(Z)-Butylidenephthalide

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    551-08-6

    Molecular formula
    C12H12O2

    SMILES
    CCC/C=C\1/C2=CC=CC=C2C(=O)O1

    Retention indicies (RI)

    • Carbowax: 2545.0

  • Odor profile

    Herbal 81.17%
    Green 68.56%
    Spicy 59.09%
    Celery 47.51%
    Sweet 35.14%
    Vegetable 34.53%
    Mint 33.97%
    Phenolic 33.01%
    Warm 29.39%
    Cortex 28.72%

    Scent© AI

  • Properties

    XLogP3-AA
    3.2

    Molecular weight
    188.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    290°C

    Flash point est.
    149.2 ˚C

  • Synonyms

    • 3-Butylidenephthalide
    • n-butylidenephthalide
    • (Z)-Butylidenephthalide
    • 72917-31-8
    • 551-08-6
    • Butylidenephthalide
    • BdPh
    • Z-butylidenephthalide
    • 1(3H)-Isobenzofuranone, 3-butylidene-, (3Z)-
    • 3-Butylideneisobenzofuran-1(3H)-one
    • (Z)-3-Butylidenephthalide
    • (3Z)-3-butylidene-2-benzofuran-1-one
    • CHEMBL249592
    • (3Z)-3-Butylidene-2-benzofuran-1(3H)-one
    • CHEBI:68233
    • 6GM611H175
    • NSC-325307
    • (Z)-3-butylideneisobenzofuran-1(3H)-one
    • 3-Butylidenephthalide, (Z)-
    • 1(3H)-ISOBENZOFURANONE, 3-BUTYLIDENE-
    • 3-Butylidene Phthalide(Cis Trans mixture)
    • UNII-6GM611H175
    • 3-Butylidene-1(3H)-isobenzofuranone; Butylidenephthalide; Ligusticum Lactone; NSC 325307;
    • MFCD00047319
    • (E)-Butylidene phthalide
    • trans-3n-butylidenephthalide
    • SCHEMBL290482
    • DTXSID30993698
    • BUTYLIDENEPHTHALIDE, (Z)-
    • HY-N0336
    • BDBM50241315
    • NSC325307
    • s6493
    • (3Z)-3-butylideneisobenzofuran-1-one
    • AKOS024286816
    • FB19574
    • AC-34145
    • BS-49282
    • 1ST164634
    • CS-0008897
    • C16924
    • F17666
    • (3Z)-3-BUTYLIDENE-1(3H)-ISOBENZOFURANONE
    • 1(3H)-ISOBENZOFURANONE, 3-BUTYLIDENE-, (Z)-
    • Q27136726
    • 3-Butylidene phthalide - mixture of cis and trans isomers
    • 3-Butylidene-1(3H)-isobenzofuranone;Butylidenephthalide;Ligusticum lactone
    • InChI=1/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8

  • Applications

    (Z)-Butylidenephthalide (CAS 551-08-6) is a natural phthalide from Angelica sinensis and other Apiaceae; in research it is utilized as: (1) a potential anticancer agent (notably for glioblastoma, liver and bladder cancers) with antiproliferative and antiangiogenic effects, induction of apoptosis and cell-cycle arrest, epigenetic modulation (DNMT1 inhibition, hypomethylation), and as a radio/chemo-sensitizer; (2) a neuroprotective and anti-inflammatory/antioxidant candidate in models of stroke, neurodegeneration and metabolic disorders; (3) a marker compound/reference standard for quality control of traditional herbal medicines (especially Dong quai) and as a standard in LC–MS/HPLC assays; (4) a characteristic phthalide-note aroma constituent for flavor and fragrance research; and (5) a target for advanced formulation development (liposomes, nanoemulsions, biopolymers) to enhance stability, solubility and tissue delivery, typically supported by preclinical pharmacokinetic, metabolism and safety evaluations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 293.31
    methanol 298.04
    isopropanol 197.83
    water 0.04
    ethyl acetate 359.87
    n-propanol 293.91
    acetone 540.91
    n-butanol 290.32
    acetonitrile 340.15
    DMF 2235.5
    toluene 449.55
    isobutanol 230.36
    1,4-dioxane 573.58
    methyl acetate 402.69
    THF 681.25
    2-butanone 547.82
    n-pentanol 199.06
    sec-butanol 255.75
    n-hexane 15.91
    ethylene glycol 67.92
    NMP 1213.03
    cyclohexane 39.17
    DMSO 711.72
    n-butyl acetate 333.76
    n-octanol 130.16
    chloroform 1278.84
    n-propyl acetate 242.23
    acetic acid 219.68
    dichloromethane 1283.06
    cyclohexanone 793.6
    propylene glycol 106.09
    isopropyl acetate 243.31
    DMAc 1112.13
    2-ethoxyethanol 265.59
    isopentanol 272.58
    n-heptane 9.3
    ethyl formate 242.04
    1,2-dichloroethane 1055.48
    n-hexanol 230.15
    2-methoxyethanol 553.25
    isobutyl acetate 167.08
    tetrachloromethane 88.99
    n-pentyl acetate 229.52
    transcutol 1192.82
    n-heptanol 114.66
    ethylbenzene 196.89
    MIBK 275.16
    2-propoxyethanol 396.61
    tert-butanol 216.28
    MTBE 263.92
    2-butoxyethanol 227.37
    propionic acid 237.19
    o-xylene 215.61
    formic acid 67.06
    diethyl ether 310.77
    m-xylene 245.28
    p-xylene 211.0
    chlorobenzene 665.68
    dimethyl carbonate 259.91
    n-octane 7.77
    formamide 177.13
    cyclopentanone 790.02
    2-pentanone 450.23
    anisole 387.92
    cyclopentyl methyl ether 364.2
    gamma-butyrolactone 708.63
    1-methoxy-2-propanol 415.44
    pyridine 1014.37
    3-pentanone 328.23
    furfural 798.22
    n-dodecane 10.52
    diethylene glycol 289.3
    diisopropyl ether 82.51
    tert-amyl alcohol 233.48
    acetylacetone 474.96
    n-hexadecane 12.73
    acetophenone 366.31
    methyl propionate 426.44
    isopentyl acetate 320.62
    trichloroethylene 1903.8
    n-nonanol 116.34
    cyclohexanol 291.25
    benzyl alcohol 335.63
    2-ethylhexanol 137.31
    isooctanol 102.6
    dipropyl ether 103.07
    1,2-dichlorobenzene 520.39
    ethyl lactate 138.4
    propylene carbonate 442.82
    n-methylformamide 560.1
    2-pentanol 192.72
    n-pentane 16.85
    1-propoxy-2-propanol 242.52
    1-methoxy-2-propyl acetate 311.89
    2-(2-methoxypropoxy) propanol 254.12
    mesitylene 129.47
    ε-caprolactone 593.96
    p-cymene 80.52
    epichlorohydrin 1110.29
    1,1,1-trichloroethane 563.6
    2-aminoethanol 161.09
    morpholine-4-carbaldehyde 878.89
    sulfolane 771.61
    2,2,4-trimethylpentane 15.13
    2-methyltetrahydrofuran 505.06
    n-hexyl acetate 361.54
    isooctane 13.04
    2-(2-butoxyethoxy)ethanol 375.68
    sec-butyl acetate 174.91
    tert-butyl acetate 247.44
    decalin 30.75
    glycerin 148.56
    diglyme 628.69
    acrylic acid 249.13
    isopropyl myristate 120.44
    n-butyric acid 342.43
    acetyl acetate 218.88
    di(2-ethylhexyl) phthalate 131.84
    ethyl propionate 218.63
    nitromethane 519.1
    1,2-diethoxyethane 324.09
    benzonitrile 535.22
    trioctyl phosphate 91.83
    1-bromopropane 432.26
    gamma-valerolactone 902.45
    n-decanol 86.68
    triethyl phosphate 103.42
    4-methyl-2-pentanol 125.83
    propionitrile 348.83
    vinylene carbonate 484.46
    1,1,2-trichlorotrifluoroethane 614.18
    DMS 328.88
    cumene 110.37
    2-octanol 96.59
    2-hexanone 284.78
    octyl acetate 159.65
    limonene 104.46
    1,2-dimethoxyethane 522.1
    ethyl orthosilicate 96.6
    tributyl phosphate 122.82
    diacetone alcohol 291.95
    N,N-dimethylaniline 232.69
    acrylonitrile 554.07
    aniline 522.74
    1,3-propanediol 241.9
    bromobenzene 748.1
    dibromomethane 792.35
    1,1,2,2-tetrachloroethane 1346.65
    2-methyl-cyclohexyl acetate 165.72
    tetrabutyl urea 170.23
    diisobutyl methanol 77.9
    2-phenylethanol 291.36
    styrene 289.85
    dioctyl adipate 167.52
    dimethyl sulfate 353.38
    ethyl butyrate 168.52
    methyl lactate 219.28
    butyl lactate 188.19
    diethyl carbonate 146.28
    propanediol butyl ether 270.11
    triethyl orthoformate 127.69
    p-tert-butyltoluene 76.15
    methyl 4-tert-butylbenzoate 223.4
    morpholine 776.38
    tert-butylamine 138.02
    n-dodecanol 67.94
    dimethoxymethane 659.25
    ethylene carbonate 359.44
    cyrene 238.77
    2-ethoxyethyl acetate 319.19
    2-ethylhexyl acetate 250.56
    1,2,4-trichlorobenzene 623.57
    4-methylpyridine 1098.89
    dibutyl ether 163.35
    2,6-dimethyl-4-heptanol 77.9
    DEF 683.15
    dimethyl isosorbide 367.5
    tetrachloroethylene 712.89
    eugenol 262.81
    triacetin 264.79
    span 80 212.57
    1,4-butanediol 96.57
    1,1-dichloroethane 735.51
    2-methyl-1-pentanol 224.47
    methyl formate 358.74
    2-methyl-1-butanol 277.45
    n-decane 14.86
    butyronitrile 363.14
    3,7-dimethyl-1-octanol 142.29
    1-chlorooctane 100.57
    1-chlorotetradecane 44.81
    n-nonane 12.53
    undecane 12.18
    tert-butylcyclohexane 24.22
    cyclooctane 13.88
    cyclopentanol 258.3
    tetrahydropyran 548.16
    tert-amyl methyl ether 219.45
    2,5,8-trioxanonane 416.67
    1-hexene 107.56
    2-isopropoxyethanol 201.17
    2,2,2-trifluoroethanol 88.57
    methyl butyrate 311.66

    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
Celery flower 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 1.3%
Celery seed 1 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 8.8%
Celery leaf 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 0.9%
Celery root 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 0.5%
Celery stem 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 0.6%
Celery seed (India) 2 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 2.64%
Geum montanum root Geum montanum L., fam. Rosaceae 1.93%