Costunolide

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  • Identifiers

    CAS number
    553-21-9

    Molecular formula
    C15H20O2

    SMILES
    C/C/1=C\CC/C(=C/[C@@H]2[C@@H](CC1)C(=C)C(=O)O2)/C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Spicy 57.12%
    Herbal 55.17%
    Mint 54.22%
    Sweet 50.23%
    Coumarinic 47.45%
    Coconut 46.05%
    Tobacco 41.95%
    Hay 35.95%
    Woody 35.23%
    Celery 34.76%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    7.53 (neutral)

    Molecular weight
    232.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    396°C

    Flash point est.
    153.03 ˚C

  • Synonyms

    • Costunolide
    • 553-21-9
    • (+)-costunolide
    • Costunlide
    • Costus lactone
    • Costunolid
    • CHEBI:3900
    • (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
    • CHEMBL86416
    • (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
    • (E,E)-6-alpha-Hydroxygermacra-1(10),4,11(13)-trien-12-oic acid gamma-lactone
    • (10S,1R)-3,7-dimethyl-11-methylene-13-oxabicyclo[8.3.0]trideca-2,6-dien-12-one
    • (E,E)-germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha-hydroxy-gamma-lactone
    • (3aS,6E,10E)-3-Methylene-6,10-dimethyl-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-2-one
    • (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one
    • CCRIS 6754
    • isocostunolide
    • C15H20O2
    • NSC 106404
    • melampolide
    • DTXSID001029520
    • NSC106404
    • NSC-106404
    • (10S,1R)-3,7-dimethyl-11-methylene-13-oxabicyclo(8.3.0)trideca-2,6-dien-12-one
    • (3aS,6E,10E)-3-methylene-6,10-dimethyl-2,3,3abeta,4,5,8,9,11aalpha-octahydrocyclodeca(b)furan-2-one
    • (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-2(3H)-one
    • (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-2(3H)-one
    • (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-2-one
    • MFCD00210262
    • Costunolide (Standard)
    • SCHEMBL92714
    • (+)-costunolide\, Costunolid
    • Costunolide, >=97% (HPLC)
    • HY-N0036R
    • Germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha-hydroxy-, gamma-lactone, (E,E)-
    • DTXCID301514754
    • HMS3269I17
    • HMS3413B19
    • HMS3677B19
    • (3AS,6E,10E,11AR)-6,10-DIMETHYL-3-METHYLENE-3,3A,4,5,8,9-HEXAHYDROCYCLODECA(B)FURAN-2(11AH)-ONE
    • Cyclodeca(b)furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS-(3aR*,6E,10E,11aS*))-
    • EX-A5462
    • HY-N0036
    • BDBM50411242
    • AKOS015840065
    • AKOS015969714
    • CS-1487
    • FC65612
    • NCGC00381718-02
    • (3aS,6E,10E,11aR)-3a,4,5,8,9,11a-Hexahydro-6,10-dimethyl-3-methylene-cyclodeca[b]furan-2(3H)-one
    • AC-28334
    • AS-17708
    • C2921
    • NS00066990
    • C09382
    • Q5175227
    • BRD-K26833429-001-01-0
    • BRD-K26833429-001-02-8
    • BRD-K26833429-001-03-6
    • (3aS,6E,10E,11aR)-6,10-dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
    • 683-148-4
    • Cyclodeca(b)furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS-(3aR*,6E,10E,11aS*))-(9CI)
    • Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aS,6E,10E,11aR)-

  • Applications

    Costunolide (CAS 553-21-9) is a natural sesquiterpene lactone bearing an α-methylene-γ-lactone Michael acceptor, used mainly in pharmaceutical and chemical-biology research: as a scaffold/lead for designing derivatives with potential anti-inflammatory, anticancer, antifibrotic, antioxidant, and antimicrobial/antiparasitic activities (evidence largely from in vitro and preclinical in vivo studies); as a covalent probe/tool that alkylates cysteine to interrogate thiol-dependent signaling and redox stress, modulating NF-κB, JAK/STAT3, MAPK and activating Nrf2; as an analytical reference standard in HPLC/LC–MS for quantification and quality control of costunolide-containing botanicals (e.g., Saussurea/Aucklandia lappa) and for formulation stability tracking; as a starting point for semisynthesis, prodrug design, or nanoformulations (liposomes, polymeric nanoparticles) to improve solubility and bioavailability; with exploratory agricultural uses as a plant-derived crop-protection agent (laboratory reports of insecticidal, antifungal, and nematicidal effects); in fragrance/cosmetics it is now used mainly as a marker/analytical standard for costus oil rather than a scent ingredient due to sensitization risk and regulatory restrictions; handle under appropriate chemical-safety practices (light/air sensitive, poorly water-soluble, soluble in common organic solvents) and comply with regulations when deploying.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 257.14
    methanol 231.96
    isopropanol 262.47
    water 0.11
    ethyl acetate 332.85
    n-propanol 301.2
    acetone 314.31
    n-butanol 298.05
    acetonitrile 206.55
    DMF 555.17
    toluene 515.12
    isobutanol 256.45
    1,4-dioxane 676.7
    methyl acetate 326.51
    THF 870.84
    2-butanone 486.26
    n-pentanol 226.8
    sec-butanol 301.14
    n-hexane 11.84
    ethylene glycol 25.08
    NMP 510.24
    cyclohexane 42.42
    DMSO 317.51
    n-butyl acetate 350.09
    n-octanol 102.31
    chloroform 1520.11
    n-propyl acetate 271.02
    acetic acid 173.9
    dichloromethane 1190.6
    cyclohexanone 667.28
    propylene glycol 65.49
    isopropyl acetate 243.24
    DMAc 528.17
    2-ethoxyethanol 243.5
    isopentanol 301.84
    n-heptane 9.64
    ethyl formate 210.57
    1,2-dichloroethane 618.43
    n-hexanol 253.61
    2-methoxyethanol 323.38
    isobutyl acetate 215.54
    tetrachloromethane 134.98
    n-pentyl acetate 216.55
    transcutol 1232.27
    n-heptanol 119.18
    ethylbenzene 199.83
    MIBK 244.72
    2-propoxyethanol 346.02
    tert-butanol 264.75
    MTBE 270.9
    2-butoxyethanol 221.84
    propionic acid 170.53
    o-xylene 231.46
    formic acid 47.7
    diethyl ether 268.51
    m-xylene 282.28
    p-xylene 260.85
    chlorobenzene 464.7
    dimethyl carbonate 126.43
    n-octane 5.39
    formamide 100.87
    cyclopentanone 626.41
    2-pentanone 351.04
    anisole 329.13
    cyclopentyl methyl ether 386.68
    gamma-butyrolactone 557.91
    1-methoxy-2-propanol 325.37
    pyridine 751.12
    3-pentanone 264.95
    furfural 501.8
    n-dodecane 7.0
    diethylene glycol 206.68
    diisopropyl ether 94.16
    tert-amyl alcohol 261.3
    acetylacetone 325.55
    n-hexadecane 8.51
    acetophenone 325.89
    methyl propionate 255.81
    isopentyl acetate 343.34
    trichloroethylene 1277.59
    n-nonanol 97.61
    cyclohexanol 302.7
    benzyl alcohol 297.39
    2-ethylhexanol 151.72
    isooctanol 106.46
    dipropyl ether 118.9
    1,2-dichlorobenzene 370.4
    ethyl lactate 115.53
    propylene carbonate 371.22
    n-methylformamide 202.92
    2-pentanol 218.32
    n-pentane 16.61
    1-propoxy-2-propanol 249.68
    1-methoxy-2-propyl acetate 314.92
    2-(2-methoxypropoxy) propanol 255.55
    mesitylene 157.8
    ε-caprolactone 524.3
    p-cymene 106.91
    epichlorohydrin 774.63
    1,1,1-trichloroethane 501.81
    2-aminoethanol 84.24
    morpholine-4-carbaldehyde 541.91
    sulfolane 485.33
    2,2,4-trimethylpentane 17.69
    2-methyltetrahydrofuran 633.55
    n-hexyl acetate 280.3
    isooctane 16.08
    2-(2-butoxyethoxy)ethanol 351.57
    sec-butyl acetate 218.26
    tert-butyl acetate 239.15
    decalin 31.65
    glycerin 86.31
    diglyme 571.83
    acrylic acid 137.74
    isopropyl myristate 108.49
    n-butyric acid 298.05
    acetyl acetate 203.94
    di(2-ethylhexyl) phthalate 136.19
    ethyl propionate 203.78
    nitromethane 291.33
    1,2-diethoxyethane 375.53
    benzonitrile 394.98
    trioctyl phosphate 86.36
    1-bromopropane 361.86
    gamma-valerolactone 689.49
    n-decanol 73.27
    triethyl phosphate 105.4
    4-methyl-2-pentanol 150.76
    propionitrile 251.24
    vinylene carbonate 358.27
    1,1,2-trichlorotrifluoroethane 386.65
    DMS 243.02
    cumene 131.15
    2-octanol 86.11
    2-hexanone 281.4
    octyl acetate 132.91
    limonene 132.72
    1,2-dimethoxyethane 442.5
    ethyl orthosilicate 102.69
    tributyl phosphate 107.93
    diacetone alcohol 248.18
    N,N-dimethylaniline 215.07
    acrylonitrile 281.71
    aniline 417.42
    1,3-propanediol 165.04
    bromobenzene 543.69
    dibromomethane 765.28
    1,1,2,2-tetrachloroethane 950.15
    2-methyl-cyclohexyl acetate 202.31
    tetrabutyl urea 131.31
    diisobutyl methanol 87.82
    2-phenylethanol 281.91
    styrene 255.55
    dioctyl adipate 163.25
    dimethyl sulfate 166.05
    ethyl butyrate 211.5
    methyl lactate 121.27
    butyl lactate 177.98
    diethyl carbonate 151.13
    propanediol butyl ether 227.76
    triethyl orthoformate 147.47
    p-tert-butyltoluene 98.34
    methyl 4-tert-butylbenzoate 222.18
    morpholine 751.06
    tert-butylamine 169.81
    n-dodecanol 57.84
    dimethoxymethane 342.45
    ethylene carbonate 298.83
    cyrene 244.99
    2-ethoxyethyl acetate 318.0
    2-ethylhexyl acetate 273.89
    1,2,4-trichlorobenzene 466.71
    4-methylpyridine 761.44
    dibutyl ether 132.48
    2,6-dimethyl-4-heptanol 87.82
    DEF 363.39
    dimethyl isosorbide 408.46
    tetrachloroethylene 551.73
    eugenol 237.72
    triacetin 258.45
    span 80 214.29
    1,4-butanediol 73.71
    1,1-dichloroethane 633.38
    2-methyl-1-pentanol 265.08
    methyl formate 150.47
    2-methyl-1-butanol 290.17
    n-decane 10.85
    butyronitrile 292.11
    3,7-dimethyl-1-octanol 133.89
    1-chlorooctane 70.2
    1-chlorotetradecane 31.35
    n-nonane 8.58
    undecane 8.36
    tert-butylcyclohexane 26.66
    cyclooctane 13.67
    cyclopentanol 274.18
    tetrahydropyran 687.27
    tert-amyl methyl ether 198.36
    2,5,8-trioxanonane 397.72
    1-hexene 95.18
    2-isopropoxyethanol 206.4
    2,2,2-trifluoroethanol 62.89
    methyl butyrate 281.1

    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 1.0%