Perillyl alcohol

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    536-59-4

    Molecular formula
    C10H16O

    SMILES
    CC(=C)C1CCC(=CC1)CO

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1301.6
    • Carbowax: 1998.57

  • Odor profile

    Sweet 76.62%
    Floral 74.34%
    Herbal 70.21%
    Green 62.31%
    Citrus 61.73%
    Fresh 59.49%
    Woody 58.39%
    Spicy 57.79%
    Mint 47.19%
    Lemon 43.74%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    230°C

    Melting point expt.

    • 244 °C

    Flash point est.
    107.23 ˚C

    Solubility expt.

    • Slightly soluble in water; soluble in alcohols and oils
    • Miscible at room temperature (in ethanol)

  • Synonyms

    • PERILLYL ALCOHOL
    • 536-59-4
    • Perilla alcohol
    • Perillol
    • Isocarveol
    • p-Mentha-1,8-dien-7-ol
    • Hydrocumin alcohol
    • 1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-
    • Dihydrocuminyl alcohol
    • Iso-carveol
    • 4-Isopropenylcyclohex-1-en-1-ylmethanol
    • 4-Isopropenyl-cyclohex-1-ene-1-methanol
    • Dihydrocuminic alcohol
    • (4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol
    • 4-Isopropenyl-1-cyclohexene carbinol
    • (4-prop-1-en-2-ylcyclohexen-1-yl)methanol
    • FEMA No. 2664
    • 1-Hydroxymethyl-4-isopropenyl-1-cyclohexene
    • 4-(1-Methylethenyl)-1-cyclohexene-1-methanol
    • [4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
    • CHEBI:15420
    • 1,8-p-Menthadien-7-ol
    • Cyclohex-1-ene-1-methanol, 4-(1-methylethenyl)-
    • Para-mentha-1,8-dien-7-ol
    • Perillic alcohol
    • CHEMBL444711
    • 319R5C7293
    • Dl-perillyl alcohol
    • NSC 641066
    • EINECS 208-639-9
    • (+/-)-PERILLYL ALCOHOL
    • perill alcohol
    • 1-perillalcohol
    • CCRIS 8461
    • UNII-319R5C7293
    • dihydrocuminyl alcoholn
    • (-)-Perillyl alcohol?
    • Spectrum2_000838
    • Spectrum3_001974
    • BSPBio_003574
    • SCHEMBL296111
    • SPECTRUM1505297
    • SPBio_000795
    • DTXSID4052180
    • KBio3_002951
    • (-)-p-Mentha-1,8-diene-7-ol
    • HY-N7000
    • 4-Isopropenyl-1-cyclohexene-methanol
    • BDBM50252404
    • CCG-40267
    • s3853
    • 4-isopropenyl-cyclohex-1-enylmethanol
    • AKOS006227854
    • CS-W019441
    • FP70326
    • SB45076
    • SDCCGMLS-0066882.P001
    • NCGC00095297-01
    • NCGC00095297-02
    • NCGC00095297-03
    • AC-35110
    • SY110506
    • P-MENTHA-1,8-DIEN-7-OL [FHFI]
    • (4-Isopropenyl-1-cyclohexen-1-yl)methanol
    • DB-065484
    • DB-071728
    • NS00013107
    • EN300-97783
    • (4-(prop-1-en-2-yl)cyclohex-1-enyl)methanol
    • 1-Hydroxymethyl-4-(1-methylvinyl)-cyclohexene
    • SR-05000002384
    • SR-05000002384-1
    • BRD-A13323580-001-03-0
    • BRD-A13323580-001-04-8
    • BRD-A13323580-001-05-5
    • Q15391928
    • (S)-[4-(1-Propen-2-yl)-1-cyclohexen-1-yl]methanol
    • Z1198147170
    • F9405E33-6136-4D27-A15E-C10CDC8C9AC4
    • (+/-)-1-CYCLOHEXENE-1-METHANOL, 4-(1-METHYLETHENYL)-

  • Applications

    Perillyl alcohol (CAS 536-59-4) is a monoterpene alcohol derived from limonene, applied broadly in pharmaceutical and biotech research for its anticancer properties (inhibits prenylation of small GTPases such as Ras via the mevalonate pathway, induces apoptosis, causes cell-cycle arrest, shows anti-angiogenic and anti-metastatic effects), investigated clinically—most notably via intranasal delivery to bypass the blood–brain barrier in recurrent glioblastoma—and as a chemo-/radiotherapy sensitizer; in formulation science, POH is incorporated into nanoemulsions, liposomes, and cyclodextrin complexes to enhance solubility and bioavailability; it also exhibits antimicrobial, antifungal, antiviral, anti-inflammatory, and antioxidant activities, supporting studies on antimicrobial coatings, “natural” preservatives, and odor control; in fragrance and flavor, it imparts citrus–herbal notes at very low levels; in green/organic synthesis, it serves as a building block for perillyl esters/ethers/acids, fine-fragrance intermediates, and bioactive probes; in agriculture, it is explored as a biopesticide/insect repellent and postharvest antifungal; it is also used as an analytical standard/reference in flavor, essential-oil, and metabolomics workflows; appropriate evaluation of toxicity, irritation potential, stability, and regulatory compliance is required prior to commercial use.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4023.53
    methanol 3911.14
    isopropanol 3180.19
    water 2.33
    ethyl acetate 3534.83
    n-propanol 3753.42
    acetone 2504.93
    n-butanol 3691.65
    acetonitrile 2708.5
    DMF 2058.56
    toluene 1004.26
    isobutanol 2126.87
    1,4-dioxane 4091.53
    methyl acetate 2221.63
    THF 3960.68
    2-butanone 2575.22
    n-pentanol 1496.01
    sec-butanol 2403.38
    n-hexane 137.12
    ethylene glycol 445.81
    NMP 1078.16
    cyclohexane 252.96
    DMSO 2300.56
    n-butyl acetate 1864.38
    n-octanol 340.16
    chloroform 3103.39
    n-propyl acetate 1240.82
    acetic acid 2114.13
    dichloromethane 2251.98
    cyclohexanone 2090.93
    propylene glycol 754.46
    isopropyl acetate 1566.79
    DMAc 1069.2
    2-ethoxyethanol 1953.07
    isopentanol 2553.69
    n-heptane 89.88
    ethyl formate 1549.52
    1,2-dichloroethane 1783.25
    n-hexanol 1528.68
    2-methoxyethanol 3963.87
    isobutyl acetate 514.69
    tetrachloromethane 666.99
    n-pentyl acetate 587.01
    transcutol 6473.94
    n-heptanol 461.73
    ethylbenzene 297.57
    MIBK 1010.15
    2-propoxyethanol 2266.36
    tert-butanol 3212.07
    MTBE 2827.46
    2-butoxyethanol 930.86
    propionic acid 1796.94
    o-xylene 429.5
    formic acid 887.45
    diethyl ether 3378.03
    m-xylene 574.69
    p-xylene 317.69
    chlorobenzene 928.33
    dimethyl carbonate 490.04
    n-octane 20.35
    formamide 1799.47
    cyclopentanone 1997.56
    2-pentanone 2263.08
    anisole 849.24
    cyclopentyl methyl ether 1811.64
    gamma-butyrolactone 2276.05
    1-methoxy-2-propanol 2612.32
    pyridine 2708.28
    3-pentanone 1419.46
    furfural 1764.83
    n-dodecane 9.62
    diethylene glycol 1299.12
    diisopropyl ether 679.04
    tert-amyl alcohol 2126.7
    acetylacetone 1448.39
    n-hexadecane 11.46
    acetophenone 535.42
    methyl propionate 1848.25
    isopentyl acetate 1234.96
    trichloroethylene 2834.32
    n-nonanol 272.43
    cyclohexanol 1738.33
    benzyl alcohol 689.61
    2-ethylhexanol 693.39
    isooctanol 317.85
    dipropyl ether 1067.91
    1,2-dichlorobenzene 673.55
    ethyl lactate 351.86
    propylene carbonate 1077.97
    n-methylformamide 2286.43
    2-pentanol 2046.76
    n-pentane 212.85
    1-propoxy-2-propanol 1685.49
    1-methoxy-2-propyl acetate 1558.56
    2-(2-methoxypropoxy) propanol 647.55
    mesitylene 313.09
    ε-caprolactone 1735.17
    p-cymene 188.18
    epichlorohydrin 2842.6
    1,1,1-trichloroethane 1628.69
    2-aminoethanol 1465.08
    morpholine-4-carbaldehyde 1689.62
    sulfolane 1478.9
    2,2,4-trimethylpentane 82.31
    2-methyltetrahydrofuran 3114.21
    n-hexyl acetate 684.37
    isooctane 80.76
    2-(2-butoxyethoxy)ethanol 1179.11
    sec-butyl acetate 741.53
    tert-butyl acetate 1421.55
    decalin 69.25
    glycerin 841.79
    diglyme 2358.23
    acrylic acid 1137.77
    isopropyl myristate 166.01
    n-butyric acid 3192.3
    acetyl acetate 1016.03
    di(2-ethylhexyl) phthalate 183.81
    ethyl propionate 979.97
    nitromethane 2874.93
    1,2-diethoxyethane 2223.74
    benzonitrile 927.29
    trioctyl phosphate 118.29
    1-bromopropane 1176.37
    gamma-valerolactone 2644.93
    n-decanol 172.95
    triethyl phosphate 241.67
    4-methyl-2-pentanol 858.05
    propionitrile 2285.63
    vinylene carbonate 997.8
    1,1,2-trichlorotrifluoroethane 1608.74
    DMS 443.0
    cumene 167.72
    2-octanol 240.55
    2-hexanone 1125.07
    octyl acetate 221.84
    limonene 310.92
    1,2-dimethoxyethane 2549.75
    ethyl orthosilicate 288.71
    tributyl phosphate 173.02
    diacetone alcohol 1289.03
    N,N-dimethylaniline 383.16
    acrylonitrile 2039.37
    aniline 1754.45
    1,3-propanediol 2501.95
    bromobenzene 829.53
    dibromomethane 1595.24
    1,1,2,2-tetrachloroethane 2169.79
    2-methyl-cyclohexyl acetate 399.61
    tetrabutyl urea 186.1
    diisobutyl methanol 389.84
    2-phenylethanol 794.1
    styrene 438.52
    dioctyl adipate 252.65
    dimethyl sulfate 524.33
    ethyl butyrate 1079.47
    methyl lactate 561.87
    butyl lactate 436.72
    diethyl carbonate 534.36
    propanediol butyl ether 701.07
    triethyl orthoformate 644.72
    p-tert-butyltoluene 198.42
    methyl 4-tert-butylbenzoate 366.46
    morpholine 5494.86
    tert-butylamine 2103.28
    n-dodecanol 113.59
    dimethoxymethane 1968.67
    ethylene carbonate 947.86
    cyrene 393.38
    2-ethoxyethyl acetate 967.39
    2-ethylhexyl acetate 861.12
    1,2,4-trichlorobenzene 802.93
    4-methylpyridine 2157.92
    dibutyl ether 550.94
    2,6-dimethyl-4-heptanol 389.84
    DEF 1913.0
    dimethyl isosorbide 890.44
    tetrachloroethylene 1634.5
    eugenol 382.32
    triacetin 479.03
    span 80 515.1
    1,4-butanediol 521.77
    1,1-dichloroethane 1937.08
    2-methyl-1-pentanol 1026.0
    methyl formate 1202.28
    2-methyl-1-butanol 2109.17
    n-decane 22.6
    butyronitrile 2384.94
    3,7-dimethyl-1-octanol 393.6
    1-chlorooctane 152.33
    1-chlorotetradecane 37.53
    n-nonane 23.12
    undecane 14.06
    tert-butylcyclohexane 71.81
    cyclooctane 70.43
    cyclopentanol 1396.66
    tetrahydropyran 4312.4
    tert-amyl methyl ether 1449.9
    2,5,8-trioxanonane 1122.17
    1-hexene 555.68
    2-isopropoxyethanol 1074.79
    2,2,2-trifluoroethanol 474.7
    methyl butyrate 1218.19

    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
Bergamot (Italy) 3 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 0.01%
Blackcurrant bud 1 68606-81-5 Ribes nigrum L., fam. Grossulariaceae 0.06%
Hortensis leaf Euodia hortensis forma hortensis, fam. Saxifragaceae (Hydrangea) 0.05%
Mastic gum (Greece) 1 61789-92-2 Pistacia lentiscus L., var. Chia, fam. Anacardiaceae 0.55%
Mentha aquatica x viridis (Italy) Mentha aquatica x viridis F. Schultz, fam. Lamiaceae (Labiatae) 0.96%
Cornmint (Mentha arvensis) (Italy) 3 68917-18-0 Mentha arvensis (L.) var. piperascens Malinv., fam. Lamiaceae (Labiatae) 0.13%
Mentha longifolia (Italy) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.01%
Mentha longifolia ssp. petiolata (Greece) 2 90063-99-3 Mentha longifolia (L.) ssp. petiolata (Chemotype II), fam. Lamiaceae 4.4%
Mentha longifolia var. crispa (Italy) 90063-99-3 Mentha longifolia (L.) var. crispa Ten., fam. Lamiaceae (Labiatae) 2.32%
Mentha spicata (Greece) Chemotype II Mentha spicata L. (Chemotype II), fam. Lamiaceae (Labiatae) 4.5%
Mentha suaveolens (Chemotype 2) Mentha suaveolens Ehrh. (Chemotype 2), fam. Lamiaceae (Labiatae) 4.71%
Mentha x villoso-nervata (Greece) 2 Mentha x villoso-nervata Opiz (M.longifolia L. x M.spicata L.) (Chemot.II) 9.0%
Narcissus tazetta absolute 2 8023-75-4 Narcissus tazetta L., fam. Amaryllidaceae 0.1%
Spearmint, scotch (USA) 1 Mentha gracilis Sole, fam. Lamiaceae (Labiatae) 1.4%
Spearmint, scotch (Italy) Mentha gracilis Sole, fam. Lamiaceae (Labiatae) 2.95%
Mapo tangelo Citrus ssp. Mapo tangelo, fam. Rutaceae 0.01%
Mandarin (Italy) 3 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.01%
Grapefruit (Italy) 1 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.01%
Melittis melissophyllum Melittis melissophylum L., ssp. albida Guss, fam. Lamiaceae (Labiatae) 0.06%
Hedychium coronarium flower (Japan) Hedychium coronarium Koenig, fam. Zingiberaceae 0.02%
Santolina chamaecyparisus (Egypt) 84961-58-0 Santolina chamaecyparisus L., fam. Asteraceae (Compositae) 0.07%
Caraway seed (Yugoslavia) 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.1%
Mandarin (Italy) 5 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.01%
Gingergrass (India) 1 Cymbopogon martini Stapf., var. sofia, fam. Poaceae (Gramineae) 15.0%
Caraway seed (Egypt) 8008-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.14%
Laser tribolum (Turkey) Laser tribolum (L.) Borkh. (Laserpitium t.L., Siler t.Crantz),fam.Apiaceae 0.53%
Orange, sweet (USA) (hydrocarbon-free) 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.1%
Yuzu (Japan) 3 Citrus junos Sieb. ex Tanaka, fam. Rutaceae 0.01%
Perilla frutescens (China) 3 crispa 90082-61-4 Perilla frutescens Brit. var. crispa (Thunb.) Hand.-Mazz, fam. Lamiaceae 0.94%
Orange, sweet (Vietnam) 1 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.65%
Chenopodium ambrosioides Chenopodium ambrosioides L., fam. Chenopodiaceae 0.15%
Cymbopogon caesius leaf Cymbopogon caesius (Nees ex Hook. et Arn.) Stapf., fam. Poaceae (Graminea) 25.61%
Juniperus oxycedrus berry Juniperus oxycedrys L., ssp. macrocarpa (Sm.) Ball., fam. Cupressaceae 0.37%
Juniperus oxycedrus leaf Juniperus oxycedrus L., ssp. macrocarpa (Sm.) Ball., fam. Cupressaceae 2.66%
Angelica root (France) 1 8015-64-3 Angelica archangelica L., fam. Apiaceae (Umbelliferae) 0.1%
Pectis prostrata leaf Pectis prostrata Cav., fam. Asteraceae (Compositae) 3.63%
Rose (China) 1a 8007-01-0 Rosa damascena Mill., fam. Rosaceae 0.05%
Rose (China) 1b 8007-01-0 Rosa species (France), fam. Rosaceae 0.18%
Rose (China) 1c 8007-01-0 Rosa damascena Mill., fam. Rosaceae 0.08%
Rose (China) 1d 8007-01-0 Rosa species (Moroccan), fam. Rosaceae 0.21%
Wormwood (Mugwort) 2 8008-93-3 Artemisia absinthium L., fam. Asteraceae (Compositae) 0.6%
Keora (India) 1 Pandanus odoratissimus L. (P. fascicularis Lam.), fam. Pandanaceae 0.01%
Clementine (Italy) 3a Citrus clementina Hort. ex Tan., cultivar Oroval, fam. Rutaceae 0.01%
Clementine (Italy) 3b Citrus clementina Hort. ex Tan., cultivar Monreal, fam. Rutaceae 0.01%
Clementine (Italy) 3c Citrus clementina Hort. ex Tan., cultivar Comune, fam. Rutaceae 0.03%
Clementine (Uruguay) 1a Citrus clementina Hort. ex Tan., cultivar Nules, fam. Rutaceae 0.01%
Clementine (Uruguay) 1b Citrus clementina Hort. ex Tan., cultivar Comune, fam. Rutaceae 0.01%
Mentha longifolia (Israel) 90063-99-3 Mentha longifolia (L.) Hudson, fam. Lamiaceae (Labiatae) 0.01%
Perilla frutescens (China) 4 acuta Perilla frutescens (L.) Brit. var. acuta (Thunb.) Kudo, fam. Lamiaceae 5.37%
Clementine x Lemon (Italy) 2 Citrus clementina Hort. ex Tan. x Citrus limon (L.) Burm., fam. Rutaceae 0.02%