PhytoHub: Showing entry for Procyanidin dimer B1

Procyanidin dimer B1

Identification

PhytoHub ID

PHUB000276

Name

Procyanidin dimer B1

Systematic Name

Not Available

Synonyms

(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,
3,3',4',5,7-Pentahydroxyflavan-(4→8)-3,3',4',5,7-pentahydroxyflavan; (2R,2'R,3R,3'S,4α)-form
Epicatechin-(4b,8)-catechin
Proanthocyanidin B1
procyanidin B1

CAS Number

20315-25-7

Average Mass

578.526

Monoisotopic Mass

578.142426277

Chemical Formula

C₃₀H₂₆O₁₂

IUPAC Name

(2R,3S)-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 Key

XFZJEEAOWLFHDH-UKWJTHFESA-N

InChI Identifier

InChI=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+/m0/s1

SMILES

O[C@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC=C(O)C(O)=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.38e-01 g/l
LogS (ALOGPS): -3.62
LogP (ALOGPS): 2.29
Hydrogen Acceptors: 12
Hydrogen Donors: 10
Rotatable Bond Count: 3
Polar Surface Area: 220.75999999999996
Refractivity: 146.508
Polarizability: 55.77368946324186
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -5.176560370760914
pKa (strongest acidic): 8.693248815093794
Number of Rings: 6
Rule of Five: No
Bioavailability: No
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: No

External Links

ChEBI: 75633
ChEBI: 75630
PubChem: 11250133
MetaboLights: MTBLC75633
Phenol-Explorer: 150
FooDB (Compounds): FDB000958
PeakForestCompound: 000242

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Flavonoids
Sub-class: Flavan-3-ols

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Flavonoids
Super-class: Phenylpropanoids and polyketides
Sub-class: Biflavonoids and polyflavonoids
Direct Parent Name: Biflavonoids and polyflavonoids
Alternative Parent Names: ["1-benzopyrans", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-hydroxyflavonoids", "3-hydroxyflavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Alkyl aryl ethers", "B-type proanthocyanidins", "Benzene and substituted derivatives", "Catechins", "Catechols", "Hydrocarbon derivatives", "Oxacyclic compounds", "Polyols", "Secondary alcohols"]
External Descriptor Annotations: ["Proanthocyanidins", "biflavonoid", "hydroxyflavan", "polyphenol", "proanthocyanidin"]
Substituent Names: ["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "3-hydroxyflavonoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Alcohol", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "B-type proanthocyanidin", "Benzenoid", "Benzopyran", "Bi- and polyflavonoid skeleton", "Catechin", "Catechol", "Chromane", "Ether", "Flavan", "Flavan-3-ol", "Hydrocarbon derivative", "Hydroxyflavonoid", "Monocyclic benzene moiety", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Polyol", "Proanthocyanidin", "Secondary alcohol"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Technology	Ion Mode	Collision Energy	View
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, energy0	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, Ionization energy 70 eV fully TMS-derivatized (structure: C[Si](C)(C)O[C@H]1CC2=C(O)C=C(O)C([C@H]3C4=C(O)C=C(O)C=C4O[C@H](C4=CC=C(O)C(O)=C4)[C@@H]3O)=C2O[C@@H]1C1=CC=C(O)C(O)=C1)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: Semi standard non polar)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=C([C@H]2C3=C(O)C=C(O)C=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H]2O)C2=C1C[C@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=C2C[C@H](O)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C1[C@H]1C2=C(O)C=C(O)C=C2O[C@H](C2=CC=C(O)C(O)=C2)[C@@H]1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)O[C@H]1[C@@H](C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C2[C@@H]1C1=C(O)C=C(O)C2=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@@H](O)C2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@H](C1=CC=C(O)C(O)=C1)[C@H](O)[C@H]2C1=C(O)C=C(O)C2=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@@H](O)C2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H](C1=C(O)C=C(O)C3=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@@H](O)C3)[C@@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3[C@H](C3=C(O)C=C(O)C4=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H](O)C4)[C@H]2O)C=C1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3[C@H](C3=C(O)C=C(O)C4=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H](O)C4)[C@H]2O)=CC=C1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC=C([C@H]2OC3=C(C[C@@H]2O)C(O)=CC(O)=C3[C@H]2C3=C(O)C=C(O)C=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H]2O)C=C1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC([C@H]2OC3=C(C[C@@H]2O)C(O)=CC(O)=C3[C@H]2C3=C(O)C=C(O)C=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H]2O)=CC=C1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=C([C@H]2C3=C(O)C=C(O)C=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H]2O)C2=C1C[C@H](O[Si](C)(C)C)[C@@H](C1=CC=C(O)C(O)=C1)O2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=C2C[C@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C1[C@H]1C2=C(O)C=C(O)C=C2O[C@H](C2=CC=C(O)C(O)=C2)[C@@H]1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H](C1=C(O)C=C(O)C3=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@@H](O[Si](C)(C)C)C3)[C@@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@H](C1=CC=C(O)C(O)=C1)[C@H](O)[C@H]2C1=C(O)C=C(O)C2=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@@H](O[Si](C)(C)C)C2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3[C@H](C3=C(O)C=C(O)C4=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H](O[Si](C)(C)C)C4)[C@H]2O)C=C1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3[C@H](C3=C(O)C=C(O)C4=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H](O[Si](C)(C)C)C4)[C@H]2O)=CC=C1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)O[C@H]1CC2=C(O)C=C(O)C([C@H]3C4=C(O)C=C(O)C=C4O[C@H](C4=CC=C(O)C(O)=C4)[C@@H]3O[Si](C)(C)C)=C2O[C@@H]1C1=CC=C(O)C(O)=C1)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC=C([C@H]2OC3=C(C[C@@H]2O[Si](C)(C)C)C(O)=CC(O)=C3[C@H]2C3=C(O)C=C(O)C=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H]2O)C=C1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC([C@H]2OC3=C(C[C@@H]2O[Si](C)(C)C)C(O)=CC(O)=C3[C@H]2C3=C(O)C=C(O)C=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H]2O)=CC=C1O)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C([C@H]2C3=C(O)C=C(O)C=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H]2O)C2=C1C[C@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=C([C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H]2O)C2=C1C[C@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@H](C1=CC=C(O)C(O)=C1)[C@H](O)[C@H]2C1=C(O)C=C(O[Si](C)(C)C)C2=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@@H](O)C2)	Positive	Not Available	View Spectrum
Predicted GC-MS	GC-MS	Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3[C@H](C3=C(O)C=C(O[Si](C)(C)C)C4=C3O[C@H](C3=CC=C(O)C(O)=C3)[C@@H](O)C4)[C@H]2O)C=C1O)	Positive	Not Available	View Spectrum
LC-MS/MS	ESI-TOF	Not Available	Negative	40V	View Spectrum
LC-MS/MS	ESI-TOF	Not Available	Negative	V	View Spectrum
LC-MS/MS	ESI-TOF	Not Available	Negative	10V	View Spectrum
LC-MS/MS	ESI-TOF	Not Available	Negative	30V	View Spectrum
LC-MS/MS	ESI-TOF	Not Available	Negative	20V	View Spectrum
LC-MS/MS	ESI-TOF	Not Available	Negative	50V	View Spectrum
LC-MS/MS	ESI-TOF	From Sumner Library	Negative	40V	View Spectrum
LC-MS/MS	ESI-TOF	From Sumner Library	Negative	V	View Spectrum
LC-MS/MS	ESI-TOF	From Sumner Library	Negative	10V	View Spectrum
LC-MS/MS	ESI-TOF	From Sumner Library	Negative	30V	View Spectrum
LC-MS/MS	ESI-TOF	From Sumner Library	Negative	20V	View Spectrum
LC-MS/MS	ESI-TOF	From Sumner Library	Negative	50V	View Spectrum
LC-MS/MS	LC-ESI-QTOF	instrument=UPLC Q-Tof Premier, Waters	negative	V	View Spectrum
LC-MS/MS	LC-ESI-QTOF	instrument=UPLC Q-Tof Premier, Waters	positive	V	View Spectrum
LC-MS/MS	Not Available	Not Available	Positive	6V	View Spectrum
LC-MS/MS	Not Available	Not Available	Positive	6V	View Spectrum
LC-MS/MS	Not Available	Not Available	Positive	6V	View Spectrum
LC-MS/MS	Not Available	Not Available	Positive	6V	View Spectrum
LC-MS/MS	Not Available	Not Available	Positive	6V	View Spectrum
Predicted LC-MS/MS	Not Available	Predicted by CFM-ID	Positive	10V	View Spectrum
Predicted LC-MS/MS	Not Available	Predicted by CFM-ID	Positive	20V	View Spectrum
Predicted LC-MS/MS	Not Available	Predicted by CFM-ID	Positive	40V	View Spectrum
Predicted LC-MS/MS	Not Available	Predicted by CFM-ID	Negative	10V	View Spectrum
Predicted LC-MS/MS	Not Available	Predicted by CFM-ID	Negative	20V	View Spectrum
Predicted LC-MS/MS	Not Available	Predicted by CFM-ID	Negative	40V	View Spectrum

Food Sources

Name	Group
Apple	Fruit, Pomes	Publications	Show
Apple cider	Beverages, Alcoholic	Publications	Show
Apple juice	Beverages, Non-alcoholic	Publications	Show
Black tea	Teas and herbal teas	Publications	Show
Cocoa	Cocoa and cocoa products	Publications	Show
Peach	Fruit, Drupes	Publications	Show
Strawberry	Fruit, Berries	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

No metabolism information available

Inter-Individual Variations in Metabolism

No data on inter-individual variations available

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Showing entry for Procyanidin dimer B1