Mezerein information

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
CAS Number	34807-41-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1675867
ChemSpider	21242853 ;
ECHA InfoCard	100.159.782
EC Number	631-545-8;
PubChem CID	24832075;
UN number	2811
CompTox Dashboard (EPA)	DTXSID3025673 ;
	InChI 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;
	SMILES 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
Chemical formula	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
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317
Precautionary statements	P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501
NFPA 704 (fire diamond)	2 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

^ "[(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.
^ ^a ^b Robertson, John. "The Poison Garden". The Poison Garden website. Robbo Services Ltd. Retrieved 28 March 2013.

[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.

[Marit-2] Robertson, John. "The Poison Garden". The Poison Garden website. Robbo Services Ltd. Retrieved 28 March 2013.

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