Berberine

Berberine

Names
Other names umbellatine; 5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
Identifiers
CAS Number	2086-83-1 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16118 Y
ChEMBL	ChEMBL12089 N
ChemSpider	2263 Y
DrugBank	DB04115 Y
ECHA InfoCard	100.016.572
PubChem	2353
UNII	0I8Y3P32UF Y
InChI InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1 Y Key: YBHILYKTIRIUTE-UHFFFAOYSA-N Y InChI=1/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1 Key: YBHILYKTIRIUTE-UHFFFAOYAJ
SMILES O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5
Properties
Chemical formula	C20H18NO4+
Molar mass	336.36122 g/mol
Appearance	yellow solid
Melting point	145 °C (293 °F; 418 K)
Solubility in water	slowly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids. It is found in such plants as Berberis (e.g. Berberis vulgaris (barberry), Berberis aristata (tree turmeric)), Mahonia aquifolium (Oregon grape), Hydrastis canadensis (goldenseal), Xanthorhiza simplicissima (yellowroot), Phellodendron amurense (Amur cork tree), Coptis chinensis (Chinese goldthread), Tinospora cordifolia, Argemone mexicana (prickly poppy), and Eschscholzia californica (Californian poppy). Berberine is usually found in the roots, rhizomes, stems, and bark.

Due to berberine's strong yellow color, Berberis species were used to dye wool, leather, and wood. Wool is still dyed with berberine today in northern India. Under ultraviolet light, berberine shows a strong yellow fluorescence, so it is used in histology for staining heparin in mast cells. As a natural dye, berberine has a colour index of 75160.

Berberine was supposedly used in China as a folk medicine by Shennong around 3000 BC. This first recorded use of Berberine is described in the ancient Chinese medical book The Divine Farmer's Herb-Root Classic.