Retinoic Acid

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  • Identifiers

    CAS number
    302-79-4

    Molecular formula
    C20H28O2

    SMILES
    CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Woody 69.68%
    Sweet 63.07%
    Floral 58.78%
    Fruity 53.53%
    Balsamic 44.13%
    Powdery 41.88%
    Berry 41.76%
    Tropical 40.62%
    Violet 35.38%
    Citrus 32.35%

     

    Flavor
    Balsam 28.83%
    Woody 27.9%
    Balsamic 24.65%
    Oriental 23.79%
    Spicy 23.29%
    Sweet 21.14%
    Wood 21.06%
    Ocimene 20.7%
    Low 20.52%
    Diterpene 20.45%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.3

    pKa est.
    7.89 (neutral)

    Molecular weight
    300.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    394°C

    Melting point expt.

    • 354 to 360 °F (NTP, 1992)
    • 372 to 374 °F (NTP, 1992)
    • 178-184
    • 180-182 °C
    • 181 °C

    Flash point

    • 208.33 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 77 °F (NTP, 1992)
    • less than 1 mg/mL at 72 °F (NTP, 1992)
    • Practically insoluble in water
    • Soluble in DMSO; slightly soluble in polyethylene glycol 400, octanol, ethanol; practically insoluble in mineral oil, glycerin
    • ... Soluble in ether; slightly soluble in ... chloroform.

  • Synonyms

    • Retinoic acid
    • tretinoin
    • 302-79-4
    • all-trans-Retinoic acid
    • Vitamin A acid
    • trans-Retinoic acid
    • ATRA
    • Aberel
    • Eudyna
    • Renova
    • Dermairol
    • all-trans-Vitamin A acid
    • Cordes vas
    • Retin A
    • Tretin M
    • Atralin
    • all-trans-Tretinoin
    • Retionic acid
    • all-trans-Vitamin A1 acid
    • beta-Ra
    • Retin-A Micro
    • Vitamin A1 acid, all-trans-
    • beta-Retinoic acid
    • Tretinoina
    • all-(E)-Retinoic acid
    • All Trans Retinoic Acid
    • Vitamin A acid, all-trans-
    • NSC-122758
    • Retinoic acid, all-trans-
    • Betarretin
    • Tretinoinum
    • A-Acido (Argentina)
    • Stieva-A
    • all trans-Retinoic acid
    • Aberela [Norway]
    • Avitoin [Norway]
    • Acnavit [Denmark]
    • Effederm [France]
    • Kerlocal
    • Refissa
    • Oristar rna
    • all-trans-beta-Retinoic acid
    • Cordes VAS [Germany]
    • Retisol-A
    • A-Vitaminsyre [Denmark]
    • Tretinoin/All-Trans Retinoic Acid
    • (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
    • Acid A Vit (Belgium, Netherlands)
    • DTXSID7021239
    • ALTRENO
    • 2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-
    • Acid, all-trans-Retinoic
    • 5688UTC01R
    • DTXCID001239
    • CHEBI:15367
    • TWYNEO COMPONENT TRETINOIN
    • VELTIN COMPONENT TRETINOIN
    • Aberela (Norway)
    • Avitoin (Norway)
    • Acnavit (Denmark)
    • Effederm (France)
    • 3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoic acid
    • Cordes VAS (Germany)
    • A-Vitaminsyre (Denmark)
    • Acid, Retinoic
    • 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
    • Acid, Vitamin A
    • 3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2E,4E,6E,8E-tetraenoic acid
    • trans Retinoic Acid
    • Acid, trans-Retinoic
    • Salt, Tretinoin Zinc
    • Zinc Salt, Tretinoin
    • Salt, Tretinoin Sodium
    • Sodium Salt, Tretinoin
    • Potassium Salt, Tretinoin
    • Salt, Tretinoin Potassium
    • beta all trans Retinoic Acid
    • Acid, beta-all-trans-Retinoic
    • Tretinoin Cream
    • Acide retinoique
    • Tretin-X
    • [All-E]-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
    • RefChem:6318
    • RETIN-A-MICRO
    • 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid
    • Tretinoin (Microsphere)
    • DERMAWERX ZMT PAK
    • D10AD01
    • L01XX14
    • ZINC OXIDE, MENTHOL, UNSPECIFIED FORM, and TRETINOIN
    • 3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
    • 206-129-0
    • CHEBI:26536
    • Retin-A
    • Vesanoid
    • Airol
    • Aknoten
    • All-trans Retinoic Acid
    • Epi-aberel
    • Aknefug
    • TRETINON
    • (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
    • Tretinoine
    • Alltrans-retinoic acid
    • Retinoate
    • MFCD00001551
    • Retacnyl
    • Vesnaroid
    • Ro 1-5488
    • Tretinoin, all-trans-
    • .beta.-Retinoic acid
    • RETINOIC ACID, ALL TRANS
    • 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
    • (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
    • MLS000028588
    • Retinoic acid (GMP)
    • Tretinoine [INN-French]
    • Tretinoinum [INN-Latin]
    • AT-RA
    • Tretinoina [INN-Spanish]
    • Tretinoino [INN-Spanish]
    • CHEMBL38
    • (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic acid
    • NSC122758
    • Retinova
    • SMR000058245
    • 15-Apo-beta-caroten-15-oic acid
    • 302-79-4

  • Applications

    Retinoic Acid (CAS 302-79-4) is used in cosmetics and personal care as a retinoid in topical formulations to influence skin-cell differentiation; in pharmaceutical manufacturing it serves as an intermediate in the synthesis of retinoid-related compounds and other vitamin A derivatives; in laboratory settings it is a common bioactive reagent for cell biology and biochemistry research, including differentiation studies in cultured cells; in industrial manufacturing it functions as a synthetic intermediate for preparing related retinoids and vitamin A derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 140.7
    methanol 139.69
    isopropanol 50.99
    water 0.02
    ethyl acetate 54.22
    n-propanol 107.78
    acetone 32.47
    n-butanol 104.4
    acetonitrile 10.95
    DMF 81.59
    toluene 45.42
    isobutanol 50.24
    1,4-dioxane 143.33
    methyl acetate 29.48
    THF 383.57
    2-butanone 69.55
    n-pentanol 85.61
    sec-butanol 66.19
    n-hexane 6.55
    ethylene glycol 1.66
    NMP 75.02
    cyclohexane 5.45
    DMSO 32.38
    n-butyl acetate 65.22
    n-octanol 30.6
    chloroform 77.45
    n-propyl acetate 44.7
    acetic acid 14.47
    dichloromethane 58.95
    cyclohexanone 90.0
    propylene glycol 8.45
    isopropyl acetate 44.85
    DMAc 105.61
    2-ethoxyethanol 92.9
    isopentanol 70.68
    n-heptane 4.23
    ethyl formate 19.79
    1,2-dichloroethane 39.46
    n-hexanol 101.05
    2-methoxyethanol 118.6
    isobutyl acetate 41.28
    tetrachloromethane 7.76
    n-pentyl acetate 45.3
    transcutol 340.1
    n-heptanol 43.56
    ethylbenzene 26.21
    MIBK 55.38
    2-propoxyethanol 168.03
    tert-butanol 54.57
    MTBE 86.84
    2-butoxyethanol 88.28
    propionic acid 14.15
    o-xylene 22.16
    formic acid 6.68
    diethyl ether 111.3
    m-xylene 35.86
    p-xylene 26.31
    chlorobenzene 29.3
    dimethyl carbonate 10.55
    n-octane 1.76
    formamide 11.02
    cyclopentanone 88.07
    2-pentanone 74.95
    anisole 66.98
    cyclopentyl methyl ether 115.08
    gamma-butyrolactone 61.85
    1-methoxy-2-propanol 111.82
    pyridine 79.37
    3-pentanone 44.06
    furfural 47.13
    n-dodecane 1.19
    diethylene glycol 44.12
    diisopropyl ether 22.41
    tert-amyl alcohol 63.69
    acetylacetone 42.39
    n-hexadecane 1.38
    acetophenone 46.24
    methyl propionate 40.39
    isopentyl acetate 71.55
    trichloroethylene 63.5
    n-nonanol 31.46
    cyclohexanol 44.41
    benzyl alcohol 44.62
    2-ethylhexanol 50.42
    isooctanol 35.96
    dipropyl ether 61.15
    1,2-dichlorobenzene 25.27
    ethyl lactate 19.28
    propylene carbonate 30.42
    n-methylformamide 27.78
    2-pentanol 53.61
    n-pentane 5.22
    1-propoxy-2-propanol 117.36
    1-methoxy-2-propyl acetate 87.04
    2-(2-methoxypropoxy) propanol 80.36
    mesitylene 20.32
    ε-caprolactone 78.47
    p-cymene 17.56
    epichlorohydrin 116.5
    1,1,1-trichloroethane 26.58
    2-aminoethanol 17.42
    morpholine-4-carbaldehyde 99.56
    sulfolane 55.9
    2,2,4-trimethylpentane 3.61
    2-methyltetrahydrofuran 189.83
    n-hexyl acetate 61.21
    isooctane 3.4
    2-(2-butoxyethoxy)ethanol 115.22
    sec-butyl acetate 45.32
    tert-butyl acetate 60.74
    decalin 4.85
    glycerin 9.89
    diglyme 168.68
    acrylic acid 7.16
    isopropyl myristate 23.54
    n-butyric acid 42.06
    acetyl acetate 17.09
    di(2-ethylhexyl) phthalate 25.84
    ethyl propionate 40.49
    nitromethane 18.73
    1,2-diethoxyethane 115.22
    benzonitrile 26.1
    trioctyl phosphate 16.11
    1-bromopropane 44.0
    gamma-valerolactone 137.08
    n-decanol 21.3
    triethyl phosphate 21.79
    4-methyl-2-pentanol 34.17
    propionitrile 22.98
    vinylene carbonate 24.26
    1,1,2-trichlorotrifluoroethane 38.99
    DMS 26.56
    cumene 19.23
    2-octanol 25.56
    2-hexanone 63.34
    octyl acetate 30.13
    limonene 25.02
    1,2-dimethoxyethane 152.18
    ethyl orthosilicate 27.46
    tributyl phosphate 18.3
    diacetone alcohol 68.66
    N,N-dimethylaniline 49.95
    acrylonitrile 16.96
    aniline 42.96
    1,3-propanediol 35.76
    bromobenzene 27.4
    dibromomethane 42.2
    1,1,2,2-tetrachloroethane 60.78
    2-methyl-cyclohexyl acetate 55.24
    tetrabutyl urea 28.39
    diisobutyl methanol 24.26
    2-phenylethanol 66.25
    styrene 26.3
    dioctyl adipate 34.71
    dimethyl sulfate 12.25
    ethyl butyrate 48.15
    methyl lactate 15.27
    butyl lactate 37.6
    diethyl carbonate 22.29
    propanediol butyl ether 53.84
    triethyl orthoformate 40.75
    p-tert-butyltoluene 18.32
    methyl 4-tert-butylbenzoate 54.56
    morpholine 246.31
    tert-butylamine 36.37
    n-dodecanol 14.01
    dimethoxymethane 116.61
    ethylene carbonate 20.56
    cyrene 59.57
    2-ethoxyethyl acetate 67.57
    2-ethylhexyl acetate 59.72
    1,2,4-trichlorobenzene 30.29
    4-methylpyridine 85.66
    dibutyl ether 36.34
    2,6-dimethyl-4-heptanol 24.26
    DEF 72.09
    dimethyl isosorbide 140.15
    tetrachloroethylene 31.99
    eugenol 58.48
    triacetin 43.25
    span 80 66.45
    1,4-butanediol 12.41
    1,1-dichloroethane 31.1
    2-methyl-1-pentanol 74.36
    methyl formate 12.49
    2-methyl-1-butanol 68.88
    n-decane 2.67
    butyronitrile 44.15
    3,7-dimethyl-1-octanol 31.7
    1-chlorooctane 15.39
    1-chlorotetradecane 4.78
    n-nonane 2.29
    undecane 1.72
    tert-butylcyclohexane 5.73
    cyclooctane 2.09
    cyclopentanol 36.67
    tetrahydropyran 202.48
    tert-amyl methyl ether 70.05
    2,5,8-trioxanonane 109.07
    1-hexene 37.18
    2-isopropoxyethanol 66.78
    2,2,2-trifluoroethanol 2.54
    methyl butyrate 51.22

    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