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LIGSTROSIDE, also known as Ligustrazine, is a chemical constituent isolated from the flowers of Osmanthus fragrans var. aurantiacus. It is a bioactive compound with various pharmacological properties, including significant inhibition of nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages.

35897-92-8

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35897-92-8 Usage

Uses

Used in Pharmaceutical Industry:
LIGSTROSIDE is used as a pharmaceutical agent for its anti-inflammatory and immunomodulatory properties. It is particularly effective in inhibiting nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages, which can be beneficial in treating various inflammatory conditions and immune disorders.
Additionally, LIGSTROSIDE may have potential applications in other industries, such as cosmetics or nutraceuticals, due to its bioactive properties. However, more research is needed to fully understand its potential uses and benefits in these areas.

Check Digit Verification of cas no

The CAS Registry Mumber 35897-92-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,8,9 and 7 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 35897-92:
(7*3)+(6*5)+(5*8)+(4*9)+(3*7)+(2*9)+(1*2)=168
168 % 10 = 8
So 35897-92-8 is a valid CAS Registry Number.
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

35897-92-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name Ligustroside

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:35897-92-8 SDS

35897-92-8Synthetic 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

(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

ligstroside

Conditions
ConditionsYield
With diethylamine In methanol at 0 - 20℃; for 6h; Inert atmosphere;71%
methanol
67-56-1

methanol

jaspolyoleoside B

jaspolyoleoside B

A

ligstroside
35897-92-8

ligstroside

B

C35H48O21

C35H48O21

Conditions
ConditionsYield
at 80℃; for 36h;
demethylligstroside, (2''R)-and (2

demethylligstroside, (2''R)-and (2"S)-2"-hydroxyoleuropeins, fraxamoside and frameroside

ligstroside
35897-92-8

ligstroside

Conditions
ConditionsYield
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

4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

ligstroside
35897-92-8

ligstroside

Conditions
ConditionsYield
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

oleuropeine

ligstroside
35897-92-8

ligstroside

Conditions
ConditionsYield
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

4-carboxymethyl-5-ethylidene-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

ligstroside
35897-92-8

ligstroside

Conditions
ConditionsYield
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

ligstroside

A

D-Glucose
2280-44-6

D-Glucose

B

p-hydroxyphenethyl alcohol
501-94-0

p-hydroxyphenethyl alcohol

Conditions
ConditionsYield
With potassium hydroxide In methanol at 60℃; for 2h;A n/a
B 2 mg
methanol
67-56-1

methanol

ligstroside
35897-92-8

ligstroside

(S)-5-Dimethoxymethyl-4-methoxycarbonylmethyl-6-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

(S)-5-Dimethoxymethyl-4-methoxycarbonylmethyl-6-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid for 4h; Heating; Yield given;
ligstroside
35897-92-8

ligstroside

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

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

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

35897-92-8Relevant articles and documents

Five trimeric secoiridoid glucosides from Jasminum polyanthum

Takenaka, Yukiko,Tanahashi, Takao,Nagakura, Naotaka

, p. 317 - 322 (1998)

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.

New semi-synthetic analogs of oleuropein show improved anticancer activity in?vitro and in?vivo

Samara, Pinelopi,Christoforidou, Nikoleta,Lemus, Christelle,Argyropoulou, Aikaterini,Ioannou, Kyriaki,Vougogiannopoulou, Konstantina,Aligiannis, Nektarios,Paronis, Efthimios,Gaboriaud-Kolar, Nicolas,Tsitsilonis, Ourania,Skaltsounis, Alexios-Leandros

, p. 11 - 29 (2017/05/29)

Oleuropein is a glucosylated seco-iridoid present in olive fruits and leaves. Due to its broad spectrum of biological activities, including anticancer properties, oleuropein has attracted scientific attention for the past 20 years. The promising antiproliferative activity of an olive leaf extract enriched in oleuropein against a series of human cancer cell lines, prompted us to proceed with the semi-synthesis of 51 analogs of oleuropein. Following their initial screening against the estrogen receptor negative breast cancer cell line SKBR3, 7 analogs were shown to display significant cytotoxicity and were further tested against 6 additional solid tumor-derived and leukemic cell lines. The analog with the most promising antitumor activity (24) was selected for more detailed studies. 24 was non-toxic to peripheral blood mononuclear cells derived from healthy blood donors when tested at concentrations close to its half maximal inhibitory concentration. In vivo administration of 24 in melanoma-bearing mice resulted in reducing tumor size in a dose-dependent manner and in inducing anti-melanoma-reactive immune responses. Our results suggest that analog 24, emerging from the initial structure of oleuropein, represents a promising lead structure for further optimization.

Secoiridoid glucosides from Fraxinus americana

Takenaka, Yukiko,Tanahashi, Takao,Shintaku, Masashi,Sakai, Takeshi,Nagakura, Naotaka,Parida

, p. 275 - 284 (2007/10/03)

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.

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