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49879

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Neoandrographolide

analytical standard

Synonym(s):

ent-19-Hydroxy-8(17),13-labdadien-16,15-olide 19-O-β-D-glucopyranoside, D-Glucopyranosyloxy)methyl]decahydro-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-2(5H)-furanone

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About This Item

Empirical Formula (Hill Notation):
C26H40O8
CAS Number:
Molecular Weight:
480.59
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

Assay

≥95% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

food and beverages

format

neat

SMILES string

C[C@]1(CCC[C@@]2(C)[C@H](CCC3=CCOC3=O)C(=C)CC[C@H]12)CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O

InChI

1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17-,18-,19-,20-,21+,22-,24-,25+,26+/m1/s1

InChI key

YGCYRQKJYWQXHG-RDNQFMDVSA-N

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General description

Neoandrographolide is a major diterpenoid isolated from Andrographis paniculata NEES (AP), a shrub belonging to the Acanthaceae family. It exhibits antihepatotoxic effect against carbon tetrachloride-induced hepatotoxicity. It also shows protective effects against galactosamine and paracetamol-induced intoxication in rats. It also helps in the suppression of human immunodeficiency virus type 1 (HIV)-induced cell cycle dysregulation and leads to a rise in CD4+ lymphocyte levels of HIV-1 infected individuals.

Application

Neoandrographolide may be used as an analytical reference standard for the quantification of the analyte in the leaves of Andrographis paniculata using chromatography techniques.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Petra H Pfisterer et al.
Planta medica, 76(15), 1698-1700 (2010-05-07)
Extracts of the traditional medicinal herb Andrographis paniculata and its main constituents are described in the literature as showing anticancer activity. The aim of this study was to isolate the main constituents of a commercially available phytotherapeutic preparation of A.
Li-Xia Chen et al.
Journal of Asian natural products research, 9(3-5), 463-469 (2007-08-19)
The biotransformation of neoandrographolide (1) was investigated by using Aspergillus niger (AS 3.739). Five products were obtained and identified as 8(17),13-ent-labdadien-16,15-olid-19-oic acid (2), 19-hydroxy-8(17),13-ent-labdadien-16,15-olide (3), 18-hydroxy-8(17),13-ent-labdadien-16,15-olid-19-oic acid (4), 3alpha-hydroxy-8(17),13-ent-labdadien-16,15-olid-19-oic acid (5) and 8beta,19-dihydroxy-ent-labd-13-en-16,15-olide (6) by spectroscopic and chemical means. Products
Alpana Srivastava et al.
Phytochemical analysis : PCA, 15(5), 280-285 (2004-10-29)
An attempt has been made to develop a method by which to determine the chemical fingerprint of Andrographis paniculata (Acanthaceae). High-performance thin layer chromatography (HPTLC) was used to analyse hexane, chloroform, methanol and water extracts of leaves of A. paniculata.
Du Qizhen et al.
Journal of chromatography. A, 984(1), 147-151 (2003-02-05)
The bioactive diterpenes andrographolide and neoandrographolide from the leaves of Andrographis paniculata NEES (Acanthaceae) were successfully separated by counter-current chromatography. A single 280-min separation yielded 189 mg of 99.9% andrographolide and 9.5 mg of 98.5% neoandrographolide applying water-methanol-ethyl acetate-n-hexane (2.5:2.5:4:1)
Javzan Batkhuu et al.
Biological & pharmaceutical bulletin, 25(9), 1169-1174 (2002-09-17)
In this study, we investigated the in vitro and ex vivo suppressive effects of Andrographis paniculata on nitric oxide (NO) production in mouse peritoneal macrophages elicited by bacillus Calmette-Guéin (BCG) and stimulated by lipopolysaccharide (LPS). Incubation of BCG-induced macrophages with

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