Limonene, (+)-

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  • Identifiers

    CAS number
    5989-27-5

    Molecular formula
    C10H16

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

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

    Retention indicies (RI)

    • DB5: 1033.0
    • Carbowax: 1193.0

  • Odor profile

    Woody 74.97%
    Herbal 72.94%
    Citrus 72.39%
    Terpenic 68.87%
    Sweet 65.88%
    Lemon 58.37%
    Fresh 56.76%
    Spicy 56.64%
    Pine 53.49%
    Mint 45.51%

    Scent© AI

  • Properties

    XLogP3-AA
    3.4

    Molecular weight
    136.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Melting point expt.

    • -142.4 °F (NTP, 1992)
    • -74 °C
    • -90 °C

    Boiling point

    • 348 to 349 °F at 760 mmHg (NTP, 1992)
    • 177.6 °C
    • 178 °C

    Flash point est.
    53.69 ˚C

    Flash point expt.

    • 119 °F (NTP, 1992)
    • 48 °C
    • 48 °C (closed cup)
    • 48 °C c.c.

    Solubility expt.

    • less than 1 mg/mL at 67.1 °F (NTP, 1992)
    • In water, 13.8 mg/L at 25 °C
    • Miscible with ethanol and ether; soluble in carbon tetrachloride
    • Miscible with fixed oils; slightly soluble in glycerin; insoluble in propylene glycol
    • Solubility in water at 25 °C: very poor
    • Insoluble in water, propylene glycol; slightly Soluble in glycerol; Soluble in oils
    • Soluble (in ethanol)

  • Synonyms

    • D-Limonene
    • 5989-27-5
    • (R)-(+)-Limonene
    • (+)-Limonene
    • (D)-Limonene
    • (+)-(4R)-Limonene
    • (4R)-Limonene
    • (R)-Limonene
    • (+)-Dipentene
    • (+)-carvene
    • D-(+)-Limonene
    • D-Limonen
    • Limonene, (+)-
    • (R)-4-Isopropenyl-1-methyl-1-cyclohexene
    • Limonene, D-
    • Citrene
    • (R)-p-Mentha-1,8-diene
    • (+)-p-Mentha-1,8-diene
    • (+)-R-Limonene
    • (4R)-4-isopropenyl-1-methylcyclohexene
    • Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-
    • FEMA No. 2633
    • d-p-Mentha-1,8-diene
    • (+)-4-Isopropenyl-1-methylcyclohexene
    • (R)-(+)-p-Mentha-1,8-diene
    • (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
    • (R)-1-Methyl-4-(1-methylethenyl)cyclohexene
    • (+)-(R)-Limonene
    • GFD7C86Q1W
    • (4R)-1-methyl-4-prop-1-en-2-ylcyclohexene
    • MFCD00062991
    • 4betaH-p-mentha-1,8-diene
    • r-(+)-limonene
    • D-limonene [JAN]
    • CHEBI:15382
    • Dipentene no. 122
    • (4R)-1-methyl-4-(1-methylethenyl)cyclohexene
    • NSC-757069
    • (4R)-1-methyl-4-isopropenylcyclohex-1-ene
    • DTXSID1020778
    • (R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
    • (+) Limonene
    • Carvene
    • Glidesafe
    • Glidsafe
    • Kautschiin
    • Refchole
    • D-LIMONENE (IARC)
    • D-LIMONENE [IARC]
    • (4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohexene
    • Biogenic SE 374
    • (+)-alpha-Limonene
    • d-Limonene (natural)
    • d-Limoneno [Spanish]
    • d limonene
    • d-Limoneno
    • Hemo-sol
    • (4R)-(+)-Limonene
    • Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-
    • (4R)-4-isopropenyl-1-methyl-cyclohexene
    • CCRIS 671
    • EC 7
    • HSDB 4186
    • D-1,8-p-Menthadiene
    • NCI-C55572
    • EINECS 227-813-5
    • UNII-GFD7C86Q1W
    • p-Mentha-1,8-diene, (R)-(+)-
    • Sulfate turpentine, distilled
    • (+)-1,8-para-Menthadiene
    • AI3-15191
    • 1-Methyl-4-(1-methylethenyl)cyclohexene, (R)-
    • 9IR
    • EINECS 266-034-5
    • D-(+)-Limonen
    • Alda341
    • ?-LIMONENE
    • Alda 341
    • Alda-341
    • EC 227-813-5
    • (+)-Limonene, stabilized with 0.03% tocopherol
    • DTXCID50778
    • (D)-LIMONENE [HSDB]
    • (+)-LIMONENE [FCC]
    • CHEMBL449062
    • Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (theta)-
    • (R)-(+)-Limonene, 95%
    • (R)-(+)-Limonene, 97%
    • CS-M3273
    • (R)-(+)-Limonene, >=93%
    • Tox21_200400
    • LIMONENE, (+)- [WHO-DD]
    • AKOS015899935
    • Purifying Balance Soothing Peeling Pad
    • (R)-4-isopropenyl-1-methylcyclohexene
    • CCG-266134
    • DB08921
    • FL45094
    • LMPR0102090013
    • NSC 757069
    • (R)-(+)-Limonene, analytical standard
    • NCGC00248591-01
    • NCGC00248591-02
    • NCGC00257954-01
    • BS-22387
    • CAS-5989-27-5
    • (+)-(R)-4-isopropenyl-1-methylcyclohexene
    • L0047
    • L0105
    • NS00008437
    • (4R)-1-methyl-4-prop-1-en-2-yl-cyclohexene
    • (R)-Limonene 2000 microg/mL in Acetonitrile
    • C06099
    • D91245
    • EN300-106573
    • SVOC Mixture 748 1000 microg/mL in Methanol
    • BRD-K20879694-001-01-7
    • Q27888324
    • Z1255486311
    • (R)-(+)-Limonene, primary pharmaceutical reference standard
    • (R)-(+)-Limonene, purum, >=96.0% (sum of enantiomers, GC)
    • (R)-(+)-Limonene, technical, ~90% (sum of enantiomers, GC)
    • (+)-Carvene;(+)-p-Mentha-1,8-diene;(R)-4-Isopropenyl-1-methyl-1-cyclohexene
    • 7705-13-7

  • Applications

    (R)-(+)-Limonene, a naturally occurring monoterpene with a fresh citrus aroma primarily obtained from orange and lemon peels, finds extensive use in the flavour and fragrance industry to impart a clean, uplifting note to perfumes, soaps, shampoos, deodorants and skincare products; in food technology it serves as an FDA-approved flavouring agent and sensory enhancer for beverages, candies, baked goods and seasonings; in household and industrial cleaners it functions as a green solvent that replaces chlorinated or petroleum solvents for metal degreasing, adhesive removal and ink cleaning thanks to its high biodegradability, pleasant odour and low toxicity; in agriculture it is explored and commercialised as a botanical insect repellent and bio-pesticide; in pharmaceuticals and biomedicine (R)-(+)-limonene is investigated as a skin-penetration enhancer, anti-inflammatory, antioxidant, potential anticancer molecule and drug carrier in nano-emulsions; additionally the compound is used as a renewable diluent or co-monomer for bioplastics, eco-friendly 3D-printing resins, and as a reference standard in essential-oil analysis.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 889.41
    methanol 368.42
    isopropanol 717.53
    water 0.08
    ethyl acetate 1411.21
    n-propanol 734.05
    acetone 606.26
    n-butanol 890.06
    acetonitrile 634.04
    DMF 269.56
    toluene 1108.56
    isobutanol 446.73
    1,4-dioxane 2616.15
    methyl acetate 655.65
    THF 3173.56
    2-butanone 816.24
    n-pentanol 505.45
    sec-butanol 641.25
    n-hexane 467.9
    ethylene glycol 29.15
    NMP 248.41
    cyclohexane 838.19
    DMSO 331.5
    n-butyl acetate 2069.71
    n-octanol 436.42
    chloroform 1912.51
    n-propyl acetate 568.76
    acetic acid 249.73
    dichloromethane 1647.94
    cyclohexanone 946.55
    propylene glycol 89.68
    isopropyl acetate 896.22
    DMAc 292.64
    2-ethoxyethanol 429.36
    isopentanol 676.64
    n-heptane 970.54
    ethyl formate 419.65
    1,2-dichloroethane 921.32
    n-hexanol 1487.84
    2-methoxyethanol 667.17
    isobutyl acetate 364.46
    tetrachloromethane 413.25
    n-pentyl acetate 545.56
    transcutol 2287.16
    n-heptanol 426.18
    ethylbenzene 391.04
    MIBK 552.55
    2-propoxyethanol 1182.83
    tert-butanol 883.46
    MTBE 1475.0
    2-butoxyethanol 452.35
    propionic acid 233.23
    o-xylene 410.16
    formic acid 36.23
    diethyl ether 2446.54
    m-xylene 574.04
    p-xylene 402.19
    chlorobenzene 638.86
    dimethyl carbonate 127.43
    n-octane 191.54
    formamide 71.22
    cyclopentanone 745.76
    2-pentanone 914.85
    anisole 581.77
    cyclopentyl methyl ether 1341.45
    gamma-butyrolactone 603.06
    1-methoxy-2-propanol 640.72
    pyridine 1493.06
    3-pentanone 582.28
    furfural 476.11
    n-dodecane 98.46
    diethylene glycol 324.1
    diisopropyl ether 751.14
    tert-amyl alcohol 665.78
    acetylacetone 620.99
    n-hexadecane 114.3
    acetophenone 316.57
    methyl propionate 546.49
    isopentyl acetate 1364.56
    trichloroethylene 1216.29
    n-nonanol 423.61
    cyclohexanol 679.45
    benzyl alcohol 250.95
    2-ethylhexanol 1050.68
    isooctanol 307.3
    dipropyl ether 2510.93
    1,2-dichlorobenzene 420.83
    ethyl lactate 119.22
    propylene carbonate 444.27
    n-methylformamide 151.49
    2-pentanol 660.27
    n-pentane 520.13
    1-propoxy-2-propanol 1146.72
    1-methoxy-2-propyl acetate 1157.77
    2-(2-methoxypropoxy) propanol 450.39
    mesitylene 320.16
    ε-caprolactone 798.11
    p-cymene 423.1
    epichlorohydrin 1059.94
    1,1,1-trichloroethane 978.47
    2-aminoethanol 127.27
    morpholine-4-carbaldehyde 560.16
    sulfolane 362.62
    2,2,4-trimethylpentane 144.67
    2-methyltetrahydrofuran 2446.14
    n-hexyl acetate 769.61
    isooctane 168.86
    2-(2-butoxyethoxy)ethanol 702.43
    sec-butyl acetate 455.44
    tert-butyl acetate 810.51
    decalin 212.23
    glycerin 86.34
    diglyme 1255.33
    acrylic acid 116.11
    isopropyl myristate 332.05
    n-butyric acid 740.85
    acetyl acetate 563.56
    di(2-ethylhexyl) phthalate 209.56
    ethyl propionate 500.34
    nitromethane 333.05
    1,2-diethoxyethane 2336.84
    benzonitrile 450.93
    trioctyl phosphate 144.55
    1-bromopropane 1327.12
    gamma-valerolactone 848.54
    n-decanol 307.87
    triethyl phosphate 249.39
    4-methyl-2-pentanol 395.77
    propionitrile 687.6
    vinylene carbonate 331.83
    1,1,2-trichlorotrifluoroethane 294.03
    DMS 296.18
    cumene 219.02
    2-octanol 280.75
    2-hexanone 590.91
    octyl acetate 400.96
    limonene 765.47
    1,2-dimethoxyethane 1179.85
    ethyl orthosilicate 302.76
    tributyl phosphate 196.19
    diacetone alcohol 481.29
    N,N-dimethylaniline 296.08
    acrylonitrile 421.18
    aniline 659.49
    1,3-propanediol 314.94
    bromobenzene 787.26
    dibromomethane 1413.93
    1,1,2,2-tetrachloroethane 944.03
    2-methyl-cyclohexyl acetate 552.21
    tetrabutyl urea 241.47
    diisobutyl methanol 528.11
    2-phenylethanol 552.48
    styrene 471.04
    dioctyl adipate 344.32
    dimethyl sulfate 99.37
    ethyl butyrate 1200.86
    methyl lactate 123.55
    butyl lactate 222.39
    diethyl carbonate 539.32
    propanediol butyl ether 258.42
    triethyl orthoformate 708.36
    p-tert-butyltoluene 422.88
    methyl 4-tert-butylbenzoate 301.39
    morpholine 2689.53
    tert-butylamine 801.63
    n-dodecanol 232.72
    dimethoxymethane 636.54
    ethylene carbonate 351.08
    cyrene 181.43
    2-ethoxyethyl acetate 666.81
    2-ethylhexyl acetate 1214.27
    1,2,4-trichlorobenzene 422.26
    4-methylpyridine 1205.61
    dibutyl ether 1222.14
    2,6-dimethyl-4-heptanol 528.11
    DEF 650.94
    dimethyl isosorbide 739.57
    tetrachloroethylene 601.36
    eugenol 233.14
    triacetin 378.82
    span 80 434.41
    1,4-butanediol 73.61
    1,1-dichloroethane 1070.78
    2-methyl-1-pentanol 443.89
    methyl formate 103.77
    2-methyl-1-butanol 554.46
    n-decane 198.29
    butyronitrile 1036.55
    3,7-dimethyl-1-octanol 487.85
    1-chlorooctane 465.41
    1-chlorotetradecane 163.68
    n-nonane 216.94
    undecane 131.67
    tert-butylcyclohexane 186.7
    cyclooctane 327.51
    cyclopentanol 471.82
    tetrahydropyran 3332.24
    tert-amyl methyl ether 873.66
    2,5,8-trioxanonane 810.33
    1-hexene 1005.98
    2-isopropoxyethanol 318.94
    2,2,2-trifluoroethanol 43.15
    methyl butyrate 551.08

    Scent© AI

1 4

IFRA standard 51

Recommendation
Specification
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 See notebox Category 7A
Rinse-off products applied to the hair with some hand contact
 See notebox
Category 2
Products applied to the axillae
 See notebox Category 7B
Leave-on products applied to the hair with some hand contact
 See notebox
Category 3
Products applied to the face/body using fingertips
 See notebox Category 8
Products with significant anogenital exposure
 See notebox
Category 4
Products related to fine fragrance
 See notebox Category 9
Products with body and hand exposure, primarily rinse off
 See notebox
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 See notebox Category 10A
Household care products with mostly hand contact
 See notebox
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 See notebox Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 See notebox
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 See notebox Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 See notebox
Category 5D
Baby Creams, baby Oils and baby talc
 See notebox Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 See notebox
Category 6
Products with oral and lip exposure
 See notebox Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 See notebox

Specification
Oxidation products of Limonene, especially hydroperoxides, have been demonstrated to be potent sensitizers.
d-, l- and dl-Limonene and natural products containing substantial amounts of it, should only be used when the level of (hydro)peroxides is kept to the lowest practical level, for instance by adding antioxidants at the time of production. The addition of 0.1% BHT or α-Tocopherol for example has shown great efficiency. Such products should have a peroxide value of less than 20 millimoles per liter, determined according to the IFRA analytical method for the determination of the peroxide value, which can be downloaded from the IFRA website (www.ifrafragrance.org).

Botanical

Name CAS Botanical Proportion
Abies sachalinensis (Finland) Abies sachalinensis (Fr. Schm.) Mast, fam. Pinaceae 0.9%
Abies mayriana (Finland) Abies mayriana Miy. et Kudo Needle, fam. Pinaceae 0.9%
Tea Tree (Australia) 9 68647-73-4 Melaleuca alternifolia (Maiden et Betche) Cheel, fam. Myrtaceae 0.51%
Bergamot (Italy, Calabria) 7 8007-75-8 Citrus bergamia Risso et Poiteau, fam. Rutaceae 40.4%