beta-Asarone

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    5273-86-9

    Molecular formula
    C12H16O3

    SMILES
    C/C=C\C1=CC(=C(C=C1OC)OC)OC

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1622.0

  • Odor profile

    Spicy 82.68%
    Floral 61.23%
    Sweet 54.15%
    Woody 51.08%
    Clove 46.94%
    Phenolic 43.52%
    Smoky 38.93%
    Warm 38.78%
    Herbal 37.94%
    Vanilla 36.96%

    Scent© AI

  • Properties

    XLogP3-AA
    3.0

    Molecular weight
    208.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    292°C

    Flash point est.
    115.7 ˚C

  • Synonyms

    • beta-Asarone
    • 5273-86-9
    • cis-Isoelemicin
    • cis-Isoasarone
    • (Z)-Asarone
    • cis-2,4,5-Trimethoxy-1-propenylbenzene
    • cis-Asarone
    • IGA3MH6IUW
    • UNII-IGA3MH6IUW
    • Cis-Asaron
    • (Z)-5-Propenyl-1,2,4-trimethoxybenzene
    • .beta.-Asarone
    • (Z)-1,2,4-Trimethoxy-5-(1-propenyl)benzene
    • 1,2,4-trimethoxy-5-[(Z)-prop-1-enyl]benzene
    • cis-.beta.-Asarone
    • CCRIS 1592
    • CHEBI:10353
    • BENZENE, 1,2,4-TRIMETHOXY-5-PROPENYL-, (Z)-
    • EINECS 226-096-6
    • 2,4,5-Trimethoxypropen-1-ylbenzene
    • BRN 1910605
    • Benzene, 1,2,4-trimethoxy-5-(1-propenyl)-, (Z)-
    • AI3-36897
    • cis-2,4,5-trimethoxyphenylpropene
    • DTXSID601020057
    • 3-06-00-06440 (Beilstein Handbook Reference)
    • 1,2,4-trimethoxy-5-propenylbenzene, z-
    • (Z)-1-(2,4,5-Trimethoxyphenyl)-1-propene
    • cis-b-Asarone (>70%)
    • Benzene, 1,2,4-trimethoxy-5-(1Z)-1-propenyl-
    • cis-beta-Asarone
    • BENZENE, 1,2,4-TRIMETHOXY-5-(1Z)-1-PROPEN-1-YL-
    • cis-1-Propenyl-2,4,5-trimethoxybenzene
    • 1,2,4-trimethoxy-5-((1Z)-prop-1-en-1-yl)benzene
    • 1,2,4-trimethoxy-5-[(1Z)-prop-1-en-1-yl]benzene
    • CHEBI:78308
    • beta-asaron
    • beta-Asarone; 1,2,4-Trimethoxy-5-[(Z)-prop-1-enyl]benzene; ss-Asarone
    • MFCD00009281
    • I(2)-Asarone
    • asarone, (Z)-isomer
    • 1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene
    • (Z)-.beta.-Asarone
    • Beta-asarone (Standard)
    • beta-ASARONE, CIS-
    • SCHEMBL528747
    • .BETA.-ASARONE, CIS-
    • CHEMBL477752
    • CHEBI:68146
    • HY-N1501R
    • DTXCID00911420
    • HMS3886B18
    • BCP23722
    • HY-N1501
    • s9118
    • AKOS030524038
    • CCG-266642
    • CS-W009103
    • DS-9662
    • AC-34897
    • FA145212
    • cis-2,4,5-Trimethoxy-1-propenylbenzene, 70%
    • 1,2,4-Trimethoxy-5-[(1Z)-1-propenyl]benzene
    • (Z)-1,2,4-Trimethoxy-5-(prop-1-en-1-yl)benzene
    • beta-Asarone, primary pharmaceutical reference standard
    • Q27089385
    • 1,2,4-Trimethoxy-5-((z)-1-propenyl)benzene, ?-asarone
    • (z)-1 pound not2 pound not4-trimethoxy-5-(1-propenyl)benzene
    • 226-096-6

  • Applications

    beta-Asarone (β-asarone, CAS 5273-86-9) is a natural phenylpropanoid from Acorus species and a historical constituent of calamus oil, now used predominantly for research and analytical purposes; in laboratories it serves as a reference/analytical standard for quantification and quality control of herbal materials, flavorings and essential-oil preparations, and as a chemotaxonomic marker; preclinical studies investigate its putative neuroprotective, anti-inflammatory, antioxidant and antimicrobial activities and its insecticidal, fumigant, repellent and larvicidal potential, and it is also employed as a structural scaffold for designing derivatives; due to toxicity and rodent genotoxic/carcinogenic findings, β-asarone is restricted or prohibited in foods, cosmetics and therapeutics in many jurisdictions, so current applications emphasize toxicology, pharmacokinetics and metabolism studies, method development (GC/MS, LC/MS), natural-products drug discovery and post-harvest protection research.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 253.14
    methanol 220.52
    isopropanol 187.08
    water 0.7
    ethyl acetate 763.14
    n-propanol 226.12
    acetone 813.54
    n-butanol 199.46
    acetonitrile 657.03
    DMF 869.61
    toluene 308.96
    isobutanol 165.03
    1,4-dioxane 1080.81
    methyl acetate 756.94
    THF 1105.53
    2-butanone 532.9
    n-pentanol 152.33
    sec-butanol 189.77
    n-hexane 40.8
    ethylene glycol 160.11
    NMP 723.8
    cyclohexane 192.25
    DMSO 825.16
    n-butyl acetate 340.97
    n-octanol 93.45
    chloroform 2642.31
    n-propyl acetate 370.11
    acetic acid 630.49
    dichloromethane 2867.06
    cyclohexanone 838.8
    propylene glycol 129.36
    isopropyl acetate 312.62
    DMAc 552.37
    2-ethoxyethanol 392.68
    isopentanol 168.63
    n-heptane 46.24
    ethyl formate 584.9
    1,2-dichloroethane 1786.58
    n-hexanol 177.61
    2-methoxyethanol 618.63
    isobutyl acetate 191.84
    tetrachloromethane 567.28
    n-pentyl acetate 205.77
    transcutol 440.25
    n-heptanol 100.17
    ethylbenzene 175.22
    MIBK 200.68
    2-propoxyethanol 345.05
    tert-butanol 300.33
    MTBE 306.23
    2-butoxyethanol 195.02
    propionic acid 392.47
    o-xylene 208.42
    formic acid 178.16
    diethyl ether 460.13
    m-xylene 195.42
    p-xylene 214.92
    chlorobenzene 600.43
    dimethyl carbonate 377.43
    n-octane 23.76
    formamide 376.32
    cyclopentanone 1046.1
    2-pentanone 423.02
    anisole 337.68
    cyclopentyl methyl ether 491.27
    gamma-butyrolactone 1361.6
    1-methoxy-2-propanol 347.15
    pyridine 910.17
    3-pentanone 388.05
    furfural 1091.91
    n-dodecane 19.07
    diethylene glycol 322.28
    diisopropyl ether 110.75
    tert-amyl alcohol 231.2
    acetylacetone 541.03
    n-hexadecane 22.25
    acetophenone 325.43
    methyl propionate 596.37
    isopentyl acetate 263.68
    trichloroethylene 3012.39
    n-nonanol 86.81
    cyclohexanol 356.99
    benzyl alcohol 278.53
    2-ethylhexanol 140.76
    isooctanol 83.9
    dipropyl ether 186.13
    1,2-dichlorobenzene 566.68
    ethyl lactate 178.01
    propylene carbonate 745.64
    n-methylformamide 516.68
    2-pentanol 142.44
    n-pentane 44.18
    1-propoxy-2-propanol 204.2
    1-methoxy-2-propyl acetate 288.62
    2-(2-methoxypropoxy) propanol 151.41
    mesitylene 130.36
    ε-caprolactone 673.16
    p-cymene 110.33
    epichlorohydrin 1492.44
    1,1,1-trichloroethane 1601.77
    2-aminoethanol 183.37
    morpholine-4-carbaldehyde 719.4
    sulfolane 1220.98
    2,2,4-trimethylpentane 32.62
    2-methyltetrahydrofuran 754.37
    n-hexyl acetate 243.21
    isooctane 22.48
    2-(2-butoxyethoxy)ethanol 193.28
    sec-butyl acetate 200.02
    tert-butyl acetate 295.08
    decalin 71.01
    glycerin 214.46
    diglyme 487.17
    acrylic acid 427.4
    isopropyl myristate 102.14
    n-butyric acid 490.6
    acetyl acetate 553.9
    di(2-ethylhexyl) phthalate 102.59
    ethyl propionate 339.75
    nitromethane 1246.32
    1,2-diethoxyethane 248.69
    benzonitrile 396.36
    trioctyl phosphate 79.05
    1-bromopropane 648.15
    gamma-valerolactone 1028.05
    n-decanol 68.33
    triethyl phosphate 168.95
    4-methyl-2-pentanol 80.64
    propionitrile 411.68
    vinylene carbonate 730.72
    1,1,2-trichlorotrifluoroethane 1044.91
    DMS 309.82
    cumene 112.03
    2-octanol 71.66
    2-hexanone 254.55
    octyl acetate 134.88
    limonene 158.8
    1,2-dimethoxyethane 635.86
    ethyl orthosilicate 154.54
    tributyl phosphate 98.61
    diacetone alcohol 263.33
    N,N-dimethylaniline 203.01
    acrylonitrile 588.6
    aniline 375.92
    1,3-propanediol 275.88
    bromobenzene 680.16
    dibromomethane 1678.54
    1,1,2,2-tetrachloroethane 2157.87
    2-methyl-cyclohexyl acetate 213.81
    tetrabutyl urea 120.86
    diisobutyl methanol 85.28
    2-phenylethanol 240.36
    styrene 244.53
    dioctyl adipate 160.64
    dimethyl sulfate 507.41
    ethyl butyrate 293.46
    methyl lactate 238.68
    butyl lactate 135.21
    diethyl carbonate 252.65
    propanediol butyl ether 130.08
    triethyl orthoformate 200.9
    p-tert-butyltoluene 107.77
    methyl 4-tert-butylbenzoate 221.71
    morpholine 1018.68
    tert-butylamine 182.54
    n-dodecanol 56.88
    dimethoxymethane 640.59
    ethylene carbonate 617.63
    cyrene 248.12
    2-ethoxyethyl acetate 273.34
    2-ethylhexyl acetate 229.25
    1,2,4-trichlorobenzene 633.08
    4-methylpyridine 642.75
    dibutyl ether 136.68
    2,6-dimethyl-4-heptanol 85.28
    DEF 516.65
    dimethyl isosorbide 339.72
    tetrachloroethylene 1480.23
    eugenol 199.68
    triacetin 248.2
    span 80 137.63
    1,4-butanediol 119.48
    1,1-dichloroethane 1372.23
    2-methyl-1-pentanol 143.7
    methyl formate 639.04
    2-methyl-1-butanol 172.18
    n-decane 29.46
    butyronitrile 391.7
    3,7-dimethyl-1-octanol 89.41
    1-chlorooctane 113.44
    1-chlorotetradecane 51.17
    n-nonane 29.2
    undecane 22.84
    tert-butylcyclohexane 52.94
    cyclooctane 58.47
    cyclopentanol 391.0
    tetrahydropyran 853.02
    tert-amyl methyl ether 230.33
    2,5,8-trioxanonane 303.33
    1-hexene 115.77
    2-isopropoxyethanol 248.34
    2,2,2-trifluoroethanol 323.16
    methyl butyrate 444.28

    Scent© AI

1 4

IFRA standard 51

Recommendation
Prohibition / Restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 See notebox Category 7A
Rinse-off products applied to the hair with some hand contact
 See notebox
Category 2
Products applied to the axillae
 See notebox Category 7B
Leave-on products applied to the hair with some hand contact
 See notebox
Category 3
Products applied to the face/body using fingertips
 See notebox Category 8
Products with significant anogenital exposure
 See notebox
Category 4
Products related to fine fragrance
 See notebox Category 9
Products with body and hand exposure, primarily rinse off
 See notebox
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 See notebox Category 10A
Household care products with mostly hand contact
 See notebox
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 See notebox Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 See notebox
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 See notebox Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 See notebox
Category 5D
Baby Creams, baby Oils and baby talc
 See notebox Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 See notebox
Category 6
Products with oral and lip exposure
 See notebox Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 See notebox

Prohibition
cis- and trans-Asarone as such should not be used as fragrance ingredients.
The natural extracts containing cis- and transAsarone should not be used as substitutes for this substance.

Restriction
On the basis of established maximum concentration levels of this substance in commercially available natural sources (like essential oils, extracts and absolutes), exposure to this substance from the use of these oils and extracts (e.g. Calamus oils) is regarded acceptable as long as the level of cis- and transAsarone in the finished consumer product does not exceed 100ppm (0.01 %).

Botanical

Name CAS Botanical Proportion
Nutmeg (Sri Lanka) 1 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.05%
Carrot seed (Japan) 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 4.1%
Orthodon calveriei (Vietnam) Orthodon calveriei Level. (Mosla calveriei), fam. Lamiaceae (Labiatae) 8.6%
Calamus (India) 1 root 8015-79-0 Acorus calamus L., fam. Araceae 92.68%
Calamus (Germany) 1a root 8015-79-0 Acorus calamus L., fam. Araceae 30.0%
Calamus (Germany) 1b root 8015-79-0 Acorus calamus L., fam. Araceae 6.4%
Calamus (China) 1c root 8015-79-0 Acorus calamus L., fam. Araceae 1.68%
Calamus (China) 1b rhizome 8015-79-0 Acorus calamus L., fam. Araceae 2.85%
Pelargonium sidoides Pelargonium sidoides DC., fam. Geraniaceae 0.1%
Eucalyptus citriodora (Bangladesh) 8000-48-4 Eucalyptus citriodora Hook. f., fam. Myrtaceae 0.02%
Cubeb 2 8007-87-2 Piper cubeba L., fam. Piperaceae 2.3%
Cubeb (India) 8007-87-2 Piper cubeba L., fam. Piperaceae 1.39%
Orthodon dianthera (Vietnam) Orthodon dianthera Maxim. (Mosla dianthera Maxim.), fam. Lamiaceae 5.5%
Calamus (Germany) 2 root 8015-79-0 Acorus calamus L., fam. Araceae 13.76%
Calamus (Bangladesh) root 8015-79-0 Acorus calamus L., fam. Araceae 81.27%
Calamus (India) 2 root 8015-79-0 Acorus calamus L., fam. Araceae 91.74%
Calamus (India) 3 root 8015-79-0 Acorus calamus L., fam. Araceae 2.01%
Calamus (Japan) 2 root 8015-79-0 Acorus calamus L., fam. Araceae 85.7%
Calamus (Japan) 1a root chemotype 1 8015-79-0 Acorus calamus L., fam. Araceae 78.4%
Calamus (Japan) 1b root chemotype 2 8015-79-0 Acorus calamus L., fam. Araceae 36.1%
Calamus (Japan) 1c root chemotype 3 8015-79-0 Acorus calamus L., fam. Araceae 7.05%
Phlomis fruticosa (Yugoslavia) Phlomis fruticosa L., fam. Lamiaceae (Labiatae) 0.1%
Calamus (Turkey) Acorus calamus L., fam. Araceae 2.4%
Asafoetida (Pakistan) 2 9000-04-8 Ferula assafoetida L., fam. Apiaceae (Umbelliferae) 0.01%
Asafoetida (Iran) 1 9000-04-8 Ferula assafoetida L., fam. Apiaceae (Umbelliferae) 0.71%