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SECOLOGANIN

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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
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
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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
pka
12.81±0.70(Predicted)
form 
Solid
color 
White to off-white
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Safety Information

WGK Germany 
3
10-21

MSDS

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SECOLOGANIN Usage And Synthesis

Description

Secologanin 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.

Definition

ChEBI: (-)-secologanin is an iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively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.

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