3-benzylidene camphor

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Structural formula
Structural formula of (E) - (1S, 4R) -3-benzylidene camphor

Structural formula of (Z) - (1S, 4R) -3-benzylidene camphor

(1 S , 4 R ) -3-Benzylidenecamphor (CAS No. 36275-29-3) with unknown geometry at the C = C double bond:
( E ) isomer (above) and ( Z ) isomer (below)
General
Surname 3-benzylidene camphor
other names
  • 3-BC
  • 3-benzylidenebon-2-one
  • 1,7,7-trimethyl-3- (phenylmethylene) bicyclo [2.2.1] heptan-2-one
  • 3-Benzylidene-1,7,7-trimethylbicyclo [2.2.1] heptan-2-one
Molecular formula C 17 H 20 O
External identifiers / databases
CAS number
  • 15087-24-8 (undefined configuration)
  • 36275-29-3 [(1 S , 4 R ) but unknown geometry at the C = C double bond]
ECHA InfoCard 100.035.567
PubChem 5901612
ChemSpider 4739980
Wikidata Q27254657
properties
Molar mass 240.35 g mol −1
Physical state

firmly

Melting point

97 ° C

solubility
safety instructions
GHS labeling of hazardous substances
08 - Dangerous to health

Caution

H and P phrases H: 361fd
P: 281
Authorization procedure under REACH

Of particular concern: there are likely to be serious effects on the environment

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3-Benzylidenecamphor (3-BC) is a mixture of several isomeric chemical compounds . The mixture was previously used in cosmetics as a component ( UV filter ) in sunscreens .

3-BC can act like a hormone , as shown in cell tests and animal studies , and harmful effects on aquatic ecosystems are likely. Germany therefore proposed 3-BC as a substance of very high concern ( SVHC ) in 2016 . In the committee of the member states of the European Chemicals Agency ( ECHA ), two states voted against inclusion in the candidate list. The decision was referred to the EU Commission . Since February 2016, the compound may no longer be used as a cosmetic ingredient ( UV-B filter). Other countries like Turkey followed the EU decision.

Individual evidence

  1. ↑ a b c d data sheet 3-Benzylidenecamphor from Sigma-Aldrich , accessed on May 28, 2017 ( PDF ).
  2. ^ A b Scientific Committee on Consumer Safety: Opinion on 3-benzylidene camphor
  3. ↑ Entry in the SVHC list of the European Chemicals Agency , accessed on January 21, 2019.
  4. ↑ Henrik Holbech, Ulrik Nørum, Bodil Korsgaard, Poul Bjerregaard: The Chemical UV-Filter 3-Benzylidene Camphor Causes an Oestrogenic Effect in an in vivo Fish Assay. In: Pharmacology & Toxicology. 91, 2002, p. 204, doi : 10.1111 / j.1742-7843.2007.auindex_1.x-i1 .
  5. ↑ Margret Schlumpf, Hubert Jarry, Wolfgang Wuttke, Risheng Ma, Walter Lichtensteiger: Estrogenic activity and estrogen receptor β binding of the UV filter 3-benzylidene camphor. In: Toxicology. 199, 2004, p. 109, doi : 10.1016 / j.tox.2004.02.015 .
  6. ↑ a b Umweltbundesamt.de: Camphor substances , accessed on May 29, 2017.
  7. ↑ Axel Trautmann, Jörg Kleine-Tebbe: Allergology in Clinic and Practice Allergens - Diagnostics - Therapy . Georg Thieme Verlag, 2013, ISBN 978-3-13-159352-8 , p. 257 ( limited preview in Google Book search).
  8. ↑ Regulation (EU) 2015/1298 of the Commission of 28 July 2015 amending Annexes II and VI of Regulation (EC) No. 1223/2009 of the European Parliament and of the Council on cosmetic products
  9. ↑ ul.com: Turkey Bans UV Filter 3-Benzylidene Camphor | Industries , accessed May 29, 2017.
  10. ↑ enhesa.com: ASEAN Cosmetic Directive: 3-benzylidene camphor to be banned from cosmetics | Enhesa , accessed May 29, 2017.