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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.
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
Yong-hong Zhang et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 27(3), 206-208 (2003-05-31)
To investigate the chemical constituents of Galeopsis bifida. Various chromatographic techniques were employed for isolation and purification of the constituents. The structures were elucidated by chemical and spectral analyses. Ten compounds were isolated and identified as chrysoeriol(1), 5,7-dihydroxy-3',4'-dimethoxyflavone(2), hederagenin(3), daucosterol(4)
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