Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

J4145

Sigma-Aldrich

Jervine

≥98% (HPLC), powder

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C27H39NO3
CAS Number:
469-59-0
Molecular Weight:
425.60
EC Number:
207-417-9
MDL number:
MFCD01684066
UNSPSC Code:
51111800
PubChem Substance ID:
24896194
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

solubility

methanol: >2 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

[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

InChI key

CLEXYFLHGFJONT-DNMILWOZSA-N

Gene Information

human ... EBP(10682)

Looking for similar products? Visit Product Comparison Guide

General description

Jervine is a steroid alkaloid present in Veratrum californicum.

Biochem/physiol Actions

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.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H360D

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Stephen T Lee et al.
Journal of agricultural and food chemistry, 51(3), 582-586 (2003-01-23)
Veratrum californicum was responsible for large losses of sheep grazing high mountain ranges in central Idaho in the 1950s. Veratrum induces various birth defects including the cyclopic-type craniofacial defect (monkey-faced lambs) that is specifically induced in lambs after pregnant ewes
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
Fadime Atalay Dumlu et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 55, 191-199 (2019-01-23)
Veratrum, hellebore is an important plant species of the Liliaceae family and jervine is the characteristic steroidal alkaloid constituent of Veratrum album. In the current study, anti-inflammatory and antioxidant effects of jervine isolated from NH4OH-benzene extract of V. album rhizomes
View All Related Papers

Articles

Cancer Stem Cells: Targets for Cancer Therapy

Cancer stem cell media, spheroid plates and cancer stem cell markers to culture and characterize CSC populations.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service