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SML0786

Sigma-Aldrich

Decursin

≥97% (HPLC)

Synonym(s):

(+)-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

Empirical Formula (Hill Notation):
C19H20O5
CAS Number:
5928-25-6
Molecular Weight:
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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Jin Sook Song et al.
Xenobiotica; the fate of foreign compounds in biological systems, 41(10), 895-902 (2011-06-11)
Decursinol is a major coumarin derived from the roots of Angelica gigas and has various pharmacological effects against inflammation, angiogenesis, nociceptive pain and Alzheimer's disease. In vitro and in vivo studies were conducted to characterize the metabolism and pharmacokinetics of
Sa-Ra Choi et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 49(10), 2517-2523 (2011-06-23)
Decursin is a major biological active component of Angelicagigas Nakai and is known to induce apoptosis of metastatic prostatic cancer cells. However, the apoptotic mechanism of decursin using primary malignant tumor (RC-58T/h/SA#4)-derived human prostate cells is not known. In the
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