M5518
瑞香素
from Daphne mezereum, ≥97% (HPLC)
别名:
12β-[(E,E)-5-Phenyl-2,4-pentadienoyloxy]daphnetoxin
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关于此项目
经验公式（希尔记法）:
C38H38O10
化学文摘社编号:
分子量:
654.70
PubChem Substance ID:
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
1675867
MDL number:
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.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Skin Irrit. 2 - Skin Sens. 1
存储类别
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
法规信息
新产品
此项目有
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
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
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
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
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