Tetramethyl bisphenol F

Tetramethyl bisphenol F
Names
	IUPAC name 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol
	Other names tetramethyl bisphenol F, valPure V70
Identifiers
CAS Number	5384-21-4;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL593206;
ECHA InfoCard	100.023.980
EC Number	226-378-9;
PubChem CID	79345;
CompTox Dashboard (EPA)	DTXSID4063820 ;
	InChI InChI=1S/C17H20O2/c1-10-5-14(6-11(2)16(10)18)9-15-7-12(3)17(19)13(4)8-15/h5-8,18-19H,9H2,1-4H3 Key: AZZWZMUXHALBCQ-UHFFFAOYSA-N;
	SMILES CC1=CC(=CC(=C1O)C)CC2=CC(=C(C(=C2)C)O)C;
Properties
Chemical formula	C17H20O2
Molar mass	256.345 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Tetramethyl bisphenol F (TMBPF), is a new coating intended as a safer replacement for bisphenol A and bisphenol F to use in epoxy linings of aluminium cans and steel cans. It was previously suggested as an insulator in electronic circuit boards.[1]

Polymerisation of tetramethyl bisphenol F occurs with epichlorohydrin when heated between 40 and 70 °C using an alkali as a catalyst to form the resin used as a coating.

Health and Environmental Effects

Causes serious eye irritation. May cause respiratory and skin irritation. Very toxic to aquatic life.[2]

Human Endocrine Effects

According to tests TMBPF does not have any effect on the endocrine system; it does not leach out of cans because unlike BPA it is fully polymerized when deposited on the metal, so there is no free chemical to leach out.[1] Tetramethyl bisphenol F was tested on rats to see if there were effects like male or female hormones. It had almost no effects like this.[3] However, a different study did find effects.[4]

References

Cornwall, Warren (23 January 2020). "To replace controversial plastic additive BPA, a chemical company teams up with unlikely allies". Science. doi:10.1126/science.aba9956. Retrieved 8 December 2020.
"Safety Data Sheet" (PDF). Toronto Research Chemicals Inc. October 11, 2019. Retrieved 8 December 2020.
Maffini, Maricel V.; Canatsey, Ryan D. (January 2020). "An expanded toxicological profile of tetramethyl bisphenol F (TMBPF), a precursor for a new food-contact metal packaging coating". Food and Chemical Toxicology. 135: 110889. doi:10.1016/j.fct.2019.110889. PMID 31629790.
"TMBPF as BPA alternative for coating epoxies | Food Packaging Forum". www.foodpackagingforum.org.

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[Cornwall-1] Cornwall, Warren (23 January 2020). "To replace controversial plastic additive BPA, a chemical company teams up with unlikely allies". Science. doi:10.1126/science.aba9956. Retrieved 8 December 2020.

[2] "Safety Data Sheet" (PDF). Toronto Research Chemicals Inc. October 11, 2019. Retrieved 8 December 2020.

[3] Maffini, Maricel V.; Canatsey, Ryan D. (January 2020). "An expanded toxicological profile of tetramethyl bisphenol F (TMBPF), a precursor for a new food-contact metal packaging coating". Food and Chemical Toxicology. 135: 110889. doi:10.1016/j.fct.2019.110889. PMID 31629790.

[4] "TMBPF as BPA alternative for coating epoxies | Food Packaging Forum". www.foodpackagingforum.org.