Elemicin

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  • Identifiers

    CAS number
    487-11-6

    Molecular formula
    C12H16O3

    SMILES
    COC1=CC(=CC(=C1OC)OC)CC=C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1555.86
    • Carbowax: 2233.0

  • Odor profile

    Spicy 84.73%
    Woody 65.34%
    Sweet 59.94%
    Floral 57.67%
    Clove 52.57%
    Phenolic 47.12%
    Warm 43.78%
    Smoky 42.04%
    Herbal 38.98%
    Balsamic 38.72%

    Scent© AI

  • Properties

    XLogP3-AA
    2.5

    Molecular weight
    208.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point

    • 152.00 to 156.00 °C. @ 17.00 mm Hg

    Flash point est.
    102.96 ˚C

    Solubility expt.

    • Practically insoluble to insoluble in water
    • Soluble (in ethanol)

  • Synonyms

    • Elemicin
    • 487-11-6
    • 5-Allyl-1,2,3-trimethoxybenzene
    • 3,4,5-Trimethoxyallylbenzene
    • Elemicine
    • 1,2,3-trimethoxy-5-prop-2-enylbenzene
    • Benzene, 1,2,3-trimethoxy-5-(2-propenyl)-
    • 1,2,3-Trimethoxy-5-(2-propenyl)benzene
    • CCRIS 6783
    • BENZENE, 5-ALLYL-1,2,3-TRIMETHOXY-
    • 4-allyl-1,2,6-trimethoxybenzene
    • HSZ191AKAN
    • EINECS 207-649-0
    • NSC 16704
    • BRN 1912664
    • 3,4,5-trimethoxyallyl benzene
    • 3-(3,4,5-Trimethoxyphenyl)-1-propene
    • AI3-20815
    • 1,2,3-trimethoxy-5-(prop-2-en-1-yl)benzene
    • NSC-16704
    • CHEBI:4771
    • DTXSID60197586
    • 4-06-00-07478 (Beilstein Handbook Reference)
    • 1-ALLYL-3,4,5-TRIMETHOXYBENZENE
    • 1,2,3-Trimethoxy-5-(2-propenyl)-benzene
    • Benzene, 5-(2-propenyl)-1,2,3-trimethoxy
    • 1-(3,4,5-TRIMETHOXYPHENYL)-2-PROPENE
    • 5-(PROP-2-ENYL)-1,2,3-TRIMETHOXYBENZENE
    • BENZENE, 1,2,3-TRIMETHOXY-5-(2-PROPEN-1-YL)-
    • 1,2,3-Trimethoxy-5-[2-propenyl]-benzene
    • UNII-HSZ191AKAN
    • MFCD01656688
    • 5'-metoxy eugenol
    • 5-allyl-1,2,3-trimethoxy-benzene
    • 3,5-Trimethoxyallylbenzene
    • 5-(Prop-2-en-1-yl)-1,2,3-trimethoxybenzene
    • SCHEMBL68542
    • 3,4, 5-Trimethoxyallylbenzene
    • CHEMBL458690
    • DTXCID20120077
    • 1,2,3-Trimethoxy-5-allylbenzene
    • HY-N6807
    • NSC16704
    • s5120
    • AKOS015896443
    • CCG-266643
    • FE22655
    • PS-4970
    • Benzene,2,3-trimethoxy-5-(2-propenyl)-
    • DB-081347
    • 1,2,3-Trimethoxy-5-allylbenzene (elemicin)
    • CS-0030665
    • NS00022224
    • 1,2,3-Trimethoxy-5-(2-propenyl)benzene, 9CI
    • Q417746
    • Benzene, 1,2,3-trimethoxy-5-(2-propenyl)-(9CI)
    • Benzene, 1,2,3-trimethoxy-5-(2-propenyl)- (9CI)
    • 1,2,3-Trimethoxy-5-(2-propen-1-yl)-benzene;5-Allyl-1,2,3-trimethoxybenzene;1-(3,4,5-Trimethoxyphenyl)-2-propene
    • 207-649-0

  • Applications

    Elemicin (CAS 487-11-6) is a trimethoxy-substituted phenylpropene found in nutmeg and several essential oils, used primarily as a flavor and fragrance ingredient that adds warm, sweet-spicy, resinous and balsamic nuances to seasonings, baked goods, confectionery and flavored beverages, and to build spicy/resinous facets in perfumes, soaps and personal-care products; in fragrance chemistry it is employed to adjust and deepen accords containing nutmeg, cinnamon, pepper and elemi resin owing to its good solubility in common organic solvents; in research and manufacturing, elemicin serves as an analytical reference for GC–MS fingerprinting of nutmeg and elemi oils for quality control and adulteration detection, and as a convenient starting material for synthesizing trimethoxybenzene derivatives and related phenylpropanoid scaffolds for bioactivity studies; in pharmacognosy and toxicology it is used as a probe to investigate metabolism, cytochrome P450 interactions and safety profiles of natural allylbenzenes; commercial use should comply with flavor safety guidelines and regional maximum-use limits, with attention to potential skin irritation/sensitization at high levels, and storage in cool, light/oxygen-protected conditions to minimize oxidative off-notes.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 419.31
    methanol 420.87
    isopropanol 293.59
    water 1.67
    ethyl acetate 755.04
    n-propanol 356.47
    acetone 1008.43
    n-butanol 296.29
    acetonitrile 784.6
    DMF 1154.26
    toluene 194.23
    isobutanol 258.27
    1,4-dioxane 1222.63
    methyl acetate 882.75
    THF 1192.56
    2-butanone 609.08
    n-pentanol 225.69
    sec-butanol 286.19
    n-hexane 36.54
    ethylene glycol 315.57
    NMP 770.58
    cyclohexane 158.1
    DMSO 1022.71
    n-butyl acetate 354.96
    n-octanol 139.1
    chloroform 2249.08
    n-propyl acetate 396.88
    acetic acid 1002.96
    dichloromethane 2350.48
    cyclohexanone 942.6
    propylene glycol 250.48
    isopropyl acetate 312.55
    DMAc 574.47
    2-ethoxyethanol 548.7
    isopentanol 221.73
    n-heptane 45.53
    ethyl formate 768.78
    1,2-dichloroethane 1551.55
    n-hexanol 245.11
    2-methoxyethanol 959.22
    isobutyl acetate 197.37
    tetrachloromethane 498.09
    n-pentyl acetate 228.54
    transcutol 568.54
    n-heptanol 145.76
    ethylbenzene 130.41
    MIBK 222.58
    2-propoxyethanol 446.53
    tert-butanol 370.57
    MTBE 299.58
    2-butoxyethanol 260.96
    propionic acid 610.68
    o-xylene 150.64
    formic acid 335.63
    diethyl ether 435.96
    m-xylene 140.7
    p-xylene 172.81
    chlorobenzene 558.47
    dimethyl carbonate 418.05
    n-octane 27.1
    formamide 568.63
    cyclopentanone 1147.83
    2-pentanone 454.41
    anisole 308.43
    cyclopentyl methyl ether 492.37
    gamma-butyrolactone 1564.52
    1-methoxy-2-propanol 538.0
    pyridine 855.03
    3-pentanone 382.82
    furfural 1249.62
    n-dodecane 22.49
    diethylene glycol 500.3
    diisopropyl ether 114.17
    tert-amyl alcohol 289.89
    acetylacetone 625.73
    n-hexadecane 25.8
    acetophenone 320.38
    methyl propionate 619.05
    isopentyl acetate 273.92
    trichloroethylene 2672.69
    n-nonanol 120.73
    cyclohexanol 426.27
    benzyl alcohol 315.32
    2-ethylhexanol 164.41
    isooctanol 117.02
    dipropyl ether 191.49
    1,2-dichlorobenzene 534.2
    ethyl lactate 236.4
    propylene carbonate 917.58
    n-methylformamide 774.55
    2-pentanol 190.06
    n-pentane 43.74
    1-propoxy-2-propanol 278.18
    1-methoxy-2-propyl acetate 318.47
    2-(2-methoxypropoxy) propanol 182.08
    mesitylene 101.88
    ε-caprolactone 786.58
    p-cymene 108.94
    epichlorohydrin 1565.8
    1,1,1-trichloroethane 1325.79
    2-aminoethanol 343.13
    morpholine-4-carbaldehyde 800.04
    sulfolane 1377.58
    2,2,4-trimethylpentane 30.32
    2-methyltetrahydrofuran 752.39
    n-hexyl acetate 298.96
    isooctane 22.77
    2-(2-butoxyethoxy)ethanol 254.03
    sec-butyl acetate 198.95
    tert-butyl acetate 283.99
    decalin 61.98
    glycerin 381.59
    diglyme 597.63
    acrylic acid 654.68
    isopropyl myristate 114.56
    n-butyric acid 693.38
    acetyl acetate 567.71
    di(2-ethylhexyl) phthalate 119.66
    ethyl propionate 345.16
    nitromethane 1695.49
    1,2-diethoxyethane 266.27
    benzonitrile 447.61
    trioctyl phosphate 103.16
    1-bromopropane 535.28
    gamma-valerolactone 1143.38
    n-decanol 95.56
    triethyl phosphate 166.51
    4-methyl-2-pentanol 99.01
    propionitrile 483.03
    vinylene carbonate 897.42
    1,1,2-trichlorotrifluoroethane 1198.76
    DMS 334.1
    cumene 98.46
    2-octanol 102.83
    2-hexanone 293.12
    octyl acetate 156.83
    limonene 157.81
    1,2-dimethoxyethane 836.03
    ethyl orthosilicate 149.72
    tributyl phosphate 121.14
    diacetone alcohol 322.51
    N,N-dimethylaniline 180.39
    acrylonitrile 729.39
    aniline 348.84
    1,3-propanediol 466.17
    bromobenzene 557.42
    dibromomethane 1407.13
    1,1,2,2-tetrachloroethane 1926.15
    2-methyl-cyclohexyl acetate 219.87
    tetrabutyl urea 147.02
    diisobutyl methanol 96.12
    2-phenylethanol 265.43
    styrene 184.67
    dioctyl adipate 176.45
    dimethyl sulfate 564.79
    ethyl butyrate 279.71
    methyl lactate 352.97
    butyl lactate 179.14
    diethyl carbonate 241.98
    propanediol butyl ether 223.16
    triethyl orthoformate 197.53
    p-tert-butyltoluene 99.36
    methyl 4-tert-butylbenzoate 237.84
    morpholine 1117.39
    tert-butylamine 207.8
    n-dodecanol 78.44
    dimethoxymethane 789.6
    ethylene carbonate 746.51
    cyrene 287.22
    2-ethoxyethyl acetate 294.67
    2-ethylhexyl acetate 226.03
    1,2,4-trichlorobenzene 608.5
    4-methylpyridine 580.84
    dibutyl ether 150.24
    2,6-dimethyl-4-heptanol 96.12
    DEF 510.76
    dimethyl isosorbide 363.43
    tetrachloroethylene 1407.28
    eugenol 225.63
    triacetin 283.21
    span 80 179.46
    1,4-butanediol 233.38
    1,1-dichloroethane 1193.66
    2-methyl-1-pentanol 173.86
    methyl formate 930.53
    2-methyl-1-butanol 231.07
    n-decane 33.54
    butyronitrile 473.5
    3,7-dimethyl-1-octanol 116.11
    1-chlorooctane 126.97
    1-chlorotetradecane 59.14
    n-nonane 34.32
    undecane 26.91
    tert-butylcyclohexane 46.28
    cyclooctane 51.56
    cyclopentanol 515.83
    tetrahydropyran 864.92
    tert-amyl methyl ether 223.06
    2,5,8-trioxanonane 351.41
    1-hexene 112.95
    2-isopropoxyethanol 309.12
    2,2,2-trifluoroethanol 456.72
    methyl butyrate 473.15

    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
Carrot leaf (India) 8015-88-1 Daucus carota L. var. sativa, fam. Apiaceae (Umbelliferae) 2.96%
Cymbopogon microstachys Cymbopogon microstachys (Hook. f.) S. Soenarko, fam. Poaceae (Gramineae) 25.3%
Elemi 1 8023-89-0 Canarium luzonicum (Miq.) A. Gray, (C. luzonicum (Blume) A.Gray) 3.5%
Tarragon 1 8016-88-4 Artemisia dracunculus L., fam. Asteraceae (Compositae) 0.34%
Indian dill Anethum sowa Roxb., fam. Apiaceae (Umbelliferae) 0.05%
Mace 1 8007-12-3 Myristica fragrans Houtt., fam. Myristicaceae 0.2%
Mace 2 8007-12-3 Myristica fragrans Houtt., fam. Myristicaceae 2.0%
Nutmeg (India) 1 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 2.35%
Nutmeg (India) 2 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.8%
Nutmeg (Sri Lanka) 1 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 1.55%
Nutmeg (India) 3 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.01%
Olibanum, Indian (India) 8016-36-2 Boswellia serrata Roxb. ex Colebr., fam. Burseraceae 0.37%
Parsley absolute (Egypt) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.31%
Parsley seed 1 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.5%
Parsley seed (Egypt) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 4.61%
Peperomia rotundifolia Peperomia rotundifolia (L.) Kth. 0.15%
Snakeroot, Canadian 8016-69-1 Asarum canadense L., fam. Aristolochiaceae 1.76%
Vanillosmopsis arborea bark Vanillosmopsis arborea Baker, fam. Asteraceae (Compositae) 2.68%
Nutmeg (West Indies) 1 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 1.3%
Sassafras 1 8006-80-2 Sassafras albidum (Nutt.) Nees, fam. Lauraceae 0.1%
Eucalyptus brassiana Eucalyptus brassiana S.T. Blake, fam. Myrtaceae 0.1%
Juniperus martinezii Juniperus martinezii Perez de la Rosa, fam. Cupressaceae 0.05%
Juniperus flaccida var. flaccida Juniperus flaccida Schlecht, var. flaccida, fam. Cupressaceae 0.1%
Empleurum fragrans Empleurum fragrans Glover, fam. Diosmeae 0.4%
Melaleuca armillaris leaf (Egypt) Melaleuca armillaris Sm., fam. Myrtaceae 0.01%
Melaleuca bracteata leaf (Egypt) Melaleuca bracteata F. Muell., fam. Myrtaceae 0.3%
Cascarilla 2 8007-06-5 Croton eluteria Bennett, fam. Euphorbiaceae 0.57%
Daphne genkwa Daphne genkwa Sieb. et Zucc., fam. Thymelaeaceae 4.45%
Parsley seed (Korea) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 2.64%
Parsley leaf (Korea) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (C. sativum Hoffm.), fam. Apiaceae 3.04%
Narcissus poeticus absolute 8023-75-4 Narcissus poeticus L., fam. Amaryllidaceae 0.1%
Nutmeg 3 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 5.46%
Nutmeg 4 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.92%
Nutmeg (Indonesia) 3 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.1%
Carrot seed (China) 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.12%
Pistacia lentiscus (Israel) 1b leaf 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.23%
Nutmeg 2 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.98%
Nutmeg (Indonesia) 4 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.9%
Nutmeg (Indonesia) 2 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.15%
Nutmeg (Sri Lanka) 4 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 1.95%
Tarragon (USA) 1 8016-88-4 Artemisia dracunculus L. (French type), fam. Asteraceae (Compositae) 0.05%
Tarragon (USA) 2 8016-88-4 Artemisia dracunculus L. (French type), fam. Asteraceae (Compositae) 0.74%
Tarragon (USA) 3 8016-88-4 Artemisia dracunculus L. (Russian type), fam. Asteraceae (Compositae) 0.52%
Tarragon (USA) 4 8016-88-4 Artemisia dracunculus L. (Russian type), fam. Asteraceae (Compositae) 52.23%
Litsea zeylanica Litsea zeylanica Nees, fam. Lauraceae 0.22%
Parsley seed (France) 1a 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 1.9%
Parsley seed (France), Giant Italian Petroselinum hortense Hoffm., fam. Apiaceae (Umbelliferae) 1.9%
Parsley seed (France) 1b 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 4.7%
Nutmeg (Sri Lanka) 3 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 2.1%
Nutmeg (India) 4 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.4%