(+)-Dihydromethysticin

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  • Identifiers

    CAS number
    19902-91-1

    Molecular formula
    C15H16O5

    SMILES
    COC1=CC(=O)O[C@H](C1)CCC2=CC3=C(C=C2)OCO3

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 58.27%
    Spicy 54.61%
    Floral 42.94%
    Coumarinic 39.07%
    Coconut 37.55%
    Vanilla 35.49%
    Lactonic 32.89%
    Creamy 32.85%
    Herbal 31.04%
    Balsamic 27.83%

     

    Flavor
    Bitter 55.11%
    Coconut 29.13%
    Tonka 26.99%
    Herbal 26.85%
    Sweet 25.68%
    Spice 22.31%
    Celery 21.69%
    Lovage 21.49%
    Floral 21.47%
    Parsley 21.23%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    6.46 (neutral)

    Molecular weight
    276.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    717°C

    Flash point

    • 167.95 ˚C est.

  • Synonyms

    • Dihydromethysticin
    • 19902-91-1
    • (+)-Dihydromethysticin
    • FZ66MQ73GS
    • NSC-112159
    • DTXSID601314143
    • (2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
    • (2S)-2-(2-(1,3-BENZODIOXOL-5-YL)ETHYL)-4-METHOXY-2,3-DIHYDROPYRAN-6-ONE
    • DTXSID3033434
    • RefChem:133875
    • GlyTouCan:G12706ZR
    • DTXCID1013434
    • DTXCID001743960
    • G12706ZR
    • 7,8-Dihydromethysticin
    • Methysticin, 7,8-dihydro-
    • Dihydromethysticin (VAN)
    • 2H-Pyran-2-one, 6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-, (6S)-
    • NSC 112159
    • (S)-6-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-4-methoxy-5,6-dihydro-2H-pyran-2-one
    • C15H16O5
    • MFCD00221731
    • 2H-Pyran-2-one, 6-(2-(1,3-benzodioxol-5-yl)ethyl)-5,6-dihydro-4-methoxy-, (S)-
    • (6S)-6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one
    • 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)phenethyl)-, (S)-
    • UNII-FZ66MQ73GS
    • CCRIS 9368
    • Methysticin,8-dihydro-
    • Dihydromethysticin (Standard)
    • CHEBI:4573
    • CHEMBL576066
    • MEGxp0_001718
    • orb1296143
    • SCHEMBL14524443
    • SCHEMBL29867658
    • ACon0_000957
    • ACon1_001371
    • HY-N0921R
    • HY-N0921
    • NSC112159
    • CCG-208398
    • CS-4245
    • EBC-616254
    • FD76570
    • (6S)-6-[2-(2H-1,3-benzodioxol-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
    • NCGC00180578-01
    • AC-34189
    • AS-79324
    • DA-62883
    • (+)-Dihydromethysticin, analytical standard
    • NS00097366
    • C09926
    • 902D911
    • SR-05000002272
    • Q5276438
    • SR-05000002272-2
    • BRD-K87171303-001-01-2
    • 2H-Pyran-2-one,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-, (S)-
    • 6-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
    • (6S)-6-[2-(1,3-dioxaindan-5-yl)ethyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
    • 2H-Pyran-2-one,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)phenethyl]-, (S)-
    • 19902-91-1

  • Applications

    (+)-Dihydromethysticin, CAS 19902-91-1, is a natural kavalactone derived from the kava plant and is commonly considered an organic intermediate for the synthesis of chiral lactone frameworks and related natural product analogs, useful in industrial chemical and pharmaceutical contexts. It is also evaluated as a fragrance material with potential for creating earthy-warm aroma notes in perfumery, and may be considered as a scent component or fixative in limited cosmetic formulations. Additionally, (+)-Dihydromethysticin can serve as a reference standard for GC/LC-MS quality control of kava extracts, and may function as a chiral building block for the synthesis of other lactone-based compounds and natural product analogs.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 26.95
    methanol 38.47
    isopropanol 30.51
    water 0.11
    ethyl acetate 61.52
    n-propanol 25.1
    acetone 115.49
    n-butanol 21.74
    acetonitrile 112.65
    DMF 129.5
    toluene 13.25
    isobutanol 19.2
    1,4-dioxane 169.57
    methyl acetate 79.32
    THF 193.52
    2-butanone 79.76
    n-pentanol 18.57
    sec-butanol 21.51
    n-hexane 0.17
    ethylene glycol 26.35
    NMP 57.67
    cyclohexane 0.72
    DMSO 455.59
    n-butyl acetate 27.51
    n-octanol 8.95
    chloroform 202.51
    n-propyl acetate 36.66
    acetic acid 71.47
    dichloromethane 206.63
    cyclohexanone 77.34
    propylene glycol 29.11
    isopropyl acetate 29.9
    DMAc 214.51
    2-ethoxyethanol 123.39
    isopentanol 20.95
    n-heptane 0.33
    ethyl formate 47.01
    1,2-dichloroethane 109.33
    n-hexanol 13.6
    2-methoxyethanol 180.5
    isobutyl acetate 23.05
    tetrachloromethane 7.64
    n-pentyl acetate 13.94
    transcutol 243.26
    n-heptanol 7.39
    ethylbenzene 7.03
    MIBK 27.57
    2-propoxyethanol 80.73
    tert-butanol 33.26
    MTBE 13.84
    2-butoxyethanol 35.27
    propionic acid 34.87
    o-xylene 8.7
    formic acid 43.81
    diethyl ether 19.13
    m-xylene 7.93
    p-xylene 11.2
    chlorobenzene 30.55
    dimethyl carbonate 39.69
    n-octane 0.3
    formamide 94.66
    cyclopentanone 98.92
    2-pentanone 49.01
    anisole 38.85
    cyclopentyl methyl ether 30.42
    gamma-butyrolactone 106.17
    1-methoxy-2-propanol 112.68
    pyridine 92.94
    3-pentanone 36.81
    furfural 120.96
    n-dodecane 0.65
    diethylene glycol 116.89
    diisopropyl ether 4.36
    tert-amyl alcohol 21.77
    acetylacetone 87.99
    n-hexadecane 0.77
    acetophenone 41.91
    methyl propionate 52.6
    isopentyl acetate 27.16
    trichloroethylene 210.57
    n-nonanol 9.86
    cyclohexanol 23.65
    benzyl alcohol 44.2
    2-ethylhexanol 9.64
    isooctanol 7.64
    dipropyl ether 10.38
    1,2-dichlorobenzene 29.06
    ethyl lactate 32.27
    propylene carbonate 49.35
    n-methylformamide 73.58
    2-pentanol 12.27
    n-pentane 0.16
    1-propoxy-2-propanol 47.85
    1-methoxy-2-propyl acetate 50.47
    2-(2-methoxypropoxy) propanol 58.81
    mesitylene 4.78
    ε-caprolactone 61.84
    p-cymene 6.29
    epichlorohydrin 201.08
    1,1,1-trichloroethane 51.78
    2-aminoethanol 35.77
    morpholine-4-carbaldehyde 130.98
    sulfolane 112.79
    2,2,4-trimethylpentane 0.32
    2-methyltetrahydrofuran 62.9
    n-hexyl acetate 22.04
    isooctane 0.24
    2-(2-butoxyethoxy)ethanol 73.99
    sec-butyl acetate 21.78
    tert-butyl acetate 28.76
    decalin 0.77
    glycerin 72.28
    diglyme 142.58
    acrylic acid 39.0
    isopropyl myristate 13.36
    n-butyric acid 47.44
    acetyl acetate 45.41
    di(2-ethylhexyl) phthalate 18.11
    ethyl propionate 32.61
    nitromethane 216.23
    1,2-diethoxyethane 53.08
    benzonitrile 53.86
    trioctyl phosphate 10.59
    1-bromopropane 24.39
    gamma-valerolactone 148.27
    n-decanol 8.46
    triethyl phosphate 19.74
    4-methyl-2-pentanol 8.9
    propionitrile 60.21
    vinylene carbonate 54.93
    1,1,2-trichlorotrifluoroethane 132.05
    DMS 35.4
    cumene 5.24
    2-octanol 5.45
    2-hexanone 33.37
    octyl acetate 15.88
    limonene 6.63
    1,2-dimethoxyethane 158.31
    ethyl orthosilicate 16.8
    tributyl phosphate 15.48
    diacetone alcohol 47.61
    N,N-dimethylaniline 19.66
    acrylonitrile 94.91
    aniline 37.44
    1,3-propanediol 66.87
    bromobenzene 29.69
    dibromomethane 89.53
    1,1,2,2-tetrachloroethane 147.35
    2-methyl-cyclohexyl acetate 24.32
    tetrabutyl urea 22.61
    diisobutyl methanol 6.96
    2-phenylethanol 31.08
    styrene 10.16
    dioctyl adipate 24.42
    dimethyl sulfate 64.9
    ethyl butyrate 25.8
    methyl lactate 49.33
    butyl lactate 20.01
    diethyl carbonate 24.59
    propanediol butyl ether 35.2
    triethyl orthoformate 23.13
    p-tert-butyltoluene 5.37
    methyl 4-tert-butylbenzoate 30.79
    morpholine 161.53
    tert-butylamine 9.3
    n-dodecanol 7.22
    dimethoxymethane 123.82
    ethylene carbonate 48.05
    cyrene 49.17
    2-ethoxyethyl acetate 35.65
    2-ethylhexyl acetate 19.89
    1,2,4-trichlorobenzene 37.85
    4-methylpyridine 71.26
    dibutyl ether 13.55
    2,6-dimethyl-4-heptanol 6.96
    DEF 50.0
    dimethyl isosorbide 79.48
    tetrachloroethylene 62.24
    eugenol 38.09
    triacetin 40.15
    span 80 30.92
    1,4-butanediol 32.71
    1,1-dichloroethane 74.74
    2-methyl-1-pentanol 16.7
    methyl formate 66.53
    2-methyl-1-butanol 17.35
    n-decane 0.84
    butyronitrile 44.32
    3,7-dimethyl-1-octanol 12.46
    1-chlorooctane 5.36
    1-chlorotetradecane 3.07
    n-nonane 0.61
    undecane 0.73
    tert-butylcyclohexane 0.58
    cyclooctane 0.27
    cyclopentanol 27.86
    tetrahydropyran 64.61
    tert-amyl methyl ether 12.31
    2,5,8-trioxanonane 115.87
    1-hexene 1.5
    2-isopropoxyethanol 66.28
    2,2,2-trifluoroethanol 38.1
    methyl butyrate 41.7

    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