Isopropyl Cloprostenate

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  • Identifiers

    CAS number
    157283-66-4

    Molecular formula
    C25H35ClO6

    SMILES
    CC(C)OC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](COC2=CC(=CC=C2)Cl)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 39.37%
    Sweet 30.03%
    Fruity 23.85%
    Milky 22.58%
    Savory 22.23%
    Spicy 21.91%
    Lactonic 21.01%
    Fresh 20.26%
    Floral 19.73%
    Peach 19.37%

     

    Flavor
    Bitter 56.57%
    Odorless 28.64%
    Mild 27.4%
    Fruity 26.4%
    Floral 24.9%
    Bland 22.33%
    Sweet-like 20.31%
    Heather 19.85%
    Cedarleaf 19.85%
    Broom 19.41%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.8

    pKa est.
    7.43 (neutral)

    Molecular weight
    467.0 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1068°C

    Flash point

    • 223.76 ˚C est.

  • Synonyms

    • 157283-66-4
    • Isopropyl cloprostenate
    • Cloprostenol isopropyl ester
    • Isopropyl cloprostenol
    • UNII-765298537G
    • 765298537G
    • CPG-611295
    • 5-Heptenoic acid, 7-((1R,2R,3R,5S)-2-((1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-buten-1-yl)-3,5-dihydroxycyclopentyl)-, 1-methylethyl ester, (5Z)-
    • 5-Heptenoic acid, 7-((1R,2R,3R,5S)-2-((1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-, 1-methylethyl ester, (5Z)-
    • CPG-6112-95
    • 5-Heptenoic acid, 7-(2-(4-(3-chlorophenoxy)-3-hydroxy-1-butenyl)-3,5-dihydroxycyclopentyl)-, 1-methylethyl ester, (1R-(1alpha(Z),2beta(1E,3R*),3alpha,5alpha))-
    • 5-HEPTENOIC ACID, 7-(2-(4-(3-CHLOROPHENOXY)-3-HYDROXY-1-BUTENYL)-3,5-DIHYDROXYCYCLOPENTYL)-, 1-METHYLETHYL ESTER, (1R-(1.ALPHA.(Z),2.BETA.(1E,3R*),3.ALPHA.,5.ALPHA.))-
    • RefChem:149814
    • ISOPROPYL CLOPROSTENATE [INCI]
    • 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl ester, (5Z)-(9CI)
    • 682-025-2
    • (+)-Cloprostenol isopropyl ester
    • propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
    • isopropyl (Z)-7-((1R,2R,3R,5S)-2-((R,E)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enoate
    • (5Z)-7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester; [1R-[1alpha(Z),2beta(1E,3R*),3alpha,5alpha]]-7-[2-[4-(3-Chlorophenoxy)-3-hydroxy-1-butenyl]-3,5-dihydroxycyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester; CPG 6112-95; Cloprostenol Isopropyl Ester
    • C25H35ClO6
    • (+)-Cloprostenolisopropylester
    • orb1986822
    • SCHEMBL30223804
    • MSK2978
    • AKOS030627123
    • FC07866
    • HY-100571
    • CS-0019712
    • D-cloprostenol isopropyl ester, 157283-66-4
    • Q27266449
    • (+)-16-m-chlorophenoxy tetranor Prostaglandin F2alpha isopropyl ester
    • isopropyl (Z)-7-[(1R,2R,3R,5S)-2-[(E,3R)-4-(3-chlorophenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl]hept-5-enoate
    • propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate
    • 157283-66-4

  • Applications

    Isopropyl cloprostenate is primarily used in pharmaceutical research and development as a lipophilic ester of cloprostenol and serves as an intermediate for prostaglandin F2α-type derivatives. It may function as a prodrug to modulate pharmacokinetic properties and tissue distribution. In industrial pharmaceutical contexts, it is considered a specialty intermediate for prostanoid APIs and related formulations. It also supports pharmacology and toxicology studies of prostanoid receptor activity in academic and industrial settings, and may have potential applications in veterinary prostaglandin analogue programs, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 12.17
    methanol 33.2
    isopropanol 3.45
    water 0.08
    ethyl acetate 2.98
    n-propanol 10.06
    acetone 18.58
    n-butanol 7.49
    acetonitrile 2.72
    DMF 73.7
    toluene 2.29
    isobutanol 5.06
    1,4-dioxane 21.42
    methyl acetate 4.57
    THF 97.47
    2-butanone 11.92
    n-pentanol 7.77
    sec-butanol 4.97
    n-hexane 0.12
    ethylene glycol 3.65
    NMP 77.38
    cyclohexane 0.25
    DMSO 163.04
    n-butyl acetate 2.93
    n-octanol 8.12
    chloroform 28.53
    n-propyl acetate 3.79
    acetic acid 32.61
    dichloromethane 26.9
    cyclohexanone 37.23
    propylene glycol 10.39
    isopropyl acetate 2.75
    DMAc 141.29
    2-ethoxyethanol 34.38
    isopentanol 5.8
    n-heptane 0.17
    ethyl formate 6.66
    1,2-dichloroethane 10.85
    n-hexanol 4.85
    2-methoxyethanol 54.93
    isobutyl acetate 3.24
    tetrachloromethane 1.91
    n-pentyl acetate 8.22
    transcutol 89.99
    n-heptanol 7.31
    ethylbenzene 1.42
    MIBK 5.84
    2-propoxyethanol 29.23
    tert-butanol 4.61
    MTBE 3.08
    2-butoxyethanol 26.54
    propionic acid 10.44
    o-xylene 1.87
    formic acid 23.56
    diethyl ether 1.69
    m-xylene 1.62
    p-xylene 1.87
    chlorobenzene 4.13
    dimethyl carbonate 6.86
    n-octane 0.14
    formamide 25.23
    cyclopentanone 46.38
    2-pentanone 7.63
    anisole 7.22
    cyclopentyl methyl ether 10.34
    gamma-butyrolactone 39.95
    1-methoxy-2-propanol 33.04
    pyridine 15.52
    3-pentanone 5.67
    furfural 40.62
    n-dodecane 0.16
    diethylene glycol 21.82
    diisopropyl ether 0.55
    tert-amyl alcohol 6.42
    acetylacetone 16.05
    n-hexadecane 0.18
    acetophenone 11.59
    methyl propionate 5.7
    isopentyl acetate 4.46
    trichloroethylene 32.79
    n-nonanol 8.39
    cyclohexanol 7.97
    benzyl alcohol 12.34
    2-ethylhexanol 2.94
    isooctanol 5.88
    dipropyl ether 2.59
    1,2-dichlorobenzene 5.27
    ethyl lactate 8.4
    propylene carbonate 15.9
    n-methylformamide 23.33
    2-pentanol 2.31
    n-pentane 0.08
    1-propoxy-2-propanol 15.87
    1-methoxy-2-propyl acetate 10.37
    2-(2-methoxypropoxy) propanol 30.23
    mesitylene 1.0
    ε-caprolactone 25.88
    p-cymene 1.17
    epichlorohydrin 49.2
    1,1,1-trichloroethane 5.7
    2-aminoethanol 12.9
    morpholine-4-carbaldehyde 65.99
    sulfolane 98.55
    2,2,4-trimethylpentane 0.15
    2-methyltetrahydrofuran 15.57
    n-hexyl acetate 11.85
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 37.62
    sec-butyl acetate 2.58
    tert-butyl acetate 5.18
    decalin 0.24
    glycerin 23.61
    diglyme 63.12
    acrylic acid 13.73
    isopropyl myristate 3.93
    n-butyric acid 13.4
    acetyl acetate 4.25
    di(2-ethylhexyl) phthalate 9.31
    ethyl propionate 3.43
    nitromethane 40.59
    1,2-diethoxyethane 10.38
    benzonitrile 7.04
    trioctyl phosphate 5.73
    1-bromopropane 3.12
    gamma-valerolactone 84.17
    n-decanol 5.07
    triethyl phosphate 4.59
    4-methyl-2-pentanol 2.17
    propionitrile 2.83
    vinylene carbonate 16.94
    1,1,2-trichlorotrifluoroethane 67.9
    DMS 7.61
    cumene 1.17
    2-octanol 3.99
    2-hexanone 7.75
    octyl acetate 6.45
    limonene 1.81
    1,2-dimethoxyethane 39.53
    ethyl orthosilicate 4.57
    tributyl phosphate 5.78
    diacetone alcohol 16.78
    N,N-dimethylaniline 6.53
    acrylonitrile 5.44
    aniline 5.9
    1,3-propanediol 16.85
    bromobenzene 3.77
    dibromomethane 10.88
    1,1,2,2-tetrachloroethane 29.55
    2-methyl-cyclohexyl acetate 7.51
    tetrabutyl urea 10.73
    diisobutyl methanol 1.55
    2-phenylethanol 9.21
    styrene 1.6
    dioctyl adipate 10.43
    dimethyl sulfate 21.01
    ethyl butyrate 3.56
    methyl lactate 15.18
    butyl lactate 14.45
    diethyl carbonate 2.85
    propanediol butyl ether 31.0
    triethyl orthoformate 5.23
    p-tert-butyltoluene 1.12
    methyl 4-tert-butylbenzoate 19.5
    morpholine 32.88
    tert-butylamine 1.54
    n-dodecanol 3.06
    dimethoxymethane 35.86
    ethylene carbonate 11.99
    cyrene 42.56
    2-ethoxyethyl acetate 14.73
    2-ethylhexyl acetate 3.24
    1,2,4-trichlorobenzene 8.32
    4-methylpyridine 10.79
    dibutyl ether 4.11
    2,6-dimethyl-4-heptanol 1.55
    DEF 16.02
    dimethyl isosorbide 44.3
    tetrachloroethylene 17.07
    eugenol 23.25
    triacetin 19.86
    span 80 26.16
    1,4-butanediol 8.08
    1,1-dichloroethane 5.03
    2-methyl-1-pentanol 7.53
    methyl formate 16.03
    2-methyl-1-butanol 7.0
    n-decane 0.34
    butyronitrile 3.24
    3,7-dimethyl-1-octanol 5.37
    1-chlorooctane 2.37
    1-chlorotetradecane 0.74
    n-nonane 0.27
    undecane 0.22
    tert-butylcyclohexane 0.19
    cyclooctane 0.13
    cyclopentanol 10.27
    tetrahydropyran 11.59
    tert-amyl methyl ether 3.92
    2,5,8-trioxanonane 47.03
    1-hexene 0.68
    2-isopropoxyethanol 18.06
    2,2,2-trifluoroethanol 11.69
    methyl butyrate 6.46

    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