(E)-Ligustilide

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  • Identifiers

    CAS number
    81944-08-3

    Molecular formula
    C12H14O2

    SMILES
    CCC/C=C/1\C2=C(C=CCC2)C(=O)O1

    Retention indicies (RI)

    • DB5: 1790.0
    • Carbowax: 2740.0

  • Odor profile

    Herbal 71.17%
    Spicy 57.0%
    Celery 48.54%
    Mint 43.36%
    Coconut 37.06%
    Lactonic 36.13%
    Green 34.83%
    Coumarinic 28.88%
    Sweet 27.1%
    Fruity 26.43%

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  • Properties

    XLogP3-AA
    2.7

    Molecular weight
    190.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    269°C

    Flash point est.
    153.63 ˚C

  • Synonyms

    • (E)-Ligustilide
    • 81944-08-3
    • (E)-3-Butylidene-4,5-dihydroisobenzofuran-1(3H)-one
    • trans-ligustilide
    • 1(3H)-Isobenzofuranone, 3-butylidene-4,5-dihydro-, (E)-
    • (3E)-3-butylidene-1,3,4,5-tetrahydro-2-benzofuran-1-one
    • (3E)-3-butylidene-4,5-dihydro-2-benzofuran-1-one
    • SCHEMBL4087024
    • IQVQXVFMNOFTMU-DHZHZOJOSA-N
    • AKOS032948223
    • (e)-3-butylidene-4,5-dihydrophthalide
    • trans-3-Butylidene-4,5-dihydrophthalide
    • 3-Butylidene-4,5-dihydrophthalide, 8CI
    • DA-69165
    • 3-Butylidene-4,5-dihydro-1(3H)-isobenzofuranone, 9CI
    • 1(3H)-Isobenzofuranone, 3-butylidene-4,5-dihydro-, (3E)-

  • Applications

    (E)-Ligustilide (CAS 81944-08-3) is a volatile phthalide that is a major bioactive of Angelica sinensis (Dang Gui) and Ligusticum chuanxiong (Chuanxiong), with applications focused on its use as a quantitative reference standard and quality marker for herbal materials, extracts, and traditional formulations; as a pharmacological probe and lead to discover and optimize derivatives with vasodilatory, antispasmodic, analgesic, anti-inflammatory, antioxidant, and neuroprotective potential (in models of cerebral ischemia, migraine, and oxidative stress), with preclinical evidence of blood-brain barrier penetration and modulation of pathways such as Nrf2/HO-1, NF-kB, and nitric oxide; as an active/marker component in formulation and drug-delivery technologies (nanoemulsions, liposomes, cyclodextrin complexes) to address its light-, heat-, and oxygen-sensitive instability and to improve bioavailability; and in the flavor and fragrance industry for its warm, spicy, celery-like note used at trace levels in foods and cosmetics; it is also used to investigate synergy with ferulic acid and other phthalides in multi-herb prescriptions and to support pharmacokinetic and metabolomic biomarker studies; however, ligustilide is currently intended primarily for research use, is not an FDA/EMA-approved drug, and any inclusion in consumer products should carefully address stability, purity, dosing, and safety, particularly for sensitive populations such as pregnant individuals.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 184.18
    methanol 175.75
    isopropanol 154.96
    water 0.04
    ethyl acetate 219.34
    n-propanol 201.23
    acetone 299.51
    n-butanol 207.19
    acetonitrile 180.86
    DMF 944.07
    toluene 317.54
    isobutanol 166.45
    1,4-dioxane 373.86
    methyl acetate 250.16
    THF 476.95
    2-butanone 339.94
    n-pentanol 154.97
    sec-butanol 199.41
    n-hexane 13.25
    ethylene glycol 39.95
    NMP 688.87
    cyclohexane 34.65
    DMSO 391.16
    n-butyl acetate 239.22
    n-octanol 100.12
    chloroform 986.42
    n-propyl acetate 168.43
    acetic acid 151.32
    dichloromethane 895.49
    cyclohexanone 536.37
    propylene glycol 66.39
    isopropyl acetate 169.73
    DMAc 567.63
    2-ethoxyethanol 177.93
    isopentanol 207.96
    n-heptane 8.13
    ethyl formate 158.92
    1,2-dichloroethane 664.01
    n-hexanol 185.65
    2-methoxyethanol 326.84
    isobutyl acetate 126.71
    tetrachloromethane 83.8
    n-pentyl acetate 176.48
    transcutol 764.06
    n-heptanol 94.62
    ethylbenzene 146.9
    MIBK 193.81
    2-propoxyethanol 288.09
    tert-butanol 170.19
    MTBE 178.41
    2-butoxyethanol 179.12
    propionic acid 165.64
    o-xylene 165.63
    formic acid 46.09
    diethyl ether 190.39
    m-xylene 188.32
    p-xylene 166.76
    chlorobenzene 458.88
    dimethyl carbonate 149.47
    n-octane 7.01
    formamide 94.93
    cyclopentanone 516.31
    2-pentanone 269.77
    anisole 262.96
    cyclopentyl methyl ether 248.43
    gamma-butyrolactone 471.0
    1-methoxy-2-propanol 265.05
    pyridine 660.17
    3-pentanone 208.36
    furfural 514.3
    n-dodecane 9.85
    diethylene glycol 208.8
    diisopropyl ether 62.29
    tert-amyl alcohol 179.1
    acetylacetone 275.31
    n-hexadecane 11.88
    acetophenone 254.44
    methyl propionate 244.38
    isopentyl acetate 237.54
    trichloroethylene 1269.73
    n-nonanol 91.76
    cyclohexanol 220.46
    benzyl alcohol 240.44
    2-ethylhexanol 114.16
    isooctanol 87.18
    dipropyl ether 78.51
    1,2-dichlorobenzene 384.63
    ethyl lactate 104.91
    propylene carbonate 307.61
    n-methylformamide 275.21
    2-pentanol 149.4
    n-pentane 15.13
    1-propoxy-2-propanol 193.23
    1-methoxy-2-propyl acetate 237.09
    2-(2-methoxypropoxy) propanol 203.96
    mesitylene 109.42
    ε-caprolactone 408.42
    p-cymene 72.35
    epichlorohydrin 681.66
    1,1,1-trichloroethane 410.37
    2-aminoethanol 96.37
    morpholine-4-carbaldehyde 521.1
    sulfolane 530.62
    2,2,4-trimethylpentane 14.22
    2-methyltetrahydrofuran 340.96
    n-hexyl acetate 263.68
    isooctane 12.76
    2-(2-butoxyethoxy)ethanol 279.47
    sec-butyl acetate 132.88
    tert-butyl acetate 170.23
    decalin 28.57
    glycerin 101.38
    diglyme 421.28
    acrylic acid 163.9
    isopropyl myristate 101.15
    n-butyric acid 240.72
    acetyl acetate 147.98
    di(2-ethylhexyl) phthalate 115.9
    ethyl propionate 154.25
    nitromethane 284.48
    1,2-diethoxyethane 218.08
    benzonitrile 382.4
    trioctyl phosphate 80.32
    1-bromopropane 314.19
    gamma-valerolactone 555.46
    n-decanol 70.97
    triethyl phosphate 86.59
    4-methyl-2-pentanol 105.43
    propionitrile 219.23
    vinylene carbonate 341.26
    1,1,2-trichlorotrifluoroethane 396.23
    DMS 231.98
    cumene 94.09
    2-octanol 80.81
    2-hexanone 189.64
    octyl acetate 131.24
    limonene 91.29
    1,2-dimethoxyethane 327.77
    ethyl orthosilicate 81.97
    tributyl phosphate 101.03
    diacetone alcohol 209.58
    N,N-dimethylaniline 168.78
    acrylonitrile 314.89
    aniline 343.34
    1,3-propanediol 158.0
    bromobenzene 539.42
    dibromomethane 581.18
    1,1,2,2-tetrachloroethane 906.84
    2-methyl-cyclohexyl acetate 140.86
    tetrabutyl urea 137.14
    diisobutyl methanol 68.79
    2-phenylethanol 236.04
    styrene 205.38
    dioctyl adipate 141.52
    dimethyl sulfate 209.97
    ethyl butyrate 133.11
    methyl lactate 146.69
    butyl lactate 149.98
    diethyl carbonate 114.31
    propanediol butyl ether 192.61
    triethyl orthoformate 105.79
    p-tert-butyltoluene 67.79
    methyl 4-tert-butylbenzoate 186.63
    morpholine 473.1
    tert-butylamine 111.51
    n-dodecanol 57.17
    dimethoxymethane 354.81
    ethylene carbonate 257.72
    cyrene 194.53
    2-ethoxyethyl acetate 233.18
    2-ethylhexyl acetate 194.17
    1,2,4-trichlorobenzene 460.35
    4-methylpyridine 654.41
    dibutyl ether 116.98
    2,6-dimethyl-4-heptanol 68.79
    DEF 380.61
    dimethyl isosorbide 303.83
    tetrachloroethylene 477.59
    eugenol 219.14
    triacetin 202.32
    span 80 176.87
    1,4-butanediol 72.36
    1,1-dichloroethane 512.26
    2-methyl-1-pentanol 174.24
    methyl formate 189.2
    2-methyl-1-butanol 208.47
    n-decane 13.49
    butyronitrile 232.8
    3,7-dimethyl-1-octanol 113.09
    1-chlorooctane 81.34
    1-chlorotetradecane 39.24
    n-nonane 11.27
    undecane 11.41
    tert-butylcyclohexane 21.56
    cyclooctane 12.7
    cyclopentanol 206.12
    tetrahydropyran 373.8
    tert-amyl methyl ether 147.15
    2,5,8-trioxanonane 307.45
    1-hexene 79.69
    2-isopropoxyethanol 146.1
    2,2,2-trifluoroethanol 59.45
    methyl butyrate 214.68

    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
Lovage root (France) 8016-31-7 Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 1.31%
Lovage headspace 8016-31-7 Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 0.66%
Lovage root (China) 1 8016-31-7 Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 0.55%
Lovage root (China) 2 8016-31-7 Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 0.67%
Celery plant 8015-90-5 Apium graveolens L. var. dulce, fam. Apiaceae (Umbelliferae) 1.4%
Lovage seed (France) 8016-31-7 Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 0.3%
Geum montanum root Geum montanum L., fam. Rosaceae 0.13%
Lovage leaf (Lithuania) Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 2.65%
Lovage stem (Lithuania) Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 0.97%
Lovage root (Lithuania) 8016-31-7 Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 1.94%