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. 2016;33(1):137-46.
doi: 10.1080/19440049.2015.1110623. Epub 2015 Nov 23.

Natural occurrence of bisphenol F in mustard

Affiliations

Natural occurrence of bisphenol F in mustard

Otmar Zoller et al. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2016.

Abstract

Bisphenol F (BPF) was found in mustard up to a concentration of around 8 mg kg(-1). Contamination of the raw products or caused by the packaging could be ruled out. Also, the fact that only the 4,4'-isomer of BPF was detected spoke against contamination from epoxy resin or other sources where technical BPF is used. Only mild mustard made of the seeds of Sinapis alba contained BPF. In all probability BPF is a reaction product from the breakdown of the glucosinolate glucosinalbin with 4-hydroxybenzyl alcohol as an important intermediate. Hot mustard made only from brown mustard seeds (Brassica juncea) or black mustard seeds (Brassica nigra) contained no BPF. BPF is structurally very similar to bisphenol A and has a similar weak estrogenic activity. The consumption of a portion of 20 g of mustard can lead to an intake of 100-200 µg of BPF. According to a preliminary risk assessment, the risk of BPF in mustard for the health of consumers is considered to be low, but available toxicological data are insufficient for a conclusive evaluation. It is a new and surprising finding that BPF is a natural food ingredient and that this is the main uptake route. This insight sheds new light on the risk linked to the family of bisphenols.

Keywords: 2,4-bis(4-hydroxybenzyl)-phenol; bamboo shoots; 4-hydroxybenzyl alcohol; Bisphenol F; Sinapis alba; bisphenols; endocrine disruptor; glucosinalbin; mustard; taxiphyllin.

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Figures

None
Graphical abstract
Figure 1.
Figure 1.
Structure of 2,4-bis(4-hydroxybenzyl)phenol.
Figure 2.
Figure 2.
(colour online) Proposed reaction mechanism for the formation of 4,4ʹ-BPF. The cleavage of the glucosinolate glucosinalbin is catalysed by the enzyme myrosinase and leads primarily to the formation of the corresponding isothiocyanate. 4-Hydroxybenzyl isothiocyanate is hydrolysed to 4-HBA. In a further reaction, 4,4ʹ-BPF is formed. The carbocation can be formed from the isothiocyanate by loss of thiocyanate or from the 4-hydroxybenzyl alcohol by protonation and loss of water. A further 4-hydroxybenzyl alcohol molecule reacts with the carbocation.
Figure 3.
Figure 3.
Results of the market survey on mustard. The products were classified according to information on the label regarding pungency. Dijon-style mustards, without further information regarding pungency, were included in the class ‘hot’. BPF was detected in 48 out of 61 samples. For visibility, values below the LOD were assigned a small value. For further details, see the text.

Comment in

References

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