Isopulegol

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  • Identifiers

    CAS number
    89-79-2

    Molecular formula
    C10H18O

    SMILES
    C[C@@H]1CC[C@H]([C@@H](C1)O)C(=C)C

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1161.0
    • Carbowax: 1575.5

  • Odor profile

    Herbal 85.33%
    Mint 74.88%
    Green 74.87%
    Floral 73.36%
    Woody 64.18%
    Fruity 61.79%
    Cooling 56.2%
    Fresh 55.09%
    Camphoreous 50.71%
    Sweet 48.92%

    Scent© AI

  • Properties

    XLogP3-AA
    3.0

    Molecular weight
    154.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Melting point expt.

    • 78 °C

    Boiling point

    • 216.00 to 218.00 °C. @ 760.00 mm Hg

    Flash point est.
    90.42 ˚C

    Solubility expt.

    • slightly soluble in water; soluble in oils
    • miscible (in ethanol)

  • Synonyms

    • (-)-Isopulegol
    • Isopulegol
    • 89-79-2
    • l-Isopulegol
    • (-)-L-Isopulegol
    • iso-Pulegol
    • coolact P
    • (1R,2S,5R)-5-METHYL-2-(PROP-1-EN-2-YL)CYCLOHEXAN-1-OL
    • Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-
    • Isopulegol (natural)
    • FEMA No. 2962
    • p-8(9)-Menthen-3-ol
    • 3TH92O3BXN
    • (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
    • (1R,2S,5R)-2-Isopropenyl-5-methylcyclohexanol
    • ISOPULEGOL [FCC]
    • EINECS 201-940-6
    • Isopulegol, (+/-)-
    • ISOPULEGOL [FHFI]
    • NVG8YK55NL
    • p-Menth-8-en-3-ol, (1R,3R,4S)-(-)-
    • 50373-36-9
    • AI3-02176
    • (1R,3R,4S)-(-)-p-Menth-8-en-3-ol
    • DTXSID5047116
    • CHEBI:70479
    • NSC1263
    • EC 201-940-6
    • NSC-1263
    • NSC-231369
    • Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-rel-
    • (1R,3R,4S)-P-METH-8-EN-3-OL
    • 5-Methyl-2-(1-methylethenyl)cyclohexanol, (1R-(1alpha,2beta,5alpha))-
    • Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R-(1alpha,2beta,5alpha))-
    • Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, [1R-(1.alpha.,2.beta.,5.alpha.)]-
    • 59905-53-2
    • MFCD00134655
    • (+/-)-(1alpha,2beta,5alpha)-5-methyl-2-(1-methylvinyl)cyclohexan-1-ol
    • UNII-3TH92O3BXN
    • rac-isopulegol
    • 1-isopulegol
    • (+/-)-isopulegol
    • UNII-NVG8YK55NL
    • ISOPULEGOL [INCI]
    • (-)-Isopulegol, 99%
    • SCHEMBL43859
    • p-Menth-8(9)-en-3-ol
    • (-)-Isopulegol, >=98%
    • CHEMBL237994
    • GTPL2462
    • ZYTMANIQRDEHIO-KXUCPTDWSA-
    • (-)-Isopulegol, technical grade
    • DTXSID90110001
    • DTXCID501764296
    • NSC 1263
    • EINECS 256-557-7
    • (-)-Isopulegol, analytical standard
    • AKOS028109164
    • AS-10358
    • FI106423
    • HY-121206
    • CS-0081229
    • NS00127398
    • (-)-Isopulegol 100 microg/mL in Acetonitrile
    • E78611
    • EN300-269447
    • Q2103922
    • (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexanol
    • 5-Methyl-2-(1-methylethenyl)-(1R,2S,5R)-Cyclohexanol
    • (-)-Isopulegol, primary pharmaceutical reference standard
    • rel-(1R,2S,5R)-5-Methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol
    • 2-Isopropenyl-5-methylcyclohexanol-, (1R-(1alpha,2beta,5alpha))-
    • (1)-(1alpha,2beta,5alpha)-5-Methyl-2-(1-methylvinyl)cyclohexan-1-ol
    • 201-940-6
    • InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1

  • Applications

    (−)-Isopulegol (CAS 89-79-2) is a chiral monoterpenoid alcohol with a characteristic minty-herbal aroma that finds broad application as the key intermediate for the selective hydrogenation to (−)-menthol, thereby underpinning the flavour and fragrance industry for toothpastes, chewing gums, confectionery and cooling tobacco products; it is also added directly to foods, beverages and mouthwashes to impart a refreshing cooling sensation with a light citrus note, and functions as a fragrance modifier in perfumes, soaps, shampoos and eco-friendly detergents to convey natural freshness; in the pharmaceutical field, (−)-Isopulegol is being investigated for its spasmolytic, gastroprotective, anxiolytic, antioxidant and anti-inflammatory properties and is formulated into gels, ointments and cooling patches, while in synthesis it serves as an important stereochemical building block for asymmetric construction of terpenoid derivatives and aromatic esters, a chemosensory test reagent, a bitterness-masking agent and an insect-repellent additive, thus increasing the bioeconomic value of essential oils from Eucalyptus and citronella.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4281.74
    methanol 4352.34
    isopropanol 3705.32
    water 1.83
    ethyl acetate 904.53
    n-propanol 2743.95
    acetone 1518.6
    n-butanol 2381.19
    acetonitrile 2286.43
    DMF 787.12
    toluene 371.99
    isobutanol 1578.98
    1,4-dioxane 3045.11
    methyl acetate 763.5
    THF 4451.37
    2-butanone 942.78
    n-pentanol 1179.27
    sec-butanol 1602.57
    n-hexane 181.18
    ethylene glycol 200.07
    NMP 422.01
    cyclohexane 364.02
    DMSO 878.63
    n-butyl acetate 1107.57
    n-octanol 501.51
    chloroform 2186.24
    n-propyl acetate 551.12
    acetic acid 1240.41
    dichloromethane 1469.28
    cyclohexanone 1205.35
    propylene glycol 403.37
    isopropyl acetate 534.54
    DMAc 331.57
    2-ethoxyethanol 822.71
    isopentanol 1376.13
    n-heptane 237.76
    ethyl formate 785.47
    1,2-dichloroethane 737.95
    n-hexanol 2026.69
    2-methoxyethanol 1841.42
    isobutyl acetate 326.61
    tetrachloromethane 330.26
    n-pentyl acetate 400.59
    transcutol 2102.83
    n-heptanol 553.93
    ethylbenzene 144.92
    MIBK 466.92
    2-propoxyethanol 1692.45
    tert-butanol 2573.65
    MTBE 1293.7
    2-butoxyethanol 686.88
    propionic acid 741.29
    o-xylene 173.63
    formic acid 347.03
    diethyl ether 1777.91
    m-xylene 243.27
    p-xylene 191.51
    chlorobenzene 455.81
    dimethyl carbonate 116.85
    n-octane 57.39
    formamide 409.83
    cyclopentanone 1154.21
    2-pentanone 863.62
    anisole 304.26
    cyclopentyl methyl ether 975.0
    gamma-butyrolactone 1197.78
    1-methoxy-2-propanol 1216.59
    pyridine 1176.31
    3-pentanone 398.54
    furfural 832.55
    n-dodecane 37.78
    diethylene glycol 743.97
    diisopropyl ether 365.9
    tert-amyl alcohol 1027.42
    acetylacetone 499.63
    n-hexadecane 42.75
    acetophenone 210.61
    methyl propionate 441.97
    isopentyl acetate 830.86
    trichloroethylene 1141.75
    n-nonanol 376.74
    cyclohexanol 1157.36
    benzyl alcohol 313.22
    2-ethylhexanol 749.07
    isooctanol 363.42
    dipropyl ether 947.35
    1,2-dichlorobenzene 293.42
    ethyl lactate 168.94
    propylene carbonate 638.66
    n-methylformamide 745.06
    2-pentanol 1177.85
    n-pentane 262.88
    1-propoxy-2-propanol 1161.14
    1-methoxy-2-propyl acetate 611.28
    2-(2-methoxypropoxy) propanol 381.38
    mesitylene 150.93
    ε-caprolactone 884.39
    p-cymene 160.0
    epichlorohydrin 1367.53
    1,1,1-trichloroethane 762.96
    2-aminoethanol 692.11
    morpholine-4-carbaldehyde 753.38
    sulfolane 642.46
    2,2,4-trimethylpentane 71.58
    2-methyltetrahydrofuran 2276.1
    n-hexyl acetate 546.12
    isooctane 90.25
    2-(2-butoxyethoxy)ethanol 681.04
    sec-butyl acetate 310.01
    tert-butyl acetate 483.79
    decalin 78.08
    glycerin 389.34
    diglyme 1115.72
    acrylic acid 411.21
    isopropyl myristate 183.82
    n-butyric acid 1635.98
    acetyl acetate 378.2
    di(2-ethylhexyl) phthalate 156.91
    ethyl propionate 325.18
    nitromethane 1263.31
    1,2-diethoxyethane 1007.97
    benzonitrile 557.16
    trioctyl phosphate 132.71
    1-bromopropane 816.87
    gamma-valerolactone 1402.73
    n-decanol 257.05
    triethyl phosphate 139.72
    4-methyl-2-pentanol 514.91
    propionitrile 1467.23
    vinylene carbonate 536.35
    1,1,2-trichlorotrifluoroethane 578.7
    DMS 204.57
    cumene 104.25
    2-octanol 328.48
    2-hexanone 581.81
    octyl acetate 227.43
    limonene 297.63
    1,2-dimethoxyethane 1407.52
    ethyl orthosilicate 162.95
    tributyl phosphate 156.22
    diacetone alcohol 474.95
    N,N-dimethylaniline 159.49
    acrylonitrile 1034.32
    aniline 557.29
    1,3-propanediol 1368.55
    bromobenzene 391.78
    dibromomethane 1111.72
    1,1,2,2-tetrachloroethane 830.16
    2-methyl-cyclohexyl acetate 322.56
    tetrabutyl urea 172.48
    diisobutyl methanol 368.11
    2-phenylethanol 461.83
    styrene 185.9
    dioctyl adipate 211.46
    dimethyl sulfate 112.36
    ethyl butyrate 535.74
    methyl lactate 185.67
    butyl lactate 284.4
    diethyl carbonate 285.22
    propanediol butyl ether 513.46
    triethyl orthoformate 357.81
    p-tert-butyltoluene 159.8
    methyl 4-tert-butylbenzoate 230.4
    morpholine 3305.44
    tert-butylamine 1747.15
    n-dodecanol 183.28
    dimethoxymethane 783.77
    ethylene carbonate 551.99
    cyrene 235.53
    2-ethoxyethyl acetate 431.79
    2-ethylhexyl acetate 574.61
    1,2,4-trichlorobenzene 305.92
    4-methylpyridine 989.86
    dibutyl ether 530.45
    2,6-dimethyl-4-heptanol 368.11
    DEF 540.23
    dimethyl isosorbide 516.59
    tetrachloroethylene 561.73
    eugenol 235.55
    triacetin 287.41
    span 80 420.29
    1,4-butanediol 316.99
    1,1-dichloroethane 1158.42
    2-methyl-1-pentanol 666.07
    methyl formate 470.19
    2-methyl-1-butanol 1060.89
    n-decane 74.83
    butyronitrile 1993.4
    3,7-dimethyl-1-octanol 413.65
    1-chlorooctane 243.79
    1-chlorotetradecane 75.96
    n-nonane 78.33
    undecane 51.03
    tert-butylcyclohexane 80.68
    cyclooctane 94.1
    cyclopentanol 1249.27
    tetrahydropyran 3328.19
    tert-amyl methyl ether 508.14
    2,5,8-trioxanonane 637.93
    1-hexene 539.73
    2-isopropoxyethanol 488.89
    2,2,2-trifluoroethanol 214.84
    methyl butyrate 487.83

    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
Mentha sylvestris var. incana Mentha sylvestris var. incana, fam Lamiacae (Labiatae) 9.58%
Lemon balm 1 8014-71-9 Melissa officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Lemon balm 2 8014-71-9 Melissa officinalis L., fam. Lamiaceae (Labiatae) 0.9%
Lemon balm 3 8014-71-9 Melissa officinalis L., fam. Lamiaceae (Labiatae) 0.17%
Bergamot (China) 1 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Blackcurrant bud 1 68606-81-5 Ribes nigrum L., fam. Grossulariaceae 0.07%
Eucalyptus citriodora (China) 1 8000-48-4 Eucalyptus citriodora Hook. f., fam. Myrtaceae 0.34%
Ginger (India) 1 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 0.1%
Mentha longifolia ssp. longifolia (Greece) 90063-99-3 Mentha longifolia (L.) ssp. longifolia, fam. Lamiaceae (Labiatae) 1.5%
Nepeta cataria 2 84929-35-1 Nepeta cataria L. var. citriodora, fam. Lamiaceae (Labiatae) 3.3%
Orange leaf, sweet (North Africa) 2 Citrus sinensis (L.) Osbeck, cultivar Sanguine, fam. Rutaceae 0.3%
Orange leaf, sweet (North Africa) 1 Citrus sinensis (L.) Osbeck, cultivar Portuguese, fam. Rutaceae 0.68%
Orange leaf, sweet (North Africa) 3 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.51%
Orange leaf, sweet (North Africa) 4 Citrus sinensis (L.) Osbeck, cultivar Washington navel, fam. Rutaceae 0.96%
Cornmint (Mentha arvensis) 68917-18-0 Mentha arvensis (L.) var. piperascens Malinv., fam. Lamiaceae (Labiatae) 0.15%
Pteronia incana 2 Pteronia incana, fam. Asteraceae (Compositae) 0.1%
Xylopia parviflora fruit (Cameroon) Xylopia parviflora (A. Rich) Benth., fam. Annonaceae 0.6%
Yuzu (Japan) 1 Citrus junos Sieb. ex Tanaka, fam. Rutaceae 0.07%
Ziziphora hispanica Ziziphora hispanica L., fam. Lamiaceae (Labiatae) 1.02%
Rosa rugosa Rosa rugosa Thunb., var. plena Regel, fam. Rosaceae 0.01%
Eucalyptus brassiana Eucalyptus brassiana S.T. Blake, fam. Myrtaceae 0.08%
Juniperus flaccida var. flaccida Juniperus flaccida Schlecht, var. flaccida, fam. Cupressaceae 0.5%
Juniperus flaccida var. poblana Juniperus flaccida var. poblana Martinez, fam. Cupressaceae 0.05%
Swangi (Citrus hystrix) leaf (Thailand) 2b Citrus hystrix DC (Swangi), fam. Rutaceae 0.32%
Swangi (Citrus hystrix) peel (Thailand) 2c Citrus hystrix DC (Swangi), fam. Rutaceae 0.27%
Swangi (Citrus hystrix) twig (Thailand) 2e Citrus hystrix DC (Swangi), fam. Rutaceae 0.69%
Swangi (Citrus hystrix) peel (Thailand) 2d Citrus hystrix DC (Swangi), fam. Rutaceae 0.01%
Phyllosma capensis Phyllosma capensis Bolus, fam. Diosmeae 0.1%
Juniper leaf (Canada) 8012-91-7 Juniperus communis L., fam. Cupressaceae 0.4%
Sage, spanish (Italy) 8016-65-7 Salvia lavandulaefolia Vahl., fam. Lamiaceae (Labiatae) 0.17%
Litsea cubeba fruit 2 68855-99-2 Litsea cubeba (Lour.) Pers. (L. citrata Blume), fam. Lauraceae 1.0%
Eucalyptus citriodora (India) 1 8008-48-4 Eucalyptus citriodora Hook. f., fam. Myrtaceae 0.34%
Citronella java (Ghana) 8000-29-1 Cymbopogon winterianus Jowitt., fam. Poaceae (Gramineae) 0.5%
Lemongrass (Ghana) 8016-84-0 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 0.13%
Litsea cubeba (India) 2a stem 68555-99-2 Litsea cubeba (Lour.) Pers. (L. citrata Blume), fam. Lauraceae 1.55%
Litsea cubeba (India) 2c fruit 68555-99-2 Litsea cubeba (Lour.) Pers. (L. citrata Blume), fam. Lauraceae 1.0%
Lemon balm (Italy) 8014-71-9 Melissa officinalis L., fam. Lamiaceae (Labiatae) 1.62%
Grapefruit (Italy) 6 8016-20-4 Citrus paradisi MacFayden, fam. Rutaceae 0.05%
Eucalyptus citriodora 1a 8008-48-4 Eucalyptus citriodora Hook. f., fam. Myrtaceae 1.1%
Lemongrass 3b headspace neat oil 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 2.47%
Lime (Mexican, West Indian, Key) (China) leaf 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.33%