Dehydrocostus lactone, (-)-

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  • Identifiers

    CAS number
    477-43-0

    Molecular formula
    C15H18O2

    SMILES
    C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1CCC3=C)OC(=O)C2=C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Nutty 38.02%
    Green 36.07%
    Spicy 35.9%
    Woody 35.06%
    Mint 28.6%
    Sweet 23.66%
    Herbal 23.26%
    Burnt 22.79%
    Odorless 21.18%
    Tobacco 21.02%

    Scent© AI

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    7.61 (neutral)

    Molecular weight
    230.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    421°C

    Flash point est.
    140.71 ˚C

  • Synonyms

    • Dehydrocostus lactone
    • 477-43-0
    • dehydrocostuslactone
    • Epiligulyl oxide
    • (-)-dehydrocostus lactone
    • 71TRF5K040
    • (-)-dehydrocostuslactone
    • COSTUS LACTONE, DEHYDRO-
    • CHEBI:244418
    • Azuleno[4,5-b]furan-2(3H)-one,decahydro-3,6,9-tris(methylene)-
    • (3aS,6aR,9aR,9bS)-3,6,9-trimethylenedecahydroazuleno[4,5-b]furan-2(3H)-one
    • DEHYDROCOSTUS LACTONE, (-)-
    • (3aS,6aR,9aR,9bS)-decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one
    • (3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
    • (3aR,6aS,9aS,9bR)-3,6,9-tris(methylidene)octahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione
    • Guaia-4(15),10(14),11(13)-trien-12-oic acid, 6alpha-hydroxy-, gamma-lactone
    • AZULENO(4,5-B)FURAN-2(3H)-ONE, DECAHYDRO-3,6,9-TRIS(METHYLENE)-, (3AS,6AR,9AR,9BS)-
    • Azuleno(4,5-b)furan-2(3H)-one, decahydro-3,6,9-tris(methylene)-, (3aS-(3a.alpha.,6a.alpha.,9a.alpha.,9b.beta.))-
    • UNII-71TRF5K040
    • 16836-47-8
    • (-)-Dehydrocostus lactone;Epiligulyl oxide
    • (3as,6ar,9ar,9bs)-3,6,9-trimethylidenedecahydroazuleno[4,5-b]furan-2(3h)-one
    • Dehydrocostus-Lactone
    • CHEMBL88985
    • SCHEMBL699070
    • Dehydrocostus Lactone (Standard)
    • HY-N0591R
    • DTXSID80891554
    • Dehydro-costus lactone (6CI,7CI)
    • HY-N0591
    • BDBM50370831
    • s3615
    • AKOS015896789
    • CCG-208469
    • CS-3636
    • FD10128
    • FD59589
    • Dehydrocostus lactone, >=98% (HPLC)
    • NCGC00385838-01
    • (3aS,6aR,9aR,9bS)-3,6,9-trimethylene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
    • AC-34569
    • Dehydrocostus lactone, analytical standard
    • D5366
    • NS00014574
    • C09387
    • Q27105152
    • (-)-Dehydrocostus lactone; Dehydrocostus lactone; Epiligulyl oxide
    • (3aR,6aS,9aS,9bR)-3,6,9-tris(methylene)octahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione
    • (3aS,6aR,9aR,9bS)-3,6,9-Trimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one
    • (3aS,6aR,9aR,9bS)-Decahydro-3,6,9-tris(methylene)-azuleno[4,5-b]furan-2(3H)-one
    • [3aS-(3aalpha,6aalpha,9aalpha,9bbeta)]-Decahydro-3,6,9-tris(methylene)-azuleno[4,5-b]furan-2(3H)-one
    • Azuleno(4,5-b)furan-2(3H)-one, decahydro-3,6,9-tris(methylene)-, (3aS-(3aalpha,6aalpha,9aalpha,9bbeta))-
    • GUAIA-4(15),10(14),11(13)-TRIEN-12-OIC ACID, 6.ALPHA.-HYDROXY-, .GAMMA.-LACTONE

  • Applications

    Dehydrocostus lactone, (-)-, CAS 477-43-0, is a sesquiterpene lactone from costus root (Saussurea costus) widely used in pharmacology research as a reactive Michael acceptor that alkylates cysteine residues, thereby modulating NF-κB, STAT3, MAPK, and Nrf2/Keap1 pathways; reported applications include anti-inflammatory action (iNOS/COX-2 inhibition, reduced NO and cytokines), anticancer effects (ROS-mediated apoptosis, cell-cycle arrest, anti-migration/invasion and anti-angiogenesis, chemosensitization/TRAIL sensitization), antibacterial/antifungal and antiparasitic activities, with exploratory antiviral and anti-fibrotic effects in preclinical models; it serves as a reference standard for quality control of costus-containing botanicals, as a covalent lead scaffold for medicinal chemistry, and as an activity-based probe for target identification, and is studied in formulation science (complexes, nano-carriers) to enhance solubility and bioavailability; beyond biomedicine, anti-feedant/insect-managing properties have been explored at a preliminary level; due to high electrophilicity and potential cytotoxicity/skin sensitization typical of sesquiterpene lactones, use is primarily research-focused with appropriate dose and lab safety controls.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 153.59
    methanol 210.5
    isopropanol 240.28
    water 0.71
    ethyl acetate 270.87
    n-propanol 216.82
    acetone 401.14
    n-butanol 215.01
    acetonitrile 212.22
    DMF 706.66
    toluene 403.87
    isobutanol 199.95
    1,4-dioxane 662.41
    methyl acetate 358.52
    THF 884.98
    2-butanone 495.28
    n-pentanol 121.09
    sec-butanol 183.89
    n-hexane 2.37
    ethylene glycol 40.79
    NMP 454.09
    cyclohexane 14.77
    DMSO 357.38
    n-butyl acetate 206.05
    n-octanol 57.6
    chloroform 1629.66
    n-propyl acetate 192.26
    acetic acid 197.75
    dichloromethane 1272.61
    cyclohexanone 711.09
    propylene glycol 61.96
    isopropyl acetate 209.4
    DMAc 457.66
    2-ethoxyethanol 199.78
    isopentanol 229.98
    n-heptane 3.66
    ethyl formate 277.51
    1,2-dichloroethane 602.79
    n-hexanol 122.35
    2-methoxyethanol 331.99
    isobutyl acetate 145.64
    tetrachloromethane 136.5
    n-pentyl acetate 150.08
    transcutol 582.81
    n-heptanol 74.47
    ethylbenzene 129.25
    MIBK 203.72
    2-propoxyethanol 252.69
    tert-butanol 224.69
    MTBE 141.25
    2-butoxyethanol 173.02
    propionic acid 213.99
    o-xylene 178.87
    formic acid 76.65
    diethyl ether 129.84
    m-xylene 214.04
    p-xylene 185.57
    chlorobenzene 456.83
    dimethyl carbonate 157.41
    n-octane 2.76
    formamide 171.74
    cyclopentanone 870.65
    2-pentanone 321.52
    anisole 239.22
    cyclopentyl methyl ether 248.85
    gamma-butyrolactone 818.27
    1-methoxy-2-propanol 282.86
    pyridine 885.11
    3-pentanone 231.01
    furfural 709.07
    n-dodecane 4.02
    diethylene glycol 211.68
    diisopropyl ether 49.14
    tert-amyl alcohol 151.85
    acetylacetone 363.43
    n-hexadecane 4.9
    acetophenone 265.93
    methyl propionate 237.08
    isopentyl acetate 206.19
    trichloroethylene 1359.68
    n-nonanol 57.1
    cyclohexanol 228.08
    benzyl alcohol 267.56
    2-ethylhexanol 76.04
    isooctanol 70.42
    dipropyl ether 53.74
    1,2-dichlorobenzene 376.18
    ethyl lactate 103.68
    propylene carbonate 431.7
    n-methylformamide 312.15
    2-pentanol 137.07
    n-pentane 4.86
    1-propoxy-2-propanol 163.34
    1-methoxy-2-propyl acetate 226.85
    2-(2-methoxypropoxy) propanol 160.76
    mesitylene 109.96
    ε-caprolactone 492.54
    p-cymene 69.63
    epichlorohydrin 930.5
    1,1,1-trichloroethane 474.52
    2-aminoethanol 88.0
    morpholine-4-carbaldehyde 542.59
    sulfolane 588.22
    2,2,4-trimethylpentane 6.24
    2-methyltetrahydrofuran 454.53
    n-hexyl acetate 174.84
    isooctane 6.02
    2-(2-butoxyethoxy)ethanol 220.05
    sec-butyl acetate 140.35
    tert-butyl acetate 175.54
    decalin 11.6
    glycerin 109.18
    diglyme 424.81
    acrylic acid 204.49
    isopropyl myristate 72.03
    n-butyric acid 312.94
    acetyl acetate 211.75
    di(2-ethylhexyl) phthalate 99.65
    ethyl propionate 146.99
    nitromethane 402.66
    1,2-diethoxyethane 185.56
    benzonitrile 450.25
    trioctyl phosphate 63.08
    1-bromopropane 228.09
    gamma-valerolactone 883.42
    n-decanol 44.0
    triethyl phosphate 75.95
    4-methyl-2-pentanol 100.27
    propionitrile 259.87
    vinylene carbonate 463.23
    1,1,2-trichlorotrifluoroethane 424.24
    DMS 203.58
    cumene 83.82
    2-octanol 53.93
    2-hexanone 196.74
    octyl acetate 87.39
    limonene 76.32
    1,2-dimethoxyethane 361.06
    ethyl orthosilicate 71.38
    tributyl phosphate 76.0
    diacetone alcohol 200.75
    N,N-dimethylaniline 139.98
    acrylonitrile 369.03
    aniline 382.74
    1,3-propanediol 186.26
    bromobenzene 482.52
    dibromomethane 695.87
    1,1,2,2-tetrachloroethane 898.55
    2-methyl-cyclohexyl acetate 130.37
    tetrabutyl urea 95.91
    diisobutyl methanol 55.18
    2-phenylethanol 221.16
    styrene 160.81
    dioctyl adipate 107.58
    dimethyl sulfate 215.74
    ethyl butyrate 143.43
    methyl lactate 138.82
    butyl lactate 133.66
    diethyl carbonate 108.85
    propanediol butyl ether 144.21
    triethyl orthoformate 97.02
    p-tert-butyltoluene 61.38
    methyl 4-tert-butylbenzoate 182.93
    morpholine 590.36
    tert-butylamine 110.9
    n-dodecanol 35.24
    dimethoxymethane 356.55
    ethylene carbonate 384.67
    cyrene 201.37
    2-ethoxyethyl acetate 230.77
    2-ethylhexyl acetate 158.2
    1,2,4-trichlorobenzene 433.86
    4-methylpyridine 769.34
    dibutyl ether 61.0
    2,6-dimethyl-4-heptanol 55.18
    DEF 264.92
    dimethyl isosorbide 288.12
    tetrachloroethylene 555.93
    eugenol 189.29
    triacetin 185.43
    span 80 137.87
    1,4-butanediol 74.86
    1,1-dichloroethane 621.91
    2-methyl-1-pentanol 134.0
    methyl formate 286.55
    2-methyl-1-butanol 177.81
    n-decane 5.84
    butyronitrile 259.49
    3,7-dimethyl-1-octanol 73.42
    1-chlorooctane 39.02
    1-chlorotetradecane 18.3
    n-nonane 4.22
    undecane 4.72
    tert-butylcyclohexane 9.58
    cyclooctane 4.79
    cyclopentanol 278.22
    tetrahydropyran 496.6
    tert-amyl methyl ether 90.03
    2,5,8-trioxanonane 262.93
    1-hexene 24.03
    2-isopropoxyethanol 152.57
    2,2,2-trifluoroethanol 120.45
    methyl butyrate 218.56

    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
Costus 8023-88-9 Saussurea lappa Clarke, fam. Zingiberaceae 10.0%