Skip to Content
Merck
CN

Key Documents

View All Documentation

M5518

Mezerein

from Daphne mezereum, ≥97% (HPLC)

Synonym(s):

12β-[(E,E)-5-Phenyl-2,4-pentadienoyloxy]daphnetoxin

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C38H38O10
CAS Number:
34807-41-5
Molecular Weight:
654.70
PubChem Substance ID:
24897019
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
1675867
MDL number:
MFCD00135953
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

biological source

Daphne mezereum

assay

≥97% (HPLC)

storage temp.

−20°C

SMILES string

[H][C@@]12C=C(C)C(=O)[C@@]1(O)[C@H](O)[C@@]3(CO)O[C@H]3C4[C@H]5OC6(O[C@]5([C@H](OC(=O)\C=C\C=C\c7ccccc7)[C@@H](C)[C@]24O6)C(C)=C)c8ccccc8

InChI

1S/C38H38O10/c1-21(2)36-30(44-27(40)18-12-11-15-24-13-7-5-8-14-24)23(4)37-26-19-22(3)29(41)35(26,43)33(42)34(20-39)31(45-34)28(37)32(36)46-38(47-36,48-37)25-16-9-6-10-17-25/h5-19,23,26,28,30-33,39,42-43H,1,20H2,2-4H3/b15-11+,18-12+/t23-,26-,28?,30-,31+,32-,33-,34+,35-,36+,37+,38?/m1/s1

InChI key

DLEDLHFNQDHEOJ-WNRHQEOASA-N

Biochem/physiol Actions

Potent second stage tumor promotor and inflammatory agent; activates protein kinase C at nanomolar concentrations.

Other Notes

Phorbol ester analog from the plant Daphne mezereum.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H317

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

新产品

This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
127H0732
126H1063
113K0993
102K1458
098H1411

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Sheng Zhuo Huang et al.
Phytochemistry, 75, 99-107 (2011-12-27)
Seven previously unreported daphnane-type diterpene esters named acutilobins A-G, together with 12 known ones, were isolated from EtOAc extract of Daphne acutiloba Rehd. Their structures were elucidated based on the spectroscopic data. The cytotoxic and anti-HIV-1 activities of these daphnane-type
Paul A Wender et al.
Organic letters, 9(9), 1829-1832 (2007-04-06)
[reaction: see text] An efficient synthetic route to the ABC tricyclic core of 1alpha-alkyldaphnanes has been developed. The conformational bias imparted by the C6-C9 oxo-bridge of BC-ring system 12 was used to elaborate the ABC-ring system precursor including the introduction
Bing-Dong Lin et al.
Journal of natural products, 73(7), 1301-1305 (2010-07-03)
Six new oxygenated daphnane-type diterpenoids, trigoxyphins A-F (1-6), a phenanthrene-type diterpenoid, trigoxyphin G (7), and two known compounds were isolated from twigs of Trigonostemon xyphophylloides. Their structures were established using spectroscopic methods. Compounds 1 and 2 exhibited strong cytotoxic activity
Craig Stewart et al.
Organic letters, 13(4), 720-723 (2011-01-19)
A short, stereoselective approach to the fused tricyclic carbon skeleton found in the tigliane and daphnane classes of diterpene natural products is described. Convergent coupling of the A- and C-rings, followed by diastereoselective cerium enolate addition and formation of a
I Rehman et al.
Molecular carcinogenesis, 27(4), 298-307 (2000-04-04)
The skin tumor initiators N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) and 7,12-dimethylbenz[a]anthracene (DMBA) differ in effectiveness when tumor formation is promoted by 12-O-tetradecanoylphorbol-13-acetate (TPA). Even at high doses, MNNG is less effective, producing fewer benign and malignant tumors with a longer latent period. In
View All Related Papers

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