Anethole, (Z)-

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  • Identifiers

    CAS number
    25679-28-1

    Molecular formula
    C10H12O

    SMILES
    C/C=C\C1=CC=C(C=C1)OC

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1251.0

  • Odor profile

    Sweet 85.72%
    Herbal 62.15%
    Spicy 62.13%
    Anisic 57.09%
    Floral 47.06%
    Green 44.32%
    Nutty 42.61%
    Phenolic 42.56%
    Warm 34.14%
    Cinnamon 32.65%

    Scent© AI

  • Properties

    XLogP3-AA
    3.3

    Molecular weight
    148.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 70.4 °F (NTP, 1992)
    • 21.3 °C
    • Liquid Molar Volume = 0.1507 cu m/kmol; Heat of Fusion @ Melting Point = 1.60E+7 J/kmol
    • 22.5 °C

    Boiling point

    • 454.1 °F at 760 mmHg (NTP, 1992)
    • 234 °C

    Flash point est.
    83.89 ˚C

    Flash point expt.

    • 195 °F (NTP, 1992)
    • 90.1 °C

    Solubility expt.

    • Slightly soluble (NTP, 1992)
    • 1:8 IN 80% ALCOHOL; 1:1 IN 90% ETHANOL
    • ALMOST WATER INSOL; MISCIBLE WITH CHLOROFORM & ETHER
    • Water solubility = 1.110E-1 g/l @ 25 °C

  • Synonyms

    • cis-Anethole
    • (Z)-Anethole
    • 25679-28-1
    • (Z)-1-Methoxy-4-(prop-1-en-1-yl)benzene
    • cis-p-Propenylanisole
    • Anethole, cis
    • ANISOLE, p-PROPENYL-, cis-
    • Anethole, (Z)-
    • 78AWK1V4GL
    • Benzene, 1-methoxy-4-(1-propenyl)-, (Z)-
    • 1-methoxy-4-[(Z)-prop-1-enyl]benzene
    • ANETHOLE, CIS-
    • DTXSID4058651
    • CHEBI:78412
    • cis-p-Anethole
    • 1-methoxy-4-[(1Z)-prop-1-en-1-yl]benzene
    • (Z-)-Anethole
    • E-anethole
    • 104-46-1
    • Methoxy-4-propenylbenzene
    • 4-06-00-03796 (Beilstein Handbook Reference)
    • EINECS 247-181-4
    • UNII-78AWK1V4GL
    • BRN 1209632
    • trans-1-(p-Methoxyphenyl)propene
    • Anistearoptene
    • cis-p-Methoxy-beta-methylstyrene
    • Anethole, USAN
    • NCGC00091493-01
    • trans-Anise camphor
    • 4-cis-propenyl-anisole
    • p-Propenylanisole, 8CI
    • 1-(methyloxy)-4-[(1E)-prop-1-en-1-yl]benzene
    • p-Propenyl-trans-Anisole
    • CIS-ANETHOLE [MI]
    • SCHEMBL57011
    • ghl.PD_Mitscher_leg0.374
    • 1-(p-Methoxyphenyl)-Propene
    • CHEMBL1468832
    • DTXCID0032283
    • FEMA 2086
    • 1-Methoxy-4-(propenyl)-Benzene
    • 1-Methoxy-4-(propen-1-yl)-Benzene
    • AKOS015840488
    • Anisole, p-propenyl-, (E)- (8CI)
    • 1-Methoxy-4-(1E)-1-propenyl-Benzene
    • 1-Methoxy-4-(1-propenyl)benzene, 9CI
    • 1-Methoxy-4-(1-propenyl)-(E)-Benzene
    • BENZENE, 1-METHOXY-4-(1-PROPENYL
    • 1-Methoxy-4-(1E)-1-propen-1-yl-Benzene
    • NS00125150
    • methyl 4-[(1Z)-prop-1-en-1-yl]phenyl ether
    • Q27147814
    • 247-181-4

  • Applications

    (Z)-Anethole (cis-anethole, CAS 25679-28-1) is used mainly as an analytical reference and stereoisomer comparator for quality control of anise, fennel and star-anise essential oils and anethole-containing flavor formulations (monitoring isomerization, purity profiling, authenticity), in GC/LC-MS method development (retention index assignment, calibration, stability/photolability studies), and as a model substrate in organic mechanism research (electrophilic additions, epoxidation, hydroboration-oxidation) and in toxicology/metabolism studies (benchmarking vs the (E) isomer for bioactivity, P450-mediated 1'-hydroxylation/epoxide formation, safety assessment); it is also used in fragrance/flavor R&D and sensory training as a comparator/off-note standard to fine-tune licorice-anise nuances and to control harsh cis-isomer impurities, in stability/packaging studies evaluating light/acid-driven cis <-> trans interconversion in essential-oil beverages, and occasionally as an intermediate toward anisyl derivatives or in structure-activity research on antimicrobial/insect effects; because it is less stable and has a less favorable safety profile than (E)-anethole, the Z isomer is rarely employed as a direct food flavor and is largely confined to research and quality-control applications.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1548.23
    methanol 1192.83
    isopropanol 1127.59
    water 0.58
    ethyl acetate 3453.26
    n-propanol 1530.09
    acetone 3320.15
    n-butanol 1299.16
    acetonitrile 3048.03
    DMF 2251.1
    toluene 1503.44
    isobutanol 974.36
    1,4-dioxane 4382.37
    methyl acetate 3095.81
    THF 3784.25
    2-butanone 2898.05
    n-pentanol 893.66
    sec-butanol 1240.81
    n-hexane 428.71
    ethylene glycol 372.5
    NMP 1873.26
    cyclohexane 597.88
    DMSO 4169.54
    n-butyl acetate 1622.9
    n-octanol 294.47
    chloroform 6144.9
    n-propyl acetate 1366.54
    acetic acid 1414.89
    dichloromethane 6893.22
    cyclohexanone 2532.44
    propylene glycol 544.57
    isopropyl acetate 1171.58
    DMAc 1535.77
    2-ethoxyethanol 1493.13
    isopentanol 965.22
    n-heptane 166.23
    ethyl formate 1087.77
    1,2-dichloroethane 5341.05
    n-hexanol 833.73
    2-methoxyethanol 2170.13
    isobutyl acetate 620.95
    tetrachloromethane 1197.42
    n-pentyl acetate 560.33
    transcutol 5640.61
    n-heptanol 267.07
    ethylbenzene 568.6
    MIBK 845.58
    2-propoxyethanol 1495.31
    tert-butanol 1563.06
    MTBE 2417.99
    2-butoxyethanol 574.9
    propionic acid 1329.68
    o-xylene 590.59
    formic acid 404.05
    diethyl ether 4216.12
    m-xylene 658.48
    p-xylene 550.93
    chlorobenzene 1859.84
    dimethyl carbonate 922.62
    n-octane 53.89
    formamide 967.41
    cyclopentanone 2892.69
    2-pentanone 2087.31
    anisole 1445.13
    cyclopentyl methyl ether 2229.07
    gamma-butyrolactone 2874.87
    1-methoxy-2-propanol 1415.36
    pyridine 3504.7
    3-pentanone 1949.53
    furfural 2157.45
    n-dodecane 33.26
    diethylene glycol 1011.23
    diisopropyl ether 703.53
    tert-amyl alcohol 1372.12
    acetylacetone 1991.42
    n-hexadecane 40.13
    acetophenone 875.98
    methyl propionate 2385.81
    isopentyl acetate 1083.17
    trichloroethylene 7662.46
    n-nonanol 255.2
    cyclohexanol 1070.55
    benzyl alcohol 721.38
    2-ethylhexanol 496.89
    isooctanol 223.62
    dipropyl ether 1064.74
    1,2-dichlorobenzene 1437.42
    ethyl lactate 393.55
    propylene carbonate 1289.76
    n-methylformamide 1368.07
    2-pentanol 930.77
    n-pentane 344.85
    1-propoxy-2-propanol 957.21
    1-methoxy-2-propyl acetate 1267.91
    2-(2-methoxypropoxy) propanol 734.2
    mesitylene 364.83
    ε-caprolactone 1938.59
    p-cymene 243.26
    epichlorohydrin 4638.61
    1,1,1-trichloroethane 4382.94
    2-aminoethanol 718.59
    morpholine-4-carbaldehyde 2283.46
    sulfolane 3383.65
    2,2,4-trimethylpentane 148.31
    2-methyltetrahydrofuran 3519.3
    n-hexyl acetate 823.55
    isooctane 117.0
    2-(2-butoxyethoxy)ethanol 1063.26
    sec-butyl acetate 801.79
    tert-butyl acetate 1271.86
    decalin 214.84
    glycerin 607.46
    diglyme 2136.92
    acrylic acid 1097.18
    isopropyl myristate 294.82
    n-butyric acid 1362.0
    acetyl acetate 1347.13
    di(2-ethylhexyl) phthalate 245.4
    ethyl propionate 1315.31
    nitromethane 3576.99
    1,2-diethoxyethane 2241.38
    benzonitrile 1047.25
    trioctyl phosphate 168.24
    1-bromopropane 3129.74
    gamma-valerolactone 2876.93
    n-decanol 189.3
    triethyl phosphate 363.23
    4-methyl-2-pentanol 403.26
    propionitrile 1939.14
    vinylene carbonate 1167.31
    1,1,2-trichlorotrifluoroethane 2451.39
    DMS 987.62
    cumene 292.55
    2-octanol 185.04
    2-hexanone 1237.58
    octyl acetate 361.26
    limonene 417.11
    1,2-dimethoxyethane 2404.1
    ethyl orthosilicate 389.1
    tributyl phosphate 282.1
    diacetone alcohol 1075.9
    N,N-dimethylaniline 617.03
    acrylonitrile 2125.62
    aniline 1542.78
    1,3-propanediol 939.22
    bromobenzene 2273.84
    dibromomethane 4689.88
    1,1,2,2-tetrachloroethane 5961.27
    2-methyl-cyclohexyl acetate 558.96
    tetrabutyl urea 312.81
    diisobutyl methanol 275.81
    2-phenylethanol 632.78
    styrene 923.1
    dioctyl adipate 437.19
    dimethyl sulfate 1351.33
    ethyl butyrate 984.72
    methyl lactate 590.99
    butyl lactate 374.66
    diethyl carbonate 661.79
    propanediol butyl ether 543.43
    triethyl orthoformate 602.21
    p-tert-butyltoluene 238.18
    methyl 4-tert-butylbenzoate 509.81
    morpholine 4487.17
    tert-butylamine 1137.6
    n-dodecanol 148.32
    dimethoxymethane 2123.32
    ethylene carbonate 1064.44
    cyrene 547.37
    2-ethoxyethyl acetate 1075.58
    2-ethylhexyl acetate 925.46
    1,2,4-trichlorobenzene 1803.66
    4-methylpyridine 2639.42
    dibutyl ether 778.82
    2,6-dimethyl-4-heptanol 275.81
    DEF 2042.09
    dimethyl isosorbide 1138.82
    tetrachloroethylene 3647.22
    eugenol 525.37
    triacetin 776.84
    span 80 536.6
    1,4-butanediol 367.52
    1,1-dichloroethane 4445.84
    2-methyl-1-pentanol 788.09
    methyl formate 1076.42
    2-methyl-1-butanol 1051.69
    n-decane 60.96
    butyronitrile 1585.26
    3,7-dimethyl-1-octanol 360.78
    1-chlorooctane 323.8
    1-chlorotetradecane 113.69
    n-nonane 67.5
    undecane 42.83
    tert-butylcyclohexane 193.0
    cyclooctane 202.75
    cyclopentanol 998.97
    tetrahydropyran 4177.51
    tert-amyl methyl ether 1518.67
    2,5,8-trioxanonane 1294.92
    1-hexene 1099.41
    2-isopropoxyethanol 961.08
    2,2,2-trifluoroethanol 463.64
    methyl butyrate 1451.51

    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
Star anise (China) 1 8007-70-3 Illicium verum Hooker fil., fam. Magnoliaceae (Illiciaceae) 0.15%
Star anise (China, Yunnan) 5 8007-70-3 Illicium verum Hooker fil., fam. Magnoliaceae (Illiciaceae) 0.42%
Anise (Spain) 2 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.31%
Anise (Spain) 1 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.36%
Anise (Turkey) 1 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.4%
Anise (USSR) 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.4%
Star anise (Vietnam) 1 8007-70-3 Illicium verum Hooker fil., fam. Magnoliaceae (Illiciaceae) 0.28%
Anise seed 1 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 2.29%
Anise seed 3 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.22%
Anise herb 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 1.18%
Star anise (Vietnam) 2 8007-70-3 Illicium verum Hooker fil., fam. Magnoliaceae (Illiciaceae) 0.11%
Fennel, bitter 1 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.1%
Fennel, sweet 1 8006-84-6 Foeniculum vulgare Miller, var. dulce DC, fam. Apiaceae (Umbelliferae) 0.3%
Star anise (China) 3 8007-70-3 Illicium verum Hooker fil., fam. Magnoliaceae (Illiciaceae) 0.01%
Wistaria sinensis headspace Wistaria sinensis DC., fam. Leguminosae (Papilionaceae) 0.1%
Backhousia anisata leaf 1 Backhousia anisata Vickery (Chemotype 1), fam. Myrtaceae 0.05%
Backhousia anisata leaf 2 Backhousia anisata Vickery (Chemotype 2), fam. Myrtaceae 0.05%
Fennel, sweet (Turkey) 8006-84-6 Foeniculum vulgare Miller, var. dulce DC, fam. Apiaceae (Umbelliferae) 0.3%
Fennel, bitter, stem (Turkey) 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.01%
Fennel, bitter, leaf (Turkey) 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.01%
Fennel, bitter, umbel flower (Turkey) 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.23%
Fennel, bitter, flower (Turkey) 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.28%
Fennel, bitter, fruit (Turkey) 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.38%
Star anise (China, Shangyou) 4 8007-70-3 Illicium verum Hooker fil., fam. Magnoliaceae (Illiciaceae) 0.2%
Scandix australis Scandix australis L., fam. Apiaceae (Umbelliferae) 0.2%
Fennel, bitter (Italy) 2 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 1.7%
Fennel, sweet (Italy) 2 8006-84-6 Foeniculum vulgare Miller, var. dulce DC, fam. Apiaceae (Umbelliferae) 3.47%
Anise seed 2 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.31%
Fennel, bitter (Hungary) 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.16%
Fennel, bitter (Spain) 1 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.08%
Fennel, sweet 2 8006-84-6 Foeniculum vulgare Miller, var. dulce DC, fam. Apiaceae (Umbelliferae) 0.73%
Star anise (China) 2 8007-70-3 Illicium verum Hooker fil., fam. Magnoliaceae (Illiciaceae) 0.39%
Fennel, bitter 2 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.3%
Fennel, sweet (Italy) 1 8006-84-6 Foeniculum vulgare Miller, var. dulce DC, fam. Apiaceae (Umbelliferae) 0.05%
Fennel, bitter, seedling (France) 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 1.75%
Clausena heptaphylla leaf (India) 1b Clausena heptaphylla W&A, fam. Rutaceae 0.33%
Clausena heptaphylla fruit (India) 1a Clausena heptaphylla W&A, fam. Rutaceae 0.02%
Fennel, bitter (Spain) 2 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.01%
Anise (Turkey) 2 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 3.7%
Anise (Colombia) 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.11%
Fitweed seed Eryngium foetidum L., fam. Apiaceae (Umbelliferae) 0.45%
Tagetes filifolia (Peru) Tagetes filifolia Lag., fam. Asteraceae (Compositae) 68.2%
Fennel, bitter 3a, fruit headspace Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.16%
Fennel, bitter 3b, fruit oil 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.18%
Fennel, bitter (Spain) 3 8006-84-6 Foeniculum vulgare Miller, var. vulgare DC, fam. Apiaceae (Umbelliferae) 0.05%
Heracleum persicum (Iran) 1a leaf a Heracleum persicum L., fam. Apiaceae (Umbelliferae) 2.3%
Heracleum persicum (Iran) 1b leaf b Heracleum persicum L., fam. Apiaceae (Umbelliferae) 4.6%
Heracleum persicum (Iran) 1c flower Heracleum persicum L., fam. Apiaceae (Umbelliferae) 4.7%
Coriander fruit (Italy) 4 8000-25-7 Coriandrum sativum L., fam. Apiaceae (Umbelliferae) 0.01%