Baicalin

Baicalin

Names
IUPAC name (2S,3S,4S,5R,6S)-6-(5,6-dihydroxy-4-oxo-2-phenyl-chromen-7-yl)oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
Other names Baicalein 7-O-glucuronide; 5,6-Dihydroxy-4-oxygen-2-phenyl-4H-1-benzopyran-7-beta-D-glucopyranose acid
Identifiers
CAS Number	21967-41-9 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:2981 Y
ChemSpider	58507 Y
ECHA InfoCard	100.133.557
PubChem CID	64982
UNII	347Q89U4M5 Y
InChI InChI=1S/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1 Y Key: IKIIZLYTISPENI-ZFORQUDYSA-N Y InChI=1/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1 Key: IKIIZLYTISPENI-ZFORQUDYBD
SMILES O=C3\C=C(/Oc2cc(O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)c(O)c(O)c23)c4ccccc4
Properties
Chemical formula	C21H18O11
Molar mass	446.36 g·mol−1
Melting point	202 to 205 °C (396 to 401 °F; 475 to 478 K)
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

Baicalin is a flavone glycoside. It is the glucuronide of baicalein.

Baicalin is found in several species in the genus Scutellaria, including Scutellaria baicalensis and Scutellaria lateriflora. There are 10 mg/g baicalin in Scutellaria galericulata leaves. It is one of the chemical ingredients of Sho-Saiko-To, an herbal supplement. It is also present in the bark isolate of the Oroxylum indicum tree.

Baicalin, along with its aglycone baicalein, is a positive allosteric modulator of the benzodiazepine site and/or a non-benzodiazepine site of the GABA_A receptor. In mice, baicalin produces anxiolytic effects without sedative or myorelaxant effects. It is thought that baicalin, along with other flavonoids, may underlie the anxiolytic effects of S. baicalensis and S. lateriflora.

Baicalin is a known prolyl endopeptidase inhibitor. It induces apoptosis in pancreatic cancer cells.