Berberine

Berberine
Names
	IUPAC name 9,10-Dimethoxy-7,8,13,13a-tetradehydro-2′H-[1,3]dioxolo[4′,5′:2,3]berbin-7-ium
	Systematic IUPAC name 9,10-Dimethoxy-5,6-dihydro-2H-7λ5-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ylium
	Other names Umbellatine;; 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;; 7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium
Identifiers
CAS Number	2086-83-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	3570374
ChEBI	CHEBI:16118 ;
ChEMBL	ChEMBL12089 ;
ChemSpider	2263 ;
DrugBank	DB04115 ;
ECHA InfoCard	100.016.572
EC Number	218-229-1;
KEGG	C00757;
PubChem CID	2353;
UNII	0I8Y3P32UF ;
CompTox Dashboard (EPA)	DTXSID9043857 ;
	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 Key: YBHILYKTIRIUTE-UHFFFAOYSA-N ; 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	336.366 g·mol−1
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). verify (what is ?) Infobox references

Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids, occurring naturally as a secondary metabolite in some plants including species of Berberis, from which its name is derived.

Due to their yellow pigmentation, raw Berberis materials were once commonly used to dye wool, leather, and wood. Under ultraviolet light, berberine shows a strong yellow fluorescence, making it useful in histology for staining heparin in mast cells. As a natural dye, berberine has a color index of 75160.

Names


IUPAC name 9,10-Dimethoxy-7,8,13,13a-tetradehydro-2′H-[1,3]dioxolo[4′,5′:2,3]berbin-7-ium
Systematic IUPAC name 9,10-Dimethoxy-5,6-dihydro-2H-7λ⁵-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ylium
Other names Umbellatine; 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium; 7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium
Identifiers
CAS Number	2086-83-1^N
3D model (JSmol)	Interactive image
Beilstein Reference	3570374
ChEBI	CHEBI:16118^Y
ChEMBL	ChEMBL12089^N
ChemSpider	2263^Y
DrugBank	DB04115^Y
ECHA InfoCard	100.016.572
EC Number	218-229-1
KEGG	C00757
PubChem CID	2353
UNII	0I8Y3P32UF^Y
CompTox Dashboard (EPA)	DTXSID9043857
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	336.366 g·mol⁻¹
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 verify (what is ^YN ?) Infobox references