9,12-Octadecadienoic Acid

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  • Identifiers

    CAS number
    2197-37-7

    Molecular formula
    C18H32O2

    SMILES
    CCCCCC=CCC=CCCCCCCCC(=O)O

    Safety labels

    Flammable
    Flammable

    Retention indicies (RI)

    • DB5: 2128.0
    • Carbowax: 3196.67

  • Odor profile

    Fatty 85.38%
    Oily 59.42%
    Waxy 52.46%
    Dairy 30.8%
    Milky 24.7%
    Meaty 23.99%
    Green 23.72%
    Creamy 23.37%
    Fishy 23.24%
    Buttery 22.33%

    Scent© AI

  • Properties

    XLogP3-AA
    6.8

    pKa est.
    7.39 (neutral)

    Molecular weight
    280.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    351°C

    Flash point est.
    203.66 ˚C

  • Synonyms

    • 9,12-Octadecadienoic acid
    • octadeca-9,12-dienoic acid
    • 2197-37-7
    • grape seed oils
    • DTXSID2075059
    • alpha-Linoleic acid
    • GrapeSeedOil
    • 85594-37-2
    • 9,12-Octadecadienoic acid (VAN)
    • 8024-22-4
    • cis-9-cis-12-Octadecadienoic acid
    • Linoleic acid- 99%
    • 9,12-octadecadienic acid
    • CBiol_001994
    • KBioGR_000094
    • KBioSS_000094
    • DTXCID8036578
    • KBio2_000094
    • KBio2_002662
    • KBio2_005230
    • KBio3_000187
    • KBio3_000188
    • Bio1_000280
    • Bio1_000769
    • Bio1_001258
    • Bio2_000094
    • Bio2_000574
    • MLA11125
    • AKOS030228545
    • FL181959
    • SY011113
    • DB-053596
    • Q27163939
    • 606-872-4

  • Applications

    9,12-Octadecadienoic acid (linoleic acid, CAS 2197-37-7) is widely used as an omega-6 fatty acid source in foods, nutraceuticals, and animal feed; in cosmetics for skin and hair as an emollient, moisturizer, and barrier-repair lipid, as well as a solvency aid to help dissolve lipophilic actives and reduce irritation; in pharmaceuticals as a lipid excipient for emulsions/microemulsions and drug delivery systems, and as a synthetic intermediate; in chemical industry as a building block for esters, amides, and surfactants, for alkyd resins, dimer acids for polyamides, epoxidized derivatives for plasticization/stabilization, biolubricants, inks, coatings/varnishes, soaps and detergents; as a transesterification feedstock for biodiesel; in agriculture as a wetting/spreading adjuvant and carrier; and in laboratories as a carbon source for microbes, an analytical standard, and a tool in lipid metabolism and oxidative-stress research; note that its polyunsaturation makes it oxidation-prone, so it is typically stored cool, air- and light-protected with antioxidants or inert gas, and may be formulated as esters (e.g., methyl/ethyl linoleate), salts, or triglycerides to improve stability, odor, and solubility.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 287.9
    methanol 220.02
    isopropanol 262.27
    water 0.01
    ethyl acetate 229.95
    n-propanol 234.12
    acetone 265.41
    n-butanol 251.37
    acetonitrile 51.22
    DMF 339.47
    toluene 80.12
    isobutanol 181.62
    1,4-dioxane 299.28
    methyl acetate 118.89
    THF 1000.94
    2-butanone 267.06
    n-pentanol 218.54
    sec-butanol 226.56
    n-hexane 65.78
    ethylene glycol 8.33
    NMP 408.1
    cyclohexane 88.34
    DMSO 660.66
    n-butyl acetate 306.66
    n-octanol 97.95
    chloroform 290.02
    n-propyl acetate 287.77
    acetic acid 81.05
    dichloromethane 314.47
    cyclohexanone 511.08
    propylene glycol 40.01
    isopropyl acetate 244.04
    DMAc 478.5
    2-ethoxyethanol 304.77
    isopentanol 276.29
    n-heptane 34.05
    ethyl formate 82.8
    1,2-dichloroethane 320.28
    n-hexanol 194.75
    2-methoxyethanol 336.65
    isobutyl acetate 214.32
    tetrachloromethane 62.43
    n-pentyl acetate 253.5
    transcutol 1320.53
    n-heptanol 108.31
    ethylbenzene 77.2
    MIBK 308.68
    2-propoxyethanol 342.87
    tert-butanol 351.49
    MTBE 406.0
    2-butoxyethanol 246.97
    propionic acid 90.42
    o-xylene 75.36
    formic acid 17.15
    diethyl ether 332.96
    m-xylene 82.16
    p-xylene 88.27
    chlorobenzene 104.53
    dimethyl carbonate 42.75
    n-octane 13.82
    formamide 35.13
    cyclopentanone 489.05
    2-pentanone 341.15
    anisole 164.1
    cyclopentyl methyl ether 446.74
    gamma-butyrolactone 350.06
    1-methoxy-2-propanol 382.14
    pyridine 201.44
    3-pentanone 190.49
    furfural 245.96
    n-dodecane 8.87
    diethylene glycol 124.73
    diisopropyl ether 129.45
    tert-amyl alcohol 303.56
    acetylacetone 302.22
    n-hexadecane 10.39
    acetophenone 180.15
    methyl propionate 159.67
    isopentyl acetate 318.23
    trichloroethylene 395.31
    n-nonanol 98.19
    cyclohexanol 253.04
    benzyl alcohol 114.66
    2-ethylhexanol 153.02
    isooctanol 114.66
    dipropyl ether 265.95
    1,2-dichlorobenzene 119.28
    ethyl lactate 99.2
    propylene carbonate 189.97
    n-methylformamide 94.41
    2-pentanol 209.1
    n-pentane 34.96
    1-propoxy-2-propanol 334.42
    1-methoxy-2-propyl acetate 300.56
    2-(2-methoxypropoxy) propanol 220.98
    mesitylene 67.05
    ε-caprolactone 398.96
    p-cymene 57.55
    epichlorohydrin 498.08
    1,1,1-trichloroethane 235.75
    2-aminoethanol 55.48
    morpholine-4-carbaldehyde 358.37
    sulfolane 633.65
    2,2,4-trimethylpentane 28.71
    2-methyltetrahydrofuran 621.55
    n-hexyl acetate 282.16
    isooctane 23.49
    2-(2-butoxyethoxy)ethanol 351.36
    sec-butyl acetate 236.37
    tert-butyl acetate 343.26
    decalin 46.84
    glycerin 53.52
    diglyme 629.51
    acrylic acid 44.68
    isopropyl myristate 104.15
    n-butyric acid 256.2
    acetyl acetate 99.06
    di(2-ethylhexyl) phthalate 81.0
    ethyl propionate 207.04
    nitromethane 143.62
    1,2-diethoxyethane 479.52
    benzonitrile 104.6
    trioctyl phosphate 65.78
    1-bromopropane 238.05
    gamma-valerolactone 591.56
    n-decanol 69.05
    triethyl phosphate 102.79
    4-methyl-2-pentanol 145.55
    propionitrile 80.28
    vinylene carbonate 120.16
    1,1,2-trichlorotrifluoroethane 282.71
    DMS 120.25
    cumene 65.25
    2-octanol 84.16
    2-hexanone 329.03
    octyl acetate 120.31
    limonene 113.92
    1,2-dimethoxyethane 536.49
    ethyl orthosilicate 118.58
    tributyl phosphate 86.11
    diacetone alcohol 365.35
    N,N-dimethylaniline 137.91
    acrylonitrile 64.12
    aniline 99.11
    1,3-propanediol 129.68
    bromobenzene 116.87
    dibromomethane 239.33
    1,1,2,2-tetrachloroethane 434.74
    2-methyl-cyclohexyl acetate 217.29
    tetrabutyl urea 127.15
    diisobutyl methanol 105.38
    2-phenylethanol 128.97
    styrene 84.17
    dioctyl adipate 160.15
    dimethyl sulfate 98.05
    ethyl butyrate 235.42
    methyl lactate 84.77
    butyl lactate 182.5
    diethyl carbonate 110.2
    propanediol butyl ether 203.08
    triethyl orthoformate 186.94
    p-tert-butyltoluene 59.32
    methyl 4-tert-butylbenzoate 188.34
    morpholine 545.77
    tert-butylamine 231.5
    n-dodecanol 49.79
    dimethoxymethane 294.08
    ethylene carbonate 116.77
    cyrene 187.68
    2-ethoxyethyl acetate 283.78
    2-ethylhexyl acetate 247.39
    1,2,4-trichlorobenzene 141.01
    4-methylpyridine 224.26
    dibutyl ether 241.4
    2,6-dimethyl-4-heptanol 105.38
    DEF 337.63
    dimethyl isosorbide 422.1
    tetrachloroethylene 252.57
    eugenol 160.18
    triacetin 233.85
    span 80 206.51
    1,4-butanediol 47.68
    1,1-dichloroethane 239.03
    2-methyl-1-pentanol 220.89
    methyl formate 45.07
    2-methyl-1-butanol 222.11
    n-decane 18.59
    butyronitrile 148.52
    3,7-dimethyl-1-octanol 128.09
    1-chlorooctane 87.48
    1-chlorotetradecane 29.06
    n-nonane 17.98
    undecane 12.06
    tert-butylcyclohexane 40.57
    cyclooctane 26.34
    cyclopentanol 230.93
    tetrahydropyran 594.5
    tert-amyl methyl ether 298.73
    2,5,8-trioxanonane 391.03
    1-hexene 182.06
    2-isopropoxyethanol 266.4
    2,2,2-trifluoroethanol 21.09
    methyl butyrate 294.97

    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
Fissitigma shangtzeense, flower extract Fissitigma shangtzeense Tsiang et P.T. Li, fam. Annonaceae 7.96%
Genet absolute 1 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 4.0%
Osmanthus absolute 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 8.7%
Parsley absolute (Egypt) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 7.63%
Saffron 1 8022-19-3 Crocus sativus L., fam. Iridaceae 0.1%
Ambrette seed (China) 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 3.78%
Orris butter 8002-73-1 Iris florentina L., fam. Iridaceae 0.01%
Diospyros discolor, fruit peel Diospyros discolor Willd., Ebenaceae (D. blancoi), fam. Ebenaceae 0.01%
Ambrette seed 2 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.5%
Ambrette seed 4 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 2.0%
Ambrette seed 3 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.3%
Angelica root (Finland) 4 8015-64-3 Angelica archangelica L. var. archangelica, fam. Apiaceae (Umbelliferae) 3.5%
Angelica root (Finland) 3 8015-64-3 Angelica archangelica L. var. sativa, fam. Apiaceae (Umbelliferae) 3.6%
Agarwood smoke 1 Aquilaria agallocha Roxb., fam. Thymelaeaceae 0.46%
Violet odorata leaf 1 8024-08-6 Viola odorata L., fam. Violaceae 29.0%
Genet absolute 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 4.0%
Elaeagnus angustifolia flower absolute (China) Elaeagnus angustifolia L., fam. Elaeagnaceae 13.59%
Zingiber zerumbet (Vietnam) 2c flower Zingiber zerumbet (L.) Sm., fam. Zingiberaceae 0.9%
Averrhoa bilimbi fruit (Malaysia) Averrhoa bilimbi L., fam. Oxalidaceae 4.6%
Indian curry leaf tree (flower) Murraya koenigii Spreng., fam. Rutaceae 1.0%
Calamus (China) 1a leaf 8015-79-0 Acorus calamus L., fam. Araceae 0.02%
Tamarind 3 fruit Tamarindus indica L., fam. Leguminosae 2.1%
Celery seed (China) 3b 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 1.04%
Lippia alba (Cuba) 1b leaf Lippia alba (Mill.) N.E. Brown, fam. Verbenaceae 37.17%
Rue (France) 8014-29-7 Ruta graveolens L., fam. Rutaceae 0.5%
Colocasia esculenta (Taro) Colocasia esculenta (L.) Schott, fam. Araceae 9.9%
Tarragon (France) 5 8016-88-4 Artemisia dracunculus L. (French type), fam. Asteraceae (Compositae) 0.5%
Patchouli (China) 3a root 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 0.11%
Patchouli (China) 3b rhizome 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.96%
Anthoxanthum odoratum (Italy) 1b hay Anthoxanthum odoratum L., fam. Poaceae (Gramineae) 1.2%
Carapa guianensis Carapa guianensis Aubl., fam. Meliaceae 0.1%
Rocket leaf 1 Eruca sativa L., fam. Brassicaceae 0.19%
Cassie absolute 1a extract 8023-82-3 Acacia farnesiana (L.) Willd., fam. Mimosaceae (Leguminosae) 5.2%
Armoise (Israel) 8008-93-3 Artemisia herba-alba Asso, fam. Asteraceae (Compositae) 0.2%
Guarea macrophylla ssp. tuberculata stem bark Guerea macrophylla Vahl. ssp. tuberculata Vellozo, fam. Meilaceae 2.7%
Croton jimenezii (Costa Rica) Croton jimenezii Standl. et Valerio, fam. Euphorbiaceae 3.05%
Neolitsea australiensis leaf (Australia) Neolitsea australiensis Kosterm., fam. Lauraceae 2.0%
Neolitsea brassii leaf (Australia) Neolitsea brassii Allen, fam. Lauraceae 3.5%