CAS 35897-92-8

methyl (3Z)-3-ethylidene-2-(beta-D-glucopyranosyloxy)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-3,4-dihydro-2H-pyran-5-carboxylate

Description:

Methyl (3Z)-3-ethylidene-2-(beta-D-glucopyranosyloxy)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-3,4-dihydro-2H-pyran-5-carboxylate, with CAS number 35897-92-8, is a complex organic compound characterized by its intricate molecular structure, which includes a pyran ring, a glucopyranosyl moiety, and various functional groups such as esters and ethers. This compound exhibits properties typical of glycosides, including potential solubility in polar solvents due to the presence of the glucopyranosyl group. Its structure suggests that it may possess biological activity, possibly acting as a natural product or a synthetic derivative with applications in pharmaceuticals or biochemistry. The presence of the hydroxyphenyl group may contribute to antioxidant properties, while the ethylidene and oxoethyl substituents could influence its reactivity and interaction with biological targets. Overall, this compound represents a fascinating example of the diversity found in organic chemistry, particularly in the realm of glycosides and their derivatives.

Formula: C₂₅H₃₂O₁₂

InChI: InChI=1/C25H32O12/c1-3-15-16(10-19(28)34-9-8-13-4-6-14(27)7-5-13)17(23(32)33-2)12-35-24(15)37-25-22(31)21(30)20(29)18(11-26)36-25/h3-7,12,16,18,20-22,24-27,29-31H,8-11H2,1-2H3/b15-3-/t16?,18-,20-,21+,22-,24?,25+/m1/s1

InChI key: InChIKey=GMQXOLRKJQWPNB-MVVLSVRYSA-N

SMILES: C(C(OCCC1=CC=C(O)C=C1)=O)[C@H]2/C(=C\C)/[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2C(OC)=O

Synonyms:

• Ligustroside
• 2H-Pyran-4-acetic acid, 3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-(4-hydroxyphenyl)ethyl ester, (2S,3E,4S)-
• 2H-Pyran-4-acetic acid, 3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-(4-hydroxyphenyl)ethyl ester, [2S-(2α,3E,4β)]-
• Ligstroside
• (2S)-3-[(E)-Ethylidene]-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4α-acetic acid 2-(4-hydroxyphenyl)ethyl ester
• (2S)-3-[(E)-Ethylidene]-2β-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4α-acetic acid 2-(4-hydroxyphenyl)ethyl ester

Ligustroside

CAS: 35897-92-8

Ligustroside analytical standard provided with chromatographic purity, to be used as reference material for qualitative determination.

Formula: C₂₅H₃₂O₁₂

Purity: (HPLC) ≥90%

Color and Shape: Powder

Molecular weight: 524.52

Ref: 11-0240

Ligstroside

CAS: 35897-92-8

Formula: C₂₅H₃₂O₁₂

Purity: %

Color and Shape: Solid

Molecular weight: 524.5144

Ref: IN-DA00CHUX

Methyl (2S,4S,E)-3-ethylidene-4-(2-(4-hydroxyphenethoxy)-2-oxoethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate

CAS: 35897-92-8

Methyl (2S,4S,E)-3-ethylidene-4-(2-(4-hydroxyphenethoxy)-2-oxoethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate

Purity: 98%

Molecular weight: 524.52g/mol

Ref: 54-OR1074656

Ligstroside

CAS: 35897-92-8

Formula: C₂₅H₃₂O₁₂

Molecular weight: 524.52

Ref: 4Z-L-201001

Ligustroside

CAS: 35897-92-8

Ligustroside mildly inhibits PGE2, has slight antioxidant and anti-inflammatory effects, and is moderately antiviral against parainfluenza 3.

Formula: C₂₅H₃₂O₁₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 524.51

Ref: TM-TN1871

Ligustroside

CAS: 35897-92-8

Formula: C₂₅H₃₂O₁₂

Purity: 95%~99%

Color and Shape: Powder

Molecular weight: 524.519

Ref: BP-SBP01648

Ligustroside

CAS: 35897-92-8

Applications Ligustroside is a chemical constituent isolated from the flowers of Osmanthus fragrans var. aurantiacus which significantly inhibited nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages.
References Liu, J., et al.: J. Nat. Med., 69, 135 (2015)

Formula: C₂₅H₃₂O₁₂

Color and Shape: Off-White

Molecular weight: 524.51

Ref: TR-L397960

Ligustroside

CAS: 35897-92-8

Ligustroside is a natural compound that has been shown to have hypoglycemic effects. It is extracted from the fructus ligustri, which is a traditional Chinese herbal medicine for treating diabetes. The extract has been found to contain acetate and coumarin derivatives, as well as 3-o-caffeoylquinic acid. Ligustroside is believed to exert its biological effects through transcriptional regulation of epidermal growth factor and p-hydroxybenzoic acid. It also inhibits the proliferation of cancer cells through surface methodology, molecular docking analysis, and preparative high performance liquid chromatography (prepHplc).

Formula: C₂₅H₃₂O₁₂

Purity: Min. 97 Area-%

Color and Shape: White Powder

Molecular weight: 524.51 g/mol

Ref: 3D-FL157864