Rosmarinic Acid

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  • Identifiers

    CAS number
    20283-92-5

    Molecular formula
    C18H16O8

    SMILES
    C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 73.05%
    Phenolic 27.37%
    Balsamic 26.33%
    Savory 25.09%
    Burnt 24.78%
    Vanilla 23.78%
    Milky 22.24%
    Spicy 20.56%
    Bitter 17.58%
    Cooked 17.09%

     

    Flavor
    Bitter 63.07%
    Odorless 56.23%
    Bland 33.54%
    Mild 30.77%
    Very mild 29.5%
    Sweet-like 23.54%
    Faint 20.56%
    Nitrile 19.8%
    Orange flower 19.74%
    Yeast 19.72%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    9.55 (weak base)

    Molecular weight
    360.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    696°C

    Melting point expt.

    • 171-175 °C

    Flash point

    • 285.43 ˚C est.

    Solubility expt.

    • Soluble in ethanol, DMSO or dimethyl formamide to approximately 25 mg/mL

  • Synonyms

    • rosmarinic acid
    • 20283-92-5
    • Rosemary acid
    • Labiatic acid
    • trans-Rosmarinic acid
    • MQE6XG29YI
    • ORISTRACT ROA
    • (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid
    • (2r)-3-(3,4-Dihydroxyphenyl)-2-{[(2e)-3-(3,4-Dihydroxyphenyl)prop-2-Enoyl]oxy}propanoic Acid
    • RM-21A
    • NPLC-0542
    • DTXSID20896987
    • R-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionic acid
    • CINNAMIC ACID, 3,4-DIHYDROXY-, 2-ESTER with 3-(3,4-DIHYDROXYPHENYL)LACTIC ACID
    • CHEBI:17226
    • Acid, Rosemary
    • Acid, Rosmarinic
    • (2R)-3-(3,4-dihydroxyphenyl)-2-(((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)propanoic acid
    • (2R)-3-(3,4-dihydroxyphenyl)-2-((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxypropanoic acid
    • RefChem:6204
    • DTXCID801326415
    • Labiatenic acid
    • Rosmarinicacid
    • (R)-rosmarinic acid
    • Rosmarinic acid racemate
    • Rosmarimic acid
    • Rosmarinic-acid
    • (R,E)-3-(3,4-dihydroxyphenyl)-2-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)propanoic acid
    • Benzenepropanoic acid,a-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-,(aR)-
    • CHEMBL324842
    • Rosemarinic Acid
    • MFCD00017740
    • (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4- dihydroxyphenyl)lactic acid
    • (2R)-3-(3,4-dihydroxyphenyl)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic acid
    • (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propanoic acid
    • Rosemaric acid
    • Benzenepropanoic acid, alpha-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-
    • UNII-MQE6XG29YI
    • rosmaric acid
    • CCRIS 9361
    • RM 21A
    • 3,4-Dihydroxycinnamic acid (R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl ester
    • HSDB 7688
    • NPLC 0542
    • (2R)-3-(3,4-DIHYDROXYPHENYL)-2-{[3-(3,4-DIHYDROXYPHENYL)PROP-2-ENOYL]OXY}PROPANOIC ACID
    • BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-
    • Benzenepropanoic acid, .alpha.-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-, (.alpha.R)-
    • Rosmarinic acid CRS
    • Rosmarinic acid, 2
    • Rosmarinic acid, 96%
    • bmse000648
    • Rosmarinic acid (Standard)
    • (R)-(+)-Rosmarinic Acid
    • ROSMARINIC ACID [MI]
    • MLS000697677
    • ROSMARINIC ACID [HSDB]
    • MEGxp0_000163
    • orb1305049
    • SCHEMBL1650675
    • SCHEMBL29438187
    • SCHEMBL29453379
    • SCHEMBL30521740
    • ACon1_001068
    • CHEBI:50371
    • CHEBI:92370
    • cid_5281792
    • HY-N0529R
    • ROSMARINIC ACID [USP-RS]
    • HMS2227A13
    • HMS3266D13
    • HMS3411K16
    • HMS3649C22
    • HMS3675K16
    • HMS3885I15
    • HMS6019J06
    • HY-N0529
    • MSK40049
    • BDBM50133496
    • s3612
    • ZB1872
    • 3,4-Dihydroxycinnamic acid 2-ester with 3-(3,4-dihydroxyphenyl)lactic acid
    • AKOS015892734
    • CCG-207919
    • CCG-208268
    • FR02310
    • NCGC00169708-01
    • AC-33965
    • AS-35341
    • SMR000445579
    • SY074011
    • NS00014042
    • C01850
    • EN300-364852
    • 225R532
    • SR-01000946599
    • SR-01000946599-1
    • (2R)-O-caffeoyl-3-(3,4-dihydroxyphenyl)lactic acid
    • BRD-K20313525-001-04-6
    • Q50380051
    • F0001-0715
    • ROSMARINIC ACID (CONSTITUENT OF ROSEMARY) [DSC]
    • 93B6A3BF-927D-4C59-8A49-29BDBC87C194
    • Rosmarinic acid, primary pharmaceutical reference standard
    • ROSMARINIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
    • Rosmarinic acid, European Pharmacopoeia (EP) Reference Standard
    • Rosmarinic acid, >=98% (HPLC), from Rosemarinus officinalis L.
    • Rosmarinic acid, United States Pharmacopeia (USP) Reference Standard
    • (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoicacid
    • (R,E)-3-(3,4-dihydroxyphenyl)-2-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)propanoicacid
    • alpha-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxybenzenepropanoic acid
    • BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-
    • Benzenepropanoic acid, .alpha.-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-, (R-(E))-
    • Benzenepropanoic acid, alpha-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-, (R-(E))-
    • Benzenepropanoic acid,a-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-,[R-(E)]
    • 20283-92-5

  • Applications

    Rosmarinic Acid (CAS 20283-92-5) is widely used as a natural antioxidant and stabilizing agent in cosmetics and personal care formulations, helping protect active ingredients and products from oxidative degradation; it is also employed in food processing as a natural antioxidant to slow lipid oxidation and extend shelf life; in industrial formulations such as polymers, coatings and inks, it functions as an antioxidant stabilizer to mitigate aging and color changes; it is commonly evaluated for use in cleaning products as an antioxidant/antimicrobial additive to improve formulation stability; and it can serve as a synthetic intermediate or starting material for the production of other polyphenolic compounds used in specialty chemicals.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1008.54
    methanol 1251.76
    isopropanol 649.94
    water 16.62
    ethyl acetate 172.82
    n-propanol 635.14
    acetone 1724.23
    n-butanol 256.66
    acetonitrile 186.41
    DMF 981.55
    toluene 7.22
    isobutanol 163.28
    1,4-dioxane 628.76
    methyl acetate 235.3
    THF 2713.57
    2-butanone 589.76
    n-pentanol 123.46
    sec-butanol 320.69
    n-hexane 0.64
    ethylene glycol 490.85
    NMP 193.53
    cyclohexane 1.34
    DMSO 5004.3
    n-butyl acetate 12.03
    n-octanol 24.5
    chloroform 2.85
    n-propyl acetate 33.67
    acetic acid 525.05
    dichloromethane 5.49
    cyclohexanone 146.81
    propylene glycol 390.22
    isopropyl acetate 66.42
    DMAc 943.67
    2-ethoxyethanol 1009.94
    isopentanol 90.08
    n-heptane 1.22
    ethyl formate 116.09
    1,2-dichloroethane 19.11
    n-hexanol 33.89
    2-methoxyethanol 2421.63
    isobutyl acetate 4.96
    tetrachloromethane 0.61
    n-pentyl acetate 14.78
    transcutol 233.12
    n-heptanol 24.62
    ethylbenzene 3.04
    MIBK 56.19
    2-propoxyethanol 235.63
    tert-butanol 540.88
    MTBE 134.26
    2-butoxyethanol 90.36
    propionic acid 192.72
    o-xylene 4.69
    formic acid 574.76
    diethyl ether 192.75
    m-xylene 3.21
    p-xylene 2.62
    chlorobenzene 1.77
    dimethyl carbonate 103.77
    n-octane 1.05
    formamide 1626.83
    cyclopentanone 481.4
    2-pentanone 286.01
    anisole 30.18
    cyclopentyl methyl ether 134.73
    gamma-butyrolactone 404.5
    1-methoxy-2-propanol 927.0
    pyridine 128.97
    3-pentanone 119.39
    furfural 102.02
    n-dodecane 1.01
    diethylene glycol 276.04
    diisopropyl ether 13.52
    tert-amyl alcohol 241.54
    acetylacetone 285.93
    n-hexadecane 1.09
    acetophenone 21.6
    methyl propionate 184.04
    isopentyl acetate 7.57
    trichloroethylene 15.29
    n-nonanol 25.07
    cyclohexanol 88.26
    benzyl alcohol 41.52
    2-ethylhexanol 7.42
    isooctanol 12.16
    dipropyl ether 36.67
    1,2-dichlorobenzene 0.97
    ethyl lactate 27.0
    propylene carbonate 34.62
    n-methylformamide 818.29
    2-pentanol 109.77
    n-pentane 1.23
    1-propoxy-2-propanol 89.53
    1-methoxy-2-propyl acetate 33.08
    2-(2-methoxypropoxy) propanol 49.69
    mesitylene 1.66
    ε-caprolactone 96.21
    p-cymene 1.33
    epichlorohydrin 457.61
    1,1,1-trichloroethane 4.36
    2-aminoethanol 703.03
    morpholine-4-carbaldehyde 313.43
    sulfolane 395.34
    2,2,4-trimethylpentane 0.43
    2-methyltetrahydrofuran 452.35
    n-hexyl acetate 19.51
    isooctane 0.21
    2-(2-butoxyethoxy)ethanol 105.27
    sec-butyl acetate 14.7
    tert-butyl acetate 60.38
    decalin 0.35
    glycerin 500.14
    diglyme 195.38
    acrylic acid 146.42
    isopropyl myristate 9.64
    n-butyric acid 138.16
    acetyl acetate 37.31
    di(2-ethylhexyl) phthalate 5.08
    ethyl propionate 36.42
    nitromethane 1230.88
    1,2-diethoxyethane 70.07
    benzonitrile 7.43
    trioctyl phosphate 6.41
    1-bromopropane 8.7
    gamma-valerolactone 501.24
    n-decanol 19.93
    triethyl phosphate 4.45
    4-methyl-2-pentanol 22.58
    propionitrile 71.42
    vinylene carbonate 20.59
    1,1,2-trichlorotrifluoroethane 120.25
    DMS 13.36
    cumene 1.34
    2-octanol 14.36
    2-hexanone 57.06
    octyl acetate 16.35
    limonene 2.36
    1,2-dimethoxyethane 637.37
    ethyl orthosilicate 4.95
    tributyl phosphate 5.04
    diacetone alcohol 183.67
    N,N-dimethylaniline 12.31
    acrylonitrile 83.25
    aniline 40.35
    1,3-propanediol 870.46
    bromobenzene 0.9
    dibromomethane 2.74
    1,1,2,2-tetrachloroethane 15.83
    2-methyl-cyclohexyl acetate 5.43
    tetrabutyl urea 14.0
    diisobutyl methanol 5.45
    2-phenylethanol 15.85
    styrene 3.57
    dioctyl adipate 12.42
    dimethyl sulfate 109.55
    ethyl butyrate 12.4
    methyl lactate 139.62
    butyl lactate 13.83
    diethyl carbonate 5.74
    propanediol butyl ether 59.25
    triethyl orthoformate 9.47
    p-tert-butyltoluene 1.55
    methyl 4-tert-butylbenzoate 18.18
    morpholine 927.88
    tert-butylamine 86.97
    n-dodecanol 14.99
    dimethoxymethane 1036.88
    ethylene carbonate 24.56
    cyrene 53.51
    2-ethoxyethyl acetate 34.92
    2-ethylhexyl acetate 3.67
    1,2,4-trichlorobenzene 2.05
    4-methylpyridine 51.85
    dibutyl ether 21.53
    2,6-dimethyl-4-heptanol 5.45
    DEF 179.08
    dimethyl isosorbide 44.61
    tetrachloroethylene 8.23
    eugenol 17.8
    triacetin 16.49
    span 80 32.33
    1,4-butanediol 258.13
    1,1-dichloroethane 10.29
    2-methyl-1-pentanol 41.54
    methyl formate 504.37
    2-methyl-1-butanol 91.36
    n-decane 1.7
    butyronitrile 51.77
    3,7-dimethyl-1-octanol 10.21
    1-chlorooctane 4.86
    1-chlorotetradecane 2.29
    n-nonane 1.46
    undecane 1.28
    tert-butylcyclohexane 0.25
    cyclooctane 0.57
    cyclopentanol 256.43
    tetrahydropyran 349.12
    tert-amyl methyl ether 78.68
    2,5,8-trioxanonane 136.65
    1-hexene 4.32
    2-isopropoxyethanol 293.2
    2,2,2-trifluoroethanol 130.47
    methyl butyrate 43.48

    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