(-)-Secologanin

cas: 19351-63-4 — see every product listed under this CAS number, including other names

(-)-Secologanin (CAS 19351-63-4) is a chemical reagent available from Chemat. Available pack sizes: 10mg, 5mg, 25mg, 50mg. Offered by: Biosynth.

brandBiosynth
catalog numberFS65469-10mg
cas19351-63-4
size10mg
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properties

categoryNatural Products
sub-category 1Terpenes
purityNo data
delivery time3-4 weeks
Structural formula: {0} (CAS {1})

(-)-secologanin is an iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively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

Source: ChEBI

Identity
Molecular formulaC17H24O10
Molecular weight388.4 g/mol
IUPAC namemethyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
InChIKeyCSKKDSFETGLMSB-NRZPKYKESA-N
SMILESCOC(=O)C1=CO[C@H]([C@@H]([C@@H]1CC=O)C=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Computed by PubChem (NCBI)

Synonyms: Secologanin, (-)-Secologanin, loniceroside, Kailian strychnoside, Loniceroside (iridoid), Secologanin (Standard), orb3177629, Secologanin, analytical standard
Isomers (same molecular formula)
[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-prop-2-enoxyoxan-2-yl]methyl acetate C17H24O10
[(2R,3R,4S,5R,6S)-3,5,6-triacetyloxy-4-prop-2-enoxyoxan-2-yl]methyl acetate C17H24O10
5-ethenyl-3-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one C17H24O10
methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate C17H24O10
(3S,4aS,5R,6S)-5-ethenyl-3-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one C17H24O10
methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate C17H24O10
[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-prop-2-enoxyoxan-2-yl]methyl acetate C17H24O10
[(3aS,5R,6R,7S,7aS)-6,7-diacetyloxy-2-methyl-2-prop-2-enoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate C17H24O10
methyl 7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate C17H24O10
methyl 7-methyl-6-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate C17H24O10
2-(hydroxymethyl)-6-[4-[3-(hydroxymethyl)oxiran-2-yl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol C17H24O10

Also listed as

Secologanin GLPBio CAS 19351-63-4
SECOLOGANIN* Sigma-Aldrich CAS 19351-63-4
Secologanin, 94.0% MedChemExpress CAS 19351-63-4
Methyl (2S,3R,4S)-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, 90% Chemat CAS 19351-63-4