cis-Dihydrocarvone

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  • Identifiers

    CAS number
    3792-53-8

    Molecular formula
    C10H16O

    SMILES
    C[C@@H]1CC[C@@H](CC1=O)C(=C)C

    Retention indicies (RI)

    • DB5: 1197.57
    • Carbowax: 1611.67

  • Odor profile

    Mint 82.06%
    Herbal 79.71%
    Camphoreous 63.54%
    Woody 54.08%
    Cooling 53.4%
    Fresh 53.15%
    Spicy 49.83%
    Citrus 43.03%
    Terpenic 42.23%
    Green 39.24%

    Scent© AI

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    8.45 (weak base)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    220°C

    Flash point est.
    78.82 ˚C

  • Synonyms

    • cis-Dihydrocarvone
    • (-)-isodihydrocarvone
    • Dihydrocarvone, cis-
    • (1R,4S)-Iso-dihydrocarvone
    • 53796-79-5
    • EXB37ICH9G
    • (1R,4S)-isodihydrocarvone
    • 3792-53-8
    • cis-(-)-Dihydrocarvone
    • Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5S)-
    • Dihydrocarvone, cis-(-)-
    • (2R,5S)-2-methyl-5-prop-1-en-2-ylcyclohexan-1-one
    • Menth-8-en-2-one, cis-p-
    • p-Menth-8-en-2-one, cis-
    • F690VV17TL
    • (1R,4S)-(-)-Isodihydrocarvone
    • CIS-P-MENTH-8-EN-2-ONE
    • Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, cis-
    • 3-Isopropenyl-6-methylcyclohexanone, cis-
    • 2-Methyl-5-(1-methylethenyl)cyclohexanone, cis-
    • Carvone, Dihydro-, trans
    • p-MENTH-8-EN-2-ONE, E-
    • 5-Isopropenyl-2-methylcyclohexanone, trans
    • UNII-EXB37ICH9G
    • UNII-F690VV17TL
    • CHEBI:155
    • SCHEMBL2562033
    • AZOCECCLWFDTAP-BDAKNGLRSA-
    • (1R,4S)-menth-8-en-2-one
    • DTXSID50332060
    • AZOCECCLWFDTAP-BDAKNGLRSA-N
    • (1R,4S)-p-menth-8-en-2-one
    • LMPR0102090037
    • NS00127657
    • (2R,5S)-2-methyl-5-isopropenylcyclohexanone
    • (2R,5S)-5-isopropenyl-2-methylcyclohexanone
    • (2R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone
    • Q27105263
    • (2R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one
    • CYCLOHEXANONE, 2-METHYL-5-(1-METHYLETHENYL)-, (2R,5S)-REL-
    • InChI=1/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9+/m1/s1

  • Applications

    cis-Dihydrocarvone (CAS 3792-53-8) is a monoterpene ketone with a minty–camphoraceous, herbal, slightly woody odour, widely used as a fragrance ingredient to fine-tune spearmint/menthol facets and impart cooling freshness in perfumes, personal-care products, soaps, detergents and air-care formulations; in flavour applications it is typically dosed at very low levels to lift mint freshness in chewing gum, confectionery, oral-care products and selected beverages; in synthesis, cis-dihydrocarvone serves as a convenient chiral-pool intermediate for assembling the p-menthane scaffold, enabling access to related structures such as menthone and menthol derivatives, and as a starting point toward certain insect pheromones, specialised flavour/fragrance ingredients and pharmaceutical precursors; it is also employed as an odour and analytical standard in GC–MS/GC–O, as a substrate in asymmetric catalysis, and as a model compound in studies of terpene ketone transformations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 734.76
    methanol 588.71
    isopropanol 794.45
    water 1.99
    ethyl acetate 465.79
    n-propanol 585.33
    acetone 366.23
    n-butanol 588.38
    acetonitrile 610.26
    DMF 371.76
    toluene 391.27
    isobutanol 418.39
    1,4-dioxane 1063.69
    methyl acetate 451.37
    THF 713.9
    2-butanone 470.26
    n-pentanol 323.91
    sec-butanol 513.22
    n-hexane 32.73
    ethylene glycol 85.95
    NMP 209.89
    cyclohexane 72.22
    DMSO 245.75
    n-butyl acetate 475.58
    n-octanol 211.05
    chloroform 1647.6
    n-propyl acetate 238.55
    acetic acid 357.54
    dichloromethane 1099.93
    cyclohexanone 534.32
    propylene glycol 169.16
    isopropyl acetate 254.12
    DMAc 328.12
    2-ethoxyethanol 330.57
    isopentanol 446.36
    n-heptane 36.64
    ethyl formate 354.74
    1,2-dichloroethane 469.4
    n-hexanol 515.6
    2-methoxyethanol 574.55
    isobutyl acetate 160.69
    tetrachloromethane 239.61
    n-pentyl acetate 221.9
    transcutol 1171.71
    n-heptanol 216.2
    ethylbenzene 185.96
    MIBK 205.04
    2-propoxyethanol 552.83
    tert-butanol 707.47
    MTBE 386.87
    2-butoxyethanol 330.67
    propionic acid 346.62
    o-xylene 212.29
    formic acid 114.78
    diethyl ether 371.86
    m-xylene 218.27
    p-xylene 255.68
    chlorobenzene 409.02
    dimethyl carbonate 85.94
    n-octane 16.94
    formamide 178.32
    cyclopentanone 411.99
    2-pentanone 321.22
    anisole 329.09
    cyclopentyl methyl ether 244.57
    gamma-butyrolactone 446.02
    1-methoxy-2-propanol 486.56
    pyridine 897.64
    3-pentanone 204.11
    furfural 578.72
    n-dodecane 15.58
    diethylene glycol 318.76
    diisopropyl ether 98.78
    tert-amyl alcohol 423.71
    acetylacetone 268.17
    n-hexadecane 18.23
    acetophenone 248.66
    methyl propionate 248.46
    isopentyl acetate 389.61
    trichloroethylene 1006.55
    n-nonanol 182.39
    cyclohexanol 373.05
    benzyl alcohol 293.24
    2-ethylhexanol 266.17
    isooctanol 174.33
    dipropyl ether 201.72
    1,2-dichlorobenzene 306.63
    ethyl lactate 109.94
    propylene carbonate 325.32
    n-methylformamide 266.5
    2-pentanol 332.75
    n-pentane 40.45
    1-propoxy-2-propanol 444.21
    1-methoxy-2-propyl acetate 315.55
    2-(2-methoxypropoxy) propanol 288.05
    mesitylene 123.57
    ε-caprolactone 467.01
    p-cymene 133.25
    epichlorohydrin 615.98
    1,1,1-trichloroethane 612.71
    2-aminoethanol 249.79
    morpholine-4-carbaldehyde 481.99
    sulfolane 277.41
    2,2,4-trimethylpentane 25.06
    2-methyltetrahydrofuran 566.5
    n-hexyl acetate 302.68
    isooctane 24.41
    2-(2-butoxyethoxy)ethanol 397.92
    sec-butyl acetate 178.0
    tert-butyl acetate 221.46
    decalin 39.56
    glycerin 185.6
    diglyme 661.42
    acrylic acid 235.26
    isopropyl myristate 118.35
    n-butyric acid 548.23
    acetyl acetate 240.86
    di(2-ethylhexyl) phthalate 125.22
    ethyl propionate 192.45
    nitromethane 477.27
    1,2-diethoxyethane 421.15
    benzonitrile 523.14
    trioctyl phosphate 81.94
    1-bromopropane 365.7
    gamma-valerolactone 688.88
    n-decanol 130.04
    triethyl phosphate 108.27
    4-methyl-2-pentanol 198.67
    propionitrile 527.25
    vinylene carbonate 365.88
    1,1,2-trichlorotrifluoroethane 369.5
    DMS 187.18
    cumene 130.36
    2-octanol 156.68
    2-hexanone 250.99
    octyl acetate 143.91
    limonene 168.86
    1,2-dimethoxyethane 532.11
    ethyl orthosilicate 111.24
    tributyl phosphate 98.61
    diacetone alcohol 264.04
    N,N-dimethylaniline 192.5
    acrylonitrile 565.86
    aniline 431.92
    1,3-propanediol 430.88
    bromobenzene 420.11
    dibromomethane 745.03
    1,1,2,2-tetrachloroethane 727.73
    2-methyl-cyclohexyl acetate 197.91
    tetrabutyl urea 119.08
    diisobutyl methanol 149.9
    2-phenylethanol 353.6
    styrene 227.9
    dioctyl adipate 157.49
    dimethyl sulfate 96.47
    ethyl butyrate 272.2
    methyl lactate 128.26
    butyl lactate 173.41
    diethyl carbonate 180.95
    propanediol butyl ether 282.08
    triethyl orthoformate 179.95
    p-tert-butyltoluene 127.6
    methyl 4-tert-butylbenzoate 217.43
    morpholine 1098.35
    tert-butylamine 435.8
    n-dodecanol 98.06
    dimethoxymethane 246.98
    ethylene carbonate 296.89
    cyrene 185.72
    2-ethoxyethyl acetate 296.72
    2-ethylhexyl acetate 283.94
    1,2,4-trichlorobenzene 352.86
    4-methylpyridine 769.71
    dibutyl ether 204.95
    2,6-dimethyl-4-heptanol 149.9
    DEF 260.4
    dimethyl isosorbide 378.19
    tetrachloroethylene 462.23
    eugenol 230.91
    triacetin 238.59
    span 80 249.25
    1,4-butanediol 142.15
    1,1-dichloroethane 708.69
    2-methyl-1-pentanol 274.5
    methyl formate 171.15
    2-methyl-1-butanol 354.59
    n-decane 27.09
    butyronitrile 612.08
    3,7-dimethyl-1-octanol 220.62
    1-chlorooctane 111.57
    1-chlorotetradecane 44.63
    n-nonane 24.22
    undecane 19.85
    tert-butylcyclohexane 40.25
    cyclooctane 21.95
    cyclopentanol 338.73
    tetrahydropyran 806.11
    tert-amyl methyl ether 213.27
    2,5,8-trioxanonane 431.35
    1-hexene 155.37
    2-isopropoxyethanol 246.64
    2,2,2-trifluoroethanol 114.52
    methyl butyrate 260.87

    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
Caraway seed 1 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.2%
Dill seed 1 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 2.0%
Indian dill Anethum sowa Roxb., fam. Apiaceae (Umbelliferae) 5.2%
Mentha longifolia var. crispa (Italy) 90063-99-3 Mentha longifolia (L.) var. crispa Ten., fam. Lamiaceae (Labiatae) 0.21%
Oregano, spanish (Greece) 1 8007-11-2 Coridothymus capitatus Rchb. (Thymus capitatus Hoffm. et Link.), Lamiaceae 0.1%
Oregano, spanish (Portugal) 1 8007-11-2 Coridothymus capitatus Rchb. (Thymus capitatus Hoffm. et Link.), Lamiaceae 0.1%
Spearmint (Italy) 8008-79-5 Mentha spicata L., fam. Lamiaceae (Labiatae) 3.14%
Spearmint, scotch (USA) 1 Mentha gracilis Sole, fam. Lamiaceae (Labiatae) 1.5%
Caraway seed (The Netherlands) 2 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.48%
Caraway seed (Yugoslavia) 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.07%
Mandarin (Italy) 5 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.01%
Thymus satureoides (Morocco) 8007-46-3 Thymus satureoides Boiss. et Reut., fam. Lamiaceae (Labiatae) 0.6%
Gingergrass (India) 1 Cymbopogon martini Stapf., var. sofia, fam. Poaceae (Gramineae) 0.15%
Caraway seed (Egypt) 8008-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.11%
Caraway seed (The Netherlands) 1 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.2%
Pepper, black 3 8006-82-4 Piper nigrum L., fam. Piperaceae 0.01%
Tansy (Canada) 2a flowers 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 3.6%
Tansy (Canada) 2b stems & sheets 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 2.2%
Marjoram, sweet (Turkey) 8015-01-8 Majorana hortensis Moench, Origanum majorana L., fam. Lamiaceae (Labiatae) 0.06%
Spearmint, scotch (USA) 3 Mentha gracilis Sole, fam. Lamiaceae (Labiatae) 1.55%
Spearmint, scotch (USA) 2 Mentha gracilis Sole, fam. Lamiaceae (Labiatae) 2.75%
Oregano, greek 1 84012-24-8 Origanum vulgare L. ssp. hirtum (Link) Ietsw., fam. Lamiaceae (Labiatae) 0.34%
Oregano, greek (Turkey) 2 84012-24-8 Origanum vulgare L. ssp. hirtum (Link) Ietsw., fam. Lamiaceae (Labiatae) 1.8%
Satureja wiedemanniana Satureja wiedemanniana (Lallem.) Velen, fam. Lamiaceae (Labiatae) 1.1%
Hyptis mutabilis Hyptis mutabilis (Rich.) Briq., fam. Lamiaceae (Labiatae) 11.38%
Dill herb (Cuba) 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 0.29%
Sphaeranthus cyathuloides (Kenya) Sphaeranthus cyathuloides O. Hoffm., fam. Asteraceae (Compositae) 26.16%
Caraway seed (Israel) 800O-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.13%
Dill herb (U.S.A.) 2 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 1.0%
Vitex agnus-castus fruit (Italy) Vitex agnus-castus L., fam. Verbenaceae 0.01%
Vitex agnus-castus inflorescence (Italy) Vitex agnus-castus L., fam. Verbenaceae 0.3%
Thyme (Denmark) 8007-46-3 Thymus vulgaris L., fam. Lamiaceae (Labiatae) 0.14%
Buchu leaf (South Africa) 1a 84649-93-4 Agathosma betulina (Berg.) Pillans (Barosma betulina Bertl.), fam. Rutacea 0.21%
Buchu leaf (South Africa) 1b (species) 84649-93-4 Agathosma crenulata Pillans, fam. Rutaceae 0.21%
Buchu leaf (South Africa) 1c (hybrid) 84649-93-4 Agathosma betulina x crenulata, fam. Rutaceae 0.19%
Dill seed (China) 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 0.26%
Spearmint (China) 8008-79-5 Mentha spicata L., fam. Lamiaceae (Labiatae) 1.82%
Celery seed (China) 3a 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 0.07%
Celery seed (China) 3b 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 0.02%
Coriander fruit (Greece) 1a 8008-52-4 Coriandrum sativum L., fam. Apiaceae (Umbelliferae) 0.1%
Coriander fruit (Greece) 1b 8008-52-4 Coriandrum sativum L., fam. Apiaceae (Umbelliferae) 0.1%
Satureja boliviana (Peru) 2 Satureja boliviana Briq. (Micromeria boliviana Benth.), fam. Lamiaceae 6.3%
Satureja brevicalix (Peru) Satureja brevicalix Epl., fam. Lamiaceae (Labiatae) 5.0%
Mentha spicata (Cuba) Chemotype Mentha spicata L., fam. Lamiaceae (Labiatae) 1.4%
Origanum husnuca-baserii (Turkey) Origanum husnucan-baserii H. Duman, Z. Aytac et A. Duran, fam. Lamiaceae 0.15%
Dill herb (Reunion Island) 8006-75-5 Anethum graveolens L., fam. Apiaceae (Umbelliferae) 0.01%
Ajowan (India) 2 seed Trachyspermum copticum (L.) Link., fam. Apiaceae (Umbelliferae) 1.1%
Lippia alba (Peru) leaf Lippia alba (Mill.) N.E. Brown, fam. Verbenaceae 0.3%
Balsamite/Costmary (Lithuania) 1a Chrysanthemum balsamita L., fam. Asteraceae (Compositae) 0.55%
Balsamite/Costmary (Lithuania) 1b Chrysanthemum balsamita L., fam. Asteraceae (Compositae) 0.53%