Baicalin

Chemical compound From Wikipedia, the free encyclopedia

Baicalin is the glucuronide of the polyphenolic compound baicalein.

Quick facts Names, Identifiers ...
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
3D model (JSmol)
70480
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.133.557 Edit this at Wikidata
EC Number
  • 606-866-1
KEGG
UNII
  • 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 checkY
    Key: IKIIZLYTISPENI-ZFORQUDYSA-N checkY
  • 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
  • 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
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:
GHS07: Exclamation mark
Warning
H315, H319, H335
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).
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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 GABAA 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]

References

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