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SML1572

Sigma-Aldrich

Gentiopicroside

≥98% (HPLC)

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Synonym(s):
(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one, (5R,6S)-5-Ethenyl-6-(-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-Pyrano[3,4-c]pyran-1-one, (5R-trans)-5-ethenyl-6-(-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one, Gentiopicrin, NSC606402
Empirical Formula (Hill Notation):
C16H20O9
CAS Number:
20831-76-9
Molecular Weight:
356.32
EC Number:
244-070-2
MDL number:
MFCD00075700
UNSPSC Code:
12352200
PubChem Substance ID:
329825970
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -185 to -205°, c = 1 in H2O

color

white to beige

solubility

H2O: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

C=C[C@H]1[C@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C3C(OCC=C31)=O

InChI

1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1

InChI key

DUAGQYUORDTXOR-GPQRQXLASA-N

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General description

Gentiopicroside is a natural Iridoid compound, found in Chinese medicinal herbs Gentiana scabra Bge. and Gentiana macrophylla Pall.

Biochem/physiol Actions

Gentiopicroside is an important active component of secoiridoid glycosides from Gentiana macrophylla Pall that exhibit anti-inflammatory, antibacterial and liver protecting activities. Gentiopicroside protects chondrocytes from IL-1β-induced inflammation response.
Gentiopicroside possesses analgesic, anti proliferative, wound healing and antioxidant properties (free radical scavenging activity). Gentiopicroside shows low oral bioavailability, hence it establishes its therapeutic action after metabolism.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Lei Zhao et al.
Journal of ethnopharmacology, 172, 100-107 (2015-06-28)
In traditional Chinese medicine, Gentiana macrophylla Pall have been prescribed for the treatment of pain and inflammatory conditions. In addition, it is a common Tibetan medicinal herb used for the treatment of tonsillitis, urticaria, and rheumatoid arthritis (RA), while the
Zhigang Wang et al.
Journal of pharmaceutical and biomedical analysis, 107, 1-6 (2015-01-06)
The metabolism of gentiopicroside in vivo was studied by LC/MS following 2,4-dinitrophenylhydrazine derivatization for the first time. The ionization efficiency of the major metabolites erythrocentaurin and gentiopicral were greatly enhanced by the new analytical method developed, and they were successfully

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