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Diethylamino hydroxybenzoyl hexyl benzoate

From Wikipedia, the free encyclopedia
Diethylamino hydroxybenzoyl hexyl benzoate
Names
Preferred IUPAC name
Hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate
Other names
Uvinul A Plus
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.103.916Edit this at Wikidata
UNII
  • InChI=1S/C24H31NO4/c1-4-7-8-11-16-29-24(28)20-13-10-9-12-19(20)23(27)21-15-14-18(17-22(21)26)25(5-2)6-3/h9-10,12-15,17,26H,4-8,11,16H2,1-3H3 checkY
    Key: FDATWRLUYRHCJE-UHFFFAOYSA-N checkY
  • InChI=1/C24H31NO4/c1-4-7-8-11-16-29-24(28)20-13-10-9-12-19(20)23(27)21-15-14-18(17-22(21)26)25(5-2)6-3/h9-10,12-15,17,26H,4-8,11,16H2,1-3H3
    Key: FDATWRLUYRHCJE-UHFFFAOYAR
  • CCCCCCOC(=O)C1=CC=CC=C1C(=O)C2=C(C(=CC=C2)N(CC)CC)O
Properties
C24H31NO4
Molar mass397.515 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Diethylamino hydroxybenzoyl hexyl benzoate (INCI) is anorganic compound used insunscreens to absorbUVA radiation. It is marketed asParsol DHHB byDSM and asUvinul A Plus byBASF. DHHB has an absorption maximum of 354 nm.[1][2]DHHB has excellent photostability and compatibility with other UV absorbers and other cosmetic ingredients.[3]

The European CommissionScientific Committee on Consumer Safety (SCCS) has expressed concerns aboutdi-n-hexyl phthalate contamination from manufacture and recommended a maximum safe level of 260 parts per million in DHHB for suncreams. They further recommended that a trace level below 1 ppm should be the target for manufacturers as the contamination is avoidable.[4] Although DHHB is a safe sunscreen ingredient, di-n-hexyl phtalate has been on the European Chemicals Agency list of Substances of Very High Concern since 2013.[5]

Synthesis

[edit]

DHHB is produced by a reaction between 3-hydroxy-N,N-diethylaniline andphthalic anhydride, followed byesterification with1-hexanol.

Regulation

[edit]

DHHB has been approved for the use in sunscreens in the European Union since 2005 with a maximum concentration of 10%[6][7] and is also approved in South America, Mexico, Japan and Taiwan.[8] In the United States it can be used for product protection.[9]

References

[edit]
  1. ^Vielhaber G, Grether-Beck S, Koch O, Johncock W, Krutmann J (March 2006). "Sunscreens with an absorption maximum of > or =360 nm provide optimal protection against UVA1-induced expression of matrix metalloproteinase-1, interleukin-1, and interleukin-6 in human dermal fibroblasts".Photochem Photobiol Sci.5 (3):275–82.doi:10.1039/b516702g.PMID 16520862.
  2. ^UV Absorber Portfolio Performance Data and Regulatory StatusArchived 2010-10-11 at theWayback Machine, cosmetics.basf.de
  3. ^"Science Links Japan | New raw materials and technologies for cosmetics. Functions and development of new UVA absorber". Archived fromthe original on 2012-02-10. Retrieved2008-08-27.
  4. ^"SCCS - Scientific Advice on the safety of Diethylamino Hydroxybenzoyl Hexyl Benzoate - DHHB – S83 - European Commission".health.ec.europa.eu. Retrieved2025-06-30.
  5. ^"Candidate List of substances of very high concern for Authorisation - ECHA".echa.europa.eu. Retrieved2025-06-30.
  6. ^"BASF Group: Uvinul® A Plus - for safer sunbathing". Archived fromthe original on 2008-10-07. Retrieved2008-08-25.
  7. ^"Archived copy"(PDF). Archived fromthe original(PDF) on 2008-08-14. Retrieved2008-08-25.{{cite web}}: CS1 maint: archived copy as title (link)
  8. ^"Archived copy"(PDF). Archived fromthe original(PDF) on 2011-07-18. Retrieved2008-08-25.{{cite web}}: CS1 maint: archived copy as title (link)
  9. ^"WebPublisher HTML Template". Archived fromthe original on 2011-07-21. Retrieved2009-07-11.
Sunscreening agentscurrently approved by one or more agencies (e.g.US FDA,SCCS,TGA)
  • UVA: 400–315 nm
  • UVB: 315–290 nm
UVA filters
UVB filters
UVA+UVB filters
Retrieved from "https://en.wikipedia.org/w/index.php?title=Diethylamino_hydroxybenzoyl_hexyl_benzoate&oldid=1298165025"
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