19351-63-4

Basic information

• Product Name: SECOLOGANIN
• Synonyms: LONICEROSIDE;(-)-SECOLOGANIN;SECOLOGANIN;(2S)-3α-Vinyl-2β-(β-D-glucopyranosyloxy)-3,4-dihydro-4α-(2-oxoethyl)-2H-pyran-5-carboxylic acid methyl ester;(4S)-4β-(2-Oxoethyl)-5β-vinyl-6α-(β-D-glucopyranosyloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester;Loniceroside【iridoid】;(2S,3R,4S)-Methyl 4-(2-oxoethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyMethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate;NSC 640525
• CAS NO: 19351-63-4
• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 507.74
• Product Categories: Iridoids;NeatsChemical Class;Polyhydroxy compoundsAlphabetic;Alcohols;Aldehydes/DNPH;AliphaticAnalytical Standards;Chemical Class;EstersChromatography;Heterocyclics;Life Sciences Standards;Natural Compounds;Natural CompoundsChemical Class;Natural Terpene StandardsChemical Class;OtherChemical Class;Oxygen containingChemical Class;S;SA - SMMore...Close...
• Mol File: 19351-63-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 595.5°Cat760mmHg
• Flash Point: 212.2°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 1.15E-16mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: −20°C
• PKA: 12.81±0.70(Predicted)
• CAS DataBase Reference: SECOLOGANIN(CAS DataBase Reference)
• NIST Chemistry Reference: SECOLOGANIN(19351-63-4)
• EPA Substance Registry System: SECOLOGANIN(19351-63-4)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 19351-63-4(Hazardous Substances Data)

Usage

Description

SECOLOGANIN, a monoterpene iridoid glycoside, is predominantly found in the Hydrangeaceae plant family. It serves as a crucial intermediate in the synthesis of monoterpene indole alkaloids, derived from geraniol. This bioactive compound is a metabolite of loganin, produced by the cytochrome P450 (CYP) isoform CYP72A1, also referred to as secologanin synthase.

Uses

Used in Pharmaceutical Industry:
SECOLOGANIN is used as an intermediate compound for the synthesis of various monoterpene indole alkaloids, which possess significant pharmacological properties. Its role in the production of these alkaloids makes it a valuable component in drug development and discovery.
Used in Anti-Inflammatory Applications:
SECOLOGANIN is utilized as an anti-inflammatory agent, particularly effective in reducing inflammation and associated discomfort. Its natural origin and bioactive properties contribute to its potential use in the development of novel anti-inflammatory medications.

InChI:InChI=1/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3

Upstream product

• 67-56-1 methanol 
• 27856-66-2 O,O,O,O-tetraacetylsecologaninn 
• 18524-94-2 loganin 
• 88204-85-7 (E)-4-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxy)but-3-en-2-one 

Downstream Products

• 19456-89-4 strictosidine 
• 22427-47-0 17β-(tetra-O-acetyl-β-D-glucopyranosyloxy)-16α-vinyl-(3ξ,15β)-18-oxa-yohimb-19-en-21-one 
• 63661-74-5 cathenamine 
• 57691-96-0 O',O',O',O'-tetraacetyl-4-(4''-bromobenzyl)vincoside 
• 1398-17-0 Bakankosid 
• 34371-11-4 5(S)-5-carboxyvincoside 
• 77988-07-9 secologanin dimethylacetal 
• 27856-66-2 O,O,O,O-tetraacetylsecologaninn 
• 131011-22-8 Methyl (4R,5aS,9S,9aS,10R)-9-(β-D-Glucopyranosyloxy)-5,5a,9,9a-tetrahydro-1-methyl-3-phenyl-4,10-methano-4H,10H-pyrano<4',3':6,7>oxocino<3,2-d>pyrazol-6-carboxylate 
• 131011-23-9 Methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-<3-(4,5-dihydro-1-methyl-5-oxo-3-phenyl-4-pyrazolyl)-2-propenyl>-2H-pyran-5-carboxylate 
• 22621-94-9 strictosamide 
• 23141-27-7 3β(R)-vincosamide 
• 19456-89-4 epi-strictosidinic acid methyl ester 
• 68727-52-6 dolichantoside 

Related news

Inter-organ transport of SECOLOGANIN (cas 19351-63-4) allows assembly of monoterpenoid indole alkaloids in a Catharanthus roseus mutant08/03/2019

The medicinal value of the monoterpenoid indole alkaloids (MIAs) such as 3′,4′-anhydrovinblastine, as well as their chemical complexity have stimulated extensive efforts to understand the biochemical and molecular pathways involved in their biosynthesis in plants such as Catharanthus roseus, R...detailed

Relevant articles and documents

Total Synthesis of (-)-Strictosidine and Interception of Aryne Natural Product Derivatives "strictosidyne" and "strictosamidyne"

Monoterpene indole alkaloids are a large class of natural products derived from a single biosynthetic precursor, strictosidine. We describe a synthetic approach to strictosidine that relies on a key facially selective Diels-Alder reaction between a glucosyl-modified alkene and an enal to set the C15-C20-C21 stereotriad. DFT calculations were used to examine the origin of stereoselectivity in this key step, wherein two of 16 possible isomers are predominantly formed. These calculations suggest the presence of a glucosyl unit, also inherent in the strictosidine structure, guides diastereoselectivity, with the reactive conformation of the vinyl glycoside dienophile being controlled by an exo-anomeric effect. (-)-Strictosidine was subsequently accessed using late-stage synthetic manipulations and an enzymatic Pictet-Spengler reaction. Several new natural product analogs were also accessed, including precursors to two unusual aryne natural product derivatives termed "strictosidyne"and "strictosamidyne". These studies provide a strategy for accessing glycosylic natural products and a new platform to access monoterpene indole alkaloids and their derivatives.

SELECTIVE TRANSFORMATIONS OF SECOLOGANIN: DIHYDROXYLATION

Sweroside tetraacetate ( 2b ) has been converted in high yield by osmylation to the epimeric glycols 3 and 4 ( R=H ) which have been separated.This reaction proceeds with high chemoselectivity for reaction at the vinyl side chain but with low stereoselectivity, leading to a small excess of the 3-R isomer.Secologanin derivatives appear to show a much lower chemoselectivity in this reaction, but the stereoselectivity is considerably higher, and opposite to that in the sweroside example.Conditions have been found for oxidizing the dimethylacetal 5b of secologanin tetraacetate in useful yields to the epimeric glycols 6 and 7 ( R=H ); in this reaction a large excess of the 3-S isomer is formed.The reasons for these differences in selectivity appear to be related to differences between the two series in conformational preference.

THE CONVERSION OF SWEROSIDE TO SECOLOGANIN

A chemical route from sweroside ( 2a ) to secologanin ( 1a ) has been established.The lactone ring of sweroside tetraacetate ( 2b ) was opened by trimethylsilyl iodide.The unstable iodo carboxylic acid 3 ( R=H; X=I ) was then formed and immediately converted to its methyl ester.The iodo function was displaced by formate, and the formate was selectively methanolized under neutral condotions.The resulting alcohol 3 ( R=Me; X=OH ) was oxidized by pyridinium chlorochromate to the aldehyde, secologanin teraacetate ( 1b ).With care, the conversion from the sweroside series to the secologanin series can be carried out in excellent yield.Secologanin can readily be recovered from its teraacetate.