Verbenol

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  • Identifiers

    CAS number
    473-67-6

    Molecular formula
    C10H16O

    SMILES
    CC1=CC(C2CC1C2(C)C)O

    Retention indicies (RI)

    • DB5: 1149.0
    • Carbowax: 1675.5

  • Odor profile

    Herbal 79.89%
    Mint 70.44%
    Sweet 66.38%
    Camphoreous 66.36%
    Spicy 62.93%
    Woody 62.61%
    Pine 61.06%
    Fresh 54.23%
    Cooling 53.21%
    Balsamic 51.62%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    9.19 (weak base)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 63.00 to 67.00 °C. @ 760.00 mm Hg

    Boiling point

    • 214.00 to 215.00 °C. @ 760.00 mm Hg

    Flash point est.
    82.94 ˚C

    Solubility expt.

    • very slightly
    • Very slightly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • VERBENOL
    • 473-67-6
    • Berbenol
    • 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol
    • d-Verbenol
    • 2-Pinen-4-ol
    • (E)-verbenol
    • Pinen-4-ol
    • cis-Verbenol
    • FEMA No. 3594
    • EINECS 207-470-8
    • (+)-Verbenol
    • UNII-G0F32F922S
    • 4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-ol
    • 4-Hydroxy-2,6,6-trimethylbicyclo(3.1.1)hept-2-ene
    • 2-Pinen-4-ol (8CI)
    • PINEN-4-O1
    • Bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-
    • 5416-53-5
    • DTXSID2042511
    • FEMA 3594
    • G0F32F922S
    • NSC44159
    • Bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-
    • NSC-408848
    • (1S)-(+)-Cis-verbenol
    • 4,6,6-Trimethyl-Bicyclo(3.1.1)hept-3-en-2-ol
    • 4,6,6-Trimethyl-bicyclo[3,1,1]hept-3-en-2-ol
    • 4,6,6-trimethyl-bicyclo[3.1.1]hept-3-en-2-ol
    • 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol, 9CI
    • (-)-trans-Verbenol
    • (-)-(Z)-Verbenol
    • 4,6,6-Trimethyl-bicyclo(3,1,1)hept-3-en-2-ol
    • 4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-ol, 9ci
    • Verbenols
    • NSC-6833
    • 4,7,7-TRIMETHYLBICYCLO[3.1.1]HEPT-3-EN-2-OL
    • VERBENOL [FHFI]
    • NCIOpen2_000769
    • (+/-)-VERBENOL
    • SCHEMBL247526
    • DTXCID0022511
    • VERBENOL, (+/-)-
    • NSC6833
    • (1S-(1.alpha.,2.beta.,5.alpha.))-4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-ol
    • CHEBI:167399
    • NSC74539
    • UAA89002
    • XAA33908
    • MFCD00001340
    • NSC-44159
    • NSC-74539
    • NSC408848
    • AKOS024365333
    • FV164125
    • DB-044683
    • NS00013255
    • F76316
    • Q2514085
    • Bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl- (9CI)

  • Applications

    Verbenol (CAS 473-67-6) is a monoterpenoid alcohol with a characteristic pine-camphor scent, widely used as a fragrance ingredient in perfumes, deodorizers, air care, and home/personal care to impart fresh resinous and herbal notes; in forestry and crop protection, its cis/trans isomers act as semiochemical/pheromone components for several bark beetles (e.g., Ips and Dendroctonus spp.), thus serving in monitoring traps, population surveillance, and push-pull pest-management schemes as well as chemical ecology research; in organic synthesis, verbenol is a bio-derived intermediate (from turpentine or essential oils) that can be oxidized to verbenone or elaborated into other bicyclic terpenoids, and it serves as a useful chiral building block for pharmaceutical and agrochemical discovery; in environmental and atmospheric analysis, it is employed as a reference standard in GC/GC-MS to track α-pinene oxidation, the formation of verbenone and secondary organic aerosol products, and to study odorant emissions from conifers and wood; additionally, verbenol can contribute trace flavor nuances in foods and beverages and is found in candles, wax melts, and “pine/forest” themed cleaners.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 468.76
    methanol 569.42
    isopropanol 308.44
    water 8.55
    ethyl acetate 280.52
    n-propanol 354.08
    acetone 334.68
    n-butanol 297.72
    acetonitrile 417.83
    DMF 236.45
    toluene 152.62
    isobutanol 209.07
    1,4-dioxane 691.81
    methyl acetate 272.15
    THF 933.13
    2-butanone 239.0
    n-pentanol 141.65
    sec-butanol 192.31
    n-hexane 36.31
    ethylene glycol 99.71
    NMP 187.76
    cyclohexane 57.7
    DMSO 203.14
    n-butyl acetate 193.8
    n-octanol 116.64
    chloroform 500.21
    n-propyl acetate 127.46
    acetic acid 295.24
    dichloromethane 392.11
    cyclohexanone 272.78
    propylene glycol 103.56
    isopropyl acetate 172.2
    DMAc 123.75
    2-ethoxyethanol 205.3
    isopentanol 211.01
    n-heptane 42.54
    ethyl formate 185.62
    1,2-dichloroethane 233.95
    n-hexanol 290.23
    2-methoxyethanol 424.14
    isobutyl acetate 93.32
    tetrachloromethane 113.97
    n-pentyl acetate 114.69
    transcutol 592.0
    n-heptanol 132.48
    ethylbenzene 62.64
    MIBK 153.02
    2-propoxyethanol 410.85
    tert-butanol 303.76
    MTBE 261.79
    2-butoxyethanol 206.85
    propionic acid 210.69
    o-xylene 82.58
    formic acid 188.95
    diethyl ether 373.17
    m-xylene 120.76
    p-xylene 80.21
    chlorobenzene 149.7
    dimethyl carbonate 94.88
    n-octane 17.43
    formamide 223.82
    cyclopentanone 370.33
    2-pentanone 226.39
    anisole 121.41
    cyclopentyl methyl ether 327.46
    gamma-butyrolactone 438.61
    1-methoxy-2-propanol 313.96
    pyridine 293.83
    3-pentanone 153.84
    furfural 271.15
    n-dodecane 12.62
    diethylene glycol 290.97
    diisopropyl ether 118.88
    tert-amyl alcohol 171.69
    acetylacetone 206.95
    n-hexadecane 14.18
    acetophenone 89.62
    methyl propionate 197.27
    isopentyl acetate 165.66
    trichloroethylene 372.31
    n-nonanol 100.69
    cyclohexanol 184.79
    benzyl alcohol 91.25
    2-ethylhexanol 129.64
    isooctanol 100.21
    dipropyl ether 170.21
    1,2-dichlorobenzene 124.45
    ethyl lactate 70.87
    propylene carbonate 197.45
    n-methylformamide 261.48
    2-pentanol 184.27
    n-pentane 57.39
    1-propoxy-2-propanol 252.39
    1-methoxy-2-propyl acetate 211.42
    2-(2-methoxypropoxy) propanol 147.45
    mesitylene 78.51
    ε-caprolactone 240.71
    p-cymene 58.43
    epichlorohydrin 425.83
    1,1,1-trichloroethane 247.45
    2-aminoethanol 193.36
    morpholine-4-carbaldehyde 273.05
    sulfolane 259.64
    2,2,4-trimethylpentane 23.78
    2-methyltetrahydrofuran 450.58
    n-hexyl acetate 162.34
    isooctane 29.24
    2-(2-butoxyethoxy)ethanol 225.51
    sec-butyl acetate 92.49
    tert-butyl acetate 183.36
    decalin 24.55
    glycerin 150.54
    diglyme 347.28
    acrylic acid 174.1
    isopropyl myristate 67.72
    n-butyric acid 259.09
    acetyl acetate 166.02
    di(2-ethylhexyl) phthalate 62.9
    ethyl propionate 116.41
    nitromethane 410.57
    1,2-diethoxyethane 231.62
    benzonitrile 138.03
    trioctyl phosphate 54.23
    1-bromopropane 190.34
    gamma-valerolactone 430.98
    n-decanol 74.0
    triethyl phosphate 58.78
    4-methyl-2-pentanol 121.71
    propionitrile 289.85
    vinylene carbonate 200.97
    1,1,2-trichlorotrifluoroethane 199.18
    DMS 122.07
    cumene 50.61
    2-octanol 82.51
    2-hexanone 122.33
    octyl acetate 81.99
    limonene 78.01
    1,2-dimethoxyethane 297.81
    ethyl orthosilicate 61.92
    tributyl phosphate 60.57
    diacetone alcohol 180.33
    N,N-dimethylaniline 75.22
    acrylonitrile 277.3
    aniline 172.49
    1,3-propanediol 261.3
    bromobenzene 145.36
    dibromomethane 287.04
    1,1,2,2-tetrachloroethane 246.13
    2-methyl-cyclohexyl acetate 94.66
    tetrabutyl urea 63.74
    diisobutyl methanol 86.24
    2-phenylethanol 149.22
    styrene 65.96
    dioctyl adipate 76.1
    dimethyl sulfate 96.99
    ethyl butyrate 123.89
    methyl lactate 102.68
    butyl lactate 92.65
    diethyl carbonate 82.96
    propanediol butyl ether 151.4
    triethyl orthoformate 95.09
    p-tert-butyltoluene 62.66
    methyl 4-tert-butylbenzoate 117.71
    morpholine 597.57
    tert-butylamine 219.96
    n-dodecanol 56.53
    dimethoxymethane 314.97
    ethylene carbonate 181.34
    cyrene 103.87
    2-ethoxyethyl acetate 171.71
    2-ethylhexyl acetate 124.62
    1,2,4-trichlorobenzene 133.77
    4-methylpyridine 233.91
    dibutyl ether 116.74
    2,6-dimethyl-4-heptanol 86.24
    DEF 156.48
    dimethyl isosorbide 207.84
    tetrachloroethylene 192.0
    eugenol 111.34
    triacetin 122.95
    span 80 128.13
    1,4-butanediol 77.94
    1,1-dichloroethane 272.11
    2-methyl-1-pentanol 104.86
    methyl formate 208.3
    2-methyl-1-butanol 171.46
    n-decane 23.04
    butyronitrile 272.88
    3,7-dimethyl-1-octanol 107.45
    1-chlorooctane 71.05
    1-chlorotetradecane 28.96
    n-nonane 22.54
    undecane 16.51
    tert-butylcyclohexane 25.62
    cyclooctane 27.24
    cyclopentanol 215.84
    tetrahydropyran 529.77
    tert-amyl methyl ether 150.47
    2,5,8-trioxanonane 220.83
    1-hexene 86.35
    2-isopropoxyethanol 139.06
    2,2,2-trifluoroethanol 130.59
    methyl butyrate 126.97

    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
Achillea wilhelmsii (Turkey) Achillea wilhelmsii C. Koch (A. santolina Auct. Mult.), fam. Asteraceae 0.5%
Angelica root (Finland) 1 8015-64-3 Angelica archangelica L., fam. Apiaceae (Umbelliferae) 0.64%
Larix conifer bark Larix decidua Mill., fam. Pinaceae 1.71%
Lavandula dentata (Chemotype A) Lavandula dentata L. (Chemotype A), fam. Lamiaceae (Labiatae) 1.1%
Lavandula dentata (Chemotype B) Lavandula dentata L. (Chemotype B), fam. Lamiaceae (Labiatae) 1.2%
Lavandula stoechas (ssp. sampaioana A) Lavandula stoechas L. (ssp. sampaioana, Chemotype A), fam. Lamiaceae 0.2%
Lavandula stoechas (ssp. pedunculata A) Lavandula stoechas L. (ssp. pedunculata, Chemotype A), fam. Lamiaceae 0.8%
Lavandula stoechas (ssp. pedunculata B) Lavandula stoechas L. (ssp. pedunculata, Chemotype B), fam. Lamiaceae 0.9%
Lavandula stoechas (ssp. sampaioana B) Lavandula stoechas L. (ssp. sampaioana, Chemotype B), fam. Lamiaceae 1.1%
Lavandula stoechas (ssp. stoechas) Lavandula stoechas L. (ssp. stoechas), fam. Lamiaceae (Labiatae) 0.4%
Lavandula viridis Lavandula viridis L., fam. Lamiaceae (Labiatae) 1.4%
Pinus pinaster (Portugal) 1 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 0.01%
Santolina canescens Santolina rosmarinifolia (L.) ssp. canescens (Lag.) Nyman, fam. Asteraceae 0.04%
Santolina pectina Santolina pectina Lag., fam. Asteraceae (Compositae) 0.04%
Santolina semidentata Santolina semidentata Hoffmanns. & Link, fam. Asteraceae (Compositae) 0.5%
Juniperus martinezii Juniperus martinezii Perez de la Rosa, fam. Cupressaceae 0.5%
Juniperus flaccida var. flaccida Juniperus flaccida Schlecht, var. flaccida, fam. Cupressaceae 2.5%
Juniperus flaccida var. poblana Juniperus flaccida var. poblana Martinez, fam. Cupressaceae 1.3%
Thymus 'Pinewood' Thymus 'Pinewood' cv. nov., fam. Lamiaceae (Labiatae) 1.28%
Pistacia lentiscus (Spain) 1a leaf 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.02%
Pistacia lentiscus (Spain) 1c ripe fruit 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.01%
Annual wormwood (Yugoslavia) 84775-74-6 Artemisia annua L., fam. Asteraceae (Compositae) 0.28%
Myrtle flower (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.02%
Myrtle ripe fruits (Spain) 8008-46-6 Myrtus communis L., fam. Myrtaceae 0.28%
Origanum solymicum (Turkey) Origanum solymicum P.H. Davis, fam. Lamiaceae (Labiatae) 0.21%
Heteromorpha trifoliata Heteromorpha trifoliata (Wendl.) Eckl. & Zey., fam.Apiaceae (Umbelliferae) 0.05%
Artemisia moorcroftiana Artemisia moorcroftiana, fam. Asteraceae (Compositae) 0.42%
Patchouli (China) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.03%
Artemisia afra Willd. (Kenia) Artemisia afra Willd., fam. Asteraceae (Compositae) 1.07%
Juniperus rigida (China) Juniperus rigida Mig., fam. Cupressaceae 0.05%
Chenopodium ambrosioides Chenopodium ambrosioides L., fam. Chenopodiaceae 1.21%
Micromeria carminea (Turkey) Micromeria carminea P.H. Davis (syn.M.cristata), fam. Lamiaceae (Labiatae) 2.74%
Achillea biebersteinii (Turkey) 2 Achillea biebersteinii Afan., fam. Asteraceae (Compositae) 0.11%
Teucrium heterophyllum (Madeira) Teucrium heterophyllum L'Her. (T. canariensis), fam. Lamiaceae (Labiatae) 0.5%
Artemisia umbelliformis (Italy) Artemisia umbelliformis Lam., fam. Asteraceae (Compositae) 0.01%
Artemisia campestris (Italy) 1 Artemisia campestris L. ssp. borealis (Pallas), H.M. Hall et Clements 2.4%
Artemisia genipi (Italy) Artemisia genipi Weber, fam. Asteraceae (Compositae) 0.01%
Artemisia petrosa (Italy) Artemisia petrosa Baumg. ssp. eriantha Ten., fam. Asteraceae (Compositae) 0.01%
Artemisia vallesiaca (Italy) Artemisia vallesiaca All., fam. Asteraceae (Compositae) 0.9%
Wormwood (Mugwort) (Italy) 2 8008-93-3 Artemisia absinthium L., fam. Asteraceae (Compositae) 0.01%
Artemisia chamaemelifolia (Italy) Artemisia chamaemelifolia Vill., fam. Asteraceae (Compositae) 0.01%
Artemisia glacialis (Italy) Artemisia glacialis L., fam. Asteraceae (Compositae) 0.01%
Artemisia campestris (Italy) 2 Artemisia campestris L. ssp. campestris, fam. Asteraceae (Compositae) 1.1%
Artemisia alba (Italy) 84775-75-7 Artemisia alba Turra, fam. Asteraceae (Compositae) 0.7%
Annual wormwood (Italy) Artemisia annua L., fam. Asteraceae (Compositae) 0.5%
Artemisia verlotiorum (Italy) Artemisia verlotiorum Lamotte, fam. Asteraceae (Compositae) 7.6%
Armoise (Italy) 8008-93-3 Artemisia vulgaris L., fam. Asteraceae (Compositae) 7.0%
Inula viscosa (Turkey) Inula viscosa (L.) Aiton (Dittrichia viscosa (L.) Greuter), fam.Asteraceae 0.2%
Teucrium haenseleri flower Teucrium haenseleri Boiss., fam. Lamiaceae (Labiatae) 2.3%
Origanum husnuca-baserii (Turkey) Origanum husnucan-baserii H. Duman, Z. Aytac et A. Duran, fam. Lamiaceae 0.25%