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J4145

Sigma-Aldrich

Jervine

≥98% (HPLC), powder

Synonyme(s) :

(3β, 23β)-17,23-Epoxy-3-hydroxyveratraman-11-one, 11-Ketocyclopamine

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About This Item

Formule empirique (notation de Hill):
C27H39NO3
Numéro CAS:
469-59-0
Poids moléculaire :
425.60
Numéro CE :
207-417-9
Numéro MDL:
MFCD01684066
Code UNSPSC :
51111800
ID de substance PubChem :
24896194
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

powder

Solubilité

methanol: >2 mg/mL
H2O: insoluble

Température de stockage

−20°C

Chaîne SMILES 

[H][C@@]12C[C@H](C)CN[C@@]1([H])[C@@H](C)[C@@]3(CC[C@]4([H])C(=C3C)C(=O)[C@@]5([H])[C@@]4([H])CC=C6C[C@@H](O)CC[C@]56C)O2

InChI

1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1

Clé InChI

CLEXYFLHGFJONT-DNMILWOZSA-N

Informations sur le gène

human ... EBP(10682)

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Description générale

Jervine is a steroid alkaloid present in Veratrum californicum.

Actions biochimiques/physiologiques

Jervine is a potent teratogenic agent. It can induce apoptosis in leukemia cells and MUTZ-1 cells. Jervine is an inhibitor of Hedgehog signaling. It exhibits anti-cancer effects on human prostate cancer. It also increases the chemosensitivity of breast cancer cells to doxorubicin treatment. Jervine may be used for treating hypertension and heart disease.
Jervine is a sonic hedgehog (Shh) pathway inhibitor.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H360D

Classification des risques

Acute Tox. 3 Oral - Repr. 1B

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
062M4709V
081M4727V
019K4707
057K4710
104K4703

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

K A El Sayed et al.
Phytochemistry, 55(1), 19-22 (2000-10-06)
Preparative-scale fermentation of the known C-nor-D-homosteroidal jerveratrum alkaloid jervine with Cunninghamella elegans (ATCC 9245) has resulted in the isolation of (-)-jervinone as the major metabolite. In addition, C. elegans ATCC 9245 was able to epimerize C-3 of jervine, producing 3-epi-jervine.
Carlos M Moran et al.
Developmental dynamics : an official publication of the American Association of Anatomists, 240(6), 1354-1364 (2011-03-09)
Signaling by the hedgehog (Hh) family of secreted growth factors is essential for development of embryonic blood vessels. Embryos lacking Hh function have abundant endothelial cells but fail to assemble vascular cords or lumenized endothelial tubes. However, the role of
F R Sim et al.
Teratogenesis, carcinogenesis, and mutagenesis, 3(2), 111-121 (1983-01-01)
The Veratrum-derived steroidal alkaloid, jervine, induces cyclopia and limb malformations in sheep, and various other craniofacial malformations in several other mammalian and avian species. In the present study, the question whether jervine acts directly or indirectly on mammalian embryos to
Miki Nagase et al.
Microvascular research, 71(2), 85-90 (2006-01-18)
Hedgehog family was reported to be involved in murine yolk sac angiogenesis. However, it has not been clarified whether impaired angiogenesis under hedgehog signaling blockade is attributable to true defect in angiogenic process or just a sequel of earlier vasculogenic
Lamia Ghezali et al.
Experimental cell research, 319(7), 1043-1053 (2013-01-30)
Erythroleukemia is generally associated with a very poor response and survival to current available therapeutic agents. Cyclooxygenase-2 (COX-2) has been described to play a crucial role in the proliferation and differentiation of leukemia cells, this enzyme seems to play an
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