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Merck
CN

07512

α-Hederin

analytical standard

Synonym(s):

(3β,4α)-3-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-α-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-28-oic acid

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About This Item

Empirical Formula (Hill Notation):
C41H66O12
CAS Number:
27013-91-8
Molecular Weight:
750.96
NACRES:
NA.24
UNSPSC Code:
85151701
EC Number:
248-166-5

Key Documents

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InChI key

KEOITPILCOILGM-LLJOFIFVSA-N

InChI

1S/C41H66O12/c1-21-28(44)30(46)31(47)33(51-21)53-32-29(45)24(43)19-50-34(32)52-27-11-12-37(4)25(38(27,5)20-42)10-13-40(7)26(37)9-8-22-23-18-36(2,3)14-16-41(23,35(48)49)17-15-39(22,40)6/h8,21,23-34,42-47H,9-20H2,1-7H3,(H,48,49)/t21-,23-,24-,25+,26+,27-,28-,29-,30+,31+,32+,33-,34-,37-,38-,39+,40+,41-/m0/s1

SMILES string

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)CO[C@H]2O[C@H]3CC[C@@]4(C)[C@@H](CC[C@]5(C)[C@@H]4CC=C6[C@@H]7CC(C)(C)CC[C@@]7(CC[C@@]56C)C(O)=O)[C@]3(C)CO)[C@H](O)[C@H](O)[C@H]1O

grade

analytical standard

assay

≥90.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

impurities

≤10.0% water

application(s)

food and beverages

format

neat

storage temp.

2-8°C

Quality Level

100

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General description

α-Hederin is a water-soluble pentacyclic triterpene compound present in the seeds of Nigella sativa.

Application

α-Hederin may be used as an internal standard for the determination of glycyrrhizin and its major metabolite glycyrrhetic acid in human plasma by liquid chromatography/tandem mass spectrometry (LC−MS/MS). It may be used as an external standard for quinovic acid glycosides assay by high performance liquid chromatography-photodiode array detection (HPLC-PDA) as well as ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF-MS). It may be used as a reference standard for the identification of α-hederin in the leaves of common ivy (Hedera helix) by liquid chromatography-electrospray ionization tandem mass spectrometry (LC-EI/MS-MS).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ5095
BCCH9041
BCCH6796
BCCH4743
BCCH2887

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HPLC-PDA method for quinovic acid glycosides assay in Cat's claw (Uncaria tomentosa) associated with UPLC/Q-TOF-MS analysis.
Pavei C, et al.
Journal of Pharmaceutical and Biomedical Analysis, 62(2), 250-257 (2012)
Simultaneous determination of glycyrrhizin, a marker component in radix Glycyrrhizae, and its major metabolite glycyrrhetic acid in human plasma by LC-MS/MS.
Lin Z, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 814(2), 201-207 (2005)
A V Lekar' et al.
Bioorganicheskaia khimiia, 37(5), 679-684 (2012-02-16)
The molecular complexation of adenine and guanine with hederagenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranoside (alpha-hederin) and its 28-O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-O-beta-D-glucopyranosyl ester (hederasaponin C) was investigated for the first time using the method of electrospray ionization mass spectrometry. Guanine forms complexes more diverse in composition than adenine.
Bo Wang et al.
Organic & biomolecular chemistry, 10(44), 8822-8834 (2012-10-09)
We synthesized a diosgenyl saponin bearing a unique disaccharide from the natural product β-hederin, together with twelve glycosylated derivatives and determined their cytotoxicity against five different human cancer cell lines. Most of them showed weak cytotoxicity, with the exception of
Marta Mendel et al.
Journal of ethnopharmacology, 146(1), 423-426 (2013-01-01)
The dry extract of Hedera helix leaves, due to its secretolytic and antispasmodic effects, is commonly used to produce pharmaceuticals applied in case of cough and other respiratory symptoms. The results of some in vitro studies as well as the
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