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SMB00118

Sigma-Aldrich

8-Acetylharpagide

≥85% (LC/MS-ELSD)

Synonym(s):

Harpagide 8-acetate

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About This Item

Empirical Formula (Hill Notation):
C17H26O11
CAS Number:
6926-14-3
Molecular Weight:
406.38
MDL number:
MFCD03700750
UNSPSC Code:
12352205
PubChem Substance ID:
329824796
NACRES:
NA.25

Assay

≥85% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

CC(=O)O[C@@]1(C)C[C@@H](O)[C@]2(O)C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12

InChI

1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1

InChI key

CAFTUQNGDROXEZ-XBDCZORHSA-N

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General description

Natural product derived from plant source.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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E Abdel-Sattar
Archives of pharmacal research, 21(6), 785-786 (1998-12-30)
The aerial parts of Teucrium yemense yielded two iridoid glycosides. Their structures were elucidated by spectral means as teucardosid and 8-O-acetylharpagid.
T Konoshima et al.
Cancer letters, 157(1), 87-92 (2000-07-14)
In the course of our continuing search for novel cancer chemopreventive agents from natural sources, several kinds of Labiatae plants were screened. Consequently, the iridoid glycoside derivative, 8-acetylharpagide (8-AcHarp), was obtained from the flowering whole plant of Ajuga decumbens as
Carlos R Pungitore et al.
Journal of natural products, 67(3), 357-361 (2004-03-27)
Growth inhibitory activities and nutritional indices of catalpol (1), 8-O-acetylharpagide (2), and harpagide (3) were determinated in larvae and adults of Tribolium castaneum, respectively. Compound 1 produced a series of allelochemical effects probably related with the DNA synthesis. This iridoid
L Dinan et al.
Insect biochemistry and molecular biology, 31(11), 1077-1082 (2001-08-25)
We have reinvestigated the activity of 8-O-acetylharpagide, an iridoid glucoside, as an ecdysteroid agonist. Elbrecht et al. (Insect Biochem. Mol. Biol. 26 (1996) 519) isolated a preparation of this compound from Ajuga reptans L. and ascribed ecdysteroid agonist activity on
M C Breschi et al.
Journal of natural products, 55(8), 1145-1148 (1992-08-01)
The traditional therapeutic indications for the use of Ajuga reptans (Labiatae) have been investigated. The H2O-soluble part of a crude and partially purified MeOH extract and two isolated iridoids (8-O-acetylharpagide and harpagide), were tested for a biological activity on isolated
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