Nepetalactone trans-cis-form

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  • Identifiers

    CAS number
    17257-15-7

    Molecular formula
    C10H14O2

    SMILES
    C[C@H]1CC[C@H]2[C@H]1C(=O)OC=C2C

    Retention indicies (RI)

    • DB5: 1395.0

  • Odor profile

    Spicy 54.3%
    Herbal 52.44%
    Mint 52.02%
    Woody 42.94%
    Sweet 39.2%
    Coumarinic 35.87%
    Tobacco 34.28%
    Coconut 32.99%
    Phenolic 31.83%
    Celery 30.0%

    Scent© AI

  • Properties

    XLogP3-AA
    1.9

    Molecular weight
    166.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    268°C

    Flash point est.
    117.4 ˚C

  • Synonyms

    • trans-cis-Nepetalactone
    • Epinepetalactone
    • Isonepetalactone
    • 17257-15-7
    • trans,cis-Nepetalactone
    • E,Z-Nepetalactone
    • Nepetalactone trans-cis-form
    • (+)-trans,cis-Nepetalactone
    • (4As,7S,7aS)-Nepetalactone
    • Nepetalactone, (+)-(4aS,7S,7aS)-
    • UNII-VZ45G6PT5C
    • VZ45G6PT5C
    • (4aS,7S,7aS)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
    • 4a.alpha.,7.alpha.,7a.beta.-Nepetalactone
    • (+)-(4aS,7S,7aS)-nepetalactone
    • Cyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS,7S,7aS)-
    • (4aS,7S,7aS)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one
    • 4aalpha,7alpha,7abeta-Nepetalactone
    • CHEBI:7519
    • SCHEMBL13039924
    • DTXSID00169348
    • ZDKZHVNKFOXMND-ZQARSLAVSA-N
    • LMPR0102070014
    • C09792
    • Q27107520
    • (4aalpha,7alpha,7abeta)-5,6,7,7a-tetrahydro-4,7-dimethylcyclopenta[c]pyran-1(4aH)-one

  • Applications

    Trans‑cis nepetalactone (CAS 17257-15-7) is the principal iridoid of catnip used as a bio-based insect repellent in sprays, topical products, candles, diffusers, treated textiles, and integrated pest management; as a feline attractant for enrichment toys, scratchers, and training sprays; as a fragrance ingredient imparting fresh green-herbal, lightly minty notes in perfumery and botanical home-care formulations; and as a reference standard and research tool in chemical ecology (probing olfactory responses, isomer-dependent structure–activity relationships, and iridoid biosynthesis), as well as a molecular scaffold for developing environmentally friendly alternatives to conventional pesticides and next-generation repellents.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 333.97
    methanol 452.42
    isopropanol 340.39
    water 2.79
    ethyl acetate 253.94
    n-propanol 296.36
    acetone 363.87
    n-butanol 231.46
    acetonitrile 370.83
    DMF 421.9
    toluene 176.53
    isobutanol 223.41
    1,4-dioxane 770.34
    methyl acetate 312.56
    THF 734.4
    2-butanone 297.31
    n-pentanol 152.58
    sec-butanol 225.03
    n-hexane 11.48
    ethylene glycol 121.56
    NMP 280.42
    cyclohexane 19.07
    DMSO 371.34
    n-butyl acetate 168.52
    n-octanol 132.39
    chloroform 941.32
    n-propyl acetate 152.71
    acetic acid 255.15
    dichloromethane 732.76
    cyclohexanone 358.83
    propylene glycol 153.22
    isopropyl acetate 174.37
    DMAc 217.55
    2-ethoxyethanol 277.37
    isopentanol 203.84
    n-heptane 8.45
    ethyl formate 187.95
    1,2-dichloroethane 409.12
    n-hexanol 209.33
    2-methoxyethanol 484.32
    isobutyl acetate 109.59
    tetrachloromethane 95.41
    n-pentyl acetate 141.98
    transcutol 873.98
    n-heptanol 121.27
    ethylbenzene 87.25
    MIBK 166.27
    2-propoxyethanol 410.48
    tert-butanol 285.74
    MTBE 201.24
    2-butoxyethanol 238.56
    propionic acid 218.74
    o-xylene 101.64
    formic acid 116.42
    diethyl ether 221.2
    m-xylene 133.46
    p-xylene 120.11
    chlorobenzene 257.13
    dimethyl carbonate 118.18
    n-octane 7.97
    formamide 163.77
    cyclopentanone 462.75
    2-pentanone 234.06
    anisole 191.62
    cyclopentyl methyl ether 248.85
    gamma-butyrolactone 519.81
    1-methoxy-2-propanol 389.87
    pyridine 457.86
    3-pentanone 159.68
    furfural 428.62
    n-dodecane 10.46
    diethylene glycol 383.71
    diisopropyl ether 66.84
    tert-amyl alcohol 195.06
    acetylacetone 277.98
    n-hexadecane 12.07
    acetophenone 159.74
    methyl propionate 199.91
    isopentyl acetate 167.79
    trichloroethylene 727.94
    n-nonanol 110.57
    cyclohexanol 183.07
    benzyl alcohol 173.07
    2-ethylhexanol 102.05
    isooctanol 103.89
    dipropyl ether 77.37
    1,2-dichlorobenzene 217.61
    ethyl lactate 108.44
    propylene carbonate 250.45
    n-methylformamide 274.03
    2-pentanol 163.11
    n-pentane 13.27
    1-propoxy-2-propanol 247.07
    1-methoxy-2-propyl acetate 218.59
    2-(2-methoxypropoxy) propanol 213.16
    mesitylene 82.17
    ε-caprolactone 310.22
    p-cymene 55.63
    epichlorohydrin 643.1
    1,1,1-trichloroethane 327.62
    2-aminoethanol 199.35
    morpholine-4-carbaldehyde 428.13
    sulfolane 438.0
    2,2,4-trimethylpentane 11.71
    2-methyltetrahydrofuran 404.68
    n-hexyl acetate 218.63
    isooctane 12.94
    2-(2-butoxyethoxy)ethanol 307.4
    sec-butyl acetate 114.78
    tert-butyl acetate 171.28
    decalin 15.44
    glycerin 205.67
    diglyme 452.87
    acrylic acid 207.59
    isopropyl myristate 88.64
    n-butyric acid 248.09
    acetyl acetate 157.4
    di(2-ethylhexyl) phthalate 97.6
    ethyl propionate 134.1
    nitromethane 429.22
    1,2-diethoxyethane 226.56
    benzonitrile 258.76
    trioctyl phosphate 72.65
    1-bromopropane 220.46
    gamma-valerolactone 558.5
    n-decanol 86.55
    triethyl phosphate 63.9
    4-methyl-2-pentanol 116.75
    propionitrile 298.25
    vinylene carbonate 257.57
    1,1,2-trichlorotrifluoroethane 327.72
    DMS 201.76
    cumene 66.43
    2-octanol 96.7
    2-hexanone 148.91
    octyl acetate 113.09
    limonene 64.69
    1,2-dimethoxyethane 360.69
    ethyl orthosilicate 62.18
    tributyl phosphate 82.15
    diacetone alcohol 214.48
    N,N-dimethylaniline 111.75
    acrylonitrile 376.53
    aniline 222.6
    1,3-propanediol 275.02
    bromobenzene 260.32
    dibromomethane 474.81
    1,1,2,2-tetrachloroethane 526.71
    2-methyl-cyclohexyl acetate 109.79
    tetrabutyl urea 94.45
    diisobutyl methanol 67.75
    2-phenylethanol 202.42
    styrene 102.29
    dioctyl adipate 110.55
    dimethyl sulfate 159.16
    ethyl butyrate 108.25
    methyl lactate 149.86
    butyl lactate 126.6
    diethyl carbonate 85.68
    propanediol butyl ether 242.5
    triethyl orthoformate 81.15
    p-tert-butyltoluene 54.01
    methyl 4-tert-butylbenzoate 171.32
    morpholine 638.71
    tert-butylamine 162.65
    n-dodecanol 66.87
    dimethoxymethane 340.29
    ethylene carbonate 214.06
    cyrene 166.89
    2-ethoxyethyl acetate 215.0
    2-ethylhexyl acetate 118.45
    1,2,4-trichlorobenzene 246.51
    4-methylpyridine 386.27
    dibutyl ether 96.22
    2,6-dimethyl-4-heptanol 67.75
    DEF 190.7
    dimethyl isosorbide 280.18
    tetrachloroethylene 325.0
    eugenol 196.51
    triacetin 180.76
    span 80 179.93
    1,4-butanediol 130.57
    1,1-dichloroethane 449.26
    2-methyl-1-pentanol 143.96
    methyl formate 239.61
    2-methyl-1-butanol 173.96
    n-decane 15.48
    butyronitrile 252.45
    3,7-dimethyl-1-octanol 121.01
    1-chlorooctane 73.56
    1-chlorotetradecane 32.89
    n-nonane 13.24
    undecane 12.49
    tert-butylcyclohexane 16.63
    cyclooctane 8.06
    cyclopentanol 230.82
    tetrahydropyran 421.22
    tert-amyl methyl ether 122.45
    2,5,8-trioxanonane 305.69
    1-hexene 57.53
    2-isopropoxyethanol 209.7
    2,2,2-trifluoroethanol 120.72
    methyl butyrate 161.95

    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
Nepeta cataria 1 84929-35-1 Nepeta cataria L., fam. Lamiaceae (Labiatae) 1.0%
Nepeta nepetella Nepeta nepetella L., fam. Lamiaceae (Labiatae) 0.3%
Nepeta nuda (Belgium) Nepeta nuda L., fam. Lamiaceae (Labiatae) 2.45%
Nepeta faassenii Nepeta faassenii Bergm. ex Stearn, fam. Lamiaceae (Labiatae) 3.1%
Nepeta caesarea (Turkey) Nepeta caesarea Boiss, fam. Lamiaceae (Labiatae) 0.24%
Nepeta nuda (Turkey) Nepeta nuda L. ssp. albiflora (Boiss.) Gams, fam. Lamiaceae (Labiatae 2.1%
Nepeta crassifolia Nepeta crassifolia Boiss. & Buhse, fam. Lamiaceae (Labiatae) 7.7%
Nepeta racemosa (Iran) Nepeta racemosa Lam. (syn. N. mussinii Spreng.), fam. Lamiaceae (Labiatae) 1.7%
Nepeta persica (Iran) Nepeta persica Boiss, fam. Lamiaceae (Labiatae) 0.5%
Inula verbascifolia ssp. methanea Inula verbascifolia ssp methanea (Hausskn.) Turin, fam. Asteraceae 0.01%
Nepeta argolica (Greece) 1b chemotype 2 Nepeta argolica Bory & Chaub. ssp. argolica, fam. Lamiaceae (Labiatae) 12.93%
Nepeta argolica (Greece) 2 Nepeta argolica Bory et Chaub. ssp. argolica, fam. Lamiaceae (Labiatae) 85.0%