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SML0786

Sigma-Aldrich

Decursin

≥97% (HPLC)

Sinónimos:

(+)-Decursin, (7S)-7,8-Dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo[1,2-b:5,4-b′]dipyran-7-yl 3-methyl-2-butenoate, 3-Methyl-2-butenoic acid (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-pyrano[3,2-g]-1-benzopyran-7-yl ester

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About This Item

Fórmula empírica (notación de Hill):
C19H20O5
Número de CAS:
5928-25-6
Peso molecular:
328.36
MDL number:
MFCD00272154
UNSPSC Code:
12352200
NACRES:
NA.77

biological source

Radix peucedani

Quality Level

100

assay

≥97% (HPLC)

form

powder

optical activity

[α]/D +120 to +160°, c = 0.5 in chloroform-d

color

white to beige

solubility

DMSO: 5 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

SMILES string

[o]1c2c(cc3c(c2)OC([C@H](C3)OC(=O)C=C(C)C)(C)C)cc[c]1=O

InChI

1S/C19H20O5/c1-11(2)7-18(21)23-16-9-13-8-12-5-6-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/t16-/m0/s1

InChI key

CUKSFECWKQBVED-INIZCTEOSA-N

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Biochem/physiol Actions

Decursin is a cumarin isolated from Radix peucedani that exhibits a number of physiological actions including anticancer, antibacterial, antinematodal and antioxidant. Decursin is potent anti-angiogenic agent targeting the VEGFR-2 signaling pathway. Decursin exhibits potent neuroprotective activity against glutamate and Ab- induced neurotoxicity. Apparently, decursin stimulates activation of Nerf2. Also, decursin inhibits androgen stimulated AR translocation to the nucleus in LNCaP prostate cancer cells.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000215000
0000214999
0000209342
0000279566
0000179113

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Kyeong Lee et al.
European journal of medicinal chemistry, 45(12), 5567-5575 (2010-10-05)
We report the synthesis of a novel series of highly potent melanin inhibitors which were obtained through structural modification of an anticancer compound S-(+)-decursinol. The in vitro inhibitory potencies of the newly synthesized compounds were evaluated against α-MSH induced melanin
Li Li et al.
Planta medica, 79(3-4), 275-280 (2013-02-01)
Decursin and decursinol angelate are the major components in the alcoholic extract of the root of Angelica gigas Nakai. Our previous work convincingly demonstrated that both decursin and decursinol angelate were rapidly converted to decursinol in mice after administration by
Seok Yun Jung et al.
Journal of cellular biochemistry, 113(5), 1478-1487 (2012-02-03)
Endothelial progenitor cells (EPCs) contribute to the tumor vasculature during tumor progression. Decursin isolated from the herb Angelica gigas is known to possess potent anti-inflammatory activities. Recently, we reported that decursin is a novel candidate for an angiogenesis inhibitor [Jung
Nam Il Park et al.
Molecular biotechnology, 50(2), 114-120 (2011-06-01)
Angelica gigas is a medicinal plant that produces pyranocoumarins, including decursin (D) and decursinol angelate (DA), which have neuroprotective, anticancer, and antiandrogenic effects. In this study, the coumarin biosynthetic pathway was engineered to increase the production of DA. Specifically, a
Li Li et al.
Planta medica, 78(3), 252-259 (2011-11-26)
The pyranocoumarin compound decursin and its isomer decursinol angelate (DA) are the major hydrophobic phytochemicals in the root of Angelica gigas Nakai (AGN, Korean Angelica), a major traditional medicinal herb. The ethanol extract of AGN and especially the purified decursin
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