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Merck
CN

G9923

Picroside I

≥98% (HPLC)

Synonym(s):

(1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-Hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl-β-D-glucopyranoside 6-[(2E)-3-phenyl-2-propenoate], 6′-Cinnamoylcatalpol

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About This Item

Empirical Formula (Hill Notation):
C24H28O11
CAS Number:
27409-30-9
Molecular Weight:
492.47
UNSPSC Code:
12352205
MDL number:
MFCD29505480
NACRES:
NA.25
EC Number:
248-445-1

Key Documents

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InChI key

XZGPUOQGERGURE-LUVHZPKESA-N

InChI

1S/C24H28O11/c25-11-24-16-13(17(27)21(24)35-24)8-9-31-22(16)34-23-20(30)19(29)18(28)14(33-23)10-32-15(26)7-6-12-4-2-1-3-5-12/h1-9,13-14,16-23,25,27-30H,10-11H2/b7-6+/t13-,14-,16-,17+,18-,19+,20-,21+,22+,23+,24-/m1/s1

SMILES string

O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(/C=C/C2=CC=CC=C2)=O)O[C@H]1O[C@@H]3OC=C[C@]4([H])[C@@]3([H])[C@](O5)(CO)[C@@H]5[C@H]4O

assay

≥98% (HPLC)

solubility

ethanol: 1 mg/mL, clear, colorless

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

Quality Level

200

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General description

Picroside I is one of the major phytochemicals found in the roots and rhizomes of Picrorhiza kurroa Royle ex Benth.

Biochem/physiol Actions

Phytochemical found within a Traditional Chinese Medicine herbal preparation. Picroside I, an iridoid glycoside, is a hepatoprotective agent.
Picroside I is a potent anti-cancer, antioxidant, and anti-inflammatory agent. Picroliv is a standardized drug that is a mixture of two iridoid glycoside components picroside I and picroside II (Kutkoside). It displays protection against ischemia-reperfusion injury, respiratory, and inflammatory diseases.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000224552
SLCQ4414
0000224552
SLBN3608V
SLBC6345V

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P Li et al.
European journal of pharmacology, 406(2), 203-208 (2000-10-06)
Natural iridoid, picroside I (beta-D-glucopyranoside, 1a,1b,2,5a,6, 6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1, 2-c]pyran-2-yl, 6-(3-phenyl-2-propenoate)) or II (beta-D-glucopyranoside, 1a,1b,2,5a,6, 6a-hexahydro-6-[(4-hydroxy-3-methoxybenzoyl)oxy]-1a-(hydroxymethyl )ox ireno[4,5]cyclopenta[1,2-c]pyran-2-yl) alone did not exhibit neuritogenic activity, but caused a concentration-dependent (>0.1 microM) enhancement of nerve growth factor (NGF, 2 ng/ml)-induced neurite outgrowth from PC12D
P Li et al.
Biological & pharmaceutical bulletin, 23(7), 890-892 (2000-08-05)
A crude methanol extract of Picrorhizae Rhizoma, the dried underground parts of Picrorhiza scrophulariiflora PENNELL, has been shown to potentiate the nerve growth factor (NGF)-induced neurite outgrowth from PC12D cells. The methanol extract was partitioned between ethyl acetate and water.
Parul Gahlan et al.
BMC genomics, 13, 126-126 (2012-04-03)
Picrorhiza kurrooa Royle ex Benth. is an endangered plant species of medicinal importance. The medicinal property is attributed to monoterpenoids picroside I and II, which are modulated by temperature. The transcriptome information of this species is limited with the availability
Pamita Bhandari et al.
Journal of chromatography. A, 1194(2), 257-261 (2008-05-21)
Sugars play a critical role in regulating overall cellular metabolism in high altitude growing plants. These plants are shown to have high levels of sugars to enhance their tolerance to abiotic stresses such as drought and freezing temperature. In the
Harsharan Singh et al.
Gene, 515(2), 320-328 (2012-12-15)
Picrorhiza kurrooa Royle ex Benth. is an economically important medicinal plant known to yield picrosides which have high medicinal value. Picroside I and picroside II are major picrosides associated with various bioactivities. The present work analyzed the expression of various
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