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80614

Pinostrobin

≥99.0% (TLC)

Synonym(s):

(S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one

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About This Item

Empirical Formula (Hill Notation):
C16H14O4
CAS Number:
480-37-5
Molecular Weight:
270.28
EC Number:
207-548-1
UNSPSC Code:
12352200
PubChem Substance ID:
329768995
Beilstein/REAXYS Number:
270230
MDL number:
MFCD06858342
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assay

≥99.0% (TLC)

SMILES string

COc1cc(O)c2C(=O)C[C@H](Oc2c1)c3ccccc3

InChI

1S/C16H14O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-8,14,17H,9H2,1H3/t14-/m0/s1

InChI key

ORJDDOBAOGKRJV-AWEZNQCLSA-N

Biochem/physiol Actions

Elicits intense apoptotic response from cultured leukemia cells in vitro. Strongly inhibits the Ca2+ signals involved in the control of G2/M phase cell cycle progression in Saccharomyces cerevisiae. Shows potent antiviral effect against herpes simplex virus-1.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Regulatory Information

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Hadi Poerwono et al.
Bioorganic & medicinal chemistry letters, 20(7), 2086-2089 (2010-03-12)
Pinostrobin (5-hydroxy-7-methoxyflavanone) obtained in relatively large amounts from fingerroot (Boesenbergia pandurata) was converted to its C-6 and C-8 prenylated derivatives. The Mitsunobu reaction, europium(III)-catalyzed Claisen-Cope rearrangement, and Claisen reaction coupled with cross-metathesis were used as the key steps. Using a
Nwet Nwet Win et al.
Journal of natural products, 70(10), 1582-1587 (2007-09-28)
The chloroform extract of rhizomes of Boesenbergia pandurata demonstrated marked preferential cytotoxicity against human pancreatic PANC-1 cancer cells in nutrient-deprived medium. Bioactivity-directed investigation of this extract yielded four new secondary metabolites, geranyl-2,4-dihydroxy-6-phenethylbenzoate ( 1), 2',4'-dihydroxy-3'-(1''-geranyl)-6'-methoxychalcone ( 2), (1' R,2' S,6'
J C Le Bail et al.
Cancer letters, 156(1), 37-44 (2000-06-07)
The interaction between the estrogen receptor and 5-hydroxy-7-methoxyflavanone (pinostrobin) was studied in the presence or absence of estradiol or dehydroepiandrosterone sulfate (DHEAS), respectively, using a stably transfected human breast cancer cell line (MVLN). We also evaluated its action on the
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