Ligustrazine

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  • Identifiers

    CAS number
    1124-11-4

    Molecular formula
    C8H12N2

    SMILES
    CC1=C(N=C(C(=N1)C)C)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1085.0
    • Carbowax: 1458.33

  • Odor profile

    Nutty 73.35%
    Roasted 69.0%
    Burnt 62.24%
    Cocoa 61.55%
    Musty 60.31%
    Earthy 57.69%
    Coffee 55.93%
    Hazelnut 54.18%
    Chocolate 51.79%
    Potato 41.92%

    Scent© AI

  • Properties

    XLogP3-AA
    1.3

    Molecular weight
    136.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Melting point expt.

    • 86 °C

    Boiling point

    • 190.00 °C. @ 760.00 mm Hg

    Flash point est.
    66.27 ˚C

    Solubility expt.

    • <0.1 [ug/mL] (The mean of the results at pH 7.4)
    • slightly soluble in water; soluble in oils, propylene glycol, organic solvents
    • very soluble (in ethanol)

  • Synonyms

    • 2,3,5,6-Tetramethylpyrazine
    • TETRAMETHYLPYRAZINE
    • 1124-11-4
    • Ligustrazine
    • Pyrazine, tetramethyl-
    • Bs factor
    • Tetrapyrazine
    • Tetramethylpyrazin
    • Chuanxiongzine
    • Liqustrazine
    • 2,3,5,6-Tetramethyl pyrazine
    • chuanxingzine
    • Ligustizine
    • FEMA No. 3237
    • Ligustrazin
    • 2,3,5,6,-Tetramethyl-1,4-pyrazine
    • EINECS 214-391-2
    • V80F4IA5XG
    • MFCD00006146
    • NSC 36080
    • NSC 46451
    • CHUANXIONGQIN
    • 2,3,5,6-Tetramethylpyrazine (natural)
    • DTXSID6047070
    • FEMA 3237
    • Pyrazine, 2,3,5,6-tetramethyl-
    • NSC-36080
    • NSC-46451
    • LIGUSTRAZINE [WHO-DD]
    • MLS000069594
    • 2,3,5,6-Tetramethyl-pyrazine
    • DTXCID4027070
    • CHEBI:133246
    • SMR000059042
    • 2,3,5,6-TETRAMETHYLPYRAZINE [FCC]
    • 2,3,5,6-TETRAMETHYLPYRAZINE [FHFI]
    • 2,5,6-Tetramethylpyrazine
    • TMPZ
    • tetramethyl pyrazine
    • UNII-V80F4IA5XG
    • Ligustrazine (Standard)
    • Opera_ID_849
    • TMP?
    • SCHEMBL77624
    • CHEMBL303697
    • FINHMKGKINIASC-UHFFFAOYSA-
    • HY-N0264R
    • 2,3,5,6-Tetra-methyl-pyrazine
    • Pyrazine, 2,3,5,6-tetramethyl
    • GLXC-10218
    • HMS2235K03
    • HMS3371J08
    • HY-N0264
    • NSC36080
    • NSC46451
    • Tox21_302313
    • BBL012277
    • s3956
    • STL163591
    • 2,3,5,6-Tetramethylpyrazine, 98%
    • AKOS003398567
    • CCG-207974
    • CS-W023183
    • FT04172
    • NCGC00247063-01
    • NCGC00256097-01
    • AC-10515
    • AC-34076
    • AS-13206
    • SY011353
    • CAS-1124-11-4
    • DB-003786
    • NS00013238
    • T0972
    • 2,3,5,6-Tetramethylpyrazine, >=98%, FG
    • EN300-113945
    • F11202
    • 2,3,5,6-Tetramethylpyrazine, analytical standard
    • A802574
    • AC-907/25014219
    • 2,3,5,6-Tetramethylpyrazine, natural, >=98%, FG
    • BRD-K25691735-001-09-5
    • Q11319317
    • Z1741976694
    • 2,3,5,6-Tetramethylpyrazine, Vetec(TM) reagent grade, 98%
    • InChI=1/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
    • 214-391-2

  • Applications

    2,3,5,6-Tetramethylpyrazine (TMP, also known as ligustrazine) is a heteroaromatic compound with a characteristic roasted, cocoa-like odor that finds diverse applications: in the food industry it is employed as a flavoring agent to impart nutty, malty, coffee and caramel notes to sauces, baked goods, chocolate, soy products and canned meat while masking off-flavors; in pharmaceuticals it is isolated or synthesized as the active ingredient of cardiovascular and cerebrovascular medications used for ischemia, stroke and angina because of its vasodilatory, anti-platelet, anti-oxidant and neuroprotective properties, appearing in injections, tablets and nano-formulations under various brand names; in agriculture it is being explored as a semiochemical for beneficial insect attraction and pest deterrence; in fragrance and tobacco it enriches smoky, woody and dark-gourmand accords in perfumes, scented candles and cigarette blends; moreover its electron-rich pyrazine core makes it a valuable intermediate in the preparation of antifungal agents, photoconductive dyes and conductive polymers.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 455.76
    methanol 882.53
    isopropanol 331.24
    water 18.18
    ethyl acetate 438.69
    n-propanol 506.15
    acetone 329.33
    n-butanol 463.87
    acetonitrile 237.95
    DMF 784.95
    toluene 345.05
    isobutanol 371.9
    1,4-dioxane 689.7
    methyl acetate 429.58
    THF 911.89
    2-butanone 455.27
    n-pentanol 286.11
    sec-butanol 400.55
    n-hexane 198.05
    ethylene glycol 150.78
    NMP 924.84
    cyclohexane 189.31
    DMSO 540.88
    n-butyl acetate 341.63
    n-octanol 183.08
    chloroform 1494.79
    n-propyl acetate 254.26
    acetic acid 241.54
    dichloromethane 1392.73
    cyclohexanone 659.74
    propylene glycol 162.24
    isopropyl acetate 280.14
    DMAc 729.76
    2-ethoxyethanol 363.92
    isopentanol 316.65
    n-heptane 108.25
    ethyl formate 369.16
    1,2-dichloroethane 787.75
    n-hexanol 289.54
    2-methoxyethanol 644.71
    isobutyl acetate 182.53
    tetrachloromethane 553.88
    n-pentyl acetate 274.96
    transcutol 462.66
    n-heptanol 182.8
    ethylbenzene 241.96
    MIBK 234.47
    2-propoxyethanol 414.6
    tert-butanol 299.2
    MTBE 404.63
    2-butoxyethanol 276.91
    propionic acid 324.76
    o-xylene 298.92
    formic acid 189.39
    diethyl ether 515.39
    m-xylene 256.35
    p-xylene 336.66
    chlorobenzene 470.14
    dimethyl carbonate 229.99
    n-octane 67.35
    formamide 232.17
    cyclopentanone 756.32
    2-pentanone 382.74
    anisole 354.32
    cyclopentyl methyl ether 579.4
    gamma-butyrolactone 834.23
    1-methoxy-2-propanol 425.84
    pyridine 520.43
    3-pentanone 400.82
    furfural 780.03
    n-dodecane 46.31
    diethylene glycol 267.52
    diisopropyl ether 192.08
    tert-amyl alcohol 360.12
    acetylacetone 362.77
    n-hexadecane 52.44
    acetophenone 314.88
    methyl propionate 410.34
    isopentyl acetate 317.91
    trichloroethylene 1161.1
    n-nonanol 160.35
    cyclohexanol 375.77
    benzyl alcohol 264.11
    2-ethylhexanol 206.69
    isooctanol 148.05
    dipropyl ether 298.93
    1,2-dichlorobenzene 502.09
    ethyl lactate 155.48
    propylene carbonate 480.35
    n-methylformamide 449.44
    2-pentanol 311.88
    n-pentane 160.52
    1-propoxy-2-propanol 299.39
    1-methoxy-2-propyl acetate 305.7
    2-(2-methoxypropoxy) propanol 197.4
    mesitylene 188.54
    ε-caprolactone 594.08
    p-cymene 174.45
    epichlorohydrin 892.2
    1,1,1-trichloroethane 817.07
    2-aminoethanol 263.5
    morpholine-4-carbaldehyde 750.04
    sulfolane 908.99
    2,2,4-trimethylpentane 89.55
    2-methyltetrahydrofuran 762.35
    n-hexyl acetate 322.44
    isooctane 51.62
    2-(2-butoxyethoxy)ethanol 244.79
    sec-butyl acetate 204.68
    tert-butyl acetate 275.95
    decalin 118.96
    glycerin 211.61
    diglyme 521.74
    acrylic acid 282.13
    isopropyl myristate 142.57
    n-butyric acid 395.12
    acetyl acetate 282.23
    di(2-ethylhexyl) phthalate 132.43
    ethyl propionate 300.24
    nitromethane 452.26
    1,2-diethoxyethane 323.31
    benzonitrile 352.74
    trioctyl phosphate 108.93
    1-bromopropane 625.72
    gamma-valerolactone 826.87
    n-decanol 122.9
    triethyl phosphate 179.42
    4-methyl-2-pentanol 149.52
    propionitrile 342.74
    vinylene carbonate 480.49
    1,1,2-trichlorotrifluoroethane 542.34
    DMS 320.95
    cumene 191.49
    2-octanol 159.16
    2-hexanone 286.16
    octyl acetate 178.92
    limonene 224.24
    1,2-dimethoxyethane 596.97
    ethyl orthosilicate 180.01
    tributyl phosphate 138.07
    diacetone alcohol 245.16
    N,N-dimethylaniline 299.03
    acrylonitrile 367.57
    aniline 341.89
    1,3-propanediol 345.49
    bromobenzene 537.75
    dibromomethane 1029.79
    1,1,2,2-tetrachloroethane 1078.86
    2-methyl-cyclohexyl acetate 237.59
    tetrabutyl urea 174.43
    diisobutyl methanol 125.95
    2-phenylethanol 258.32
    styrene 256.16
    dioctyl adipate 175.1
    dimethyl sulfate 355.88
    ethyl butyrate 271.15
    methyl lactate 209.88
    butyl lactate 189.05
    diethyl carbonate 207.89
    propanediol butyl ether 193.12
    triethyl orthoformate 231.03
    p-tert-butyltoluene 169.5
    methyl 4-tert-butylbenzoate 271.44
    morpholine 669.49
    tert-butylamine 245.1
    n-dodecanol 96.87
    dimethoxymethane 558.9
    ethylene carbonate 416.37
    cyrene 239.15
    2-ethoxyethyl acetate 305.63
    2-ethylhexyl acetate 297.84
    1,2,4-trichlorobenzene 553.25
    4-methylpyridine 589.65
    dibutyl ether 275.33
    2,6-dimethyl-4-heptanol 125.95
    DEF 533.3
    dimethyl isosorbide 389.37
    tetrachloroethylene 863.54
    eugenol 237.7
    triacetin 244.47
    span 80 176.37
    1,4-butanediol 165.07
    1,1-dichloroethane 738.8
    2-methyl-1-pentanol 251.98
    methyl formate 392.73
    2-methyl-1-butanol 371.93
    n-decane 75.95
    butyronitrile 373.62
    3,7-dimethyl-1-octanol 163.33
    1-chlorooctane 206.31
    1-chlorotetradecane 90.55
    n-nonane 79.82
    undecane 57.32
    tert-butylcyclohexane 119.4
    cyclooctane 93.59
    cyclopentanol 461.15
    tetrahydropyran 650.41
    tert-amyl methyl ether 394.28
    2,5,8-trioxanonane 327.96
    1-hexene 317.09
    2-isopropoxyethanol 230.87
    2,2,2-trifluoroethanol 193.89
    methyl butyrate 358.19

    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
Orris butter 8002-73-1 Iris florentina L., fam. Iridaceae 0.01%
Rhubarb root Rheum palmatum L., fam. Polygonaceae 0.2%