(S)-lipoic acid

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  • Identifiers

    CAS number
    1077-27-6

    Molecular formula
    C8H14O2S2

    SMILES
    C1CSS[C@H]1CCCCC(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Meaty 55.75%
    Roasted 50.25%
    Sulfurous 44.28%
    Savory 38.93%
    Nutty 36.9%
    Cooked 34.7%
    Fatty 34.52%
    Beefy 24.84%
    Onion 22.89%
    Cheesy 20.86%

     

    Flavor
    Fatty 33.8%
    Odorless 29.78%
    Sulfury 28.2%
    Sulfurous 27.48%
    Mild 26.76%
    Fruity 24.89%
    Tropical 24.35%
    Cheese 24.05%
    Roasted 23.76%
    Oily 23.35%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.7

    pKa est.
    6.08 (neutral)

    Molecular weight
    206.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 60.5 °C

    Boiling point

    • 162.5 °C

    Flash point

    • 179.26 ˚C est.

    Solubility expt.

    • Insoluble
    • 2.24e-01 g/L

  • Synonyms

    • 1077-27-6
    • (S)-lipoic acid
    • 5-[(3S)-dithiolan-3-yl]pentanoic acid
    • (S)-Thioctic Acid
    • (-)-Thioctic Acid
    • (S)-(-)-lipoic acid
    • Thioctic acid l-form
    • 5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid
    • L-6-thioctic acid
    • L-6,8-thioctic acid
    • S-Lipoate
    • Thioctic acid, (-)-
    • L-1,2-dithiolane 3-valeric acid
    • s-(-)-alpha-lipoic acid
    • UNII-J2Y905FQ57
    • (S)-1,2-Dithiolane-3-pentanoic acid
    • ESLIPOIC ACID
    • 1,2-Dithiolane-3-pentanoic acid, (3S)-
    • J2Y905FQ57
    • CHEBI:43796
    • DTXSID40904735
    • THIOCTIC ACID L-FORM [MI]
    • S-(-)-.ALPHA.-LIPOIC ACID
    • .ALPHA.-LIPOIC ACID, (-)-
    • 5-((3S)-dithiolan-3-yl)pentanoic acid
    • 5-((3S)-1,2-dithiolan-3-yl)pentanoic acid
    • RefChem:70490
    • DTXCID601333842
    • ALPHA-LIPOIC ACID, (-)-
    • (S)-5-(1,2-Dithiolan-3-yl)pentanoic acid
    • (S)-alpha-Lipoic Acid
    • L-Thioctic acid
    • S-LA
    • (s)-(-)-alpha-lipoic acid
    • lipoic acid
    • MFCD01863481
    • (3S)-1,2-Dithiolane-3-pentanoic Acid
    • (S)-(-)-a-Lipoic Acid
    • 1,2-Dithiolane-3-pentanoic acid, (S)-
    • C8H14O2S2
    • SLA
    • thioctic-acid
    • (+)-1,2-Dithiolane-3-valeric Acid
    • Lopac-T-5625
    • (S)-(-)-?-Lipoic acid
    • (S)-(-)-a -Lipoic acid
    • orb2939763
    • SCHEMBL2128472
    • (S)-(-)-|A -Lipoic acid
    • CHEMBL1234071
    • AKOS016842424
    • CS-W015306
    • EBC-253308
    • FL24905
    • HY-W014590
    • NCGC00016032-01
    • AS-35195
    • SY258856
    • (S)-5-(1,2-Dithiolan-3-yl)pentanoicacid
    • NS00120065
    • ( inverted exclamation markA)-|A-Lipoic acid
    • EN300-7416584
    • (S)-(-)-alpha -Lipoic acid, >=97% (HPLC)
    • 077L276
    • F091890
    • Q21097956
    • Z1269169215
    • 1077-27-6

  • Applications

    (S)-lipoic acid, CAS 1077-27-6 is used in several real-world applications: as a dietary supplement ingredient due to its antioxidant properties; as an antioxidant additive and stabilizer in cosmetics and personal care formulations; as a chiral building block and intermediate in organic synthesis and pharmaceutical manufacturing; as an antioxidant stabilizer in polymers, plastics, and coatings to improve oxidative stability and durability; and as a reducing agent or precursor for thiol-containing compounds in chemical synthesis, and as a source of dithiol-containing building blocks for research and metal complex preparation.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 184.79
    methanol 202.84
    isopropanol 121.12
    water 0.24
    ethyl acetate 459.55
    n-propanol 136.38
    acetone 710.06
    n-butanol 118.57
    acetonitrile 85.62
    DMF 1113.24
    toluene 115.28
    isobutanol 105.54
    1,4-dioxane 451.15
    methyl acetate 287.1
    THF 1102.75
    2-butanone 438.45
    n-pentanol 127.8
    sec-butanol 105.47
    n-hexane 2.42
    ethylene glycol 90.07
    NMP 953.67
    cyclohexane 7.08
    DMSO 1975.21
    n-butyl acetate 290.23
    n-octanol 64.34
    chloroform 268.66
    n-propyl acetate 328.21
    acetic acid 346.49
    dichloromethane 217.77
    cyclohexanone 735.7
    propylene glycol 167.96
    isopropyl acetate 355.63
    DMAc 880.07
    2-ethoxyethanol 500.91
    isopentanol 141.6
    n-heptane 2.6
    ethyl formate 219.14
    1,2-dichloroethane 227.6
    n-hexanol 137.36
    2-methoxyethanol 704.51
    isobutyl acetate 217.54
    tetrachloromethane 30.82
    n-pentyl acetate 197.85
    transcutol 2165.28
    n-heptanol 77.97
    ethylbenzene 48.7
    MIBK 313.09
    2-propoxyethanol 494.37
    tert-butanol 221.35
    MTBE 180.41
    2-butoxyethanol 266.88
    propionic acid 262.1
    o-xylene 72.4
    formic acid 191.09
    diethyl ether 92.35
    m-xylene 104.16
    p-xylene 65.31
    chlorobenzene 181.87
    dimethyl carbonate 211.73
    n-octane 1.48
    formamide 357.91
    cyclopentanone 1227.68
    2-pentanone 435.98
    anisole 242.72
    cyclopentyl methyl ether 407.99
    gamma-butyrolactone 1244.87
    1-methoxy-2-propanol 659.68
    pyridine 404.04
    3-pentanone 230.35
    furfural 1125.02
    n-dodecane 1.69
    diethylene glycol 480.97
    diisopropyl ether 49.65
    tert-amyl alcohol 178.77
    acetylacetone 916.36
    n-hexadecane 2.13
    acetophenone 326.41
    methyl propionate 372.66
    isopentyl acetate 295.79
    trichloroethylene 729.55
    n-nonanol 60.4
    cyclohexanol 172.0
    benzyl alcohol 264.25
    2-ethylhexanol 82.34
    isooctanol 72.34
    dipropyl ether 59.32
    1,2-dichlorobenzene 205.42
    ethyl lactate 194.1
    propylene carbonate 665.44
    n-methylformamide 463.07
    2-pentanol 88.08
    n-pentane 1.92
    1-propoxy-2-propanol 364.49
    1-methoxy-2-propyl acetate 493.09
    2-(2-methoxypropoxy) propanol 329.91
    mesitylene 64.62
    ε-caprolactone 694.62
    p-cymene 41.14
    epichlorohydrin 1081.58
    1,1,1-trichloroethane 210.92
    2-aminoethanol 190.93
    morpholine-4-carbaldehyde 1250.87
    sulfolane 1761.11
    2,2,4-trimethylpentane 3.59
    2-methyltetrahydrofuran 557.7
    n-hexyl acetate 246.38
    isooctane 4.11
    2-(2-butoxyethoxy)ethanol 506.58
    sec-butyl acetate 233.0
    tert-butyl acetate 468.44
    decalin 6.21
    glycerin 358.37
    diglyme 906.71
    acrylic acid 260.26
    isopropyl myristate 81.98
    n-butyric acid 437.64
    acetyl acetate 324.73
    di(2-ethylhexyl) phthalate 108.56
    ethyl propionate 240.7
    nitromethane 847.9
    1,2-diethoxyethane 310.7
    benzonitrile 264.24
    trioctyl phosphate 70.86
    1-bromopropane 51.53
    gamma-valerolactone 1734.81
    n-decanol 44.6
    triethyl phosphate 99.26
    4-methyl-2-pentanol 78.69
    propionitrile 87.8
    vinylene carbonate 536.41
    1,1,2-trichlorotrifluoroethane 840.45
    DMS 252.03
    cumene 39.11
    2-octanol 54.74
    2-hexanone 306.4
    octyl acetate 111.63
    limonene 53.59
    1,2-dimethoxyethane 601.63
    ethyl orthosilicate 90.5
    tributyl phosphate 97.28
    diacetone alcohol 624.04
    N,N-dimethylaniline 146.73
    acrylonitrile 179.8
    aniline 225.66
    1,3-propanediol 276.83
    bromobenzene 162.54
    dibromomethane 112.36
    1,1,2,2-tetrachloroethane 562.13
    2-methyl-cyclohexyl acetate 184.73
    tetrabutyl urea 136.76
    diisobutyl methanol 54.6
    2-phenylethanol 228.97
    styrene 67.47
    dioctyl adipate 155.57
    dimethyl sulfate 493.27
    ethyl butyrate 196.18
    methyl lactate 304.04
    butyl lactate 222.92
    diethyl carbonate 125.45
    propanediol butyl ether 347.5
    triethyl orthoformate 140.31
    p-tert-butyltoluene 42.73
    methyl 4-tert-butylbenzoate 257.05
    morpholine 615.95
    tert-butylamine 72.26
    n-dodecanol 31.88
    dimethoxymethane 556.47
    ethylene carbonate 429.91
    cyrene 388.01
    2-ethoxyethyl acetate 384.66
    2-ethylhexyl acetate 201.1
    1,2,4-trichlorobenzene 266.72
    4-methylpyridine 429.75
    dibutyl ether 62.48
    2,6-dimethyl-4-heptanol 54.6
    DEF 473.37
    dimethyl isosorbide 587.01
    tetrachloroethylene 315.3
    eugenol 279.69
    triacetin 338.76
    span 80 283.83
    1,4-butanediol 143.96
    1,1-dichloroethane 175.94
    2-methyl-1-pentanol 133.55
    methyl formate 342.74
    2-methyl-1-butanol 115.94
    n-decane 2.8
    butyronitrile 111.47
    3,7-dimethyl-1-octanol 82.65
    1-chlorooctane 25.74
    1-chlorotetradecane 9.51
    n-nonane 2.32
    undecane 2.1
    tert-butylcyclohexane 6.26
    cyclooctane 2.94
    cyclopentanol 236.31
    tetrahydropyran 311.34
    tert-amyl methyl ether 136.64
    2,5,8-trioxanonane 592.88
    1-hexene 19.4
    2-isopropoxyethanol 356.16
    2,2,2-trifluoroethanol 190.28
    methyl butyrate 357.58

    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