| Identification | Back Directory | [Name]
SECOLOGANIN | [CAS]
19351-63-4 | [Synonyms]
NSC 640525
SECOLOGANIN
LONICEROSIDE
(-)-SECOLOGANIN
Loniceroside【iridoid】
(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
2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, (2S,3R,4S)-
(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 | [Molecular Formula]
C17H24O10 | [MDL Number]
MFCD00013361 | [MOL File]
19351-63-4.mol | [Molecular Weight]
388.37 |
| Chemical Properties | Back Directory | [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 | [pka]
12.81±0.70(Predicted) | [color ]
White to off-white | [Major Application]
food and beverages | [InChIKey]
CSKKDSFETGLMSB-NRZPKYKESA-N | [SMILES]
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC=O |
| Hazard Information | Back Directory | [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(-)-secologanin is an iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively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. | [References]
[1] A. BATTERSBY P P A R Burnett. Alkaloid biosynthesis. Part XIV. Secologanin: its conversion into ipecoside and its role as biological precursor of the indole alkaloids[J]. Journal of The Chemical Society C: Organic, 1969, 61 1: 1187-1192. DOI: 10.1039/j39690001187
[2] KAREL MIETTINEN. The seco-iridoid pathway from Catharanthus roseus.[J]. ACS Combinatorial Science, 2014: 3606. DOI: 10.1038/ncomms4606
[3] S IRMLER. Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase.[J]. The Plant Journal, 2000, 24 6: 797-804. DOI: 10.1046/j.1365-313x.2000.00922.x |
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