8-O-acetylharpagide Chemical Properties

Melting point:

227-229℃

Boiling point:

607.2±55.0 °C(Predicted)

Density 

1.58

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Soluble in DMSO and methanol;

form 

Powder

pka

11.88±0.70(Predicted)

color 

White to off-white

Water Solubility 

insoluble in water

InChIKey

CAFTUQNGDROXEZ-XBDCZORHSA-N

SMILES

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

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29389090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

8-O-acetylharpagide Usage And Synthesis

Chemical Properties

White crystalline powder, easily soluble in water and methanol, from the whole herb of Ajuga decumbens Thunb. in the genus Sinews, family Labiatae, and Scrophularia ningpoensis Hemsl in the family Genseng.

Uses

3-Acetylharpagide is an iridoid glycoside displaying antibacterial, antiinflammatory and antiviral effects.

Synthesis

Dried and pulverized whole grass of Solanum vulgare (3.0 kg) was soaked in acetone (20 L) at room temperature for 48 h. The filtrate was extracted three times in the same way by recovering the solvent under reduced pressure to obtain 92.0 . g acetone extract. The residue of the herb continued to be soaked in methanol (12 L) for 72 h, the filtrate was decompressed to recover the solvent, and extracted twice in the same way to obtain 222.6 g of methanol extract. g methanol extract. The acetone extract and methanol extract were combined, dissolved in 90% methanol, and extracted with hexane and dichloromethane sequentially to obtain 71.0 g of hexane extract, 30.4 of dichloromethane extract and 197.5 g of aqueous parts. The aqueous part (197.5 g) was extracted by D101 macromolecule. g) was passed through a D101 macroporous resin and eluted sequentially with water, 20%, 40%, 60% and 80% ethanol-water in a gradient to obtain the aqueous eluted site Fr.W1 (about 160 ), the 20% ethanol-water eluted site Fr. g), 20% ethanol site Fr. W2 (13.2 g), 40% ethanol site Fr. W3 (15.0 g), 60% ethanol site Fr. W4 (ca. 3.0 ) and 80% ethanol site Fr. W4 (ca. 3.0 ). g), 60% ethanol site Fr.W4 (ca. 3.0 ) and 80% ethanol site Fr.W5 (ca. 2.0 g). Fr.W2 was chromatographed on a Sephadex LH-20 column. LH-20 column chromatography, eluting with 50% methanol to give 8 flow fractions (Fr. W2a to W2h). Fr. W2d was purified by silica gel column chromatography and semi-preparative HPLC to give compound l (16.4 ). mg).

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