. Sapindaceae 22.28%
Patchouli (Indonesia) 4 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 12.0%
Basil (France) 2 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.06%
Alseuosmia macrophylla Alseuosmia macrophylla A. Cunn, fam. Alseuosmiaceae 13.2%
Uromyrtus australis (Australia) Uromyrtus australis A.J. Scott, fam. Myrtaceae 0.21%
Uromyrtus metrosideros (Australia) Uromyrtus metrosideros (F.M. Bailey) A.J. Scott, fam. Myrtaceae 0.06%
Tea Tree (Australia) 9 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.19%
Patchouli (Indonesia) 6 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 18.7%
Eugenia ovalifolia leaf Eugenia ovalifolia Camb., fam. Myrtaceae 0.7%
Eugenia nitida (Brazil) Eugenia nitida Camb., fam. Myrtaceae 0.6%
Eugenia uniflora leaf (Brazil) 2 Eugenia uniflora L. (E. michelii Lam., E. pitanga (Berg), fam. Myrtaceae 0.7%
Mandarin (Uruguay) 3 8008-31-9 Citrus deliciosa Tenore cv. Nova (C. reticulata Blanco), fam. Rutaceae 0.01%
Rollinia mucosa fruit Rollinia mucosa (Jacq.) Baill, fam. Annonaceae 0.1%
Manuka (Australia) 1b Leptospermum scoparium J.R. et F. Forst, var. eximium, fam. Myrtaceae 0.01%
Manuka (Australia) 1a Leptospermum scoparium J.R. et F. Forst, var. scoparium, fam. Myrtaceae 0.1%
Eucalyptus globulus (Spain) 2a old leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.25%
Eucalyptus globulus (Spain) 2c mature fruits 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.44%
Eucalyptus globulus (Yugoslavia) 1a leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.1%
Eucalyptus globulus (Yugoslavia) 1b flower buds 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.34%
Eucalyptus globulus (Yugoslavia) 1c branches 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.4%
Kanuka (New Zealand) 3 Kunzea ericoides (A. Rich.) J. Thompson, fam. Myrteceae 1.1%
Geranium (Cuba) 8000-46-2 Pelargonium species, fam. Geraniaceae 2.4%
Patchouli (China) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 21.99%
Patchouli (India) 2 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 7.31%
Patchouli (Indonesia) 5 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 11.1%
Pepper, black (India) 6a distilled 8006-82-4 Piper nigrum L., fam. Piperaceae 0.6%
Pepper, black (India) 6b free volatiles 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Sweetie peel Citrus paradisi Macfayden x Citrus maxima Merill, fam. Rutaceae 0.01%
Calamus (Germany) 2 root 8015-79-0 Acorus calamus L., fam. Araceae 5.48%
Baga fruit Annona glabra L., fam. Annonaceae 0.01%
Lippia lupulina stalk & leaf (Brazil) Lippia lupulina Cham., fam. Verbenaceae 0.2%
Chenopodium botrys Chenopodium botrys L., fam. Chenopodiaceae 0.2%
Desmos goezeanus leaf (Australia) Desmos goezeanus (F. Muell.) L.W. Jessup, fam. Annonaceae 0.15%
Desmos wardianus leaf (Australia) Desmos wardianus (F.M. Bailey) L.W. Jessup, fam. Annonaceae 0.6%