(-)-Santonin

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  • Identifiers

    CAS number
    481-06-1

    Molecular formula
    C15H18O3

    SMILES
    C[C@H]1[C@@H]2CC[C@]3(C=CC(=O)C(=C3[C@H]2OC1=O)C)C

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 51.04%
    Caramellic 43.78%
    Woody 37.01%
    Coumarinic 35.78%
    Coconut 34.65%
    Burnt 34.38%
    Tobacco 33.54%
    Spicy 33.08%
    Nutty 31.6%
    Lactonic 28.61%

     

    Flavor
    Bitter 82.77%
    Lovage 21.07%
    Cedarleaf 20.21%
    Basil 19.98%
    Fenugreek 19.78%
    Ripe apricot 19.75%
    Red fruit 19.39%
    Leaves 19.36%
    Seedy 19.07%
    Parsley 18.92%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    6.95 (neutral)

    Molecular weight
    246.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    451°C

    Flash point

    • 186.82 ˚C est.

  • Synonyms

    • santonin
    • alpha-Santonin
    • 481-06-1
    • Semenen
    • Santoninum
    • Santoninic anhydride
    • (-)-Santonin
    • L-alpha-Santonin
    • DTXSID7045312
    • NSC-4900
    • 1VL8J38ERO
    • (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
    • (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione
    • DTXCID5025312
    • CHEBI:16363
    • (3S,3AS,5AS)-3,5A,9-TRIMETHYL-3A,4,5,5A-TETRAHYDRONAPHTHO(1,2-B)FURAN-2,8(3H,9BH)-DIONE
    • (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo(g)(1)benzofuran-2,8-dione
    • (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,5,5a,9b-tetrahydronaphtho(1,2-b)furan-2,8(3H,4H)-dione
    • RefChem:56700
    • Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S-(3alpha,3aalpha,5abeta,9bbeta))-
    • CHEBI:26604
    • (3R,3aR,5aR,9bR)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo(g)(1)benzofuran-2,8-dione
    • 207-560-7
    • (-)-alpha-Santonin
    • (-)-Santonine
    • MFCD00135865
    • NSC4900
    • .alpha.-Santonin
    • C15H14O3
    • NSC 4900
    • (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g]benzofuran-2,8-dione
    • l-.alpha.-Santonin
    • Santonin [JAN]
    • (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,5a-tetrahydronaphtho[1,2-b]furan-2,8(3H,9bH)-dione
    • (3S,3aS,5aS,9bS)-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione
    • naphtho[1,2-b]furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-
    • (-)-.alpha.-Santonin
    • Santonin [JAN:NF]
    • SR-01000635568
    • UNII-1VL8J38ERO
    • Santonin-a
    • Santonin CRS
    • (3S,5aS,9bS)-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)dione
    • XJHDMGJURBVLLE-BOCCBSBMSA-N
    • NCGC00016461-01
    • (3S,3AS,5AS,9BS)-3A,5,5A,9B-TETRAHYDRO-3,5A,9-TRIMETHYLNAPHTHO(1,2-B)FURAN-2,8(3H,4H)-DIONE
    • CAS-481-06-1
    • Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-
    • ()-alpha-Santonin
    • EINECS 207-560-7
    • NSC 41311
    • Santonin (Standard)
    • SANTONINE
    • Santonin (JP18)
    • Spectrum_000790
    • SpecPlus_000318
    • AI3-19471
    • (-)- alpha -Santonin
    • Prestwick0_001070
    • Prestwick1_001070
    • Prestwick2_001070
    • Prestwick3_001070
    • Spectrum2_000699
    • Spectrum3_001245
    • Spectrum4_001476
    • Spectrum5_000151
    • SANTONINUM [HPUS]
    • SANTONIN [MART.]
    • SANTONIN [WHO-DD]
    • UPCMLD-DP084
    • BSPBio_001060
    • BSPBio_002750
    • KBioGR_002051
    • KBioSS_001270
    • SPECTRUM300542
    • MLS002154141
    • DivK1c_006414
    • SPBio_000857
    • SPBio_002970
    • alpha-Santonin; (-)-Santonin
    • BPBio1_001166
    • CHEMBL259254
    • MEGxp0_001636
    • SCHEMBL1133565
    • .ALPHA.-SANTONIN [MI]
    • UPCMLD-DP084:001
    • GTPL12448
    • HY-B1761R
    • KBio1_001358
    • KBio2_001270
    • KBio2_003838
    • KBio2_006406
    • KBio3_002250
    • (-)-alpha-Santonin, >=99%
    • HMS1571E22
    • HMS2098E22
    • HMS2268H12
    • BB_NC-03265
    • HY-B1761
    • Tox21_110445
    • CCG-40021
    • EBC-47480
    • s3999
    • 11-Epiisoeusantona-1,4-dienic acid, 6alpha-hydroxy-3-oxo-, gamma-lactone
    • AKOS015895177
    • Tox21_110445_1
    • FS65157
    • LMPR0103190001
    • SDCCGMLS-0066491.P001
    • (3S)-2,3,3a,4,5,5a,8,9bbeta-Octahydro-3,5abeta,9-trimethylnaphtho(1,2-b)furan-2,8-dion
    • Eudesma-1,4-dien-12-oic acid, 6-alpha-hydroxy-3-oxo-, gamma-lactone, (11S)-(-)-
    • Naphtho(1,2-b)puran-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-
    • (-)-alpha-Santonin, analytical standard
    • NCGC00161640-01
    • NCGC00161640-02
    • NCGC00161640-03
    • NCGC00263447-01
    • (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione
    • SMR000112520
    • SY231845
    • AB00376930
    • CS-0013789
    • NS00022216
    • S0521
    • EN300-34530
    • C02206
    • D00154
    • 481-06-1

  • Applications

    (-)-Santonin is used as a chiral building block for asymmetric synthesis in pharmaceutical and fine-chemical contexts; it serves as an intermediate in pharmaceutical synthesis and product development; it is used as a general organic-synthesis reagent in laboratory research; and it is employed as an analytical reference standard for method development and structural verification.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 15.33
    methanol 25.72
    isopropanol 21.49
    water 0.39
    ethyl acetate 52.52
    n-propanol 19.28
    acetone 63.87
    n-butanol 22.13
    acetonitrile 32.33
    DMF 146.52
    toluene 122.74
    isobutanol 18.57
    1,4-dioxane 126.59
    methyl acetate 67.23
    THF 137.26
    2-butanone 81.02
    n-pentanol 14.8
    sec-butanol 14.49
    n-hexane 0.44
    ethylene glycol 7.89
    NMP 138.12
    cyclohexane 2.81
    DMSO 68.79
    n-butyl acetate 52.84
    n-octanol 12.47
    chloroform 325.01
    n-propyl acetate 44.54
    acetic acid 35.98
    dichloromethane 229.62
    cyclohexanone 144.59
    propylene glycol 6.46
    isopropyl acetate 48.15
    DMAc 136.62
    2-ethoxyethanol 36.3
    isopentanol 29.61
    n-heptane 0.6
    ethyl formate 40.0
    1,2-dichloroethane 109.07
    n-hexanol 25.8
    2-methoxyethanol 58.06
    isobutyl acetate 40.75
    tetrachloromethane 31.8
    n-pentyl acetate 41.94
    transcutol 113.15
    n-heptanol 18.84
    ethylbenzene 38.28
    MIBK 48.96
    2-propoxyethanol 75.9
    tert-butanol 29.77
    MTBE 16.44
    2-butoxyethanol 47.11
    propionic acid 33.64
    o-xylene 61.59
    formic acid 20.86
    diethyl ether 15.68
    m-xylene 69.31
    p-xylene 60.85
    chlorobenzene 119.68
    dimethyl carbonate 49.61
    n-octane 0.59
    formamide 41.74
    cyclopentanone 156.7
    2-pentanone 54.77
    anisole 65.27
    cyclopentyl methyl ether 45.83
    gamma-butyrolactone 167.1
    1-methoxy-2-propanol 50.23
    pyridine 177.78
    3-pentanone 52.3
    furfural 165.43
    n-dodecane 0.98
    diethylene glycol 68.1
    diisopropyl ether 9.83
    tert-amyl alcohol 17.28
    acetylacetone 87.38
    n-hexadecane 1.22
    acetophenone 83.33
    methyl propionate 53.68
    isopentyl acetate 59.24
    trichloroethylene 301.51
    n-nonanol 14.56
    cyclohexanol 33.11
    benzyl alcohol 69.08
    2-ethylhexanol 18.99
    isooctanol 18.94
    dipropyl ether 11.05
    1,2-dichlorobenzene 104.52
    ethyl lactate 28.8
    propylene carbonate 92.82
    n-methylformamide 53.24
    2-pentanol 13.81
    n-pentane 0.66
    1-propoxy-2-propanol 43.99
    1-methoxy-2-propyl acetate 70.4
    2-(2-methoxypropoxy) propanol 53.16
    mesitylene 35.35
    ε-caprolactone 106.64
    p-cymene 22.62
    epichlorohydrin 166.75
    1,1,1-trichloroethane 106.93
    2-aminoethanol 13.67
    morpholine-4-carbaldehyde 164.19
    sulfolane 142.25
    2,2,4-trimethylpentane 1.14
    2-methyltetrahydrofuran 62.99
    n-hexyl acetate 44.56
    isooctane 1.23
    2-(2-butoxyethoxy)ethanol 57.59
    sec-butyl acetate 37.38
    tert-butyl acetate 48.49
    decalin 2.91
    glycerin 19.12
    diglyme 109.07
    acrylic acid 39.57
    isopropyl myristate 21.8
    n-butyric acid 49.16
    acetyl acetate 59.54
    di(2-ethylhexyl) phthalate 36.37
    ethyl propionate 38.91
    nitromethane 89.74
    1,2-diethoxyethane 38.66
    benzonitrile 106.12
    trioctyl phosphate 22.57
    1-bromopropane 34.8
    gamma-valerolactone 193.17
    n-decanol 11.54
    triethyl phosphate 29.39
    4-methyl-2-pentanol 16.35
    propionitrile 40.68
    vinylene carbonate 111.25
    1,1,2-trichlorotrifluoroethane 92.22
    DMS 72.77
    cumene 25.67
    2-octanol 12.01
    2-hexanone 40.95
    octyl acetate 26.61
    limonene 20.82
    1,2-dimethoxyethane 73.68
    ethyl orthosilicate 27.5
    tributyl phosphate 25.45
    diacetone alcohol 53.63
    N,N-dimethylaniline 45.25
    acrylonitrile 72.28
    aniline 97.01
    1,3-propanediol 27.24
    bromobenzene 128.48
    dibromomethane 121.78
    1,1,2,2-tetrachloroethane 189.37
    2-methyl-cyclohexyl acetate 46.89
    tetrabutyl urea 32.81
    diisobutyl methanol 14.64
    2-phenylethanol 73.95
    styrene 44.71
    dioctyl adipate 36.06
    dimethyl sulfate 76.86
    ethyl butyrate 37.75
    methyl lactate 35.5
    butyl lactate 36.01
    diethyl carbonate 34.42
    propanediol butyl ether 31.1
    triethyl orthoformate 31.71
    p-tert-butyltoluene 20.45
    methyl 4-tert-butylbenzoate 62.98
    morpholine 94.21
    tert-butylamine 14.34
    n-dodecanol 9.22
    dimethoxymethane 80.93
    ethylene carbonate 86.81
    cyrene 71.54
    2-ethoxyethyl acetate 67.17
    2-ethylhexyl acetate 46.76
    1,2,4-trichlorobenzene 124.58
    4-methylpyridine 181.96
    dibutyl ether 11.81
    2,6-dimethyl-4-heptanol 14.64
    DEF 57.26
    dimethyl isosorbide 98.62
    tetrachloroethylene 129.99
    eugenol 67.44
    triacetin 61.15
    span 80 39.8
    1,4-butanediol 12.48
    1,1-dichloroethane 100.68
    2-methyl-1-pentanol 21.55
    methyl formate 52.59
    2-methyl-1-butanol 20.92
    n-decane 1.37
    butyronitrile 35.23
    3,7-dimethyl-1-octanol 16.81
    1-chlorooctane 8.39
    1-chlorotetradecane 4.51
    n-nonane 0.93
    undecane 1.14
    tert-butylcyclohexane 2.32
    cyclooctane 1.1
    cyclopentanol 30.85
    tetrahydropyran 62.72
    tert-amyl methyl ether 14.39
    2,5,8-trioxanonane 80.06
    1-hexene 3.23
    2-isopropoxyethanol 34.28
    2,2,2-trifluoroethanol 31.22
    methyl butyrate 49.04

    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