Procyanidin B1

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  • Identifiers

    CAS number
    20315-25-7

    Molecular formula
    C30H26O12

    SMILES
    C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O

    Safety labels

    Corrosive
    Corrosive

  • Odor profile

    Fragrance
    Odorless 69.73%
    Phenolic 50.71%
    Burnt 30.03%
    Smoky 26.31%
    Vanilla 22.17%
    Spicy 21.88%
    Medicinal 20.73%
    Savory 19.87%
    Balsamic 18.06%
    Bitter 15.94%

     

    Flavor
    Bitter 91.86%
    Bland 26.9%
    Odorless 26.36%
    Sweet-like 23.71%
    Cedarleaf 20.19%
    Eugenol 18.98%
    Parsley 18.93%
    Very strong 18.89%
    Indole 18.78%
    Lovage 18.77%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    9.92 (weak base)

    Molecular weight
    578.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    4570°C

    Melting point expt.

    • 231 - 232 °C

    Flash point

    • 330.32 ˚C est.

  • Synonyms

    • Procyanidin B1
    • 20315-25-7
    • Proanthocyanidin B1
    • CHEBI:75633
    • DTXSID401030238
    • 0566J48E7X
    • (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
    • (4,8-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-
    • 2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-(4,8-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol
    • (2R,3S)-2-(3,4-dihydroxyphenyl)-8-((2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl)-3,4-dihydro-2H-chromene-3,5,7-triol
    • RefChem:45384
    • DTXCID301515340
    • Endotelon
    • Procyanidin dimer B1
    • (2R,2'R,3R,3'S,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichromane]-3,3',5,5',7,7'-hexaol
    • MFCD01861512
    • Epicatechin-(4beta->8)-ent-epicatechin
    • (+)-PROCYANIDIN B1
    • [4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3R,3'S,4R)-
    • EC-(4b,8)-C
    • C30H26O12
    • Procyanidin D
    • Procyanidol D
    • procyandin B1
    • Procyanidin-B1
    • UNII-0566J48E7X
    • procyanidin B-1
    • procyanidin-B-2
    • (4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, 2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-, (2R,2'R,3R,3'S,4R)-
    • PROCYANIDOL B1
    • Procyanidin B1 (Standard)
    • Epicatechin(4b->8)catechin
    • cis,trans''-4,8''-Bi-(3,3',4',5,7-Pentahydroxyflavane)
    • SCHEMBL676745
    • Epicatechin(4beta->8)catechin
    • CHEMBL504937
    • orb1296133
    • SCHEMBL29640987
    • SCHEMBL29761662
    • SCHEMBL29833218
    • SCHEMBL30096664
    • HY-N0795R
    • epicatechin-(4beta->8)-catechin
    • PROCYANIDIN B1, (+)-
    • 71328-22-8
    • HY-N0795
    • Procyanidin B1, analytical standard
    • BDBM50553252
    • LMPK12030001
    • MSK000324
    • AKOS030530133
    • CS-5955
    • EBC-615786
    • FP45625
    • AC-34943
    • AS-78072
    • DA-57055
    • 4,8-Bi-(3,3',4',5,7-Pentahydroxyflavane)
    • Q7247551
    • (-)-EPICATECHIN-(4.BETA.-8)-(+)-CATECHIN
    • BRD-K72093555-001-01-0
    • BRD-K72093555-001-02-8
    • PROCYANIDIN B1 (CONSTITUENT OF MARITIME PINE) [DSC]
    • (2R,2'R,3R,3'S,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichroman]-3,3',5,5',7,7'-hexaol
    • (2R,2'R,3R,3'S,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol
    • (2R,3R,4R)-2-(3,4-DIHYDROXYPHENYL)-4-[(2R,3S)-2-(3,4-DIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-3,4-DIHYDRO-2H-1-BENZOPYRAN-8-YL]-3,4-DIHYDRO-2H-1-BENZOPYRAN-3,5,7-TRIOL
    • (2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]chromane-3,5,7-triol
    • (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol
    • (4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, 2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-, (2R-(2.ALPHA.,3.ALPHA.,4.BETA.(2'R*,3'S*)))-
    • 20315-25-7

  • Applications

    Procyanidin B1, CAS 20315-25-7, is a natural proanthocyanidin in the tannin class, used primarily as an antioxidant and stabilizer in cosmetics and personal care formulations; it is also evaluated for food processing applications as an antioxidant ingredient and evaluated for potential natural colorant roles; in the leather industry it acts as a tanning agent for processing and finishing hides; in coatings and inks it may contribute as a natural stabilizer and color source; in polymers and plastics it is explored as a natural antioxidant stabilizer to improve aging resistance; and in early stage nutraceutical or pharmaceutical research it is being evaluated for potential bioactive polyphenol applications. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.73
    methanol 5.19
    isopropanol 0.45
    water 0.06
    ethyl acetate 1.11
    n-propanol 1.44
    acetone 1.35
    n-butanol 0.71
    acetonitrile 0.45
    DMF 50.85
    toluene 0.07
    isobutanol 0.31
    1,4-dioxane 6.09
    methyl acetate 1.44
    THF 11.45
    2-butanone 1.98
    n-pentanol 0.2
    sec-butanol 0.45
    n-hexane 0.0
    ethylene glycol 7.94
    NMP 29.9
    cyclohexane 0.0
    DMSO 40.36
    n-butyl acetate 0.32
    n-octanol 0.38
    chloroform 0.13
    n-propyl acetate 0.37
    acetic acid 14.95
    dichloromethane 0.14
    cyclohexanone 1.64
    propylene glycol 10.39
    isopropyl acetate 0.47
    DMAc 39.0
    2-ethoxyethanol 18.47
    isopentanol 0.25
    n-heptane 0.01
    ethyl formate 2.19
    1,2-dichloroethane 0.15
    n-hexanol 0.12
    2-methoxyethanol 77.66
    isobutyl acetate 0.09
    tetrachloromethane 0.02
    n-pentyl acetate 0.54
    transcutol 16.14
    n-heptanol 0.36
    ethylbenzene 0.02
    MIBK 0.27
    2-propoxyethanol 11.12
    tert-butanol 0.24
    MTBE 0.18
    2-butoxyethanol 6.14
    propionic acid 3.31
    o-xylene 0.04
    formic acid 29.56
    diethyl ether 0.37
    m-xylene 0.04
    p-xylene 0.02
    chlorobenzene 0.03
    dimethyl carbonate 3.44
    n-octane 0.0
    formamide 27.93
    cyclopentanone 5.38
    2-pentanone 1.03
    anisole 0.28
    cyclopentyl methyl ether 0.81
    gamma-butyrolactone 10.75
    1-methoxy-2-propanol 33.06
    pyridine 2.3
    3-pentanone 0.64
    furfural 10.49
    n-dodecane 0.0
    diethylene glycol 16.78
    diisopropyl ether 0.03
    tert-amyl alcohol 0.29
    acetylacetone 2.73
    n-hexadecane 0.0
    acetophenone 0.38
    methyl propionate 2.47
    isopentyl acetate 0.21
    trichloroethylene 0.48
    n-nonanol 0.42
    cyclohexanol 0.24
    benzyl alcohol 0.48
    2-ethylhexanol 0.08
    isooctanol 0.2
    dipropyl ether 0.38
    1,2-dichlorobenzene 0.03
    ethyl lactate 2.06
    propylene carbonate 2.11
    n-methylformamide 20.11
    2-pentanol 0.2
    n-pentane 0.0
    1-propoxy-2-propanol 5.65
    1-methoxy-2-propyl acetate 2.63
    2-(2-methoxypropoxy) propanol 4.4
    mesitylene 0.02
    ε-caprolactone 2.85
    p-cymene 0.02
    epichlorohydrin 7.4
    1,1,1-trichloroethane 0.04
    2-aminoethanol 10.35
    morpholine-4-carbaldehyde 44.86
    sulfolane 21.15
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 1.37
    n-hexyl acetate 0.65
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 7.24
    sec-butyl acetate 0.15
    tert-butyl acetate 0.45
    decalin 0.0
    glycerin 46.61
    diglyme 14.45
    acrylic acid 6.13
    isopropyl myristate 0.19
    n-butyric acid 2.8
    acetyl acetate 0.73
    di(2-ethylhexyl) phthalate 0.34
    ethyl propionate 0.57
    nitromethane 23.78
    1,2-diethoxyethane 1.55
    benzonitrile 0.17
    trioctyl phosphate 0.31
    1-bromopropane 0.05
    gamma-valerolactone 41.34
    n-decanol 0.24
    triethyl phosphate 0.32
    4-methyl-2-pentanol 0.07
    propionitrile 0.42
    vinylene carbonate 2.19
    1,1,2-trichlorotrifluoroethane 19.59
    DMS 0.84
    cumene 0.01
    2-octanol 0.17
    2-hexanone 0.29
    octyl acetate 0.41
    limonene 0.03
    1,2-dimethoxyethane 14.42
    ethyl orthosilicate 0.29
    tributyl phosphate 0.27
    diacetone alcohol 2.68
    N,N-dimethylaniline 0.2
    acrylonitrile 1.23
    aniline 0.33
    1,3-propanediol 10.97
    bromobenzene 0.02
    dibromomethane 0.05
    1,1,2,2-tetrachloroethane 0.38
    2-methyl-cyclohexyl acetate 0.21
    tetrabutyl urea 0.64
    diisobutyl methanol 0.06
    2-phenylethanol 0.29
    styrene 0.02
    dioctyl adipate 0.57
    dimethyl sulfate 7.55
    ethyl butyrate 0.49
    methyl lactate 11.36
    butyl lactate 1.81
    diethyl carbonate 0.31
    propanediol butyl ether 7.33
    triethyl orthoformate 0.67
    p-tert-butyltoluene 0.02
    methyl 4-tert-butylbenzoate 1.23
    morpholine 11.9
    tert-butylamine 0.05
    n-dodecanol 0.13
    dimethoxymethane 20.8
    ethylene carbonate 1.36
    cyrene 5.71
    2-ethoxyethyl acetate 2.16
    2-ethylhexyl acetate 0.14
    1,2,4-trichlorobenzene 0.08
    4-methylpyridine 0.73
    dibutyl ether 0.25
    2,6-dimethyl-4-heptanol 0.06
    DEF 3.9
    dimethyl isosorbide 5.83
    tetrachloroethylene 0.25
    eugenol 1.84
    triacetin 1.78
    span 80 3.67
    1,4-butanediol 1.78
    1,1-dichloroethane 0.05
    2-methyl-1-pentanol 0.1
    methyl formate 13.27
    2-methyl-1-butanol 0.33
    n-decane 0.01
    butyronitrile 0.27
    3,7-dimethyl-1-octanol 0.16
    1-chlorooctane 0.05
    1-chlorotetradecane 0.02
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.64
    tetrahydropyran 0.94
    tert-amyl methyl ether 0.24
    2,5,8-trioxanonane 8.77
    1-hexene 0.01
    2-isopropoxyethanol 3.78
    2,2,2-trifluoroethanol 4.55
    methyl butyrate 0.84

    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