35897-92-8

Basic information

• Product Name: LIGSTROSIDE
• Synonyms: 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 NO: 35897-92-8
• Molecular Formula: C₂₅H₃₂O₁₂
• Molecular Weight: 524.52188
• Mol File: 35897-92-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 736.9 °C at 760 mmHg
• Flash Point: 245.1 °C
• Appearance: /
• Density: 1.44 g/cm³
• Vapor Pressure: 8.5E-23mmHg at 25°C
• Refractive Index: 1.613
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.91±0.15(Predicted)
• CAS DataBase Reference: LIGSTROSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: LIGSTROSIDE(35897-92-8)
• EPA Substance Registry System: LIGSTROSIDE(35897-92-8)

Safety Data

• Hazardous Substances Data: 35897-92-8(Hazardous Substances Data)

Usage

Uses

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.

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

Synthetic route

(2S,3S,4R,5S,6R)-2-(acetoxymethyl)-6-(((E)-3-ethylidene-4-(2-(4-hydroxyphenethoxy)-2-oxoethyl)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate → ligstroside (35897-92-8)

Conditions	Yield
With diethylamine In methanol at 0 - 20℃; for 6h; Inert atmosphere;	71%

methanol (67-56-1) + jaspolyoleoside B → ligstroside (35897-92-8) + C35H48O21

Conditions	Yield
at 80℃; for 36h;

diazomethane (186581-53-3, 908094-01-9) + demethylligstroside, (2''R)-and (2"S)-2"-hydroxyoleuropeins, fraxamoside and frameroside → ligstroside (35897-92-8)

Conditions	Yield
In methanol; diethyl ether Methylation;	0.5 mg

4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (60539-23-3) → ligstroside (35897-92-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: pyridine / 2 h / 0 - 20 °C / Inert atmosphere 2.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 2 h / 0 - 20 °C 2.2: 2 h / 0 - 20 °C 3.1: diethylamine / methanol / 6 h / 0 - 20 °C / Inert atmosphere View Scheme

oleuropeine (32619-42-4) → ligstroside (35897-92-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water / 0.17 h / 100 °C / Microwave irradiation 2.1: pyridine / 2 h / 0 - 20 °C / Inert atmosphere 3.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 2 h / 0 - 20 °C 3.2: 2 h / 0 - 20 °C 4.1: diethylamine / methanol / 6 h / 0 - 20 °C / Inert atmosphere View Scheme

4-carboxymethyl-5-ethylidene-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (911438-61-4) → ligstroside (35897-92-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 2 h / 0 - 20 °C 1.2: 2 h / 0 - 20 °C 2.1: diethylamine / methanol / 6 h / 0 - 20 °C / Inert atmosphere View Scheme

ligstroside (35897-92-8) → D-Glucose (2280-44-6) + p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With potassium hydroxide In methanol at 60℃; for 2h;	A n/a B 2 mg

methanol (67-56-1) + ligstroside (35897-92-8) → (S)-5-Dimethoxymethyl-4-methoxycarbonylmethyl-6-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

Conditions	Yield
With sulfuric acid for 4h; Heating; Yield given;

ligstroside (35897-92-8) → (2R,3S,4S)-4-{[2-(4-hydroxyphenyl)ethoxy]carbonyl}-3-formyl-3,4-dihydro-2H-pyran-5-acetic acid methyl ester

Conditions	Yield
With β-glucosidase from almonds In water at 34℃; for 24h; Enzymatic reaction;	25 mg

Upstream product

• 67-56-1 methanol 
• 911438-61-4 4-carboxymethyl-5-ethylidene-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 
• 32619-42-4 oleuropeine 
• 60539-23-3 4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 
• 186581-53-3 diazomethane 

Downstream Products

• 2280-44-6 D-Glucose 
• 501-94-0 p-hydroxyphenethyl alcohol 

Relevant articles and documents

Five trimeric secoiridoid glucosides from Jasminum polyanthum

Investigation of the crude drug 'Ye su xin', the dried flowers of Jasminum polyanthum, has led to the isolation of five new secoiridoid glucosides, oleopolyanthosides A and B, and jaspolyoleosides A, B, and C. The structures of the new compounds were elucidated by spectroscopic and chemical means.

Secoiridoid glucosides from Fraxinus americana

Investigation of the leaves of Fraxinus americana led to the isolation of five secoiridoid glucosides, demethylligstroside, (2'' R)- and (2'' S)-2''-hydroxyoleuropeins, fraxamoside and frameroside, together with 18 known compounds. Their structures were determined on the basis of spectroscopic studies and chemical evidence. (C) 2000 Elsevier Science Ltd.