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Merck
CN

SML0932

Psoralidin

≥98% (HPLC)

Synonym(s):

3,9-Dihydroxy-2-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one, 3,9-Dihydroxy-2-prenylcoumestan

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About This Item

Empirical Formula (Hill Notation):
C20H16O5
CAS Number:
18642-23-4
Molecular Weight:
336.34
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD10566617

Key Documents

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InChI

1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3

SMILES string

CC(C)=CCC1=C(C=C(OC2=O)C(C(OC3=C4)=C2C3=CC=C4O)=C1)O

InChI key

YABIJLLNNFURIJ-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

Quality Level

100

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Biochem/physiol Actions

Psoralidin is a coumestan derivative extracted from Psoralea corylifolia seeds. It exhibits anti-inflammatory property by inhibiting both cyclooxygenases-2 (COX-2) and 5-lipoxygenase (5-LOX) expression. In addition to its anti-cancer and anti-inflammatory activities, psoralidin also exhibits anti-oxidant, anti-bacterial, and anti-depressant activities. Psoralidin is implicated in the regulation of insulin signaling. It is used as a key ingredient in traditional medicines for bleeding, enuresis, pollakiuria, vitiligo, and psoriasis.
Psoralidin is a furanocoumarin natural product used in Chinese medicine. Psoralidin, a PTP1B inhibitor, has been shown to have anticancer activity with a variety of mechanisms proposed. Psoralidin induces ROS generation in androgen-independent prostate cancer cells, leading to inhibition of cell proliferation. Psoralidin has been found to downregulate NOTCH1 signaling, causing growth arrest in both breast cancer stem cells and breast cancer cells.
Psoralidin is a furanocoumarin natural product with anticancer activity; PTP1B inhibitor.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000353447
0000353446
0000353447
0000353446
0000145056

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Hee Jung Yang et al.
Biochemical pharmacology, 82(5), 524-534 (2011-06-15)
Radiotherapy is the most significant non-surgical cure for the elimination of tumor, however it is restricted by two major problems: radioresistance and normal tissue damage. Efficiency improvement on radiotherapy is demanded to achieve cancer treatment. We focused on radiation-induced normal
Li-Tao Yi et al.
Progress in neuro-psychopharmacology & biological psychiatry, 32(2), 510-519 (2007-11-17)
The antidepressant-like effects of psoralidin isolated from the seeds of Psoralea corylifolia were investigated in the forced swimming test (FST) in ICR strain of male mice. Psoralidin significantly decreased immobility time and increased swimming behavior without altering climbing behavior in
Pallab Pahari et al.
The Journal of organic chemistry, 74(7), 2750-2754 (2009-03-04)
A base-catalyzed condensation of phenyl acetate with acid chloride, followed by intramolecular cyclization and microwave-assisted cross-metathesis reaction, leads to the first total synthesis of psoralidin, a natural product with a broad range of biological activities, in a highly convergent and
Luhua Zhao et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 821(1), 67-74 (2005-05-21)
High-performance liquid chromatography (HPLC) was developed for fingerprint analysis of Psoralea corylifolia. Liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MSn) technique was first employed to identify the components of the fingerprint. The samples were separated with an Alltima C18 column (250 mm
Raj Kumar et al.
Molecular cancer therapeutics, 9(9), 2488-2496 (2010-08-26)
Epidermal growth factor receptor (EGFR) activation is an important event that regulates mitogenic signaling, such as the Raf, mitogen-activated protein kinase (MAPK), and extracellular signal-regulated kinase 1/2 cascades. EGFR activation has been implicated in the transition of prostate cancer from
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