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Cinnamtannin B1

Names
IUPAC name -(2-oxy-7,8→4)--(4→8)-
Systematic IUPAC name (2R,3R,4S,8S,14R,15R)-2,8-Bis(3,4-dihydroxyphenyl)-4--3,4-dihydro-2H,8H,14H-8,14-methanobenzopyranobenzodioxocine-3,5,11,13,15-pentol
Identifiers
CAS Number	88082-60-4
3D model (JSmol)	Interactive image
ChemSpider	417255
PubChem CID	475277
UNII	H1059K9GIN
InChI 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/s1Key: BYSRPHRKESMCPO-LQNPQWRQSA-N InChI=1/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/s1Key: BYSRPHRKESMCPO-LQNPQWRQBE
SMILES Oc1cc(O)c2c(c1)O1((2c2c(O1)cc(c1c2O(c2ccc(c(c2)O)O)(1c1c(O)cc(c2c1O((C2)O)c1ccc(c(c1)O)O)O)O)O)O)c1ccc(c(c1)O)O
Properties
Chemical formula	C45H36O18
Molar mass	864.75 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Cinnamtannin B1 is a condensed tannin found in Cinnamomum verum. It falls under the category of type A proanthocyanidin.

Cinnamon could potentially exhibit pharmacological effects in treating type 2 diabetes mellitus and insulin resistance. The plant material predominantly employed in the study was sourced from Chinese cinnamon (see Chinese cinnamon's medicinal uses). Recent phytochemical research has suggested that cinnamtannin B1, extracted from C. Verum, might have a potential therapeutic impact on type 2 diabetes, with the exception of postmenopausal patients studied using Cinnamomum aromaticum.

Cinnamtannin B1 possesses multiple phenolic hydroxyl groups and is noted for its antioxidant properties, antimicrobial activities, and ability to inhibit platelet aggregation, which could contribute to the protection of damaged tissues in wounds.

References

1. Anderson; Broadhurst, CL; Polansky, MM; Schmidt, WF; Khan, A; Flanagan, VP; Schoene, NW; Graves, DJ (January 2004). "Isolation and characterization of polyphenol type-A polymers from cinnamon with insulin-like biological activity". J Agric Food Chem. 52 (1): 65–70. doi:10.1021/jf034916b. PMID 14709014.
2. Khan A, Safdar M, Ali Khan MM, Khattak KN, Anderson RA (December 2003). "Cinnamon improves glucose and lipids of people with type 2 diabetes". Diabetes Care. 26 (12): 3215–8. doi:10.2337/diacare.26.12.3215. PMID 14633804.
3. Verspohl, Eugen J.; Bauer, K; Neddermann, E; et al. (2005). "Antidiabetic effect of Cinnamomum cassia and Cinnamomum zeylanicum In vivo and In vitro". Phytotherapy Research. 19 (3): 203–206. doi:10.1002/ptr.1643. PMID 15934022. S2CID 32335294.
4. Taher, Muhammad; et al. "A proanthocyanidin from Cinnamomum zeylanicum stimulates phosphorylation of insulin receptor in 3T3-L1 adipocyties" (PDF). Archived from the original (PDF) on 2008-05-28. Retrieved 2008-05-11.
5. Vanschoonbeek, Kristof; et al. (2006). "Cinnamon Supplementation Does Not Improve Glycemic Control in Postmenopausal Type 2 Diabetes Patients". The Journal of Nutrition. 136 (4): 977–980. doi:10.1093/jn/136.4.977. PMID 16549460. Retrieved 2008-05-11.
6. López, J. J., Jardín, I., Salido, G. M., & Rosado, J. A. (2008). Cinnamtannin B-1 as an antioxidant and platelet aggregation inhibitor. Life sciences, 82(19), 977-982. doi:10.1016/j.lfs.2008.03.009
7. ^ Fujita K, Kuge K, Ozawa N, Sahara S, Zaiki K, Nakaoji K, et al. (2015) Cinnamtannin B-1 Promotes Migration of Mesenchymal Stem Cells and Accelerates Wound Healing in Mice. PLoS ONE 10(12): e0144166. doi:10.1371/journal.pone.0144166 This article incorporates text from this source, which is available under the CC BY 4.0 license.

• Procyanidins
• Natural phenol trimers