Cinnamtannin B-1

Specifications / Handling

More Information
Product Details
Synonyms	Epicatechin-(4β→8,2β→O→7)-epicatechin-(4α→8)-epicatechin; Cinnamtannin B1; CB1
Product Type	Chemical
Properties
Formula	C₄₅H₃₆O₁₈
MW	864.7
CAS	88082-60-4
Source/Host Chemicals	Isolated from Laurus nobilis L.
Purity Chemicals	≥95% (HPLC)
Appearance	Brown solid.
Solubility	Soluble in ethanol, methanol or a DMSO:water mixture.
Identity	Determined by ¹H-NMR.
Other Product Data	Stable in methanol solution for up to 4 weeks when stored at -20°C.
InChi Key	BYSRPHRKESMCPO-LQNPQWRQSA-N
Smiles	O[C@@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=C5[C@@H]6[C@@H](O)[C@@](OC7=CC(O)=CC(O)=C67)(OC5=CC(O)=C34)C3=CC(O)=C(O)C=C3)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC(O)=C(O)C=C1
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Keep under inert gas. Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

A-Type proanthocyanidine.
Selective cytotoxic agent [1].
Potent antioxidant [2, 4, 8, 9].
Lipid peroxidation inhibitor [2].
Antidiabetic, with similar effects to insulin activity in adipogenesis [3].
Free radical scavenger [4].
Antithrombotic. Inhibits platelet aggregation [5, 6, 8].
Apoptosis inhibitor [7, 12].
Reduces intracellular Ca(2+) overload and ROS production [8, 10].
Antibacterial [9].
Cyclooxygenase-2 (COX-2) inhibitor in vitro [11].
LDL oxidation inhibitor [13].

Product References

Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents: Y. Kashiwada, et al.; J. Nat. Prod. 55, 1033 (1992)
Antioxidant activity of tannin components from Vaccinium vitis-idaea L: K.Y. Ho, et al.; J. Pharm. Pharmacol. 51, 1075 (1999)
Cinnamtannin B1 activity on adipocytes formation: M. Taher, et al.; Med. J. Malaysia 59, 97 (2004)
Phenolic constituents in the fruits of Cinnamomum zeylanicum and their antioxidant activity: G.K. Jayaprakasha, et al.; J. Agric. Food Chem. 54, 1672 (2006)
Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets: N. Ben Amor, et al.; J. Med. Chem. 50, 3937 (2007)
Cinnamtannin B-1 from bay wood reduces abnormal intracellular Ca2+ homeostasis and platelet hyperaggregability in type 2 diabetes mellitus patients: A. Bouaziz, et al.; Arch. Biochem. Biophys. 457, 235 (2007)
Cinnamtannin B-1 from bay wood exhibits antiapoptotic effects in human platelets: A. Bouaziz, et al.; Apoptosis 12, 489 (2007)
Cinnamtannin B-1 as an antioxidant and platelet aggregation inhibitor: J.J. López, et al.; Life Sci. 82, 977 (2008)
Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties : T.O. Idowu, et al.; Phytochemistry 71, 2092 (2010)
Effect of cinnamtannin B-1 on cholecystokinin-8-evoked responses in mouse pancreatic acinar cells: R. Rivera-Barreno, et al.; Clin. Exp. Pharmacol. Physiol. 37, 980 (2010)
Bioactive A-type proanthocyanidins from Cinnamomum cassia: K.B. Killday, et al.; J. Nat. Prod. 74, 1833 (2011)
Cinnamtannin B-1 regulates cell proliferation of spinal cord astrocytes and protects the cell from oxygen-glucose-serum deprivation/reoxygenation-induced apoptosis: Z. Chi, et al.; Int. J. Mol. Sci. 14, 15827 (2013)
Flavonoids from Lindera glauca Blume as low-density lipoprotein oxidation inhibitors: G.W. Huh, et al.; Nat. Prod. Res. 28, 831 (2014)
Quantitative and fngerprint analysis of proanthocyanidins and phenylpropanoids in Cinnamomum verum bark, Cinnamomum cassia bark, and Cassia twig by UPLC combined with chemometrics: C. Liu, et al.; Eur. Food Res. Technol. (2021)
Recovery and Seasonal Variation of Cinnamtannin B-1 from Laurel (Laurus nobilis L.) Pruning Wood Wastes: A. Alejo-Armijo, et al.; Chem. Biodivers. e202100807 ahead of print (2022)

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