SECOLOGANIN

SECOLOGANIN 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:19351-63-4
MF:C17H24O10
MW:388.37
EINECS:
Product Categories:Natural Terpene StandardsChemical Class;OtherChemical Class;Iridoids;Oxygen containingChemical Class;S;SA - SMMore...Close...;NeatsChemical Class;Polyhydroxy compoundsAlphabetic;Alcohols;Aldehydes/DNPH;AliphaticAnalytical Standards;Chemical Class;EstersChromatography;Heterocyclics;Life Sciences Standards;Natural Compounds;Natural CompoundsChemical Class
Mol File:19351-63-4.mol
SECOLOGANIN Structure
SECOLOGANIN Chemical Properties
Boiling point 595.5±50.0 °C(Predicted)
density 1.42±0.1 g/cm3(Predicted)
storage temp. −20°C
solubility Water: Slightly Soluble
form neat
pka12.81±0.70(Predicted)
Safety Information
WGK Germany 3
10-21
MSDS Information
ProviderLanguage
SigmaAldrich English
SECOLOGANIN Usage And Synthesis
DescriptionSecologanin is a monoterpene that has been found in V. rosea and is an intermediate in the synthesis of monoterpene indole alkaloids from geraniol. It is a metabolite of loganin formed by the cytochrome P450 (CYP) isoform CYP72A1, also known as secologanin synthase.
Uses(-?)?-?Secologanin is an iridoid glycoside found in Hydrangeaceae used in anti-inflammatory.
DefinitionChEBI: (-)-secologanin is an iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer). It has a role as a plant metabolite. It is a beta-D-glucoside, a methyl ester, an aldehyde, an enoate ester, a secoiridoid glycoside and a member of pyrans.
SECOLOGANIN Preparation Products And Raw materials
Preparation ProductsTETRAHYDROALSTONINE
5-(methoxymethoxy)-Pentanoicacidmethylester 5-HEXENOIC ACID n-Butyl vinyl ether 3-ETHOXYMETHACROLEIN Propoxyethylene 3,4-DIHYDRO-2-METHOXY-4-METHYL-2H-PYRAN ETHYLENE GLYCOL MONOISOBUTYL ETHER SECOLOGANIN ethyl D-glucopyranoside 3,4-Dihydro-2H-pyran Chloroform BUTYL-BETA-D-GLUCOPYRANOSIDE METHYL 3-METHYLPENTANOATE METHYL BETA-D-GLUCOPYRANOSIDE HEMIHYDRATE Methyl 3-methoxyacrylate 5-HEXENOIC ACID METHYL ESTER 2-Ethoxy-3,4-dihydro-4-methyl-2H-pyran PENT-4-ENYL-D-GLUCOPYRANOSIDE

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