secoxyloganin
secoxyloganin Basic information
- Product Name:
- secoxyloganin
- Synonyms:
-
- secoxyloganin
- (2S)-3α-Ethenyl-2β-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4α-acetic acid
- Secologanoside 11-methyl ester
- Secoxyloganin, >=98%
- 2H-Pyran-4-acetic acid,3-ethenyl-2-(b-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-,(2S,3R,4S)-
- 2H-Pyran-4-acetic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2S,3R,4S)-
- (2S,3R,4S)-2-(β-D-Glucopyranosyloxy)-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]aceticaci
- 2-[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetic acid
- CAS:
- 58822-47-2
- MF:
- C17H24O11
- MW:
- 404.37
- Product Categories:
-
- reagent
- standard substance
- Mol File:
- 58822-47-2.mol
secoxyloganin Chemical Properties
- Boiling point:
- 649.5±55.0 °C(Predicted)
- Density
- 1.49±0.1 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- DMF: 5mg/mL; DMSO: 5mg/mL; Ethanol: 10mg/mL; PBS (pH 7.2): 10mg/mL
- form
- A crystalline solid
- pka
- 4.40±0.10(Predicted)
secoxyloganin Usage And Synthesis
Description
Secoxyloganin is a secoiridoid glycoside that has been found in L. japonica and has diverse biological activities. It is active against E. coli and S. aureus in a disc assay when used at a concentration of 2 mg/disc. Secoxyloganin is cytotoxic to human dermal fibroblasts (IC50 = 78.1 μM). In vivo, secoxyloganin (10 mg/ml) prevents hen egg white lysozyme-induced decreases in tail vein blood flow, a marker of allergic inflammation, in hen egg white lysozyme-sensitized mice.
Uses
Secoxyloganin is a component of Poraqueiba sericea stems and may be used for its cytotoxic activity.
Definition
ChEBI: Secoxyloganin is a secoiridoid glycoside that is [(2R,3R,4S)-2-hydroxy-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid in which the anometric hydroxy group has been converted to the corresponding beta-D-glucoside. It has been isolated from several plant species and exhibits antioxidant and anti-allergic properties. It has a role as a plant metabolite, an antioxidant and an anti-allergic agent. It is a methyl ester, a member of pyrans, an enoate ester, a beta-D-glucoside, a monosaccharide derivative, a dicarboxylic acid monoester and a secoiridoid glycoside. It is a conjugate acid of a secoxyloganin(1-).
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