Alpha-muurolene, (-)-

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  • Identifiers

    CAS number
    31983-22-9

    Molecular formula
    C15H24

    SMILES
    CC1=C[C@@H]2[C@H](CC1)C(=CC[C@H]2C(C)C)C

    Retention indicies (RI)

    • DB5: 1501.14
    • Carbowax: 1711.14

  • Odor profile

    Woody 82.01%
    Spicy 64.43%
    Herbal 60.93%
    Green 51.95%
    Fresh 48.61%
    Citrus 46.73%
    Terpenic 41.8%
    Dry 37.43%
    Pine 34.48%
    Oily 31.04%

    Scent© AI

  • Properties

    XLogP3-AA
    4.1

    pKa est.
    10.06 (weak base)

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    261°C

    Flash point est.
    97.25 ˚C

  • Synonyms

    • alpha-Muurolene
    • Muurolene
    • B1-Cadinene
    • 10208-80-7
    • D2ZGB75M36
    • alpha-Muurolene, (-)-
    • (-)-alpha-muurolene
    • (-)-.alpha.-Muurolene
    • UNII-D2ZGB75M36
    • .alpha.-Muurolene, (-)-
    • CHEBI:64797
    • DTXSID90144629
    • .alpha.-Muurolene
    • 1.BETA.-CADINA-4,9-DIENE
    • (+)-alpha-muurolene
    • Naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-(1alpha,4aalpha,8aalpha))-
    • (1S,4aS,8aR)-1-isopropyl-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalene
    • (1S,4aS,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene
    • Naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S,4aS,8aR)-
    • (1S,4AS,8AR)-1,2,4A,5,6,8A-HEXAHYDRO-4,7-DIMETHYL-1-(1-METHYLETHYL)NAPHTHALENE
    • (1S,4aS,8aR)-4,7-dimethyl-1-propan-2-yl-1,2,4a,5,6,8a-hexahydronaphthalene
    • 31983-22-9
    • NAPHTHALENE, 1,2,4A,5,6,8A-HEXAHYDRO-4,7-DIMETHYL-1-(1-METHYLETHYL)-, (1S-(1.ALPHA.,4A.ALPHA.,8A.ALPHA.))-
    • DTXCID1067120
    • 1BETA-CADINA-4,9-DIENE
    • QMAYBMKBYCGXDH-ZNMIVQPWSA-N
    • NS00095990
    • C20272
    • Q27133436
    • Naphthalene, 1,2,4a,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-,(1R,4aR,8aS)-rel-

  • Applications

    Alpha-muurolene [(-)-], a tricyclic sesquiterpene hydrocarbon found in many plant essential oils, is used primarily as an analytical reference in GC–MS/GC–FID and secondary-metabolite studies (identification/quantification, retention-index assignment, essential-oil fingerprinting, provenance verification, and quality control of botanicals, foods, and fragrances); as a chemotaxonomic marker and a tool for terpenoid biosynthesis/enzymology research (e.g., probing muurolene synthase, FPP flux, and stereochemical profiling); and as a natural aroma component imparting warm woody–resinous nuances to fine-fragrance and flavor formulations at trace levels to adjust the depth and dryness of woody/spicy accords; in biological and agronomic contexts it is often employed as a reference to study volatile-mediated plant–insect interactions and potential crop-protection roles (antimicrobial/antifungal effects are typically assessed within essential-oil matrices rather than claimed as therapeutic), while in atmospheric chemistry it serves as a highly reactive VOC for modeling O3/OH oxidation and secondary organic aerosol formation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 58.2
    methanol 19.74
    isopropanol 71.43
    water 0.02
    ethyl acetate 211.7
    n-propanol 77.24
    acetone 165.8
    n-butanol 111.66
    acetonitrile 74.07
    DMF 94.48
    toluene 498.81
    isobutanol 72.17
    1,4-dioxane 506.25
    methyl acetate 143.9
    THF 916.97
    2-butanone 234.21
    n-pentanol 75.49
    sec-butanol 84.03
    n-hexane 124.53
    ethylene glycol 3.24
    NMP 148.0
    cyclohexane 289.63
    DMSO 80.71
    n-butyl acetate 483.67
    n-octanol 126.63
    chloroform 501.95
    n-propyl acetate 153.34
    acetic acid 33.58
    dichloromethane 462.04
    cyclohexanone 429.22
    propylene glycol 10.6
    isopropyl acetate 183.38
    DMAc 129.1
    2-ethoxyethanol 60.07
    isopentanol 115.26
    n-heptane 260.01
    ethyl formate 78.94
    1,2-dichloroethane 296.36
    n-hexanol 250.19
    2-methoxyethanol 71.02
    isobutyl acetate 147.54
    tetrachloromethane 129.6
    n-pentyl acetate 215.8
    transcutol 425.24
    n-heptanol 118.4
    ethylbenzene 216.22
    MIBK 178.31
    2-propoxyethanol 187.4
    tert-butanol 109.47
    MTBE 256.39
    2-butoxyethanol 121.54
    propionic acid 41.82
    o-xylene 235.87
    formic acid 2.97
    diethyl ether 318.63
    m-xylene 293.41
    p-xylene 249.67
    chlorobenzene 292.17
    dimethyl carbonate 45.5
    n-octane 72.99
    formamide 7.11
    cyclopentanone 428.16
    2-pentanone 231.09
    anisole 235.08
    cyclopentyl methyl ether 425.2
    gamma-butyrolactone 269.73
    1-methoxy-2-propanol 91.24
    pyridine 442.17
    3-pentanone 196.2
    furfural 181.06
    n-dodecane 48.15
    diethylene glycol 57.91
    diisopropyl ether 143.79
    tert-amyl alcohol 108.09
    acetylacetone 203.82
    n-hexadecane 56.98
    acetophenone 183.69
    methyl propionate 129.1
    isopentyl acetate 408.53
    trichloroethylene 444.19
    n-nonanol 127.55
    cyclohexanol 176.68
    benzyl alcohol 106.88
    2-ethylhexanol 256.7
    isooctanol 109.94
    dipropyl ether 479.73
    1,2-dichlorobenzene 223.39
    ethyl lactate 46.12
    propylene carbonate 175.42
    n-methylformamide 28.16
    2-pentanol 96.35
    n-pentane 113.49
    1-propoxy-2-propanol 207.46
    1-methoxy-2-propyl acetate 287.27
    2-(2-methoxypropoxy) propanol 168.71
    mesitylene 196.25
    ε-caprolactone 307.58
    p-cymene 237.31
    epichlorohydrin 353.83
    1,1,1-trichloroethane 344.17
    2-aminoethanol 11.28
    morpholine-4-carbaldehyde 189.32
    sulfolane 213.94
    2,2,4-trimethylpentane 52.37
    2-methyltetrahydrofuran 653.72
    n-hexyl acetate 289.05
    isooctane 51.18
    2-(2-butoxyethoxy)ethanol 202.02
    sec-butyl acetate 141.48
    tert-butyl acetate 214.93
    decalin 107.65
    glycerin 12.6
    diglyme 355.41
    acrylic acid 25.45
    isopropyl myristate 164.47
    n-butyric acid 106.06
    acetyl acetate 134.72
    di(2-ethylhexyl) phthalate 118.93
    ethyl propionate 141.07
    nitromethane 56.64
    1,2-diethoxyethane 393.78
    benzonitrile 178.68
    trioctyl phosphate 86.68
    1-bromopropane 365.29
    gamma-valerolactone 331.94
    n-decanol 106.24
    triethyl phosphate 115.89
    4-methyl-2-pentanol 81.73
    propionitrile 111.95
    vinylene carbonate 134.87
    1,1,2-trichlorotrifluoroethane 99.25
    DMS 149.68
    cumene 146.58
    2-octanol 93.52
    2-hexanone 185.25
    octyl acetate 181.13
    limonene 324.93
    1,2-dimethoxyethane 224.77
    ethyl orthosilicate 129.11
    tributyl phosphate 102.16
    diacetone alcohol 140.33
    N,N-dimethylaniline 165.16
    acrylonitrile 80.24
    aniline 197.05
    1,3-propanediol 30.87
    bromobenzene 400.24
    dibromomethane 412.19
    1,1,2,2-tetrachloroethane 339.2
    2-methyl-cyclohexyl acetate 247.3
    tetrabutyl urea 135.22
    diisobutyl methanol 159.22
    2-phenylethanol 203.74
    styrene 235.17
    dioctyl adipate 178.99
    dimethyl sulfate 53.03
    ethyl butyrate 300.63
    methyl lactate 34.01
    butyl lactate 99.52
    diethyl carbonate 161.76
    propanediol butyl ether 83.74
    triethyl orthoformate 209.01
    p-tert-butyltoluene 227.05
    methyl 4-tert-butylbenzoate 185.38
    morpholine 432.99
    tert-butylamine 107.89
    n-dodecanol 89.94
    dimethoxymethane 142.7
    ethylene carbonate 126.62
    cyrene 111.98
    2-ethoxyethyl acetate 228.73
    2-ethylhexyl acetate 392.15
    1,2,4-trichlorobenzene 256.06
    4-methylpyridine 411.68
    dibutyl ether 307.17
    2,6-dimethyl-4-heptanol 159.22
    DEF 175.19
    dimethyl isosorbide 335.78
    tetrachloroethylene 202.94
    eugenol 134.41
    triacetin 181.1
    span 80 162.64
    1,4-butanediol 13.92
    1,1-dichloroethane 286.37
    2-methyl-1-pentanol 94.5
    methyl formate 27.35
    2-methyl-1-butanol 101.79
    n-decane 83.02
    butyronitrile 162.84
    3,7-dimethyl-1-octanol 154.1
    1-chlorooctane 185.8
    1-chlorotetradecane 85.62
    n-nonane 87.01
    undecane 60.44
    tert-butylcyclohexane 89.94
    cyclooctane 140.77
    cyclopentanol 142.88
    tetrahydropyran 778.13
    tert-amyl methyl ether 188.61
    2,5,8-trioxanonane 265.68
    1-hexene 237.81
    2-isopropoxyethanol 71.82
    2,2,2-trifluoroethanol 10.04
    methyl butyrate 160.83

    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
Abies alba from cones 8021-27-0 Abies alba Mill., fam. Pinaceae 0.4%
Lemon balm 2 8014-71-9 Melissa officinalis L., fam. Lamiaceae (Labiatae) 0.3%
Bergamot (Italy) 1 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Cedarleaf 2 8000-27-9 Thuja occidentalis L., fam. Taxodiaceae 0.1%
Cedrela odorata Cedrela odorata L., fam. Meliaceae 1.0%
Chamomile, german (Bulgaria) 8002-66-2 Chamomilla recutita (L.) Rausch.(Matricaria chamomilla L.), fam.Asteraceae 3.41%
Citronella java (China) 8000-29-1 Cymbopogon winterianus Jowitt., fam. Poaceae (Gramineae) 0.52%
Citronella java (Argentina) 2 8000-29-1 Cymbopogon winterianus Jowitt., fam. Poaceae (Gramineae) 0.7%
Citronella java (S. America) 8000-29-1 Cymbopogon winterianus Jowitt., fam. Poaceae (Gramineae) 0.49%
Citronella java 3 8000-29-1 Cymbopogon winterianus Jowitt., fam. Poaceae (Gramineae) 0.46%
Citronella ceylon 5 8000-29-1 Cymbopogon nardus (L.) Rendle, fam. Poaceae (Gramineae) 0.46%
Clove bud 3 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison (E.caryophyllata Thunb.) 0.4%
Clove bud (Malagasy) 8000-34-8 Eugenia caryophyllus (Spreng.) Bullock & Harrison (E.caryophyllata Thunb.) 0.03%
Cubeb 1 8007-87-2 Piper cubeba L., fam. Piperaceae 1.2%
Cymbopogon distans 1 (Himalaya) Cymbopogon distans (Steud.) Wats. (Chemotype 1), fam. Poaceae (Gramineae) 2.3%
Hemizygia welwitschii Hemizygia welwitschii (Rolfe) M.Ashby (Orthosiphon welwitschii) 0.2%
Hinoki leaf Chamaecyparis obtusa (Sieb. et Zucc.) Endl., fam. Cupressaceae 3.81%
Hinoki root Chamaecyparis obtusa (Sieb. et Zucc.) Endl., fam. Cupressaceae 1.71%
Hinoki wood Chamaecyparis obtusa (Sieb. et Zucc.) Endl., fam. Cupressaceae 5.78%
Homalomena aromatica rhizome (Vietnam) Homalomena aromatica Schott. (Calla aromatica), fam. Araceae 0.3%
Juniper berry 1 8012-91-7 Juniperus communis L., fam. Cupressaceae 0.68%
Juniperus foetidissima leaf Juniperus foetidissima Willd., fam. Cupressaceae 0.1%
Larix conifer bark Larix decidua Mill., fam. Pinaceae 0.01%
Larix conifer needle Larix decidua Mill., fam. Pinaceae 0.76%
Lotus flower Nelumbo nucifera L., fam. Nelumbonaceae 0.01%
Lovage root (France) 8016-31-7 Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 0.3%
Mace 2 8007-12-3 Myristica fragrans Houtt., fam. Myristicaceae 0.1%
Mentha longifolia (France) Chemotype 1 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 2.0%
Mentha longifolia (France) Chemotype 2 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 6.0%
Muhuhu Brachylaena hutchinsii Hutch. (Synchodendron hutchii Hutch.), Asteraceae 3.0%
Oregano, greek (European) 84012-24-8 Origanum vulgare L. ssp. vulgare, fam. Lamiaceae (Labiatae) 0.15%
Peperomia rotundifolia Peperomia rotundifolia (L.) Kth. 0.4%
Peppermint (Greece) 1 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 0.5%
Peppermint (Greece) 2 8006-90-4 Mentha piperita L., fam. Lamiaceae (Labiatae) 0.5%
Picea engelmanni needle Picea engelmanni (Parry) Engelm., fam. Pinaceae 0.06%
Picea engelmanni twigs with needles Picea engelmanni (Parry) Engelm., fam. Pinaceae 0.07%
Pimento (Allspice) 2 8006-77-7 Pimenta dioica (L.) Merr. (P. officinalis Lindl.), fam. Myrtaceae 1.05%
Pinus pinaster (France) 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 0.01%
Rose (Turkey) 6 8007-01-0 Rosa damascena Mill., fam. Rosaceae 0.14%
Tea Tree (Australia) 1 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.01%
Xylopia aethiopica fruit (Cameroon) Xylopia aethiopica (Dunal) A. Richard, fam. Annonaceae 4.3%
Zdravets Geranium macrorrhizum L., fam. Geraniaceae 0.5%
Eucalyptus maculata (Uruguay) Eucalyptus maculata Hook., fam. Myrtaceae 2.1%
Juniperus martinezii Juniperus martinezii Perez de la Rosa, fam. Cupressaceae 0.05%
Juniperus flaccida var. flaccida Juniperus flaccida Schlecht, var. flaccida, fam. Cupressaceae 0.05%
Baccharis genistelloides Baccharis genistelloides Pers. (Carqueja), fam. Asteraceae (Compositae) 0.52%
Swangi (Citrus hystrix) leaf (Thailand) 2b Citrus hystrix DC (Swangi), fam. Rutaceae 0.01%
Swangi (Citrus hystrix) peel (Thailand) 2d Citrus hystrix DC (Swangi), fam. Rutaceae 0.01%
Marigold pot 1 70892-20-5 Calendula officinalis L. (Pot Marigold), fam. Asteraceae (Compositae) 0.33%
Cascarilla 2 8007-06-5 Croton eluteria Bennett, fam. Euphorbiaceae 1.44%
Hyptis crenata (Brazil) Hyptis crenata Pohl ex Benth, fam. Lamiaceae (Labiatae) 0.02%
Kanuka (New Zealand) 2 Kunzea ericoides (A. Rich.) J. Thompson, fam. Myrtaceae 0.2%
Tejpat leaf Cinnamomum tamala (Ham.) Nees et Eberm., fam. Lauraceae 0.8%
Lemon (Italy-Sicily) 14d Torchi method 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.04%
Turmeric (India) 5a rhizome 8024-37-1 Curcuma longa L., cv. Roma (C. domestica Val.), fam. Zingiberaceae 0.3%
Turmeric (India) 5b leaf 8024-37-1 Curcuma longa L., cv. Roma (C. domestica Val.), fam. Zingiberaceae 0.1%
Juniperus cedrus (Portugal-Madeira) Juniperus cedrus Webb & Berth. (J. oxycedrus L), fam. Cupressaceae 0.1%
Sage, dalmatian (Serbia-Montenegro) 1b flower 8016-20-4 Salvia officinalis L., fam. Lamiaceae (Labiatae) 0.2%
Geranium (India) 14a 8000-46-2 Pelargonium species, cultivar Bourbon, fam. Geraniaceae 0.1%
Licaria salicifolia Licaria salicifolia (Sw.) Kosterm., fam. Lauraceae 0.4%
Helichrysum hypnoides (Madagascar) 2 Helichrysum hypnoides (DC.) R.Vig. et Humbert, fam.Asteraceae (Compositae) 0.05%
Calamintha vardarensis Calamintha vardarensis (Greuter et Burdet) Silic, fam.Lamiaceae (Labiatae) 0.1%
Siparuna guianensis stem wood Siparuna guianensis Aublet, fam. Monimiaceae 0.8%
Salvia pomifera Salvia pomifera L. ssp. calycina (Sm.) Hayek, fam. Lamiaceae (Labiatae) 0.01%
Cinnamomum aureofulvum bark Cinnamomum aureofulvum Gamb., fam. Lauraceae 0.6%
Lepechinia salviaefolia (Venezuela) Lepechinia salviaefolia (Kunth) Epl., fam. Lamiaceae (Labiatae) 0.1%
Mikania cordata leaf Mikania cordata (Burm.f.) B.L. Robinson var. cordata, fam. Asteraceae 1.1%
Protium heptaphyllum 2a leaf Protium heptaphyllum (Aubl.) March., fam. Burseraceae 1.0%
Myrrhinium atropurpureum leaf (Brazil) Myrrhinium atropurpureum Schot, fam. Myrtaceae 1.1%
Hyptis suaveolens (Mali) Hyptis suaveolens (L.) Poit., fam. Lamiaceae (Labiatae) 0.35%
Plectranthus glandulosus (Cameroon) 2 Plectranthus glandulosus Hook f., fam. Lamiaceae (Labiatae) 0.1%
Cinnamon fruit (India) 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 6.1%
Cassinia laevis flower Cassinia laevis R.Br., fam. Asteraceae (Compositae) 2.7%
Cassinia laevis leaf Cassinia laevis R.Br., fam. Asteraceae (Compositae) 7.0%
Pepper, black (India) 4 8006-82-4 Piper nigrum L., fam. Piperaceae 0.12%
Pepper, black (Sao Tome) 8006-82-4 Piper nigrum L., fam. Piperaceae 0.5%
Laurel leaf (Turkey) 4 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.01%
Pinus canariensis (Greece) Pinus canariensis Sweet ex Sprengel, fam. Pinaceae 0.8%
Pinus brutia (Greece) Pinus brutia Tenore, fam. Pinaceae 0.1%
Pinus halepensis (Greece) Pinus halepensis Miller, fam. Pinaceae 0.3%
Aristolochia odoratissima Aristolochia odoratissima L., fam. Aristolochaceae 2.2%
Pinus sylvestris (Greece) 8023-99-2 Pinus sylvestris L. (Scotch pine), fam. Pinaceae 0.9%
Pinus mugo (Dwarf pine) 3 (Greece) 8000-26-8 Pinus mugo Turra, fam. Pinaceae 2.4%
Pinus pumila 2 Pinus pumila (Pall.) Regel, fam. Pinaceae 0.4%
Microglossa pyrrhopappa Microglossa pyrrhopappa (A. Rich) Agnew var. Phyrropappa, fam. Asteraceae 3.8%
Myrtle leaf (Greece) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.5%
Neomitranthes cordifolia Neomitranthes cordifolia (D. Legrand) D. Legrand, fam. Myrtaceae 1.0%
Abies alba needle (Montenegro) 8021-27-0 Abies alba Mill., fam. Pinaceae 0.05%
Yarrow (Estonia) 1a flower 84082-83-7 Achillea millefolium L., fam. Asteraceae (Compositae) 0.5%
Yarrow (Estonia) 1b leaf 84082-83-7 Achillea millefolium L., fam. Asteraceae (Compositae) 0.1%
Yarrow (Estonia) 1c stem 84082-83-7 Achillea millefolium L., fam. Asteraceae (Compositae) 0.05%
Pinus canariensis (Morocco) needle Pinus canariensis Sweet ex Sprengel, fam. Pinaceae 1.3%
Pinus halepensis (Morocco) needle Pinus halepensis Miller, fam. Pinaceae 0.5%
Pinus pinaster (Morocco) needle 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 1.7%
Sweetie peel Citrus paradisi Macfayden x Citrus maxima Merill, fam. Rutaceae 0.01%
Pineapple pulp Ananas comosus (L.) Merr., fam. Bromeliaceae 0.77%
Amorpha fruticosa flower Amorpha fruticosa L., fam. Papilionaceae 2.8%
Amorpha fruticosa leaf Amorpha fruticosa L., fam. Papilionaceae 1.1%
Amorpha fruticosa fruit Amorpha fruticosa L., fam. Papilionaceae 4.8%
Inula verbascifolia ssp. parnassica Inula verbascifolia Hausskn., ssp. parnassia Tutin, fam. Asteraceae 0.01%