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M5518

Sigma-Aldrich

Mezerein

from Daphne mezereum, ≥97% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C38H38O10
CAS Number:
34807-41-5
Molecular Weight:
654.70
Beilstein/REAXYS Number:
1675867
MDL number:
MFCD00135953
UNSPSC Code:
12352200
PubChem Substance ID:
24897019

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

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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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

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

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Paul A Wender et al.
Nature chemistry, 3(8), 615-619 (2011-07-23)
The daphnane diterpene orthoesters constitute a structurally fascinating family of natural products that exhibit a remarkable range of potent biological activities. Although partial activity information is available for some natural daphnanes, little information exists for non-natural congeners or on how
Michelle R Staudt et al.
Journal of cellular physiology, 218(2), 304-314 (2008-10-11)
Cancer cells are commonly less differentiated than their normal progenitors; a phenotype that correlates with loss of specialized functions and an increased capability to self-renew. Melanoma is an ideal model to analyze cancer progression and differentiation since a well-characterized process
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
C A O'Brian et al.
Cancer metastasis reviews, 8(3), 199-214 (1989-12-01)
Protein kinase C (PKC) is composed of a family of isozymes that transduce signals of certain hormones, growth factors, lectins, and neurotransmitters. This review addresses the role of PKC in the regulation of cellular proliferation and its disorders. PKC is
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
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