(2-cis,6-trans)-Farnesol

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  • Identifiers

    CAS number
    3790-71-4

    Molecular formula
    C15H26O

    SMILES
    CC(=CCC/C(=C/CC/C(=C\CO)/C)/C)C

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

    Retention indicies (RI)

    • DB5: 1709.4
    • Carbowax: 2311.0

  • Odor profile

    Floral 90.45%
    Rose 65.81%
    Waxy 64.52%
    Sweet 60.12%
    Citrus 50.64%
    Green 48.91%
    Fruity 48.09%
    Fresh 47.42%
    Balsamic 46.27%
    Muguet 42.06%

    Scent© AI

  • Properties

    XLogP3-AA
    4.8

    Molecular weight
    222.37 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point

    • 230 to 235 °F at 760 mmHg (NTP, 1992)
    • 110-113 °C
    • BP: 145-146 °C at 3 mm Hg

    Flash point est.
    136.37 ˚C

    Solubility expt.

    • Soluble in three volumes of 70% alcohol
    • SOL IN ALCOHOL: 1:3 IN 70% ALCOHOL
    • Solubility in alcohol: 1 mL in 1 mL 95% ethanol
    • Insoluble in water
    • Insoluble in water; soluble in oils
    • soluble (in ethanol)

  • Synonyms

    • (2Z,6E)-Farnesol
    • (Z,E)-Farnesol
    • cis,trans-Farnesol
    • 2-cis,6-trans-Farnesol
    • 3790-71-4
    • (2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
    • (2-cis,6-trans)-farnesol
    • (Z,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
    • Farnesol, (2Z,6E)-
    • SQ4TI19PXT
    • (2-cis,6-trans)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
    • (2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol
    • CIS-TRANS-FARNESOL
    • 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (Z,E)-
    • CHEBI:16774
    • 3,7,11-trimethyldodeca-2Z,6E,10-trien-1-ol
    • Farnesyl alcohol
    • UNII-SQ4TI19PXT
    • NSC60597
    • (Z)-Farnesol
    • cis,trans-.alpha.-Farnesol
    • SCHEMBL806894
    • CHEMBL5185759
    • CIS-2-TRANS-6-FARNESOL
    • DTXSID30274196
    • 4602-84-0
    • LMPR0103010013
    • FEMA NO. 2478, (2Z,6E)-
    • 2-cis,6-trans-Farnesol, >=95.0% (GC)
    • C03220
    • EN300-7460532
    • 3,7,11-trimethyl-dodeca-2cis,6trans,10-trien-1-ol
    • Q27102070
    • 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (2Z,6E)-

  • Applications

    (2-cis,6-trans)-Farnesol is a sesquiterpenoid alcohol with a soft floral, warm, slightly woody odor, widely used as a fragrance ingredient and fixative in fine fragrances, personal care and household products to enhance diffusion, longevity and smooth muguet-rose accords; thanks to its antimicrobial activity against odor-causing bacteria it is also employed as a deodorant/preservation booster at low levels, with allergen labeling and compliance to IFRA, EU and local regulations required; in flavor applications this isomer may be used at very low levels to impart honeyed, floral-fruity nuances in beverages and confectionery where permitted; in biological and pharmaceutical R&D, (2-cis,6-trans)-farnesol serves as a reference compound to probe the mevalonate pathway, modulation of HMG-CoA reductase and protein prenylation, as a model quorum-sensing molecule of Candida albicans, and in studies on antifungal/antibiofilm effects, transdermal permeation enhancement and as a synthetic scaffold for esters, farnesylated derivatives and functional materials; its lipophilicity and tendency to oxidize call for airtight, light/oxygen-protected storage and the use of antioxidants in formulations, and selecting the 2-cis,6-trans isomer allows fine-tuning of odor character versus other farnesol isomers.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 589.99
    methanol 313.58
    isopropanol 467.1
    water 0.06
    ethyl acetate 448.5
    n-propanol 466.84
    acetone 269.13
    n-butanol 567.9
    acetonitrile 148.96
    DMF 114.22
    toluene 195.66
    isobutanol 285.96
    1,4-dioxane 938.53
    methyl acetate 224.77
    THF 1268.53
    2-butanone 340.02
    n-pentanol 383.19
    sec-butanol 432.9
    n-hexane 250.19
    ethylene glycol 15.9
    NMP 118.23
    cyclohexane 311.35
    DMSO 196.82
    n-butyl acetate 441.74
    n-octanol 159.08
    chloroform 548.9
    n-propyl acetate 294.68
    acetic acid 118.8
    dichloromethane 400.61
    cyclohexanone 421.5
    propylene glycol 72.04
    isopropyl acetate 287.81
    DMAc 171.47
    2-ethoxyethanol 368.93
    isopentanol 399.66
    n-heptane 213.29
    ethyl formate 128.9
    1,2-dichloroethane 303.29
    n-hexanol 546.98
    2-methoxyethanol 418.43
    isobutyl acetate 205.39
    tetrachloromethane 110.75
    n-pentyl acetate 219.53
    transcutol 1278.27
    n-heptanol 205.26
    ethylbenzene 132.1
    MIBK 254.0
    2-propoxyethanol 525.23
    tert-butanol 595.01
    MTBE 738.93
    2-butoxyethanol 295.94
    propionic acid 109.68
    o-xylene 118.89
    formic acid 21.11
    diethyl ether 1050.92
    m-xylene 141.76
    p-xylene 140.26
    chlorobenzene 139.51
    dimethyl carbonate 34.6
    n-octane 49.25
    formamide 32.37
    cyclopentanone 296.67
    2-pentanone 390.06
    anisole 221.38
    cyclopentyl methyl ether 493.26
    gamma-butyrolactone 215.93
    1-methoxy-2-propanol 384.5
    pyridine 344.33
    3-pentanone 233.26
    furfural 185.39
    n-dodecane 21.6
    diethylene glycol 160.15
    diisopropyl ether 277.51
    tert-amyl alcohol 469.61
    acetylacetone 212.45
    n-hexadecane 25.27
    acetophenone 150.29
    methyl propionate 181.93
    isopentyl acetate 374.95
    trichloroethylene 393.38
    n-nonanol 155.52
    cyclohexanol 362.89
    benzyl alcohol 131.59
    2-ethylhexanol 342.96
    isooctanol 167.63
    dipropyl ether 773.56
    1,2-dichlorobenzene 125.47
    ethyl lactate 86.12
    propylene carbonate 147.27
    n-methylformamide 57.96
    2-pentanol 409.65
    n-pentane 204.54
    1-propoxy-2-propanol 504.44
    1-methoxy-2-propyl acetate 334.82
    2-(2-methoxypropoxy) propanol 260.73
    mesitylene 102.84
    ε-caprolactone 346.76
    p-cymene 111.42
    epichlorohydrin 408.11
    1,1,1-trichloroethane 308.37
    2-aminoethanol 80.41
    morpholine-4-carbaldehyde 257.08
    sulfolane 206.78
    2,2,4-trimethylpentane 68.42
    2-methyltetrahydrofuran 873.45
    n-hexyl acetate 281.64
    isooctane 59.09
    2-(2-butoxyethoxy)ethanol 403.13
    sec-butyl acetate 252.5
    tert-butyl acetate 326.53
    decalin 90.93
    glycerin 68.15
    diglyme 684.96
    acrylic acid 50.69
    isopropyl myristate 121.96
    n-butyric acid 324.0
    acetyl acetate 152.1
    di(2-ethylhexyl) phthalate 90.23
    ethyl propionate 227.86
    nitromethane 120.91
    1,2-diethoxyethane 704.59
    benzonitrile 131.22
    trioctyl phosphate 67.61
    1-bromopropane 398.7
    gamma-valerolactone 418.03
    n-decanol 110.16
    triethyl phosphate 122.62
    4-methyl-2-pentanol 208.29
    propionitrile 190.3
    vinylene carbonate 105.72
    1,1,2-trichlorotrifluoroethane 182.13
    DMS 113.08
    cumene 101.51
    2-octanol 130.03
    2-hexanone 329.53
    octyl acetate 136.99
    limonene 201.35
    1,2-dimethoxyethane 747.3
    ethyl orthosilicate 153.68
    tributyl phosphate 87.84
    diacetone alcohol 274.07
    N,N-dimethylaniline 145.97
    acrylonitrile 105.09
    aniline 174.25
    1,3-propanediol 187.18
    bromobenzene 149.18
    dibromomethane 353.07
    1,1,2,2-tetrachloroethane 396.37
    2-methyl-cyclohexyl acetate 256.5
    tetrabutyl urea 101.64
    diisobutyl methanol 190.66
    2-phenylethanol 189.81
    styrene 135.46
    dioctyl adipate 158.13
    dimethyl sulfate 41.17
    ethyl butyrate 377.74
    methyl lactate 57.98
    butyl lactate 138.57
    diethyl carbonate 186.61
    propanediol butyl ether 186.86
    triethyl orthoformate 292.36
    p-tert-butyltoluene 115.14
    methyl 4-tert-butylbenzoate 171.51
    morpholine 1162.49
    tert-butylamine 482.36
    n-dodecanol 83.07
    dimethoxymethane 241.68
    ethylene carbonate 114.56
    cyrene 142.94
    2-ethoxyethyl acetate 274.77
    2-ethylhexyl acetate 314.31
    1,2,4-trichlorobenzene 137.74
    4-methylpyridine 305.89
    dibutyl ether 394.31
    2,6-dimethyl-4-heptanol 190.66
    DEF 270.86
    dimethyl isosorbide 381.62
    tetrachloroethylene 242.63
    eugenol 147.47
    triacetin 191.68
    span 80 249.85
    1,4-butanediol 60.75
    1,1-dichloroethane 320.45
    2-methyl-1-pentanol 297.06
    methyl formate 34.79
    2-methyl-1-butanol 339.37
    n-decane 48.76
    butyronitrile 342.76
    3,7-dimethyl-1-octanol 174.54
    1-chlorooctane 138.66
    1-chlorotetradecane 49.13
    n-nonane 52.13
    undecane 30.19
    tert-butylcyclohexane 89.39
    cyclooctane 101.28
    cyclopentanol 225.46
    tetrahydropyran 1376.34
    tert-amyl methyl ether 469.95
    2,5,8-trioxanonane 416.47
    1-hexene 496.8
    2-isopropoxyethanol 280.76
    2,2,2-trifluoroethanol 21.09
    methyl butyrate 288.3

    Scent© AI

1 4

IFRA standard 51

Recommendation
Restriction / Specification
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0.21 % Category 7A
Rinse-off products applied to the hair with some hand contact
 2.4 %
Category 2
Products applied to the axillae
 0.062 % Category 7B
Leave-on products applied to the hair with some hand contact
 2.4 %
Category 3
Products applied to the face/body using fingertips
 1.2 % Category 8
Products with significant anogenital exposure
 0.12 %
Category 4
Products related to fine fragrance
 1.2 % Category 9
Products with body and hand exposure, primarily rinse off
 2.3 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0.29 % Category 10A
Household care products with mostly hand contact
 8.1 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0.29 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 8.1 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0.29 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 4.5 %
Category 5D
Baby Creams, baby Oils and baby talc
 0.29 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 4.5 %
Category 6
Products with oral and lip exposure
 0.68 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Specification
Farnesol should only be used as a fragrance ingredient if it contains a minimum of 96% of farnesol isomers as determined by GLC.

Botanical

Name CAS Botanical Proportion
Ambrette seed 1 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.61%
Cedrela odorata Cedrela odorata L., fam. Meliaceae 0.11%
Palmarosa (India) 3 8014-19-5 Cymbopogon martini (Roxb.) Wats, var. martini, fam. Poaceae (Gramineae) 0.64%
Ambrette seed (China) 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.13%
Pepper, black 6 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Rose (Bulgaria) 2 8007-01-0 Rosa damascena Mill., fam. Rosaceae 0.15%
Ambrette seed 2 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.3%
Ambrette seed 3 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.2%
Orange, bitter (Italy) 72968-50-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.01%
Yuzu (Japan) 3 Citrus junos Sieb. ex Tanaka, fam. Rutaceae 0.01%
Lemon (Japan) 4 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Neroli bigarade (bitter orange flower) China 3 8016-38-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.36%
Rosa rugosa (China) 2 Rosa rugosa Thunb., fam. Rosaceae 0.91%
Eucalyptus globulus (China) 2 fruit 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.95%
Ylang Ylang 2a 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.9%
Ylang Ylang 2b 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 1.8%
Ylang Ylang 2c 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 2.3%
Clausena dunniana (China) 1 Clausena dunniana Levl., fam. Rutaceae 0.1%
Cymbidium sinense flower headspace (China) Cymbidium sinense (Andr.) Willd., fam. Orchidaceae 1.82%
Pterodon polygalaeflorus Pterodon polygalaeflorus Benth., fam. Leguminosae 1.6%
Eucalyptus robusta (China) Eucalyptus robusta Smith, fam. Myrtaceae 1.54%
Jasmine (China) 1 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 3.06%
Couroupita guaianensis flower (Malaysia) Couroupita guianensis Auble, fam. Lecythidaceae 0.9%
Coleus aromaticus (Mauritius) Coleus aromaticus Benth. (wild oregano), fam. Lamiaceae (Labiatae) 0.5%
Chamomile, german (Italy) 2 8002-66-2 Chamomilla recutita (L.) Rausch.(Matricaria chamomilla L.), fam.Asteraceae 0.42%
Neroli bigarade (bitter orange flower) Italy 3 8016-38-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.98%
Ylang Ylang (China) 4 68606-83-7 Cananga odorata (Lamk.) Hook. f. et Thomson, fam. Annonaceae 0.21%
Rosa odorata (China) Rosa odorata Sweet, fam. Rosaceae 1.1%
Citronella java (Cuba) 8000-29-1 Cymbopogon winterianus Jowitt., fam. Poaceae (Graminae) 0.07%
Lavender (Lithuania) 8000-28-0 Lavandula angustifolia Mill., fam. Lamiaceae (Labiatae) 0.01%
Lemon flower headspace (clone SG) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.1%
Lemon flower headspace (clone ZH) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 1.0%
Rose (Turkey) 4 8007-01-7 Rosa damascena Mill., fam. Rosaceae 0.38%
Rosa rugosa (China) 1 Rosa rugosa Thunb. (hybrids), fam. Rosaceae 1.0%
Annona squamosa leaf Annona squamosa L., fam. Annonaceae (sweetsop or custard apple) 1.2%
Phalaenopsis schilleriana headspace Phalaenopsis schilleriana Rehb. f., fam. Orchidaceae 0.1%
Tagetes filifolia (Peru) Tagetes filifolia Lag., fam. Asteraceae (Compositae) 0.1%
Canella winterana (Cuba) 2 Canella winterana (L.) Gaertn., fam. Canellaceae 0.4%
Couroupita guianensis flower (Brazil) Couroupita guainensis Auble., fam. Lecythidaceae 1.5%
Rollinia mucosa fruit Rollinia mucosa (Jacq.) Baill, fam. Annonaceae 0.1%
Cinnamomum aureofulvum bark Cinnamomum aureofulvum Gamb., fam. Lauraceae 0.2%
Geranium (Cuba) 8000-46-2 Pelargonium species, fam. Geraniaceae 0.4%
Patchouli (China) 3a root 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.77%
Patchouli (China) 3b rhizome 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.63%
Pepper, black (India) 6a distilled 8006-82-4 Piper nigrum L., fam. Piperaceae 3.1%
Pepper, black (India) 6b free volatiles 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Pepper, black (India) 4 8006-82-4 Piper nigrum L., fam. Piperaceae 4.59%
Eupatorium cannabinum Eupatorium cannabinum L. ssp. cannabinum, fam. Astercaceae (Compositae) 0.7%
Lime (Mexican, West Indian, Key) (Vietnam) 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.02%
Croton ovalifolius (Venezuela) Croton ovalifolius Vahl, fam. Euphorbiaceae 1.7%