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Secologanin

analytical standard

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About This Item

Formule empirique (notation de Hill):
C17H24O10
Numéro CAS:
19351-63-4
Poids moléculaire :
388.37
Numéro MDL:
MFCD16661163
Code UNSPSC :
85151701
ID de substance PubChem :
329757628
Nomenclature NACRES :
NA.24

Qualité

analytical standard

Niveau de qualité

100

Pureté

≥88% (HPLC)

Technique(s)

HPLC: suitable
gas chromatography (GC): suitable

Application(s)

food and beverages

Format

neat

Température de stockage

−20°C

Chaîne 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

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

Clé InChI

CSKKDSFETGLMSB-NRZPKYKESA-N

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Catégories apparentées

Application

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (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
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
Liuqing Yang et al.
Chemistry & biodiversity, 7(4), 860-870 (2010-04-17)
Strictosidine synthase (STR1) catalyzes the stereoselective formation of 3alpha(S)-strictosidine from tryptamine and secologanin. Strictosidine is the key intermediate in the biosynthesis of 2,000 plant monoterpenoid indole alkaloids, and it is a key precursor of enzyme-mediated synthesis of alkaloids. An improved
Gyula Beke et al.
Journal of natural products, 65(5), 649-655 (2002-05-25)
The reaction of secologanin (1) (mainly in its tetraacetylated form 1a) with histamine (2) and its benzyl derivative (2b) was investigated. With the benzylated amine (2b), the main product was the normal, tetraacetylated benzyl derivative of histeloside having the R
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