Meso-Dihydroguaiaretic Acid

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  • Identifiers

    CAS number
    66322-34-7

    Molecular formula
    C20H26O4

    SMILES
    C[C@H](CC1=CC(=C(C=C1)O)OC)[C@@H](C)CC2=CC(=C(C=C2)O)OC

    Safety labels

  • Odor profile

    Fragrance
    Spicy 65.96%
    Phenolic 58.3%
    Woody 44.93%
    Smoky 43.61%
    Balsamic 39.76%
    Sweet 35.16%
    Vanilla 34.85%
    Clove 32.6%
    Burnt 32.19%
    Powdery 30.74%

     

    Flavor
    Spice 41.1%
    Phenolic 40.73%
    Woody 40.36%
    Spicy 34.32%
    Bitter 32.97%
    Medicinal 31.58%
    Mild 28.67%
    Herbal 28.34%
    Camphor 27.02%
    Smoky 25.93%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    5.0

    pKa est.
    9.84 (weak base)

    Molecular weight
    330.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    475°C

    Flash point

    • 191.55 ˚C est.

  • Synonyms

    • meso-dihydroguaiaretic acid
    • 66322-34-7
    • Dihydroguaiaretic acid, meso-
    • S81Z40PSJ4
    • 4-[(2S,3R)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
    • CHEBI:68169
    • DTXSID301019954
    • Guaiacol, 4,4'-(2,3-dimethyltetramethylene)di-, meso-
    • Phenol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis(2-methoxy-, (R*,S*)-
    • Phenol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis[2-methoxy-, (R*,S*)-
    • REL-4,4'-((2R,3S)-2,3-dimethyl-1,4-butanediyl)bis(2-methoxyphenol)
    • Phenol, 4,4'-((2R,3S)-2,3-dimethyl-1,4-butanediyl)bis(2-methoxy-, rel-
    • 4-((2S,3R)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl)-2-methoxyphenol
    • RefChem:34601
    • Mesodihydroguaiaretic Acid
    • DTXCID201477814
    • rel-4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(2-methoxyphenol)
    • 4,4'-[(2R,3S)-2,3-dimethylbutane-1,4-diyl]bis(2-methoxyphenol)
    • 4-[(2S,3R)-4-(4-hydroxy-3-methoxy-phenyl)-2,3-dimethyl-butyl]-2-methoxy-phenol
    • dihydroguaiac acid
    • Dihydroguaiareticacid
    • Meso-Dihyroguaiareticacid
    • UNII-S81Z40PSJ4
    • MLS002473306
    • SCHEMBL974725
    • CHEMBL430464
    • orb1684645
    • HY-N6087R
    • HMS2202B04
    • HY-N6087
    • MFCD02752706
    • 4,4'-dihydroxy-3,3'-dimethoxylignan
    • AKOS028109653
    • meso-Dihydroguaiaretic acid (Standard)
    • DA-52545
    • FD145227
    • MS-24966
    • SMR001397390
    • CS-0032514
    • F82185
    • Q27136661
    • meso-1,4-Bis-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutane
    • 2,2'-Dimethoxy-4,4'-[rel-(2R,3S)-2,3-dimethylbutane- 1,4-diyl]diphenol
    • 4-[(2r,3s)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-methylbutyl]-2-methoxyphenol
    • 66322-34-7

  • Applications

    Meso-Dihydroguaiaretic Acid (CAS 66322-34-7) is used as a versatile building block in lignan-based synthetic chemistry, acting as a key intermediate for the preparation of bioactive lignan derivatives used in pharmaceutical and agrochemical research. It also functions as an antioxidant and stabilizer in polymers, coatings, and inks, helping to improve long-term oxidative stability. In cosmetics and personal care, it may be used as an antioxidant additive or a dermatologist-friendly polyphenol component, subject to regulatory limits. In the laboratory, it serves as a research reagent in organic synthesis and may be evaluated for fragrance-related applications.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 37.61
    methanol 30.07
    isopropanol 37.88
    water 0.05
    ethyl acetate 205.97
    n-propanol 50.15
    acetone 246.12
    n-butanol 37.17
    acetonitrile 65.43
    DMF 230.12
    toluene 38.05
    isobutanol 32.81
    1,4-dioxane 219.46
    methyl acetate 189.08
    THF 648.47
    2-butanone 174.78
    n-pentanol 30.11
    sec-butanol 45.25
    n-hexane 4.12
    ethylene glycol 8.15
    NMP 125.32
    cyclohexane 10.52
    DMSO 502.58
    n-butyl acetate 77.85
    n-octanol 16.0
    chloroform 482.42
    n-propyl acetate 83.5
    acetic acid 95.1
    dichloromethane 483.48
    cyclohexanone 201.88
    propylene glycol 19.53
    isopropyl acetate 118.7
    DMAc 264.1
    2-ethoxyethanol 112.65
    isopentanol 36.4
    n-heptane 3.85
    ethyl formate 65.06
    1,2-dichloroethane 351.58
    n-hexanol 35.29
    2-methoxyethanol 150.37
    isobutyl acetate 47.07
    tetrachloromethane 50.06
    n-pentyl acetate 57.99
    transcutol 269.66
    n-heptanol 23.16
    ethylbenzene 20.51
    MIBK 80.98
    2-propoxyethanol 109.1
    tert-butanol 85.61
    MTBE 129.78
    2-butoxyethanol 66.4
    propionic acid 74.02
    o-xylene 27.82
    formic acid 22.76
    diethyl ether 148.96
    m-xylene 25.03
    p-xylene 24.43
    chlorobenzene 68.0
    dimethyl carbonate 105.7
    n-octane 2.51
    formamide 86.48
    cyclopentanone 371.14
    2-pentanone 146.02
    anisole 63.36
    cyclopentyl methyl ether 152.85
    gamma-butyrolactone 351.14
    1-methoxy-2-propanol 122.51
    pyridine 117.02
    3-pentanone 131.68
    furfural 182.13
    n-dodecane 1.57
    diethylene glycol 74.87
    diisopropyl ether 39.03
    tert-amyl alcohol 74.99
    acetylacetone 228.29
    n-hexadecane 1.85
    acetophenone 70.63
    methyl propionate 177.09
    isopentyl acetate 78.56
    trichloroethylene 531.25
    n-nonanol 17.78
    cyclohexanol 52.07
    benzyl alcohol 43.85
    2-ethylhexanol 24.71
    isooctanol 22.34
    dipropyl ether 47.21
    1,2-dichlorobenzene 78.68
    ethyl lactate 44.81
    propylene carbonate 129.78
    n-methylformamide 90.18
    2-pentanol 34.58
    n-pentane 3.91
    1-propoxy-2-propanol 74.72
    1-methoxy-2-propyl acetate 131.69
    2-(2-methoxypropoxy) propanol 64.31
    mesitylene 17.62
    ε-caprolactone 157.2
    p-cymene 18.07
    epichlorohydrin 481.45
    1,1,1-trichloroethane 240.96
    2-aminoethanol 22.24
    morpholine-4-carbaldehyde 183.3
    sulfolane 382.53
    2,2,4-trimethylpentane 4.74
    2-methyltetrahydrofuran 210.04
    n-hexyl acetate 57.06
    isooctane 3.13
    2-(2-butoxyethoxy)ethanol 86.12
    sec-butyl acetate 58.25
    tert-butyl acetate 146.99
    decalin 5.55
    glycerin 35.78
    diglyme 212.44
    acrylic acid 65.5
    isopropyl myristate 23.61
    n-butyric acid 92.48
    acetyl acetate 135.47
    di(2-ethylhexyl) phthalate 23.3
    ethyl propionate 84.9
    nitromethane 311.52
    1,2-diethoxyethane 103.88
    benzonitrile 42.15
    trioctyl phosphate 18.5
    1-bromopropane 112.97
    gamma-valerolactone 322.93
    n-decanol 13.12
    triethyl phosphate 43.83
    4-methyl-2-pentanol 24.41
    propionitrile 61.39
    vinylene carbonate 105.66
    1,1,2-trichlorotrifluoroethane 245.13
    DMS 89.64
    cumene 16.24
    2-octanol 16.09
    2-hexanone 68.61
    octyl acetate 29.14
    limonene 24.61
    1,2-dimethoxyethane 208.39
    ethyl orthosilicate 42.85
    tributyl phosphate 23.9
    diacetone alcohol 126.31
    N,N-dimethylaniline 41.53
    acrylonitrile 80.99
    aniline 52.24
    1,3-propanediol 43.55
    bromobenzene 73.95
    dibromomethane 261.58
    1,1,2,2-tetrachloroethane 430.81
    2-methyl-cyclohexyl acetate 54.2
    tetrabutyl urea 29.04
    diisobutyl methanol 21.26
    2-phenylethanol 50.61
    styrene 24.17
    dioctyl adipate 39.65
    dimethyl sulfate 187.27
    ethyl butyrate 65.38
    methyl lactate 73.08
    butyl lactate 44.09
    diethyl carbonate 51.69
    propanediol butyl ether 46.6
    triethyl orthoformate 54.11
    p-tert-butyltoluene 18.82
    methyl 4-tert-butylbenzoate 70.59
    morpholine 260.58
    tert-butylamine 39.58
    n-dodecanol 9.88
    dimethoxymethane 250.55
    ethylene carbonate 99.15
    cyrene 78.1
    2-ethoxyethyl acetate 105.3
    2-ethylhexyl acetate 56.78
    1,2,4-trichlorobenzene 92.49
    4-methylpyridine 84.61
    dibutyl ether 29.85
    2,6-dimethyl-4-heptanol 21.26
    DEF 132.09
    dimethyl isosorbide 147.73
    tetrachloroethylene 245.21
    eugenol 58.65
    triacetin 80.12
    span 80 48.63
    1,4-butanediol 18.54
    1,1-dichloroethane 226.36
    2-methyl-1-pentanol 30.96
    methyl formate 87.46
    2-methyl-1-butanol 33.43
    n-decane 3.08
    butyronitrile 42.39
    3,7-dimethyl-1-octanol 20.52
    1-chlorooctane 14.64
    1-chlorotetradecane 5.72
    n-nonane 2.78
    undecane 2.09
    tert-butylcyclohexane 5.09
    cyclooctane 3.96
    cyclopentanol 64.84
    tetrahydropyran 215.63
    tert-amyl methyl ether 87.69
    2,5,8-trioxanonane 130.94
    1-hexene 15.13
    2-isopropoxyethanol 80.67
    2,2,2-trifluoroethanol 58.46
    methyl butyrate 89.57

    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