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50741

Supelco

Secologanin

analytical standard

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About This Item

Empirical Formula (Hill Notation):
C17H24O10
CAS Number:
19351-63-4
Molecular Weight:
388.37
MDL number:
MFCD16661163
UNSPSC Code:
85151701
PubChem Substance ID:
329757628
NACRES:
NA.24

grade

analytical standard

Quality Level

100

Assay

≥88% (HPLC)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

food and beverages

format

neat

storage temp.

−20°C

SMILES string

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

InChI

1S/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/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1

InChI key

CSKKDSFETGLMSB-NRZPKYKESA-N

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM1061
BCCK8017
BCCJ8380
BCCH7282
BCCG0287

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Kenichiro Inoue
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 125(1), 31-49 (2005-01-07)
Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine which are biosynthesized via strictosidine, an alkaloidal glucoside, formed from secologanin and tryptamine. In secologanin biosynthesis
Christie A M Peebles et al.
Biotechnology and bioengineering, 93(3), 534-540 (2005-10-22)
Among the pharmacologically important terpenoid indole alkaloids produced by Catharanthus roseus are the anti-cancer drugs vinblastine and vincristine. These two drugs are produced in small yields within the plant, which makes them expensive to produce commercially. Metabolic engineering has focused
Souvik Kusari et al.
Journal of natural products, 74(4), 764-775 (2011-02-26)
Fungal endophytes inhabit healthy tissues of all terrestrial plant taxa studied and occasionally produce host-specific compounds. We recently isolated an endophytic fungus, Fusarium solani, from Camptotheca acuminata, capable of biosynthesizing camptothecin (CPT, 1), but this capability substantially decreased on repeated
G Beke et al.
Chirality, 13(8), 483-487 (2001-07-24)
In the presence of the enzyme strictosidine synthase, the coupling reaction of secologanin and tryptamine is completely stereoselective and affords strictosidine with 3S configuration, exclusively. The stereoselectivity is transferred and retained in most indole alkaloids of type I in which
Yasuyo Yamazaki et al.
Plant physiology, 134(1), 161-170 (2003-12-06)
Camptothecin derivatives are clinically used antitumor alkaloids that belong to monoterpenoid indole alkaloids. In this study, we investigated the biosynthetic pathway of camptothecin from [1-13C]glucose (Glc) by in silico and in vivo studies. The in silico study measured the incorporation
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