4-Allyl-2,6-dimethoxyphenol

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    6627-88-9

    Molecular formula
    C11H14O3

    SMILES
    COC1=CC(=CC(=C1O)OC)CC=C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 2494.5

  • Odor profile

    Spicy 87.56%
    Phenolic 69.07%
    Woody 67.18%
    Smoky 63.78%
    Sweet 63.78%
    Clove 60.25%
    Vanilla 41.63%
    Warm 41.4%
    Balsamic 40.26%
    Burnt 38.45%

    Scent© AI

  • Properties

    XLogP3-AA
    2.6

    Molecular weight
    194.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point

    • 168.00 to 169.00 °C. @ 11.00 mm Hg

    Flash point est.
    118.39 ˚C

    Solubility expt.

    • insoluble in water; soluble in fat
    • miscible (in ethanol)

  • Synonyms

    • 4-Allyl-2,6-dimethoxyphenol
    • 6627-88-9
    • Methoxyeugenol
    • 2,6-dimethoxy-4-prop-2-enylphenol
    • 4-Allylsyringol
    • 2,6-Dimethoxychavicol
    • Phenol, 2,6-dimethoxy-4-(2-propenyl)-
    • Phenol, 4-allyl-2,6-dimethoxy-
    • 2,6-Dimethoxy-4-allylphenol
    • 4-Allyl-2,6-dimetoxyphenol
    • 4-Hydroxy-3,5-dimethoxyallylbenzene
    • FEMA No. 3655
    • CHEBI:86562
    • 6-methoxyeugenol
    • UNII-8VF00YWP89
    • 2,6-dimethoxy-4-(2-propenyl)phenol
    • 8VF00YWP89
    • EINECS 229-600-2
    • NSC 16953
    • NSC 60246
    • NSC-16953
    • NSC-60246
    • Phenol, 4-(2-propenyl)-2,6-dimethoxy
    • 2,6-dimethoxy-4-(prop-2-en-1-yl)phenol
    • AI3-23057
    • Phenol,2,6-dimethoxy-4-(2-propen-1-yl)-
    • 4-(2-PROPENYL)SYRINGOL
    • DTXSID30216470
    • CHAVICOL, 2,6-DIMETHOXY-
    • Phenol,6-dimethoxy-
    • 4-ALLYL-2,6-DIMETHOXYPHENOL [FHFI]
    • PHENOL, 2,6-DIMETHOXY-4-(2-PROPEN-1-YL)-
    • 4-(2-Propenyl)-2,6-dimethoxyphenol (4-allylsyringol)
    • Phenol,6-dimethoxy-4-(2-propenyl)-
    • MFCD00008655
    • bmse010054
    • SCHEMBL293977
    • 4-allyl-2,6-dimethoxy-phenol
    • CHEMBL2059292
    • DTXCID30138961
    • NSC16953
    • NSC60246
    • 4-Allyl-2,6-dimethoxyphenol, 8CI
    • BDBM50242963
    • 4-(2-Propenyl)-2,6-dimethoxyphenol
    • AKOS015888171
    • 2,6-dimethoxy-4-(2-propenyl)-phenol
    • 2,6-Dimethoxy-4-(2-propenyl) phenol
    • 4-Allyl-2,6-dimethoxyphenol, >=95%
    • Phenol, 4-allyl-2,6-dimethoxy-(8CI)
    • AS-36789
    • BP-10517
    • Phenol, 4-allyl-2,6-dimethoxy- (8CI)
    • DB-054902
    • 2,6-Dimethoxy-4-(2-propenyl)phenol, 9CI
    • 4-Allyl-2,6-dimethoxyphenol, >=95%, FG
    • CS-0158007
    • NS00022639
    • Phenol, 2,6-dimethoxy-4-(2-propenyl)-(9CI)
    • Phenol, 2,6-dimethoxy-4-(2-propenyl)- (9CI)
    • Q27159248
    • 229-600-2

  • Applications

    4-Allyl-2,6-dimethoxyphenol (CAS 6627-88-9) is a naturally occurring phenolic derivative found in several essential oils; its pronounced antioxidant power, antimicrobial action and warm spicy fragrance make it valuable as a bio-preservative and flavour modulator in foods and beverages, as a fragrance ingredient and product-stabilising agent in cosmetics, and as a scaffold under pharmaceutical investigation for analgesic, anti-inflammatory and tyrosinase-inhibiting leads; furthermore, the allyl-substituted aromatic core allows it to serve as a versatile intermediate for the synthesis of vanillin analogues, lignans and bio-based epoxy resins, while its well-defined chromatographic behaviour qualifies it as an analytical reference standard for gas-chromatography/mass-spectrometry quality control of essential oil compositions.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 246.55
    methanol 280.62
    isopropanol 149.3
    water 0.53
    ethyl acetate 277.07
    n-propanol 188.1
    acetone 420.11
    n-butanol 142.76
    acetonitrile 266.9
    DMF 558.35
    toluene 60.35
    isobutanol 113.33
    1,4-dioxane 484.9
    methyl acetate 350.39
    THF 590.39
    2-butanone 269.69
    n-pentanol 106.33
    sec-butanol 127.92
    n-hexane 6.51
    ethylene glycol 156.35
    NMP 296.3
    cyclohexane 27.72
    DMSO 688.7
    n-butyl acetate 142.48
    n-octanol 60.49
    chloroform 520.87
    n-propyl acetate 155.66
    acetic acid 400.22
    dichloromethane 584.74
    cyclohexanone 336.82
    propylene glycol 127.4
    isopropyl acetate 109.47
    DMAc 272.09
    2-ethoxyethanol 279.41
    isopentanol 103.67
    n-heptane 10.3
    ethyl formate 295.71
    1,2-dichloroethane 433.04
    n-hexanol 116.65
    2-methoxyethanol 528.99
    isobutyl acetate 82.25
    tetrachloromethane 84.43
    n-pentyl acetate 81.86
    transcutol 345.74
    n-heptanol 66.55
    ethylbenzene 47.0
    MIBK 94.23
    2-propoxyethanol 230.58
    tert-butanol 215.96
    MTBE 137.35
    2-butoxyethanol 136.57
    propionic acid 220.5
    o-xylene 53.11
    formic acid 146.87
    diethyl ether 158.65
    m-xylene 49.98
    p-xylene 58.56
    chlorobenzene 155.01
    dimethyl carbonate 142.98
    n-octane 6.61
    formamide 281.07
    cyclopentanone 449.8
    2-pentanone 183.73
    anisole 123.86
    cyclopentyl methyl ether 167.98
    gamma-butyrolactone 586.57
    1-methoxy-2-propanol 271.49
    pyridine 307.39
    3-pentanone 137.63
    furfural 473.65
    n-dodecane 6.64
    diethylene glycol 257.65
    diisopropyl ether 35.28
    tert-amyl alcohol 150.53
    acetylacetone 229.8
    n-hexadecane 7.66
    acetophenone 132.99
    methyl propionate 223.65
    isopentyl acetate 112.56
    trichloroethylene 719.13
    n-nonanol 54.11
    cyclohexanol 152.46
    benzyl alcohol 130.32
    2-ethylhexanol 71.67
    isooctanol 53.4
    dipropyl ether 67.35
    1,2-dichlorobenzene 145.76
    ethyl lactate 95.1
    propylene carbonate 298.8
    n-methylformamide 356.57
    2-pentanol 78.14
    n-pentane 7.64
    1-propoxy-2-propanol 135.09
    1-methoxy-2-propyl acetate 133.75
    2-(2-methoxypropoxy) propanol 103.02
    mesitylene 35.68
    ε-caprolactone 278.59
    p-cymene 39.76
    epichlorohydrin 607.31
    1,1,1-trichloroethane 300.58
    2-aminoethanol 186.94
    morpholine-4-carbaldehyde 331.98
    sulfolane 546.68
    2,2,4-trimethylpentane 8.96
    2-methyltetrahydrofuran 293.97
    n-hexyl acetate 109.31
    isooctane 6.98
    2-(2-butoxyethoxy)ethanol 149.08
    sec-butyl acetate 77.87
    tert-butyl acetate 115.8
    decalin 15.4
    glycerin 200.87
    diglyme 315.09
    acrylic acid 230.73
    isopropyl myristate 45.48
    n-butyric acid 267.02
    acetyl acetate 173.4
    di(2-ethylhexyl) phthalate 52.68
    ethyl propionate 116.27
    nitromethane 688.48
    1,2-diethoxyethane 118.45
    benzonitrile 165.04
    trioctyl phosphate 43.66
    1-bromopropane 144.12
    gamma-valerolactone 456.96
    n-decanol 43.36
    triethyl phosphate 64.66
    4-methyl-2-pentanol 45.89
    propionitrile 180.12
    vinylene carbonate 287.95
    1,1,2-trichlorotrifluoroethane 428.14
    DMS 116.97
    cumene 36.9
    2-octanol 43.37
    2-hexanone 124.03
    octyl acetate 60.89
    limonene 56.92
    1,2-dimethoxyethane 400.41
    ethyl orthosilicate 59.67
    tributyl phosphate 48.91
    diacetone alcohol 159.64
    N,N-dimethylaniline 77.54
    acrylonitrile 274.01
    aniline 126.92
    1,3-propanediol 256.96
    bromobenzene 145.45
    dibromomethane 349.78
    1,1,2,2-tetrachloroethane 516.99
    2-methyl-cyclohexyl acetate 91.08
    tetrabutyl urea 62.1
    diisobutyl methanol 42.87
    2-phenylethanol 118.38
    styrene 62.34
    dioctyl adipate 73.44
    dimethyl sulfate 203.44
    ethyl butyrate 106.2
    methyl lactate 140.3
    butyl lactate 75.0
    diethyl carbonate 87.85
    propanediol butyl ether 115.85
    triethyl orthoformate 73.33
    p-tert-butyltoluene 38.6
    methyl 4-tert-butylbenzoate 103.35
    morpholine 512.74
    tert-butylamine 101.49
    n-dodecanol 34.12
    dimethoxymethane 339.35
    ethylene carbonate 238.5
    cyrene 142.02
    2-ethoxyethyl acetate 116.35
    2-ethylhexyl acetate 86.98
    1,2,4-trichlorobenzene 167.95
    4-methylpyridine 217.09
    dibutyl ether 55.51
    2,6-dimethyl-4-heptanol 42.87
    DEF 195.62
    dimethyl isosorbide 172.74
    tetrachloroethylene 356.0
    eugenol 108.06
    triacetin 115.3
    span 80 91.37
    1,4-butanediol 105.41
    1,1-dichloroethane 320.55
    2-methyl-1-pentanol 87.21
    methyl formate 396.36
    2-methyl-1-butanol 99.78
    n-decane 10.01
    butyronitrile 168.34
    3,7-dimethyl-1-octanol 52.83
    1-chlorooctane 42.38
    1-chlorotetradecane 19.7
    n-nonane 9.2
    undecane 7.99
    tert-butylcyclohexane 12.86
    cyclooctane 9.44
    cyclopentanol 177.18
    tetrahydropyran 327.92
    tert-amyl methyl ether 95.23
    2,5,8-trioxanonane 191.58
    1-hexene 29.49
    2-isopropoxyethanol 156.77
    2,2,2-trifluoroethanol 161.87
    methyl butyrate 174.9

    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
Nutmeg (Indonesia) 3 8008-45-5 Myristica fragrans Houtt., fam. Myristicaceae 0.1%
Mimusops elengi flower headspace Mimusops elengi L., fam. Sapotaceae 0.7%
Pineapple pulp Ananas comosus (L.) Merr., fam. Bromeliaceae 0.07%