Procyanidin A2

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  • Identifiers

    CAS number
    41743-41-3

    Molecular formula
    C30H24O12

    SMILES
    C1[C@H]([C@H](OC2=C1C(=CC3=C2[C@@H]4[C@H]([C@](O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O)C7=CC(=C(C=C7)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 69.5%
    Phenolic 50.25%
    Burnt 28.52%
    Smoky 25.79%
    Vanilla 23.48%
    Spicy 22.35%
    Medicinal 19.8%
    Savory 19.15%
    Balsamic 19.01%
    Bitter 15.29%

     

    Flavor
    Bitter 92.96%
    Bland 27.04%
    Odorless 23.52%
    Sweet-like 23.29%
    Cedarleaf 19.88%
    Parsley 18.83%
    Eugenol 18.72%
    Lovage 18.61%
    Very strong 18.5%
    Indole 18.45%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    9.79 (weak base)

    Molecular weight
    576.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    4043°C

    Melting point expt.

    • 300 °C

    Flash point

    • 333.31 ˚C est.

  • Synonyms

    • Procyanidin A2
    • Proanthocyanidin A2
    • 41743-41-3
    • Proanthocyanidin A-2
    • Epicatechin-(2beta->7,4beta->8)-epicatechin
    • UQN6668Q4R
    • CHEBI:28472
    • (1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
    • (2r,3r,8s,14r,15r)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-2h,14h-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5,11,13,15-pentol
    • LITCHIDERM LS-9704 COMPONENT
    • (1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo(11.7.1.02,11.03,8.015,20)henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
    • (2R,3R,8S,14R,15R)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanochromeno(7,8-d)(1,3)benzodioxocine-3,5,11,13,15-pentol
    • RefChem:47048
    • DTXCID001332096
    • DTXSID00904175
    • Procyanidol A2
    • Procyanidin dimer A2
    • CHEMBL286933
    • (2R,3R,8S,14R,15R)-2,8-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol
    • C30H24O12
    • (+)-Proanthocyanidin A2
    • Dimeric catechin
    • (+)-Epicatechin-(4.beta.-8,2.beta.-O-7)-epicatechin
    • bis(3,4-dihydroxyphenyl)[?]pentol
    • 8,14-Methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R,8S,14R,15R)-
    • Procyanidoepicatechin
    • 8,14-METHANO-2H,14H-1-BENZOPYRANO(7,8-D)(1,3)BENZODIOXOCIN-3,5,11,13,15-PENTOL, 2,8-BIS(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3R,8S,14R,15R)-
    • Procyanidin A2 (Standard)
    • UNII-UQN6668Q4R
    • SCHEMBL981582
    • orb1297536
    • SCHEMBL29373082
    • SCHEMBL29551197
    • SCHEMBL30096674
    • HY-N2343R
    • Procyanidin A2, analytical standard
    • BDBM50478905
    • EC-(4b,8)(2b,7)-EC
    • AKOS037514797
    • EBC-459144
    • FP75067
    • 2,14-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-8,14-methano-2H,8H,14H-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol
    • AC-35008
    • DA-77078
    • Epicatechin-(2b->7,4b->8)-epicatechin
    • MS-30365
    • epicatechin-(2beta->O->7,4beta->8)-epicatechin
    • Q7247550
    • Epicatechin-(4.beta.-->8,2.beta.-->O-->7)epicatechin
    • (1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
    • 8,14-Methano-2H,14H-1,7,9-trioxabenzo[6,7]cycloocta[1,2-a]naphthalene-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R,8S,14R,15R)-
    • 8,14-Methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, [2R-(2.alpha,3.alpha.,8.beta.,14.beta.,15R*)]-
    • 8,14-Methano-2H,8H,14H-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol, 2,14-bis(3,4-dihydroxyphenyl)-3,4-dihydro-
    • Proanthocyanidin A2\, Procyanidol A2\, Procyanidoepicatechin\, Epicatechin-(2beta->7\,4beta->8)-epicatechin
    • 41743-41-3

  • Applications

    Procyanidin A2 is a dimeric proanthocyanidin primarily used as a natural antioxidant and color-related polyphenol. In cosmetics and personal care, it can function as an antioxidant ingredient and formulation stabilizer. In food processing and nutraceuticals, it is evaluated as a natural antioxidant and color stabilizer and may appear as an ingredient in functional foods or dietary supplements. In coatings and inks, it is investigated as a natural colorant and stabilizing additive. In polymer/plastics formulations, it is explored as a natural stabilizer/antioxidant alternative to synthetic additives. In beverages, it may act as a natural pigment source and contribute to tannin-related coloration. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.82
    methanol 17.01
    isopropanol 1.8
    water 0.2
    ethyl acetate 3.24
    n-propanol 4.2
    acetone 2.75
    n-butanol 2.06
    acetonitrile 1.1
    DMF 87.01
    toluene 0.17
    isobutanol 0.99
    1,4-dioxane 10.07
    methyl acetate 4.2
    THF 18.88
    2-butanone 4.02
    n-pentanol 0.69
    sec-butanol 1.48
    n-hexane 0.01
    ethylene glycol 22.23
    NMP 60.04
    cyclohexane 0.01
    DMSO 54.57
    n-butyl acetate 1.25
    n-octanol 0.83
    chloroform 0.38
    n-propyl acetate 1.24
    acetic acid 38.48
    dichloromethane 0.45
    cyclohexanone 3.53
    propylene glycol 24.92
    isopropyl acetate 1.48
    DMAc 69.0
    2-ethoxyethanol 30.36
    isopentanol 0.73
    n-heptane 0.02
    ethyl formate 5.27
    1,2-dichloroethane 0.44
    n-hexanol 0.47
    2-methoxyethanol 123.77
    isobutyl acetate 0.31
    tetrachloromethane 0.06
    n-pentyl acetate 1.58
    transcutol 25.28
    n-heptanol 0.98
    ethylbenzene 0.06
    MIBK 0.68
    2-propoxyethanol 21.63
    tert-butanol 0.79
    MTBE 0.44
    2-butoxyethanol 10.88
    propionic acid 10.13
    o-xylene 0.11
    formic acid 73.5
    diethyl ether 1.13
    m-xylene 0.1
    p-xylene 0.05
    chlorobenzene 0.09
    dimethyl carbonate 10.54
    n-octane 0.01
    formamide 65.38
    cyclopentanone 10.37
    2-pentanone 2.3
    anisole 0.65
    cyclopentyl methyl ether 2.09
    gamma-butyrolactone 22.93
    1-methoxy-2-propanol 60.15
    pyridine 4.5
    3-pentanone 1.63
    furfural 18.12
    n-dodecane 0.01
    diethylene glycol 36.14
    diisopropyl ether 0.12
    tert-amyl alcohol 0.83
    acetylacetone 5.67
    n-hexadecane 0.01
    acetophenone 0.98
    methyl propionate 6.96
    isopentyl acetate 0.73
    trichloroethylene 1.2
    n-nonanol 0.9
    cyclohexanol 0.78
    benzyl alcohol 1.26
    2-ethylhexanol 0.25
    isooctanol 0.53
    dipropyl ether 1.0
    1,2-dichlorobenzene 0.09
    ethyl lactate 5.63
    propylene carbonate 5.6
    n-methylformamide 44.48
    2-pentanol 0.71
    n-pentane 0.01
    1-propoxy-2-propanol 11.78
    1-methoxy-2-propyl acetate 7.03
    2-(2-methoxypropoxy) propanol 7.53
    mesitylene 0.05
    ε-caprolactone 6.71
    p-cymene 0.07
    epichlorohydrin 12.5
    1,1,1-trichloroethane 0.11
    2-aminoethanol 24.09
    morpholine-4-carbaldehyde 73.51
    sulfolane 34.32
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 2.95
    n-hexyl acetate 1.59
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 11.96
    sec-butyl acetate 0.55
    tert-butyl acetate 1.25
    decalin 0.01
    glycerin 94.88
    diglyme 22.31
    acrylic acid 18.31
    isopropyl myristate 0.46
    n-butyric acid 7.69
    acetyl acetate 2.1
    di(2-ethylhexyl) phthalate 0.83
    ethyl propionate 1.67
    nitromethane 50.54
    1,2-diethoxyethane 3.1
    benzonitrile 0.45
    trioctyl phosphate 0.77
    1-bromopropane 0.14
    gamma-valerolactone 59.92
    n-decanol 0.54
    triethyl phosphate 0.95
    4-methyl-2-pentanol 0.26
    propionitrile 1.18
    vinylene carbonate 6.25
    1,1,2-trichlorotrifluoroethane 36.13
    DMS 2.63
    cumene 0.03
    2-octanol 0.48
    2-hexanone 0.76
    octyl acetate 0.97
    limonene 0.1
    1,2-dimethoxyethane 21.0
    ethyl orthosilicate 0.78
    tributyl phosphate 0.68
    diacetone alcohol 6.06
    N,N-dimethylaniline 0.49
    acrylonitrile 3.11
    aniline 0.94
    1,3-propanediol 26.6
    bromobenzene 0.05
    dibromomethane 0.14
    1,1,2,2-tetrachloroethane 1.11
    2-methyl-cyclohexyl acetate 0.64
    tetrabutyl urea 1.42
    diisobutyl methanol 0.17
    2-phenylethanol 0.9
    styrene 0.07
    dioctyl adipate 1.24
    dimethyl sulfate 18.66
    ethyl butyrate 1.43
    methyl lactate 29.78
    butyl lactate 4.57
    diethyl carbonate 1.01
    propanediol butyl ether 12.47
    triethyl orthoformate 1.68
    p-tert-butyltoluene 0.07
    methyl 4-tert-butylbenzoate 2.64
    morpholine 20.17
    tert-butylamine 0.15
    n-dodecanol 0.32
    dimethoxymethane 40.45
    ethylene carbonate 4.21
    cyrene 10.97
    2-ethoxyethyl acetate 5.12
    2-ethylhexyl acetate 0.5
    1,2,4-trichlorobenzene 0.23
    4-methylpyridine 1.65
    dibutyl ether 0.5
    2,6-dimethyl-4-heptanol 0.17
    DEF 9.23
    dimethyl isosorbide 10.34
    tetrachloroethylene 0.8
    eugenol 3.96
    triacetin 4.29
    span 80 6.63
    1,4-butanediol 5.12
    1,1-dichloroethane 0.16
    2-methyl-1-pentanol 0.34
    methyl formate 28.61
    2-methyl-1-butanol 0.96
    n-decane 0.02
    butyronitrile 0.72
    3,7-dimethyl-1-octanol 0.36
    1-chlorooctane 0.12
    1-chlorotetradecane 0.04
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.0
    cyclooctane 0.01
    cyclopentanol 1.92
    tetrahydropyran 2.11
    tert-amyl methyl ether 0.63
    2,5,8-trioxanonane 14.37
    1-hexene 0.03
    2-isopropoxyethanol 7.79
    2,2,2-trifluoroethanol 13.18
    methyl butyrate 2.29

    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