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MedKoo Cat#: 330128 | Name: Columbianadin
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Description:

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

Columbianadin, also known as CBN, is a natural coumarin from Angelica decursiva (Umbelliferae). CBN is known to have various biological activities including anti-inflammatory and anti-cancer effects.

Chemical Structure

Columbianadin
CAS#5058-13-9

Theoretical Analysis

MedKoo Cat#: 330128

Name: Columbianadin

CAS#: 5058-13-9

Chemical Formula: C19H20O5

Exact Mass: 328.1311

Molecular Weight: 328.36

Elemental Analysis: C, 69.50; H, 6.14; O, 24.36

Price and Availability

Size Price Availability Quantity
25mg USD 450.00 2 Weeks
100mg USD 1,150.00 2 Weeks
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Related CAS #
No Data
Synonym
Columbianadin; Columbianetin; CBN; Columbianetin angelate; Zosimin
IUPAC/Chemical Name
(S)-2-(2-Oxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-yl)propan-2-yl (Z)-2-Methylbut-2-enoate
InChi Key
JRIBPWOXWIRQOQ-GHAIFCDISA-N
InChi Code
InChI=1S/C19H20O5/c1-5-11(2)18(21)24-19(3,4)15-10-13-14(22-15)8-6-12-7-9-16(20)23-17(12)13/h5-9,15H,10H2,1-4H3/b11-5-/t15-/m0/s1
SMILES Code
C/C=C(C)\C(OC(C)([C@@H](O1)CC2=C1C=CC3=C2OC(C=C3)=O)C)=O
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 328.36 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: Yang YF, Zhang L, Yang XW. Distribution Assessments of Coumarins from Angelicae Pubescentis Radix in Rat Cerebrospinal Fluid and Brain by Liquid Chromatography Tandem Mass Spectrometry Analysis. Molecules. 2018 Jan 20;23(1). pii: E225. doi: 10.3390/molecules23010225. PubMed PMID: 29361720. 2: Yang YF, Zhang L, Zhang YB, Yang XW. Simultaneous assessment of absorption characteristics of coumarins from Angelicae Pubescentis Radix: In vitro transport across Caco-2 cell and in vivo pharmacokinetics in rats after oral administration. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Aug 15;1060:308-315. doi: 10.1016/j.jchromb.2017.06.020. Epub 2017 Jun 13. PubMed PMID: 28654868. 3: Li R, Zhao C, Yao M, Song Y, Wu Y, Wen A. Analgesic effect of coumarins from Radix angelicae pubescentis is mediated by inflammatory factors and TRPV1 in a spared nerve injury model of neuropathic pain. J Ethnopharmacol. 2017 Jan 4;195:81-88. doi: 10.1016/j.jep.2016.11.046. Epub 2016 Nov 30. PubMed PMID: 27915078. 4: Li YC, Wang LY, Li R, Wu YZ, Guo QL, Qu YH, Wang SJ, Yang YC, Lin S. [Chemical constituents from ethyl acetate exaction of root of Paeonia lactiflora]. Zhongguo Zhong Yao Za Zhi. 2016 Jun;41(12):2255-2260. doi: 10.4268/cjcmm20161214. Chinese. PubMed PMID: 28901069. 5: Yrjönen T, Eeva M, Kauppila TJ, Martiskainen O, Summanen J, Vuorela P, Vuorela H. Profiling of Coumarins in Peucedanum palustre (L.) Moench Populations Growing in Finland. Chem Biodivers. 2016 Jun;13(6):700-9. doi: 10.1002/cbdv.201500198. Epub 2016 May 24. PubMed PMID: 27133212. 6: Kang JI, Hong JY, Choi JS, Lee SK. Columbianadin Inhibits Cell Proliferation by Inducing Apoptosis and Necroptosis in HCT116 Colon Cancer Cells. Biomol Ther (Seoul). 2016 May 1;24(3):320-7. doi: 10.4062/biomolther.2015.145. PubMed PMID: 27098859; PubMed Central PMCID: PMC4859796. 7: Yang YF, Xu W, Song W, Ye M, Yang XW. Transport of Twelve Coumarins from Angelicae Pubescentis Radix across a MDCK-pHaMDR Cell Monolayer-An in Vitro Model for Blood-Brain Barrier Permeability. Molecules. 2015 Jun 25;20(7):11719-32. doi: 10.3390/molecules200711719. PubMed PMID: 26121397. 8: Zhang YB, Yang XW. Tissue distribution study of columbianadin and its active metabolite columbianetin in rats. Biomed Chromatogr. 2016 Feb;30(2):256-62. doi: 10.1002/bmc.3543. Epub 2015 Aug 17. PubMed PMID: 26115176. 9: Chang YX, Wang CP, Li J, Bai Y, Luo Q, He J, Lu B, Wang T, Zhang BL, Gao XM. LC-MS/MS determination and pharmacokinetic study of columbianadin in rat plasma after intravenous administration of pure columbianadin. Chem Cent J. 2014 Nov 21;8(1):64. doi: 10.1186/s13065-014-0064-1. eCollection 2014. PubMed PMID: 25550710; PubMed Central PMCID: PMC4280029. 10: Sarkhail P. Traditional uses, phytochemistry and pharmacological properties of the genus Peucedanum: a review. J Ethnopharmacol. 2014 Oct 28;156:235-70. doi: 10.1016/j.jep.2014.08.034. Epub 2014 Sep 3. Review. PubMed PMID: 25193684. 11: Lim HJ, Lee JH, Choi JS, Lee SK, Kim YS, Kim HP. Inhibition of airway inflammation by the roots of Angelica decursiva and its constituent, columbianadin. J Ethnopharmacol. 2014 Sep 11;155(2):1353-61. doi: 10.1016/j.jep.2014.07.033. Epub 2014 Jul 25. PubMed PMID: 25068578. 12: Dai D, Pei L, Tang L, Chen F, Chen X. LC-MS/MS determination of bakkenolide D in rats plasma and its application in pharmacokinetic studies. Biomed Chromatogr. 2013 Sep;27(9):1200-7. doi: 10.1002/bmc.2927. Epub 2013 May 30. PubMed PMID: 23723093. 13: Zhang YB, Li W, Yang XW. Biotransformation of columbianadin by rat hepatic microsomes and inhibition of biotransformation products on NO production in RAW 264.7 cells in vitro. Phytochemistry. 2012 Sep;81:109-16. doi: 10.1016/j.phytochem.2012.06.015. Epub 2012 Jul 9. PubMed PMID: 22784551. 14: Bahadır O, Çitoğlu GS, Ozbek H, Dall'Acqua S, Hošek J, Smejkal K. Hepatoprotective and TNF-α inhibitory activity of Zosima absinthifolia extracts and coumarins. Fitoterapia. 2011 Apr;82(3):454-9. doi: 10.1016/j.fitote.2010.12.007. Epub 2010 Dec 24. PubMed PMID: 21185922. 15: Zhang YB, Yang XW. A simple RP-HPLC method for quantification of columbianadin in rat plasma and its application to pharmacokinetic study. Biomed Chromatogr. 2010 Apr;24(4):433-7. doi: 10.1002/bmc.1310. PubMed PMID: 19662622. 16: Yang XW, Guo QM, Wang Y. [Absorption and transport of 6 coumarins isolated from the roots of Angelica pubescens f. biserrata in human Caco-2 cell monolayer model]. Zhong Xi Yi Jie He Xue Bao. 2008 Apr;6(4):392-8. doi: 10.3736/jcim20080413. Chinese. PubMed PMID: 18405608. 17: Wu YN, Luan LB. [In situ rats single pass perfusion intestinal absorption of the effectivein components in Radix Angelicae Pubescentis]. Yao Xue Xue Bao. 2008 Jan;43(1):102-7. Chinese. PubMed PMID: 18357742. 18: Yang XW, Xu B, Ran FX, Wang RQ, Wu J, Cui JR. [Inhibitory effects of 11 coumarin compounds against growth of human bladder carcinoma cell line E-J in vitro]. Zhong Xi Yi Jie He Xue Bao. 2007 Jan;5(1):56-60. Chinese. PubMed PMID: 17214937. 19: Muckensturm B, Boulanger A, Ouahabi S, Reduron JP. A new irregular diterpenoid from Opopanax chironium. Fitoterapia. 2005 Dec;76(7-8):768-70. Epub 2005 Oct 17. PubMed PMID: 16229971. 20: Tammela P, Wennberg T, Vuorela H, Vuorela P. HPLC micro-fractionation coupled to a cell-based assay for automated on-line primary screening of calcium antagonistic components in plant extracts. Anal Bioanal Chem. 2004 Oct;380(4):614-8. Epub 2004 Aug 21. PubMed PMID: 15322796.