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Sigma-Aldrich

Pinobanksin

≥95% (HPLC)

Synonym(s):

(2R,3R)-3,5,7-Trihydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one, (2R,3R)-3,5,7-Trihydroxy-2-phenyl-chroman-4-one, (2R,3R)-3,5,7-Trihydroxyflavanone

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About This Item

Empirical Formula (Hill Notation):
C15H12O5
CAS Number:
548-82-3
Molecular Weight:
272.25
Beilstein:
91238
MDL number:
MFCD07784478
UNSPSC Code:
12352200
PubChem Substance ID:
329760961
NACRES:
NA.25

Assay

≥95% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

O[C@@H]1[C@H](Oc2cc(O)cc(O)c2C1=O)c3ccccc3

InChI

1S/C15H12O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,14-17,19H/t14-,15+/m0/s1

InChI key

SUYJZKRQHBQNCA-LSDHHAIUSA-N

Related Categories

General description

Pinobanksin is a flavonoid that is widely available in honey and different propolis.

Application

Pinobanksin has been used as a reference standard to identify and measure its presence in eleven different acacia honey samples using high-performance liquid chromatography with photo-diode array detection (HPLC-PDA).

Biochem/physiol Actions

Pinobanksin is a potent antioxidant. It displays several anti-cancer properties as an apoptosis inducer, anti-proliferative and antiangiogenic agent in B-cell lymphoma (M12.C3.F6) cells and human umbilical vein endothelial cells, respectively. Pinobanksin also exerts antimicrobial and antifungal properties.

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

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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Potential antimicrobial activity of honey phenolic compounds against Gram positive and Gram negative bacteria
Leyva-Jimenez F J, et al.,
Lebensm. Wiss. Technol., 101, 236-245 (2019)
Cui Shi et al.
Phytochemistry, 71(4), 435-442 (2009-12-22)
Phenolic compounds, named integracin D (1), (7'R, 8'S, 8S)-8-hydroxyisoguaiacin (3), (2R, 3R) pinobanksin-3-caffeoylate (5) and threo-8S-7-methoxysyringylglycerol (6), respectively, were isolated from the Chinese mangrove plant Laguncularia racemosa (L) Gaertn. f. (Combretaceae), together with 23 known phenolic metabolites. Their structures were
Yan-Zhen Zheng et al.
Food chemistry, 240, 323-329 (2017-09-28)
The effects of the ester group and solvent on the structure and antioxidant activity of pinobanksin were carried out using DFT calculation. First, the properties of the intramolecular hydrogen-bonds in the investigated compounds were studied. Second, the antioxidant capacities of
Xiaolan Xu et al.
Molecules (Basel, Switzerland), 24(19) (2019-10-09)
The chemical compositions of ethanol extracts of propolis from China (EEP-C) and the United States (EEP-A) and their antifungal activity against Penicillium notatum were determined. The result showed that a total of 49 compounds were detected by UPLC-Q-TOF-MS, 30 of
Antiangiogenic effect of pinobanksin on human umbilical vein endothelial cells
Bang, Ho-Jeong and Ahn, Mok-Ryeon
Journal of functional foods, 79, 104408-104408 (2021)
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