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Key Documents

82415

Sigma-Aldrich

Prunetin

≥98.0% (TLC)

Synonym(s):

4′,5-Dihydroxy-7-methoxyisoflavone

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About This Item

Empirical Formula (Hill Notation):
C16H12O5
CAS Number:
Molecular Weight:
284.26
Beilstein:
292155
EC Number:
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98.0% (TLC)

form

powder

SMILES string

COc1cc(O)c2C(=O)C(=COc2c1)c3ccc(O)cc3

InChI

1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

InChI key

KQMVAGISDHMXJJ-UHFFFAOYSA-N

Biochem/physiol Actions

Inhibitor of both cytoplasmic and mitochondrial human liver aldehyde dehydrogenases, possibly by binding at an allosteric site.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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N S Nagarajan et al.
Natural product research, 20(2), 195-200 (2005-12-02)
Two isoflavonoids isolated from Dalbergia sympathetica were identified as 5,4'-dihydroxy-7-methoxyisoflavone (1) (Prunetin) and Prunetin-4'-O-beta-D-gentiobioside (2) (Dalsympathetin). The natural occurrence of Dalsympathetin is reported for the first time. The position of glycosylation in Dalsympathetin at 4'-position has been confirmed by 2D-NMR
Ruth N Muchiri et al.
Journal of AOAC International, 103(4), 1160-1166 (2020-11-27)
Extracts of red clover (Trifolium pratense L.) containing estrogenic and pro-estrogenic isoflavones are used in dietary supplements primarily for the management of menopausal symptoms in women. A UHPLC-MS/MS assay was developed and validated for the quantitative analysis of the six
Nattaya Ngamrojanavanich et al.
Journal of ethnopharmacology, 109(2), 354-358 (2006-09-16)
A carpin (3-hydroxy-9-methoxypterocarpan) (Medicarpin) (1) and four isoflavones, 7-hydroxy-4'-methoxy-isoflavone (Formononetin) (2); 7,4'-dimethoxyisoflavone (3); 5,4'-dihydroxy-7-methoxy-isoflavone (Prunetin) (4) and 7-hydroxy-6,4'-dimethoxyisoflavone (5) were isolated from the tuber roots of Butea superba Roxb. Compounds 2 and 4 showed moderate cytotoxic activity on KB cell
Hyun Jae Lee et al.
Phytotherapy research : PTR, 25(8), 1196-1200 (2011-02-10)
This study investigated whether prunetin significantly affects the secretion, production and gene expression of mucin from cultured airway epithelial cells. Confluent primary rat tracheal surface epithelial (RTSE) cells were pretreated with adenosine triphosphate (ATP) for 5 min and then chased for
Stephen W J Wang et al.
The Journal of pharmacology and experimental therapeutics, 329(3), 1023-1031 (2009-03-07)
Flavonoids have poor bioavailabilities largely because of metabolism via UDP-glucuronosyltransferases (UGTs). This study aims to further understand the functions of UGT in metabolizing genistein and apigenin, two compounds metabolized more extensively in the gut than in the liver. Because Gunn

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