Record Information
Version1.0
Creation date2010-04-08 22:10:03 UTC
Update date2018-05-02 12:53:13 UTC
Primary IDFDB012204
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProcyanidin B2
DescriptionProcyanidin B2, also known as procyanidol B2 or ec-(4b,8)-ec, belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Thus, procyanidin B2 is considered to be a flavonoid lipid molecule. Procyanidin B2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Procyanidin B2 is found, on average, in the highest concentration in a few different foods, such as cocoa powders, chocolates, and broad beans and in a lower concentration in rubus (blackberry, raspberry), yellow wax beans, and hot chocolates. Procyanidin B2 has also been detected, but not quantified in, several different foods, such as green zucchinis, apple ciders, bilberries, alcoholic beverages, and chickpea. This could make procyanidin B2 a potential biomarker for the consumption of these foods.
CAS Number29106-49-8
Structure
Thumb
Synonyms
SynonymSource
EC-(4b,8)-ecChEBI
Epicathechin-(4beta->8)-epicathechinChEBI
Proanthocyanidin b2ChEBI
Procyanidol b2ChEBI
Epicathechin-(4b->8)-epicathechinGenerator
Epicathechin-(4β->8)-epicathechinGenerator
(+)-Procyanidin b2HMDB
2,3-cis-ProanthocyanidinHMDB
cis,Cis"-4,8"-bi(3,3',4',5,7-pentahydroxyflavane)HMDB
Procyanidin dimer b2HMDB
(+)-Procyanidin B2biospider
cis,cis"-4,8"-Bi(3,3',4',5,7-pentahydroxyflavane)biospider
EC-(4b,8)-ECdb_source
Proanthocyanidin B2db_source
Procyanidin B2db_source
Procyanidin dimer B2manual
Procyanidol B2biospider
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.29ALOGPS
logP3.12ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area220.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity146.51 m³·mol⁻¹ChemAxon
Polarizability57.15 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H26O12
IUPAC name(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1
InChI KeyXFZJEEAOWLFHDH-NFJBMHMQSA-N
Isomeric SMILES[H][C@]1([C@@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C(O)C=C(O)C2=C1O[C@@H]([C@H](O)C2)C1=CC(O)=C(O)C=C1
Average Molecular Weight578.526
Monoisotopic Molecular Weight578.142426277
Classification
Description belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
Substituents
  • B-type proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Catechin
  • Flavan-3-ol
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Foods
  • Cocoa and cocoa products
  • Nuts and legumes:

    Fruits and vegetables:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateNot Available
    Physical DescriptionNot Available
    Mass CompositionC 62.28%; H 4.53%; O 33.19%DFC
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical Rotation[a]D +26 (H2O)DFC
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03mj-0500790000-0d28ce5601f00c17eaa5JSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9400124000-e693e1a36e8e5fdd34e2JSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0551-0790100000-ba210c828673adbc07c8JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0300090000-f0366f761dd35900f408JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0000190000-82899b68a12b3ff7f0a3JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0050950000-7c3e401e0cdbb5a2fabaJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0191600000-9a516f7211ac18d6e0feJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-052r-0191600000-9a516f7211ac18d6e0feJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0551-0790100000-ba210c828673adbc07c8JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0300090000-f0366f761dd35900f408JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0000190000-82899b68a12b3ff7f0a3JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0050950000-7c3e401e0cdbb5a2fabaJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-052r-0191600000-9a516f7211ac18d6e0feJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-052r-0391200000-f0bdc661ae52358a3a75JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-002u-0290300000-42d1534f346f0b46137eJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0ika-0019605000-2910ce23bfd62dd5d6b1JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0550-0291810000-cae7840ddc5a7ce6e9c3JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0970640000-534c1d685846bd293495JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0551-0790100000-ba210c828673adbc07c8JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0000190000-82899b68a12b3ff7f0a3JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0050950000-7c3e401e0cdbb5a2fabaJSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0110980000-5100aeb456b72604bfbeJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0334920000-f9222e1bae7f0bca6417JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0076-0491110000-c8af712677eef1677727JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000290000-ae7911e8a6b7e2e8867eJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kbr-0920440000-53d4ef58d673c17bbbb2JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0910000000-851c43689a6c620aa704JSpectraViewer
    ChemSpider ID109417
    ChEMBL IDCHEMBL38714
    KEGG Compound IDC17639
    Pubchem Compound ID122738
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID151
    DrugBank IDNot Available
    HMDB IDHMDB33973
    CRC / DFC (Dictionary of Food Compounds) IDHGT19-P:HFC08-X
    EAFUS IDNot Available
    Dr. Duke IDPROANTHOCYANIDIN-B2|EPICATECHIN-(4-BETA->8)5-EPICATECHIN|PROCYANIDIN-B-2
    BIGG IDNot Available
    KNApSAcK IDC00009077
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID151
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    beta-adrenergic receptor blocker37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.CHEBI
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).