Baicalin

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Not to be confused with baicalein.
Baicalin
Baicalin.svg
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
21967-41-9 N
ChEBI CHEBI:2981 YesY
ChEMBL ChEMBL485818 YesY
ChemSpider 58507 YesY
Jmol 3D model Interactive image
PubChem 64982
UNII 347Q89U4M5 YesY
  • 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 YesY
    Key: IKIIZLYTISPENI-ZFORQUDYSA-N YesY
  • 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 446.36 g·mol−1
Melting point 202 to 205 °C (396 to 401 °F; 475 to 478 K)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Baicalin is a flavone, a type of flavonoid. It is the glucuronide of baicalein.

Natural occurrences

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.[1] 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.

Medical uses

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.[2][3][4] In mice, baicalin produces anxiolytic effects without sedative or myorelaxant effects.[5][6] It is thought that baicalin, along with other flavonoids, may underlie the anxiolytic effects of S. baicalensis and S. lateriflora.[7][8]

Baicalin is a known prolyl endopeptidase inhibitor.[9] It induces apoptosis in pancreatic cancer cells.[10]

References

  1. ↑ P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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