Prenol

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    556-82-1

    Molecular formula
    C5H10O

    SMILES
    CC(=CCO)C

    Safety labels

    Flammable
    Flammable

    Corrosive
    Corrosive

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 778.5
    • Carbowax: 1326.75

  • Odor profile

    Fruity 89.46%
    Green 80.53%
    Sweet 71.91%
    Fermented 55.34%
    Ethereal 53.77%
    Alcoholic 52.55%
    Herbal 50.29%
    Pungent 45.53%
    Winey 44.19%
    Musty 41.65%

    Scent© AI

  • Properties

    XLogP3-AA
    1.0

    Molecular weight
    86.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Melting point expt.

    • -59.3 °C

    Boiling point

    • 138.00 to 174.00 °C. @ 760.00 mm Hg
    • 140 °C

    Flash point est.
    47.14 ˚C

    Flash point expt.

    • 50 °C c.c.

    Solubility expt.

    • Solubility in water, g/100ml at 20 °C: 17 (good)
    • Insoluble in water; soluble in fats
    • soluble (in ethanol)

  • Synonyms

    • 3-METHYL-2-BUTEN-1-OL
    • Prenol
    • 556-82-1
    • 3-Methylbut-2-en-1-ol
    • 3,3-Dimethylallyl alcohol
    • 2-Buten-1-ol, 3-methyl-
    • Prenyl alcohol
    • 3-Methyl-2-butenol
    • Dimethylallyl alcohol
    • 3-Methylcrotyl alcohol
    • 3-Methyl-2-butenyl alcohol
    • 3-Methyl-2-butene-1-ol
    • butenol methyl
    • FEMA No. 3647
    • 2-Butenol, 3-methyl
    • NSC 158709
    • EINECS 209-141-4
    • Methyl-3-but-2-en-1-ol
    • MFCD00002916
    • .gamma.,.gamma.-Dimethylallyl alcohol
    • UNII-55MY0HM445
    • BRN 1633479
    • DTXSID2027206
    • CHEBI:16019
    • 2-methyl-2-buten-4-ol
    • NSC-158709
    • 3-methyl-but-2-en-1-ol
    • ISOPENT-2-EN-1-OL
    • DTXCID507206
    • FEMA 3647
    • EC 209-141-4
    • 55MY0HM445
    • 4-01-00-02129 (Beilstein Handbook Reference)
    • 3-METHYLBUT-2-EN-1-OL [FHFI]
    • CAS-556-82-1
    • 3Methyl2butenol
    • 2Methyl2buten4ol
    • 3Methylbut2en1ol
    • 3Methylbuten2ol1
    • 3,3-Dimethylallyl alcohol; 3-Methyl-2-butenyl alcohol; Dimethylallyl alcohol; Prenol; Prenyl alcohol
    • 3-methylbut-2-enol
    • 3Methylcrotyl alcohol
    • 2Buten1ol, 3methyl
    • 3Methyl2butenyl alcohol
    • 3-methyl-2-buten-1ol
    • 3,3Dimethylallyl alcohol
    • gamma-Methylcrotyl Alcohol
    • 3-methyl-2 -buten-1-ol
    • gamma,gammaDimethylallyl alcohol
    • CHEMBL3184952
    • 3-Methyl-2-buten-1-ol, 99%
    • Tox21_202234
    • Tox21_303419
    • BBL011665
    • LMFA05000106
    • NSC158709
    • s3123
    • STL163363
    • AKOS005716671
    • CS-W013751
    • HY-W013035
    • SB83755
    • NCGC00249194-01
    • NCGC00257241-01
    • NCGC00259783-01
    • 3-Methyl-2-buten-1-ol, >=98%, FG
    • M0714
    • NS00005818
    • EN300-73249
    • C01390
    • F20316
    • Q425512
    • Z431953402
    • 209-141-4

  • Applications

    3-Methyl-2-buten-1-ol (also known as isoprenol) is a versatile branched allylic alcohol whose applications span industry and research: it serves as a key feedstock in the synthesis of isoprenoid flavor and fragrance chemicals, especially for manufacturing citral, geraniol, nerol, linalool, ionones and other aroma ingredients used in perfumes, cosmetics and soaps; it is an essential intermediate in the production of vitamin A, vitamin E, carotenoids and other terpene-derived pharmaceuticals and veterinary drugs; the molecule is employed as a precursor for agrochemicals, plant growth regulators, polyisoprene resins, plasticizers and advanced biofuel additives; in the laboratory it functions as a prenylating agent, reaction solvent, leaving-group carrier in C-C coupling processes, and as a model compound for studying the enzymatic mevalonate pathway, thereby linking bench-scale research with large-scale commercial manufacturing.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 567.22
    methanol 605.83
    isopropanol 401.35
    water 22.22
    ethyl acetate 132.36
    n-propanol 440.35
    acetone 165.29
    n-butanol 408.09
    acetonitrile 161.66
    DMF 156.61
    toluene 19.58
    isobutanol 258.0
    1,4-dioxane 333.81
    methyl acetate 136.42
    THF 414.71
    2-butanone 147.65
    n-pentanol 174.7
    sec-butanol 336.66
    n-hexane 44.9
    ethylene glycol 193.05
    NMP 231.85
    cyclohexane 47.7
    DMSO 173.32
    n-butyl acetate 134.57
    n-octanol 133.42
    chloroform 228.94
    n-propyl acetate 73.9
    acetic acid 627.98
    dichloromethane 128.99
    cyclohexanone 189.08
    propylene glycol 276.98
    isopropyl acetate 65.65
    DMAc 119.45
    2-ethoxyethanol 219.46
    isopentanol 209.22
    n-heptane 69.93
    ethyl formate 93.0
    1,2-dichloroethane 76.83
    n-hexanol 334.06
    2-methoxyethanol 420.53
    isobutyl acetate 48.48
    tetrachloromethane 73.1
    n-pentyl acetate 77.25
    transcutol 469.28
    n-heptanol 154.3
    ethylbenzene 14.16
    MIBK 60.89
    2-propoxyethanol 352.84
    tert-butanol 374.18
    MTBE 142.06
    2-butoxyethanol 209.26
    propionic acid 373.73
    o-xylene 21.78
    formic acid 283.19
    diethyl ether 169.48
    m-xylene 20.6
    p-xylene 21.16
    chlorobenzene 43.07
    dimethyl carbonate 30.93
    n-octane 17.58
    formamide 198.28
    cyclopentanone 215.83
    2-pentanone 114.95
    anisole 49.35
    cyclopentyl methyl ether 162.92
    gamma-butyrolactone 258.08
    1-methoxy-2-propanol 263.75
    pyridine 120.06
    3-pentanone 88.1
    furfural 190.15
    n-dodecane 12.61
    diethylene glycol 269.24
    diisopropyl ether 45.93
    tert-amyl alcohol 290.02
    acetylacetone 82.26
    n-hexadecane 12.96
    acetophenone 45.39
    methyl propionate 97.9
    isopentyl acetate 96.61
    trichloroethylene 145.66
    n-nonanol 115.16
    cyclohexanol 252.33
    benzyl alcohol 59.09
    2-ethylhexanol 166.72
    isooctanol 105.59
    dipropyl ether 149.93
    1,2-dichlorobenzene 44.04
    ethyl lactate 57.25
    propylene carbonate 137.13
    n-methylformamide 157.16
    2-pentanol 235.32
    n-pentane 53.23
    1-propoxy-2-propanol 276.05
    1-methoxy-2-propyl acetate 106.11
    2-(2-methoxypropoxy) propanol 137.4
    mesitylene 16.92
    ε-caprolactone 182.4
    p-cymene 32.12
    epichlorohydrin 175.56
    1,1,1-trichloroethane 103.47
    2-aminoethanol 357.4
    morpholine-4-carbaldehyde 220.98
    sulfolane 234.89
    2,2,4-trimethylpentane 23.63
    2-methyltetrahydrofuran 289.86
    n-hexyl acetate 117.32
    isooctane 17.25
    2-(2-butoxyethoxy)ethanol 214.66
    sec-butyl acetate 48.53
    tert-butyl acetate 78.62
    decalin 15.92
    glycerin 300.34
    diglyme 267.18
    acrylic acid 297.45
    isopropyl myristate 49.4
    n-butyric acid 346.76
    acetyl acetate 72.82
    di(2-ethylhexyl) phthalate 50.86
    ethyl propionate 65.75
    nitromethane 308.12
    1,2-diethoxyethane 128.23
    benzonitrile 62.06
    trioctyl phosphate 44.71
    1-bromopropane 77.47
    gamma-valerolactone 257.05
    n-decanol 84.1
    triethyl phosphate 43.57
    4-methyl-2-pentanol 97.41
    propionitrile 135.49
    vinylene carbonate 106.19
    1,1,2-trichlorotrifluoroethane 216.2
    DMS 55.51
    cumene 16.95
    2-octanol 90.62
    2-hexanone 81.85
    octyl acetate 71.23
    limonene 61.8
    1,2-dimethoxyethane 185.49
    ethyl orthosilicate 46.95
    tributyl phosphate 48.6
    diacetone alcohol 137.01
    N,N-dimethylaniline 35.52
    acrylonitrile 125.78
    aniline 83.15
    1,3-propanediol 401.85
    bromobenzene 29.57
    dibromomethane 108.5
    1,1,2,2-tetrachloroethane 142.66
    2-methyl-cyclohexyl acetate 80.11
    tetrabutyl urea 58.22
    diisobutyl methanol 77.75
    2-phenylethanol 91.93
    styrene 16.45
    dioctyl adipate 68.36
    dimethyl sulfate 44.13
    ethyl butyrate 90.79
    methyl lactate 80.17
    butyl lactate 81.74
    diethyl carbonate 54.07
    propanediol butyl ether 169.94
    triethyl orthoformate 73.34
    p-tert-butyltoluene 33.57
    methyl 4-tert-butylbenzoate 84.93
    morpholine 401.85
    tert-butylamine 237.24
    n-dodecanol 63.6
    dimethoxymethane 103.27
    ethylene carbonate 96.92
    cyrene 96.83
    2-ethoxyethyl acetate 82.41
    2-ethylhexyl acetate 80.66
    1,2,4-trichlorobenzene 56.61
    4-methylpyridine 79.54
    dibutyl ether 91.12
    2,6-dimethyl-4-heptanol 77.75
    DEF 113.74
    dimethyl isosorbide 167.6
    tetrachloroethylene 122.55
    eugenol 94.55
    triacetin 86.72
    span 80 172.79
    1,4-butanediol 128.24
    1,1-dichloroethane 96.39
    2-methyl-1-pentanol 119.08
    methyl formate 91.56
    2-methyl-1-butanol 230.0
    n-decane 21.53
    butyronitrile 147.97
    3,7-dimethyl-1-octanol 105.67
    1-chlorooctane 57.65
    1-chlorotetradecane 24.53
    n-nonane 21.95
    undecane 15.77
    tert-butylcyclohexane 21.5
    cyclooctane 15.88
    cyclopentanol 298.84
    tetrahydropyran 298.23
    tert-amyl methyl ether 116.94
    2,5,8-trioxanonane 191.36
    1-hexene 80.49
    2-isopropoxyethanol 137.51
    2,2,2-trifluoroethanol 199.11
    methyl butyrate 81.52

    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
Ylang Ylang 4 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.13%
Orange leaf, sweet (Israel) 3 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.02%
Orange leaf, sweet (Israel) 2 Citrus sinensis (L.) Osbeck, cultivar Ruby (Blood orange), fam. Rutaceae 0.01%
Agathosma rosmarinifolia Agathosma rosmarinifolia (Bartl.) Williams, fam. Diosmea (Rutaceae) 3.1%
Phyllosma capensis Phyllosma capensis Bolus, fam. Diosmeae 2.1%
Narcissus (Japan) 1a 8023-75-4 Narcissus tazetta L. (N. poeticus L.), fam. Amarillidaceae 0.36%
Narcissus (Japan) 1b 8023-75-4 Narcissus tazetta L. (N. poeticus L.), fam. Amaryllidaceae 0.56%
Rose (Bulgaria) 2 8007-01-0 Rosa damascena Mill., fam. Rosaceae 0.01%
Lavender (France) 6 8000-28-0 Lavandula angustifolia Mill., fam. Lamiaceae (Labiatae) 0.01%
Ylang Ylang (Colombia) 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.05%
Jonquil (France) flower headspace 8023-75-4 Narcissus jonquilla L., fam. Amaryllidaceae 0.5%
Lawsonia inermis flower 1a Lawsonia inermis L. (syn. L. alba Lam.), fam. Lythraceae 0.1%
Lawsonia inermis flower 1b Lawsonia inermis L. (syn. L. alba Lam.), fam. Lytraceae 0.3%
Indian curry leaf tree (leaf) Murraya koenigii Spreng., fam. Rutaceae 0.01%
Colocasia esculenta (Taro) Colocasia esculenta (L.) Schott, fam. Araceae 0.1%
Carob bean extract 1 9000-40-2 Ceratonia siliqua L., fam. Leguminoseae 0.01%
Soursop, wild fruit Annona montana Macf., fam. Annonaceae 3.8%
Lavender (France) 8 8000-28-0 Lavandula angustifolia Mill. (L. officinalis Chaix), fam. Lamiaceae 0.01%
Lavender (Bulgaria) 2 8000-28-0 Lavandula angustifolia Mill. (L. officinalis Chaix), fam. Lamiaceae 0.01%
Lavender (Moldova) 8000-28-0 Lavandula angustifolia Mill., (L. officinalis Chaix), fam. Lamiaceae 0.01%