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Merck
CN

50741

Secologanin

analytical standard

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About This Item

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

Key Documents

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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

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 key

CSKKDSFETGLMSB-NRZPKYKESA-N

grade

analytical standard

assay

≥88% (HPLC)

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

food and beverages

format

neat

storage temp.

−20°C

Quality Level

100

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN8744
BCCM7278
BCCM1061
BCCK8017
BCCJ8380

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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
Atsuko Itoh et al.
Phytochemistry, 62(3), 359-369 (2003-03-07)
From the dried roots of Neonauclea sessilifolia, two new chromone-secoiridoid glycosides, sessilifoside and 7"-O-beta-D-glucopyranosylsessilifoside, and three novel indole alkaloid glycosides, neonaucleosides A, B, and C, were isolated along with the main known glycosides, 5-hydroxy-2-methylchromone-7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, sweroside, loganin, grandifloroside, and quinovic acid
Oriol Bassas et al.
Organic letters, 7(14), 2817-2820 (2005-07-01)
[reaction: see text] Racemic oxodiester 1 undergoes stereoselective cyclocondensation with (S)-tryptophanol, (S)-(3,4-dimethoxyphenyl)alaninol, or the corresponding amino acids, in a process involving a tandem dynamic kinetic resolution/desymmetrization of diastereotopic groups, to give bicyclic lactams, which are cyclized to substituted indolo[2,3-a]- and
Shi Chen et al.
Chemistry & biology, 13(11), 1137-1141 (2006-11-23)
Plant alkaloids exhibit a diverse array of structures and pharmaceutical activities, though metabolic engineering efforts in these eukaryotic pathways have been limited. Strictosidine synthase (STR) is the first committed step in the biosynthesis of over two thousand terpene indole alkaloids.
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