Meranzin

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  • Identifiers

    CAS number
    23971-42-8

    Molecular formula
    C15H16O4

    SMILES
    CC1([C@@H](O1)CC2=C(C=CC3=C2OC(=O)C=C3)OC)C

  • Odor profile

    Sweet 42.49%
    Floral 31.3%
    Powdery 30.46%
    Fruity 29.04%
    Vanilla 28.66%
    Creamy 24.78%
    Animal 24.29%
    Phenolic 23.63%
    Woody 21.67%
    Coumarinic 20.5%

    Scent© AI

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    6.64 (neutral)

    Molecular weight
    260.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    414°C

    Flash point est.
    155.83 ˚C

  • Synonyms

    • Meranzin
    • 23971-42-8
    • Merancin
    • (-)-Meranzin
    • 8-[[(2S)-3,3-dimethyloxiran-2-yl]methyl]-7-methoxychromen-2-one
    • Coumarin, 8-(2,3-epoxy-3-methylbutyl)-7-methoxy-, (-)-
    • (S)-8-((3,3-Dimethyloxiran-2-yl)methyl)-7-methoxy-2H-chromen-2-one
    • 2H-1-Benzopyran-2-one, 8-[(3,3-dimethyloxiranyl)methyl]-7-methoxy-, (S)-
    • 2H-1-Benzopyran-2-one, 8-[[(2S)-3,3-dimethyloxiranyl]methyl]-7-methoxy-
    • 2H-1-Benzopyran-2-one, 8-[[(2S)-3,3-dimethyl-2-oxiranyl]methyl]-7-methoxy-
    • 2H-1-Benzopyran-2-one, 8-(((2S)-3,3-dimethyloxiranyl)methyl)-7-methoxy-
    • 8-{[(2S)-3,3-DIMETHYLOXIRAN-2-YL]METHYL}-7-METHOXYCHROMEN-2-ONE
    • 2H-1-Benzopyran-2-one, 8-(((2S)-3,3-dimethyl-2-oxiranyl)methyl)-7-methoxy-
    • 2H-1-Benzopyran-2-one, 8-((3,3-dimethyloxiranyl)methyl)-7-methoxy-, (S)-
    • Meranzin (Standard)
    • SCHEMBL14315527
    • HY-N3298R
    • 8-[[(2S)-3,3-Dimethyl-2-oxiranyl]methyl]-7-methoxy-2H-1-benzopyran-2-one; (-)-Meranzin
    • 489-53-2
    • HY-N3298
    • MFCD02683834
    • AKOS040760112
    • AC-34114
    • DA-75419
    • MS-23666
    • CS-0023841
    • G13151

  • Applications

    Meranzin (CAS 23971-42-8) is a natural coumarin mainly isolated from Citrus species; in research it is commonly used as an analytical reference standard (HPLC/LC-MS) for quality control of herbal materials such as Fructus/Pericarpium aurantii and related formulas, and as a bioactive probe in studies of pharmacodynamics, pharmacokinetics, metabolism, and mechanism, particularly in models of gastrointestinal hypomotility and smooth-muscle spasm (reported prokinetic and antispasmodic effects), as well as exploratory areas like antioxidant and anti-inflammatory activity, serotonergic/cholinergic modulation, and antidepressant-like effects; it is also employed as a scaffold for designing new coumarin derivatives and as a comparator in target screening, and is intended for laboratory R&D use only.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 22.01
    methanol 24.87
    isopropanol 12.78
    water 0.04
    ethyl acetate 50.47
    n-propanol 15.05
    acetone 51.26
    n-butanol 11.22
    acetonitrile 41.66
    DMF 168.65
    toluene 11.87
    isobutanol 10.84
    1,4-dioxane 125.85
    methyl acetate 73.69
    THF 160.82
    2-butanone 56.17
    n-pentanol 8.21
    sec-butanol 10.53
    n-hexane 0.12
    ethylene glycol 13.02
    NMP 97.76
    cyclohexane 0.42
    DMSO 98.92
    n-butyl acetate 26.64
    n-octanol 2.27
    chloroform 131.58
    n-propyl acetate 32.56
    acetic acid 63.78
    dichloromethane 151.15
    cyclohexanone 60.8
    propylene glycol 12.83
    isopropyl acetate 32.09
    DMAc 232.04
    2-ethoxyethanol 64.71
    isopentanol 14.12
    n-heptane 0.16
    ethyl formate 25.83
    1,2-dichloroethane 77.64
    n-hexanol 7.31
    2-methoxyethanol 117.32
    isobutyl acetate 25.24
    tetrachloromethane 4.04
    n-pentyl acetate 10.7
    transcutol 211.69
    n-heptanol 3.48
    ethylbenzene 5.34
    MIBK 22.94
    2-propoxyethanol 64.4
    tert-butanol 17.67
    MTBE 24.17
    2-butoxyethanol 25.07
    propionic acid 28.35
    o-xylene 6.69
    formic acid 32.59
    diethyl ether 18.23
    m-xylene 6.3
    p-xylene 9.29
    chlorobenzene 23.5
    dimethyl carbonate 39.09
    n-octane 0.07
    formamide 64.58
    cyclopentanone 84.16
    2-pentanone 30.59
    anisole 33.13
    cyclopentyl methyl ether 32.45
    gamma-butyrolactone 107.11
    1-methoxy-2-propanol 59.34
    pyridine 96.19
    3-pentanone 26.72
    furfural 110.63
    n-dodecane 0.12
    diethylene glycol 70.11
    diisopropyl ether 4.6
    tert-amyl alcohol 15.43
    acetylacetone 68.54
    n-hexadecane 0.15
    acetophenone 38.37
    methyl propionate 48.07
    isopentyl acetate 31.1
    trichloroethylene 203.67
    n-nonanol 2.87
    cyclohexanol 11.58
    benzyl alcohol 27.47
    2-ethylhexanol 5.58
    isooctanol 3.95
    dipropyl ether 7.44
    1,2-dichlorobenzene 24.89
    ethyl lactate 19.6
    propylene carbonate 50.63
    n-methylformamide 56.67
    2-pentanol 5.91
    n-pentane 0.12
    1-propoxy-2-propanol 30.41
    1-methoxy-2-propyl acetate 63.83
    2-(2-methoxypropoxy) propanol 43.8
    mesitylene 3.35
    ε-caprolactone 60.31
    p-cymene 4.55
    epichlorohydrin 204.88
    1,1,1-trichloroethane 39.3
    2-aminoethanol 21.23
    morpholine-4-carbaldehyde 173.37
    sulfolane 95.64
    2,2,4-trimethylpentane 0.36
    2-methyltetrahydrofuran 71.22
    n-hexyl acetate 13.2
    isooctane 0.2
    2-(2-butoxyethoxy)ethanol 49.22
    sec-butyl acetate 25.19
    tert-butyl acetate 35.25
    decalin 0.54
    glycerin 28.81
    diglyme 120.82
    acrylic acid 35.29
    isopropyl myristate 6.7
    n-butyric acid 31.23
    acetyl acetate 44.32
    di(2-ethylhexyl) phthalate 11.04
    ethyl propionate 30.06
    nitromethane 161.45
    1,2-diethoxyethane 40.58
    benzonitrile 27.46
    trioctyl phosphate 5.33
    1-bromopropane 15.72
    gamma-valerolactone 184.65
    n-decanol 2.28
    triethyl phosphate 16.96
    4-methyl-2-pentanol 6.14
    propionitrile 26.81
    vinylene carbonate 54.97
    1,1,2-trichlorotrifluoroethane 117.62
    DMS 44.38
    cumene 4.29
    2-octanol 1.81
    2-hexanone 23.81
    octyl acetate 7.63
    limonene 4.91
    1,2-dimethoxyethane 123.42
    ethyl orthosilicate 15.5
    tributyl phosphate 8.58
    diacetone alcohol 42.18
    N,N-dimethylaniline 19.8
    acrylonitrile 47.74
    aniline 25.62
    1,3-propanediol 32.88
    bromobenzene 22.51
    dibromomethane 52.75
    1,1,2,2-tetrachloroethane 123.72
    2-methyl-cyclohexyl acetate 23.64
    tetrabutyl urea 11.44
    diisobutyl methanol 4.55
    2-phenylethanol 25.13
    styrene 7.54
    dioctyl adipate 14.36
    dimethyl sulfate 64.35
    ethyl butyrate 22.66
    methyl lactate 28.65
    butyl lactate 12.6
    diethyl carbonate 20.98
    propanediol butyl ether 17.19
    triethyl orthoformate 20.26
    p-tert-butyltoluene 4.13
    methyl 4-tert-butylbenzoate 24.36
    morpholine 142.42
    tert-butylamine 6.79
    n-dodecanol 1.84
    dimethoxymethane 102.59
    ethylene carbonate 43.94
    cyrene 43.77
    2-ethoxyethyl acetate 37.25
    2-ethylhexyl acetate 23.08
    1,2,4-trichlorobenzene 39.07
    4-methylpyridine 69.43
    dibutyl ether 4.94
    2,6-dimethyl-4-heptanol 4.55
    DEF 51.45
    dimethyl isosorbide 75.53
    tetrachloroethylene 54.68
    eugenol 26.88
    triacetin 34.16
    span 80 20.57
    1,4-butanediol 10.9
    1,1-dichloroethane 47.74
    2-methyl-1-pentanol 11.68
    methyl formate 46.03
    2-methyl-1-butanol 11.95
    n-decane 0.17
    butyronitrile 20.0
    3,7-dimethyl-1-octanol 5.07
    1-chlorooctane 1.37
    1-chlorotetradecane 0.78
    n-nonane 0.11
    undecane 0.14
    tert-butylcyclohexane 0.46
    cyclooctane 0.12
    cyclopentanol 15.86
    tetrahydropyran 46.22
    tert-amyl methyl ether 17.74
    2,5,8-trioxanonane 81.86
    1-hexene 1.1
    2-isopropoxyethanol 40.62
    2,2,2-trifluoroethanol 28.19
    methyl butyrate 35.55

    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
Orange, bitter (Spain) 1 72968-50-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.5%
Orange, bitter (Spain) 2 72968-50-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.4%