Baicalin

Not to be confused with baicalein.

Baicalin is the glucuronide of the polyphenolic compound baicalein.

Baicalin

Names
IUPAC name 5,6-Dihydroxy-4-oxoflav-2-en-7-yl β-D-glucopyranosiduronic acid
Systematic IUPAC name (2S,3S,4S,5R,6S)-6-[(5,6-Dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Other names Baicalein 7-O-glucuronide; 5,6-Dihydroxy-4-oxygen-2-phenyl-4H-1-benzopyran-7-β-D-glucopyranose acid
Identifiers
CAS Number	21967-41-9 N
3D model (JSmol)	Interactive image
Beilstein Reference	70480
ChEBI	CHEBI:2981 Y
ChEMBL	ChEMBL485818 Y
ChemSpider	58507 Y
ECHA InfoCard	100.133.557
EC Number	606-866-1
KEGG	C10025
PubChem CID	64982
UNII	347Q89U4M5 Y
CompTox Dashboard (EPA)	DTXSID701346569
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	446.364 g·mol−1
Melting point	202 to 205 °C (396 to 401 °F; 475 to 478 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
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

Natural occurrences

Baicalin is found in several species in the genus Scutellaria, including Scutellaria baicalensis,^[1] and Scutellaria lateriflora. There are 10 mg/g baicalin in Scutellaria galericulata leaves.^[2] It is also present in the bark isolate of the Oroxylum indicum tree.

Medical uses

Baicalin is one of the chemical ingredients of at least two herbal supplements: Shuanghuanglian^[1] and Sho-Saiko-To, which is a Chinese classic herbal formula, and listed in Japan as Kampo medicine.^{[citation needed]}

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.^[3][4][5] In mice, baicalin produces anxiolytic effects without sedative or myorelaxant effects.^[6][7] It is thought that baicalin, along with other flavonoids, may underlie the anxiolytic effects of S. baicalensis and S. lateriflora.^[8][9]

Baicalin is a known prolyl endopeptidase inhibitor.^[10] It induces apoptosis in pancreatic cancer cells.^[11]