Rotundifolone

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  • Identifiers

    CAS number
    5945-46-0

    Molecular formula
    C10H14O2

    SMILES
    CC(=C1CC[C@]2([C@@H](C1=O)O2)C)C

    Retention indicies (RI)

    • DB5: 1366.43
    • Carbowax: 1963.0

  • Odor profile

    Mint 70.04%
    Herbal 65.14%
    Camphoreous 46.29%
    Sweet 38.58%
    Woody 36.7%
    Tobacco 36.03%
    Fresh 35.72%
    Cooling 32.62%
    Spicy 31.22%
    Citrus 30.69%

    Scent© AI

  • Properties

    XLogP3-AA
    1.8

    Molecular weight
    166.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    250°C

    Flash point est.
    110.17 ˚C

    Solubility expt.

    • Soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • Rotundifolone
    • Piperitenone oxide
    • Lippione
    • 3564-96-3
    • cis-Piperitenone epoxide
    • Piperitenone oxide [FHFI]
    • (+-)-Rotundifolone
    • FEMA No. 4199
    • (+-)-Piperitenone oxide
    • UNII-6FR5IOD112
    • (+)-Rotundifolone
    • Piperitenone oxide, (+-)-
    • 6FR5IOD112
    • (1S,6S)-6-methyl-3-propan-2-ylidene-7-oxabicyclo[4.1.0]heptan-2-one
    • 7-Oxabicyclo(4.1.0)heptan-2-one, 6-methyl-3-(1-methylethylidene)-, (1S)-
    • 7-Oxabicyclo(4.1.0)heptan-2-one, 6-methyl-3-(1-methylethylidene)-, (1S,6S)-
    • (1S,6S)-3-isopropylidene-6-methyl-7-oxabicyclo(4.1.0)heptan-2-one
    • (1S,6S)-3-isopropylidene-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one
    • (1S,6S)-6-methyl-3-propan-2-ylidene-7-oxabicyclo(4.1.0)heptan-2-one
    • CHEBI:8900
    • SCHEMBL2317471
    • (+)-PIPERITENONE OXIDE
    • DTXSID301317536
    • PIPERITENONE OXIDE, (+)-
    • AKOS040753565
    • HY-134013
    • CS-0136507
    • C09896
    • Q27108176

  • Applications

    Rotundifolone (CAS 5945-46-0) is a natural monoterpene ketone predominantly found in Mentha essential oils (notably Mentha × villosa/M. suaveolens), investigated for smooth‑muscle and vascular relaxation (involving K+ channels, NO/cGMP signaling, and TRPM8), antispasmodic effects in the gastrointestinal tract, experimental antihypertensive activity, analgesic and anti‑inflammatory actions; it shows antimicrobial and antifungal properties and larvicidal activity against Aedes mosquitoes, with additional antiprotozoal potential (e.g., Leishmania), supporting exploration as a bio‑pesticide/repellent and natural preservative; in flavor and fragrance work it contributes a minty‑herbal note and serves as a chemical marker for chemotype identification and quality control of Mentha oils; in synthesis its menthane ketone scaffold is used as a building block for monoterpene derivatives; in pharma/materials research it is formulated into carriers (nanoemulsions, cyclodextrins) to enhance stability/solubility; note that biomedical uses remain largely preclinical and subject to local regulation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 84.48
    methanol 111.49
    isopropanol 64.14
    water 1.57
    ethyl acetate 60.4
    n-propanol 65.75
    acetone 71.18
    n-butanol 61.75
    acetonitrile 92.31
    DMF 87.59
    toluene 51.24
    isobutanol 47.67
    1,4-dioxane 161.29
    methyl acetate 77.64
    THF 139.52
    2-butanone 69.17
    n-pentanol 48.03
    sec-butanol 55.23
    n-hexane 3.16
    ethylene glycol 30.47
    NMP 81.08
    cyclohexane 9.67
    DMSO 52.23
    n-butyl acetate 57.29
    n-octanol 34.17
    chloroform 236.89
    n-propyl acetate 47.99
    acetic acid 80.59
    dichloromethane 171.09
    cyclohexanone 97.89
    propylene glycol 34.91
    isopropyl acetate 40.2
    DMAc 83.47
    2-ethoxyethanol 80.79
    isopentanol 50.28
    n-heptane 4.09
    ethyl formate 70.29
    1,2-dichloroethane 76.08
    n-hexanol 62.77
    2-methoxyethanol 124.39
    isobutyl acetate 37.17
    tetrachloromethane 36.67
    n-pentyl acetate 40.54
    transcutol 178.03
    n-heptanol 32.92
    ethylbenzene 32.95
    MIBK 39.95
    2-propoxyethanol 107.2
    tert-butanol 64.65
    MTBE 41.71
    2-butoxyethanol 62.22
    propionic acid 54.05
    o-xylene 35.01
    formic acid 52.12
    diethyl ether 42.22
    m-xylene 35.12
    p-xylene 49.97
    chlorobenzene 67.65
    dimethyl carbonate 28.46
    n-octane 2.67
    formamide 75.81
    cyclopentanone 92.72
    2-pentanone 49.85
    anisole 62.73
    cyclopentyl methyl ether 48.49
    gamma-butyrolactone 104.95
    1-methoxy-2-propanol 82.31
    pyridine 126.03
    3-pentanone 38.77
    furfural 132.93
    n-dodecane 3.53
    diethylene glycol 107.33
    diisopropyl ether 15.78
    tert-amyl alcohol 49.18
    acetylacetone 60.55
    n-hexadecane 4.04
    acetophenone 62.47
    methyl propionate 47.66
    isopentyl acetate 56.75
    trichloroethylene 161.78
    n-nonanol 32.81
    cyclohexanol 55.48
    benzyl alcohol 64.27
    2-ethylhexanol 37.97
    isooctanol 26.9
    dipropyl ether 26.35
    1,2-dichlorobenzene 63.89
    ethyl lactate 37.01
    propylene carbonate 76.7
    n-methylformamide 65.49
    2-pentanol 37.49
    n-pentane 4.28
    1-propoxy-2-propanol 71.33
    1-methoxy-2-propyl acetate 61.69
    2-(2-methoxypropoxy) propanol 67.63
    mesitylene 21.28
    ε-caprolactone 91.72
    p-cymene 23.38
    epichlorohydrin 120.69
    1,1,1-trichloroethane 81.37
    2-aminoethanol 51.68
    morpholine-4-carbaldehyde 120.63
    sulfolane 79.3
    2,2,4-trimethylpentane 3.88
    2-methyltetrahydrofuran 88.25
    n-hexyl acetate 54.43
    isooctane 3.22
    2-(2-butoxyethoxy)ethanol 87.48
    sec-butyl acetate 35.96
    tert-butyl acetate 41.24
    decalin 6.69
    glycerin 54.14
    diglyme 129.75
    acrylic acid 51.56
    isopropyl myristate 26.45
    n-butyric acid 70.2
    acetyl acetate 51.26
    di(2-ethylhexyl) phthalate 33.8
    ethyl propionate 41.28
    nitromethane 112.91
    1,2-diethoxyethane 59.36
    benzonitrile 85.92
    trioctyl phosphate 22.85
    1-bromopropane 45.54
    gamma-valerolactone 140.5
    n-decanol 25.52
    triethyl phosphate 30.41
    4-methyl-2-pentanol 28.89
    propionitrile 71.89
    vinylene carbonate 87.12
    1,1,2-trichlorotrifluoroethane 90.07
    DMS 51.86
    cumene 24.36
    2-octanol 24.16
    2-hexanone 48.09
    octyl acetate 32.18
    limonene 26.89
    1,2-dimethoxyethane 115.83
    ethyl orthosilicate 29.41
    tributyl phosphate 26.08
    diacetone alcohol 56.26
    N,N-dimethylaniline 40.45
    acrylonitrile 86.9
    aniline 60.91
    1,3-propanediol 79.01
    bromobenzene 66.98
    dibromomethane 109.41
    1,1,2,2-tetrachloroethane 117.0
    2-methyl-cyclohexyl acetate 48.38
    tetrabutyl urea 32.78
    diisobutyl methanol 23.46
    2-phenylethanol 74.33
    styrene 35.48
    dioctyl adipate 36.59
    dimethyl sulfate 33.31
    ethyl butyrate 45.25
    methyl lactate 36.39
    butyl lactate 39.66
    diethyl carbonate 40.91
    propanediol butyl ether 59.2
    triethyl orthoformate 37.7
    p-tert-butyltoluene 21.18
    methyl 4-tert-butylbenzoate 49.59
    morpholine 149.44
    tert-butylamine 39.47
    n-dodecanol 19.5
    dimethoxymethane 67.69
    ethylene carbonate 71.01
    cyrene 67.86
    2-ethoxyethyl acetate 57.57
    2-ethylhexyl acetate 47.0
    1,2,4-trichlorobenzene 74.94
    4-methylpyridine 109.03
    dibutyl ether 28.91
    2,6-dimethyl-4-heptanol 23.46
    DEF 50.6
    dimethyl isosorbide 92.54
    tetrachloroethylene 85.56
    eugenol 57.2
    triacetin 54.76
    span 80 54.96
    1,4-butanediol 37.53
    1,1-dichloroethane 82.95
    2-methyl-1-pentanol 45.99
    methyl formate 58.68
    2-methyl-1-butanol 45.03
    n-decane 5.09
    butyronitrile 76.05
    3,7-dimethyl-1-octanol 35.9
    1-chlorooctane 19.43
    1-chlorotetradecane 9.83
    n-nonane 4.08
    undecane 4.18
    tert-butylcyclohexane 5.98
    cyclooctane 3.32
    cyclopentanol 56.56
    tetrahydropyran 99.4
    tert-amyl methyl ether 31.7
    2,5,8-trioxanonane 98.8
    1-hexene 15.33
    2-isopropoxyethanol 60.11
    2,2,2-trifluoroethanol 38.86
    methyl butyrate 53.26

    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
Calamintha nepeta (Greece) 1 Calamintha nepeta (L.) Savi (Melissa nepeta L.), fam. Lamiaceae (Labiatae) 0.45%
Mentha longifolia (Italy) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 77.43%
Mentha longifolia (The Netherlands) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.19%
Mentha longifolia (France) Chemotype 1 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.2%
Mentha longifolia (France) Chemotype 2 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 15.0%
Mentha longifolia ssp. himalaiensis 90063-99-3 Mentha longifolia (L.) Hudson, ssp. himalaiensis Briq., fam. Lamiaceae 58.9%
Mentha longifolia ssp. longifolia (Greece) 90063-99-3 Mentha longifolia (L.) ssp. longifolia, fam. Lamiaceae (Labiatae) 2.5%
Mentha longifolia ssp. petiolata (Greece) 1 90063-99-3 Mentha longifolia (L.) ssp. petiolata (Chemotype I), fam. Lamiaceae 1.95%
Mentha rotundifolia (Greece) 1 Mentha x rotundifolia (L.) Hudson (Chemotype I), fam. Lamiaceae (Labiatae) 1.0%
Mentha rotundifolia (Japan) Mentha rotundifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 36.0%
Mentha spicata (Greece) Chemotype IIIa Mentha spicata L. (Chemotype IIIa), fam. Lamiaceae (Labiatae) 2.5%
Mentha spicata (Greece) Chemotype IIIb Mentha spicata L. (Chemotype IIIb), fam. Lamiaceae (Labiatae) 67.25%
Mentha suaveolens (Chemotype 1) Mentha suaveolens Ehrh. (Chemotype 1), fam. Lamiaceae (Labiatae) 4.91%
Mentha suaveolens (Greece) Mentha suaveolens Ehrh., fam Lamiacae (Labiatae) 75.83%
Mentha x villosa (Greece) 2 Mentha x villosa Hudson, fam. Lamiaceae (Labiatae) 61.18%
Mentha x villoso-nervata (Greece) 1 Mentha x villoso-nervata Opiz (M.longifolia L. x M.spicata L.) (Chemot.I) 33.0%
Minthostachys glabrescens Minthostachys glabrescens Epling, fam. Lamiaceae (Labiatae) 0.6%
Calamintha nepeta (Greece) 2 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 1.2%
Buchu leaf 84649-93-4 Agathosma betulina (Berg.) Pillans (Barosma betulina Bertl.), fam. Rutacea 9.5%
Calamintha nepeta (Turkey) 2 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 43.8%
Micromeria congesta (Turkey) Micromeria congesta Boiss. et Hausskn. ex Boiss., fam. Lamiaceae (Labiat. 42.3%
Fennel, pepper (France) Foeniculum vulgare Miller, ssp. piperitum, fam. Apiaceae (Umbelliferae) 17.85%
Calamintha incana (Turkey) Calamintha incana (Sm.) Boiss., fam. Lamiaceae (Labiatae) 66.6%
Mentha longifolia (Lithuania) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 44.2%
Mentha longifolia (Israel) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 1.7%
Mentha spicata (Cuba) Chemotype Mentha spicata L., fam. Lamiaceae (Labiatae) 52.3%
Calamintha nepeta (Italy) Calamintha nepeta (L.) Savi ssp. nepeta, fam. Lamiaceae (Labiatae) 3.6%
Mentha longifolia (Iran) 1 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 23.5%
Thapsia garganica root Thapsia garganica L., fam. Apiaceae (Umbelliferae) 0.7%
Calamintha vardarensis Calamintha vardarensis (Greuter et Burdet) Silic, fam.Lamiaceae (Labiatae) 1.4%
Mentha longifolia (Iran) 3 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.3%
Calamintha nepeta (Montenegro) Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball, fam.Lamiaceae 1.8%
Calamintha nepeta (Greece) 3 Calamintha nepeta (L.) Savi ssp. glandulosa (Req.) P.W.Ball,fam. Lamiaceae 1.0%
Plectranthus glandulosus (Cameroon) 2 Plectranthus glandulosus Hook f., fam. Lamiaceae (Labiatae) 10.9%
Tanacetum balsamita Tanacetum balsamita L., fam. Asteraceae (Compositae) 0.05%
Calamintha sylvatica (Yugoslavia) Calamintha sylvatica Bromf., ssp. sylvatica, fam. Lamiaceae (Labiatae) 0.6%
Calamintha nepeta (France) Calamintha nepeta (L.) Savi ssp. nepeta, fam. Lamiaceae (Labiatae) 0.2%
Mentha longifolia (Jordan) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 83.7%
Satureja parvifolia (Argentina) Satureja parvifolia (Phil.) Epl., fam. Lamiaceae (Labiatae) 69.8%
Teucrium salviastrum (Portugal) Teucrium salviastrum Schreber, fam. Lamiaceae (Lagiatae) 0.1%
Oregano, greek (Greece) 2 84012-24-8 Origanum vulgare L. ssp. hirtum (Link) Ietsw., fam. Lamiaceae (Labiatae) 0.15%