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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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Preclinical and clinical effects of Nigella sativa and its constituent, thymoquinone: A review.
Gholamnezhad Z, et al.
Journal of Ethnopharmacology, 190, 372-386 (2016)
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)
Yang Liu et al.
Molecules (Basel, Switzerland), 15(11), 7871-7883 (2010-11-10)
Thirteen novel triterpenoid saponins, designed as amide derivatives of the natural cytotoxic saponin β-hederin, were synthesized by a stepwise glycosylation strategy. The in vitro cytotoxic activity of these compounds was evaluated against five different tumor cell lines. Most of the
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
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