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Mezerein

Mezerein
Names
Other names
meserein; 12β-[(E,E)-5-Phenyl-2,4-pentadienoyloxy]daphnetoxin; daphnetoxin,12-[(1-oxo-5-phenyl-2,4-pentadienyl)oxy]-,12-beta(E,E)]
Identifiers
3D model (JSmol)
1675867
ChemSpider
ECHA InfoCard 100.159.782 Edit this at Wikidata
EC Number
  • 631-545-8
UN number 2811
  • 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
    Key: DLEDLHFNQDHEOJ-UDTOXTEMSA-N
  • OC[C@]12O[C@H]1[C@H]1[C@H]3O[C@]4(O[C@]1([C@H]1[C@@]([C@@H]2O)(O)C(=O)C(=C1)C)[C@@H]([C@H]([C@@]3(O4)C(=C)C)OC(=O)/C=C/C=C/c1ccccc1)C)c1ccccc1
Properties
C38H38O10
Molar mass 654.712 g·mol−1
Melting point 258.0 to 262.0 °C; 496.4 to 503.6 °F; 531.1 to 535.1 K
Hazards[1]
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H317
P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mezerein is a toxic diterpene ester found in the sap of Daphne mezereum and related plants. Plants of the genera Euphorbiaceae and Thymelaeaceae possess a wide variety of different phorbol esters, which share the capacity of mimicking diacylglycerol (DAG) and thus activating different isoforms of protein kinase C. Mezerein was first isolated in 1975. It has antileukemic properties in mice, but it is also defined as a weak promoter of skin cancers in the same species.[2] All parts of the plants contain an acrid and irritant sap that contains mezerein, thought to be the principal poison. The sap is especially prevalent in the bark and berries.

Mezerein is highly liposoluble and can cause vomiting, diarrhea and burning of the mouth. When a large dose is taken, there can be shivering, dilation of the pupils, damage to the oral passages and the intestine and even death. It can also irritate the skin, resulting in redness by slight damage of the veins. Because of causing this redness, the sap used to be applied as rouge.[2]

  1. ^ "[(1R,2R,6S,7S,8R,10S,11S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] (2E,4E)-5-phenylpenta-2,4-dienoate". pubchem.ncbi.nlm.nih.gov.
  2. ^ a b Robertson, John. "The Poison Garden". The Poison Garden website. Robbo Services Ltd. Retrieved 28 March 2013.
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