procyanidin B1

2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-(4,8-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol

CAS: 20315-25-7 C30 H26 O12 MW: 578.52762000

Identification

Nameprocyanidin B1
IUPAC(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
CAS Number20315-25-7
FDA UNII0566J48E7X
Molecular FormulaC30 H26 O12
Molecular Weight578.52762000
MDL NumberMFCD01861512
Nikkaji NumberJ56.252A

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 955.30 °C. @ 760.00 mm Hg (est)
Flash Point 989.00 °F. TCC ( 531.60 °C. ) (est)
logP (o/w) 0.300 (est)
Soluble in water, 20.86 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for procyanidin B1 usage levels up tonot for fragrance use.
Recommendation for procyanidin B1 flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

apple fruit apple fruit juice apple leaf apple pericarp bean fava bean bean fava bean testa bilberry fruit bilberry leaf cacao cassia bark cinnamomum spp. cinnamon ceylon cinnamon bark grape leaf grape pericarp grape seed guava bark guava leaf hazelnut bark lingonberry malus spp. pomegranate fruit rubus spp. star fruit wine red wine

Synonyms

(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 PubMed: Phenolic compounds, organic acids and antioxidant activity of grape juices produced from new Brazilian varieties planted in the Northeast Region of Brazil. PubMed: Development of a fluorometric microplate antiadhesion assay using uropathogenic Escherichia coli and human uroepithelial cells. PubMed: Variation of quantitative composition of phenolic compounds in rowan (Sorbus aucuparia L.) leaves during the growth season. PubMed: Inhibitory activity of synthesized acetylated Procyanidin B1 analogs against HeLa S3 cells proliferation. PubMed: The phenolic content and its involvement in the graft incompatibility process of various pear rootstocks (Pyrus communis L.). PubMed: Peroxidase as the major protein constituent in areca nut and identification of its natural substrates. PubMed: Radical-scavenging-linked antioxidant activities of extracts from black chokeberry and blueberry cultivated in Korea. PubMed: Polyphenols and triterpenes from Chaenomeles fruits: chemical analysis and antioxidant activities assessment. PubMed: Effect of growing zone and vintage on the prediction of extractable flavanols in winegrape seeds by a FT-NIR method. PubMed: A targeted metabolomics approach to understand differences in flavonoid biosynthesis in red and yellow raspberries. PubMed: Effect of pyrogallol on the physiology and biochemistry of litchi fruit during storage. PubMed: Evaluation of cardiovascular protective effect of different apple varieties - Correlation of response with composition. PubMed: Ultrasound-assisted extraction, HPLC analysis, and antioxidant activity of polyphenols from unripe apple. PubMed: Antithrombin effect of polyphenol-rich extracts from black chokeberry and grape seeds. PubMed: The relationship between antiglycation activity and procyanidin and phenolic content in commercial grape seed products. PubMed: HPLC-DAD-ESI-MS analysis of flavonoid compounds in 5 seedless table grapes grown in Apulian Region. PubMed: Characterization of polyphenolic metabolites in the seeds of Vitis germplasm. PubMed: Flavangenol (pine bark extract) and its major component procyanidin B1 enhance fatty acid oxidation in fat-loaded models. PubMed: Omega-3 docosahexaenoic acid and procyanidins inhibit cyclo-oxygenase activity and attenuate NF-κB activation through a p105/p50 regulatory mechanism in macrophage inflammation. PubMed: Inhibition of ulcerative colitis in mice after oral administration of a polyphenol-enriched cocoa extract is mediated by the inhibition of STAT1 and STAT3 phosphorylation in colon cells. PubMed: Procyanidin dimer B1 and trimer C1 impair inflammatory response signalling in human monocytes. PubMed: Effects of thermal and high hydrostatic pressure processing and storage on the content of polyphenols and some quality attributes of fruit smoothies. PubMed: Flavan-3-ol compounds from wine wastes with in vitro and in vivo antioxidant activity. PubMed: Plasma protein binding of polyphenols from maritime pine bark extract (USP). PubMed: Procyanidin B1 purified from Cinnamomi cortex suppresses hepatitis C virus replication. PubMed: Phenolic compounds in different barley varieties: identification by tandem mass spectrometry (QStar) and NMR; quantification by liquid chromatography triple quadrupole-linear ion trap mass spectrometry (Q-Trap). PubMed: Isolation and identification of antioxidant and hyaluronidase inhibitory compounds from Ficus microcarpa L. fil. bark. PubMed: Influence of apple polyphenols on inflammatory gene expression. PubMed: Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L. PubMed: Procyanidins and butanol extract of Cinnamomi Cortex inhibit SARS-CoV infection. PubMed: Densitometric determination of (+)-catechin and (-)-epicatechin by 4-dimethylaminocinnamaldehyde reagent. PubMed: An analysis on flavonoids, phenolics and organic acids contents in brewed red wines of both non-skin contact and skin contact fermentation techniques of Mao Luang ripe fruits (Antidesma bunius) harvested from Phupan Valley in Northeast Thailand. PubMed: An analysis on flavonoids contents in Mao Luang fruits of fifteen cultivars (Antidesma bunius), grown in northeast Thailand. PubMed: Tyrosinase inhibition by extracts and constituents of Sideroxylon inerme L. stem bark, used in South Africa for skin lightening. PubMed: Structure of polymeric polyphenols of cinnamon bark deduced from condensation products of cinnamaldehyde with catechin and procyanidins. PubMed: Analysis of CYP3A inhibitory components of star fruit (Averrhoa carambola L.) using liquid chromatography-mass spectrometry. PubMed: [Evaluation of gambir quality based on quantitative analysis of polyphenolic constituents]. PubMed: Revised structures of gambiriins A1, A2, B1, and B2, chalcane-flavan dimers from gambir (Uncaria gambir extract). PubMed: Unravelling the total antioxidant capacity of pinotage wines: contribution of phenolic compounds. PubMed: Separation of eight selected flavan-3-ols on cellulose thin-layer chromatographic plates. PubMed: Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases. PubMed: Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. PubMed: Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance. PubMed: Varietal differences among the polyphenol profiles of seven table grape cultivars studied by LC-DAD-MS-MS.