CAS 19351-63-4

Secologanin

Description:

Secologanin is a naturally occurring iridoid glycoside, primarily found in various plant species, particularly in the genus *Vinca* and *Gentiana*. It is characterized by its complex molecular structure, which includes a cyclopentane ring and a glucose moiety. The substance is known for its potential pharmacological properties, including anti-inflammatory and neuroprotective effects, making it of interest in medicinal chemistry and herbal medicine. Secologanin is also a precursor in the biosynthesis of several important alkaloids, such as vincamine and other compounds with therapeutic applications. Its solubility is generally moderate in polar solvents, and it exhibits stability under standard conditions, although it may be sensitive to extreme pH levels and light. The compound's biological activity is attributed to its ability to interact with various biological targets, which has led to ongoing research into its mechanisms of action and potential health benefits. Overall, secologanin represents a significant compound in the study of natural products and their applications in health and disease.

Formula: C₁₇H₂₄O₁₀

InChI: InChI=1/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3

InChI key: InChIKey=CSKKDSFETGLMSB-NRZPKYKESA-N

SMILES: C(=C)[C@@H]1[C@H](CC=O)C(C(OC)=O)=CO[C@H]1O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O

Synonyms:

• 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(β-<span class="text-smallcaps">D</span>-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, (2S,3R,4S)-
• 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(β-<span class="text-smallcaps">D</span>-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, [2S-(2α,3β,4β)]-
• Loniceroside
• Loniceroside (iridoid)
• NSC 640525
• methyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
• methyl 3-ethenyl-2-(hexopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
• Secologanin
• 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, [2S-(2α,3β,4β)]-
• 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, (2S,3R,4S)-
• (-)-SECOLOGANIN
• (4S)-4β-(2-Oxoethyl)-5β-vinyl-6α-(β-D-glucopyranosyloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester
• (2S)-3α-Vinyl-2β-(β-D-glucopyranosyloxy)-3,4-dihydro-4α-(2-oxoethyl)-2H-pyran-5-carboxylic acid methyl ester

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

CAS: 19351-63-4

Formula: C₁₇H₂₄O₁₀

Purity: 90%

Molecular weight: 388.3665

Ref: IN-DA00APG6

Secologanin

CAS: 19351-63-4

Formula: C₁₇H₂₄O₁₀

Purity: 95%~99%

Molecular weight: 388.369

Ref: BP-BP1722

(-)-Secologanin

CAS: 19351-63-4

(-)-Secologanin is a monoterpenoid glycoside, which is a key intermediate in the biosynthesis of indole alkaloids, found primarily in plants such as those in the Apocynaceae and Rubiaceae families. It plays a crucial role in the natural production of complex alkaloids, forming the backbone for numerous pharmacologically active compounds, including quinine, camptothecin, and ajmalicine.

Formula: C₁₇H₂₄O₁₀

Purity: Min. 88 Area-%

Color and Shape: Powder

Molecular weight: 388.37 g/mol

Ref: 3D-FS65469