Alpha-Longipinene

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  • Identifiers

    CAS number
    5989-08-2

    Molecular formula
    C15H24

    SMILES
    CC1=CC[C@@H]2[C@@H]3[C@H]1[C@]2(CCCC3(C)C)C

    Retention indicies (RI)

    • DB5: 1360.0

  • Odor profile

    Woody 89.64%
    Dry 52.15%
    Amber 50.97%
    Spicy 48.5%
    Sweet 45.31%
    Cedar 44.8%
    Sandalwood 36.79%
    Vetiver 35.88%
    Balsamic 34.07%
    Fresh 33.2%

    Scent© AI

  • Properties

    XLogP3-AA
    4.6

    pKa est.
    9.71 (weak base)

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    265°C

    Flash point est.
    79.16 ˚C

  • Synonyms

    • Longipinene
    • alpha-Longipinene
    • (+)-alpha-Longipinene
    • 104AN9V5Q1
    • 5989-08-2
    • UNII-104AN9V5Q1
    • (1R,2S,7R,8R)-2,6,6,9-tetramethyltricyclo[5.4.0.02,8]undec-9-ene
    • 3,3,7,9-Tetramethyltricyclo(5.4.0.0(2,8))undec-9-ene
    • Longipinene (~75%)
    • Tricyclo(5.4.0.0(2,8))undec-9-ene, 3,3,7,9-tetramethyl-
    • (1R,2S,7R,8R)-2,6,6,9-tetramethyltricyclo[5.4.0.0(2,8)]undec-9-ene
    • TRICYCLO(5.4.0.02,8)UNDEC-9-ENE, 2,6,6,9-TETRAMETHYL-, (1R,2S,7R,8R)-
    • (+)-.alpha.-Longipinene
    • CHEBI:62753
    • 2,6,6,9-tetramethyltricyclo(5.4.0.0(2,8))undec-9-ene
    • CHEBI:62752
    • DTXSID30975297
    • HICYDYJTCDBHMZ-COMQUAJESA-N
    • Q27132143
    • (1R,2S,7R,8R)-2,6,6,9-tetramethyltricyclo[5.4.0.0?,?]undec-9-ene
    • 2,6,6,9-Tetramethyl-tricyclo[5.4.0.02,8]undec-9-ene Stereoisomer; alpha-Longipinene; (1R,2S,7R,8R)-2,6,6,9-Tetramethyltricyclo[5.4.0.02,8]undec-9-ene; (+)-alpha-Longipinene

  • Applications

    Alpha-Longipinene (CAS 5989-08-2) is a chiral sesquiterpene with a characteristic piney–resinous, woody note; it is used or explored as: (1) a fragrance ingredient in fine fragrances, deodorants, soaps, detergents, scented candles, personal care and air-care to impart warm woody/resin nuances; (2) a trace flavoring for herbal/resinous tonalities in beverages, confectionery, chewing gum and other foods where permitted by flavor regulations; (3) a renewable terpene feedstock and chiral building block in organic synthesis to access fragrance/cosmetic intermediates, agrochemical leads and pharmaceutical scaffolds via transformations such as isomerization, oxidation and hydrogenation; (4) a raw material in the development of terpene-based resins, tackifiers and bio-based plasticizers for adhesives, inks and specialty coatings; (5) a subject of R&D for bioactivity (antimicrobial, anti-inflammatory, insect-repellent, antioxidant) and for encapsulation/controlled-release systems in home- and crop-care; (6) a fragrance carrier in terpene-based solutions/emulsions that can enable greener formulations as alternatives to petroleum solvents.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 155.24
    methanol 121.05
    isopropanol 193.43
    water 0.68
    ethyl acetate 440.67
    n-propanol 210.63
    acetone 499.18
    n-butanol 228.38
    acetonitrile 271.61
    DMF 529.44
    toluene 643.54
    isobutanol 194.84
    1,4-dioxane 903.36
    methyl acetate 381.86
    THF 1578.86
    2-butanone 475.67
    n-pentanol 141.3
    sec-butanol 177.16
    n-hexane 122.38
    ethylene glycol 39.87
    NMP 465.37
    cyclohexane 241.49
    DMSO 264.2
    n-butyl acetate 472.66
    n-octanol 212.89
    chloroform 897.71
    n-propyl acetate 257.42
    acetic acid 101.41
    dichloromethane 705.9
    cyclohexanone 775.01
    propylene glycol 59.55
    isopropyl acetate 393.85
    DMAc 374.88
    2-ethoxyethanol 182.94
    isopentanol 226.88
    n-heptane 150.54
    ethyl formate 219.25
    1,2-dichloroethane 544.56
    n-hexanol 372.27
    2-methoxyethanol 308.03
    isobutyl acetate 254.1
    tetrachloromethane 247.97
    n-pentyl acetate 321.54
    transcutol 533.9
    n-heptanol 216.17
    ethylbenzene 285.08
    MIBK 379.77
    2-propoxyethanol 498.54
    tert-butanol 245.75
    MTBE 447.15
    2-butoxyethanol 311.58
    propionic acid 150.37
    o-xylene 353.73
    formic acid 27.47
    diethyl ether 526.38
    m-xylene 476.65
    p-xylene 326.27
    chlorobenzene 464.69
    dimethyl carbonate 253.15
    n-octane 74.34
    formamide 53.16
    cyclopentanone 1008.55
    2-pentanone 472.81
    anisole 398.79
    cyclopentyl methyl ether 788.52
    gamma-butyrolactone 812.08
    1-methoxy-2-propanol 315.14
    pyridine 621.56
    3-pentanone 410.24
    furfural 528.64
    n-dodecane 50.57
    diethylene glycol 256.07
    diisopropyl ether 271.68
    tert-amyl alcohol 202.99
    acetylacetone 540.33
    n-hexadecane 59.89
    acetophenone 305.61
    methyl propionate 379.74
    isopentyl acetate 474.93
    trichloroethylene 815.36
    n-nonanol 192.76
    cyclohexanol 314.26
    benzyl alcohol 204.39
    2-ethylhexanol 267.17
    isooctanol 185.41
    dipropyl ether 442.76
    1,2-dichlorobenzene 410.02
    ethyl lactate 143.09
    propylene carbonate 435.71
    n-methylformamide 192.24
    2-pentanol 194.49
    n-pentane 141.34
    1-propoxy-2-propanol 396.8
    1-methoxy-2-propyl acetate 509.24
    2-(2-methoxypropoxy) propanol 256.2
    mesitylene 334.31
    ε-caprolactone 578.39
    p-cymene 227.72
    epichlorohydrin 839.25
    1,1,1-trichloroethane 597.89
    2-aminoethanol 77.51
    morpholine-4-carbaldehyde 582.9
    sulfolane 683.91
    2,2,4-trimethylpentane 70.35
    2-methyltetrahydrofuran 868.98
    n-hexyl acetate 432.38
    isooctane 81.07
    2-(2-butoxyethoxy)ethanol 321.85
    sec-butyl acetate 236.92
    tert-butyl acetate 430.11
    decalin 115.77
    glycerin 89.31
    diglyme 605.91
    acrylic acid 122.22
    isopropyl myristate 211.34
    n-butyric acid 250.52
    acetyl acetate 319.28
    di(2-ethylhexyl) phthalate 153.77
    ethyl propionate 281.83
    nitromethane 256.94
    1,2-diethoxyethane 366.18
    benzonitrile 332.54
    trioctyl phosphate 144.18
    1-bromopropane 445.59
    gamma-valerolactone 908.57
    n-decanol 146.55
    triethyl phosphate 180.94
    4-methyl-2-pentanol 176.38
    propionitrile 342.66
    vinylene carbonate 396.98
    1,1,2-trichlorotrifluoroethane 343.13
    DMS 371.22
    cumene 198.68
    2-octanol 163.52
    2-hexanone 287.47
    octyl acetate 233.53
    limonene 300.67
    1,2-dimethoxyethane 452.0
    ethyl orthosilicate 182.13
    tributyl phosphate 163.23
    diacetone alcohol 327.11
    N,N-dimethylaniline 258.58
    acrylonitrile 320.91
    aniline 350.3
    1,3-propanediol 140.15
    bromobenzene 563.69
    dibromomethane 547.62
    1,1,2,2-tetrachloroethane 635.08
    2-methyl-cyclohexyl acetate 294.32
    tetrabutyl urea 187.88
    diisobutyl methanol 196.15
    2-phenylethanol 340.13
    styrene 310.94
    dioctyl adipate 219.36
    dimethyl sulfate 307.25
    ethyl butyrate 336.86
    methyl lactate 177.66
    butyl lactate 205.07
    diethyl carbonate 230.23
    propanediol butyl ether 220.06
    triethyl orthoformate 268.78
    p-tert-butyltoluene 245.49
    methyl 4-tert-butylbenzoate 330.17
    morpholine 737.68
    tert-butylamine 209.12
    n-dodecanol 116.94
    dimethoxymethane 562.04
    ethylene carbonate 367.55
    cyrene 229.12
    2-ethoxyethyl acetate 376.45
    2-ethylhexyl acetate 411.33
    1,2,4-trichlorobenzene 449.17
    4-methylpyridine 644.63
    dibutyl ether 312.0
    2,6-dimethyl-4-heptanol 196.15
    DEF 404.73
    dimethyl isosorbide 483.57
    tetrachloroethylene 437.93
    eugenol 262.23
    triacetin 318.37
    span 80 224.21
    1,4-butanediol 60.11
    1,1-dichloroethane 538.88
    2-methyl-1-pentanol 145.85
    methyl formate 197.25
    2-methyl-1-butanol 202.37
    n-decane 87.94
    butyronitrile 341.5
    3,7-dimethyl-1-octanol 210.53
    1-chlorooctane 223.49
    1-chlorotetradecane 103.91
    n-nonane 90.78
    undecane 65.23
    tert-butylcyclohexane 102.66
    cyclooctane 141.07
    cyclopentanol 317.5
    tetrahydropyran 936.5
    tert-amyl methyl ether 323.98
    2,5,8-trioxanonane 384.89
    1-hexene 222.24
    2-isopropoxyethanol 174.12
    2,2,2-trifluoroethanol 75.06
    methyl butyrate 308.71

    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
Abies sachalinensis (Finland) Abies sachalinensis (Fr. Schm.) Mast, fam. Pinaceae 0.2%
Abies mayriana (Finland) Abies mayriana Miy. et Kudo Needle, fam. Pinaceae 0.3%
Pistacia vera fruit hull (Turkey) Pistacia vera L., fam. Anacardiaceae 0.07%
Pinus sylvestris (Yugoslavia) 8023-99-2 Pinus sylvestris L. (Scotch pine), fam. Pinaceae 0.9%