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MedKoo Cat#: 598522 | Name: Cinnamtannin B1
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cinnamtannin B1 is an A-type proanthocyanidin contained in several plant species such as Laurus nobilis L., Vaccinium vitis-idaea, Parameria laevigata, Cinnamomum zeylanicum and Lindera umbellata. Cinnamtannin B-1 is a potent antioxidant and protective agent against oxidative stress and apoptosis in human platelets. Cinnamtannin B-1 is a Cox-2 (cyclooxygenase-2) inhibitor.

Chemical Structure

Cinnamtannin B1
Cinnamtannin B1
CAS#88082-60-4

Theoretical Analysis

MedKoo Cat#: 598522

Name: Cinnamtannin B1

CAS#: 88082-60-4

Chemical Formula: C45H36O18

Exact Mass: 864.1902

Molecular Weight: 864.76

Elemental Analysis: C, 62.50; H, 4.20; O, 33.30

Price and Availability

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5mg USD 550.00 2 Weeks
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Synonym
Cinnamtannin B1; Cinnamtannin B-1; LDN-0022358; LDN 0022358; LDN0022358; Cinnamtannin B1 (constituent of cinnamomum verum bark) [DSC];
IUPAC/Chemical Name
(2R,3R,4S,8S,14R,15R)-2,8-bis(3,4-dihydroxyphenyl)-4-((2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-8-yl)-3,4-dihydro-2H,14H-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol
InChi Key
BYSRPHRKESMCPO-LQNPQWRQSA-N
InChi Code
InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38-,39-,40-,41-,44-,45+/m1/s1
SMILES Code
OC1=CC([C@H]2OC(C([C@@H]3[C@@H](O)[C@@H](C4=CC=C(O)C(O)=C4)OC5=C3C(O)=CC6=C5[C@@H](C(C(O)=CC(O)=C7)=C7O8)[C@](O)([H])[C@]8(C9=CC=C(O)C(O)=C9)O6)=C(O)C=C%10O)=C%10C[C@H]2O)=CC=C1O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 864.76 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Ito Y, Ohmori K, Suzuki K. Annulation approach to doubly linked (A-type) oligocatechins: syntheses of (+)-procyanidin A₂ and (+)-cinnamtannin B₁. Angew Chem Int Ed Engl. 2014 Sep 15;53(38):10129-33. doi: 10.1002/anie.201405600. Epub 2014 Jul 28. PubMed PMID: 25070773. 2: Wen L, You L, Yang X, Yang J, Chen F, Jiang Y, Yang B. Identification of phenolics in litchi and evaluation of anticancer cell proliferation activity and intracellular antioxidant activity. Free Radic Biol Med. 2015 Jul;84:171-184. doi: 10.1016/j.freeradbiomed.2015.03.023. Epub 2015 Apr 7. PubMed PMID: 25857215. 3: Taher M, Abdul Majid FA, Sarmidi MR. Cinnamtannin B1 activity on adipocytes formation. Med J Malaysia. 2004 May;59 Suppl B:97-8. PubMed PMID: 15468836. 4: Gonzalez A, Santofimia-Castaño P, Rivera-Barreno R, Salido GM. Cinnamtannin B-1, a natural antioxidant that reduces the effects of H(2)O(2) on CCK-8-evoked responses in mouse pancreatic acinar cells. J Physiol Biochem. 2012 Jun;68(2):181-91. doi: 10.1007/s13105-011-0130-2. Epub 2011 Nov 26. PubMed PMID: 22120978. 5: Fujita K, Kuge K, Ozawa N, Sahara S, Zaiki K, Nakaoji K, Hamada K, Takenaka Y, Tanahashi T, Tamai K, Kaneda Y, Maeda A. Cinnamtannin B-1 Promotes Migration of Mesenchymal Stem Cells and Accelerates Wound Healing in Mice. PLoS One. 2015 Dec 11;10(12):e0144166. doi: 10.1371/journal.pone.0144166. eCollection 2015. PubMed PMID: 26657737; PubMed Central PMCID: PMC4686113. 6: Chi Z, Ma X, Cui G, Li M, Li F. Cinnamtannin B-1 regulates cell proliferation of spinal cord astrocytes and protects the cell from oxygen-glucose-serum deprivation/reoxygenation-induced apoptosis. Int J Mol Sci. 2013 Jul 30;14(8):15827-37. doi: 10.3390/ijms140815827. PubMed PMID: 23903044; PubMed Central PMCID: PMC3759888. 7: Rivera-Barreno R, del Castillo-Vaquero A, Salido GM, Gonzalez A. Effect of cinnamtannin B-1 on cholecystokinin-8-evoked responses in mouse pancreatic acinar cells. Clin Exp Pharmacol Physiol. 2010 Oct;37(10):980-8. doi: 10.1111/j.1440-1681.2010.05424.x. PubMed PMID: 20626416. 8: Ben Amor N, Bouaziz A, Romera-Castillo C, Salido S, Linares-Palomino PJ, Bartegi A, Salido GM, Rosado JA. Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets. J Med Chem. 2007 Aug 9;50(16):3937-44. Epub 2007 Jun 29. PubMed PMID: 17602466. 9: Bouaziz A, Salido S, Linares-Palomino PJ, Sanchez A, Altarejos J, Bartegi A, Salido GM, Rosado JA. Cinnamtannin B-1 from bay wood reduces abnormal intracellular Ca2+ homeostasis and platelet hyperaggregability in type 2 diabetes mellitus patients. Arch Biochem Biophys. 2007 Jan 15;457(2):235-42. Epub 2006 Nov 7. PubMed PMID: 17118329. 10: López JJ, Jardín I, Salido GM, Rosado JA. Cinnamtannin B-1 as an antioxidant and platelet aggregation inhibitor. Life Sci. 2008 May 7;82(19-20):977-82. doi: 10.1016/j.lfs.2008.03.009. Epub 2008 Mar 29. Review. PubMed PMID: 18433795. 11: Bouaziz A, Romera-Castillo C, Salido S, Linares-Palomino PJ, Altarejos J, Bartegi A, Rosado JA, Salido GM. Cinnamtannin B-1 from bay wood exhibits antiapoptotic effects in human platelets. Apoptosis. 2007 Mar;12(3):489-98. Epub 2006 Dec 29. PubMed PMID: 17195094. 12: Chen L, Yang Y, Yuan P, Yang Y, Chen K, Jia Q, Li Y. Immunosuppressive Effects of A-Type Procyanidin Oligomers from Cinnamomum tamala. Evid Based Complement Alternat Med. 2014;2014:365258. doi: 10.1155/2014/365258. Epub 2014 Oct 30. PubMed PMID: 25530780; PubMed Central PMCID: PMC4230008. 13: Huh GW, Park JH, Kang JH, Jeong TS, Kang HC, Baek NI. Flavonoids from Lindera glauca Blume as low-density lipoprotein oxidation inhibitors. Nat Prod Res. 2014;28(11):831-4. doi: 10.1080/14786419.2013.879583. Epub 2014 Feb 5. PubMed PMID: 24499267. 14: Esatbeyoglu T, Wray V, Winterhalter P. Isolation of dimeric, trimeric, tetrameric and pentameric procyanidins from unroasted cocoa beans (Theobroma cacao L.) using countercurrent chromatography. Food Chem. 2015 Jul 15;179:278-89. doi: 10.1016/j.foodchem.2015.01.130. Epub 2015 Feb 4. PubMed PMID: 25722166. 15: Engemann A, Hübner F, Rzeppa S, Humpf HU. Intestinal metabolism of two A-type procyanidins using the pig cecum model: detailed structure elucidation of unknown catabolites with Fourier transform mass spectrometry (FTMS). J Agric Food Chem. 2012 Jan 25;60(3):749-57. doi: 10.1021/jf203927g. Epub 2012 Jan 13. PubMed PMID: 22175758. 16: Sun P, Wang T, Chen L, Yu BW, Jia Q, Chen KX, Fan HM, Li YM, Wang HY. Trimer procyanidin oligomers contribute to the protective effects of cinnamon extracts on pancreatic β-cells in vitro. Acta Pharmacol Sin. 2016 Aug;37(8):1083-90. doi: 10.1038/aps.2016.29. Epub 2016 May 30. PubMed PMID: 27238208; PubMed Central PMCID: PMC4973380. 17: Dudek Jamróz MK, Kaźmierski S, Stefaniak K, Gliński VB, Gliński JA. Conformational equilibria in selected A-type trimeric procyanidins. Org Biomol Chem. 2014 Dec 28;12(48):9837-44. doi: 10.1039/c4ob02086c. PubMed PMID: 25355183. 18: Park HJ, Kim SY, Song NY, Cho JG, Kang JH, Jeong TS, Lee DY, Kim GS, Kim YB, Kang HC, Baek NI. Procyanidins from the stem wood of Machilus japonica and their inhibitory effect on LDL oxidation. Arch Pharm Res. 2014 Nov;37(11):1403-10. doi: 10.1007/s12272-013-0304-2. Epub 2013 Dec 3. PubMed PMID: 24297667. 19: Bicker J, Petereit F, Hensel A. Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L. Fitoterapia. 2009 Dec;80(8):483-95. doi: 10.1016/j.fitote.2009.08.015. Epub 2009 Aug 18. PubMed PMID: 19695312. 20: Chen L, Yuan P, Chen K, Jia Q, Li Y. Oxidative conversion of B- to A-type procyanidin trimer: evidence for quinone methide mechanism. Food Chem. 2014 Jul 1;154:315-22. doi: 10.1016/j.foodchem.2014.01.018. Epub 2014 Jan 17. PubMed PMID: 24518348.