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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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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
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
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
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