Phantolid

Structural formula
	Nonspecific stereochemistry
General
Surname	Phantolid
other names	1- (1,1,2,3,3,6-hexamethyl-2 H -inden-5-yl) ethanone; 6-acetyl-1,1,2,3,3,5-hexamethyl-indane; AHMI;
Molecular formula	C 17 H 24 O
Brief description	Solid with a sweet musk odor
External identifiers / databases
EC number	239-360-0
ECHA InfoCard	100.035.766
PubChem	47167
Wikidata	Q21099107
properties
Molar mass	244.43 g mol −1
Physical state	firmly
density	0.9937 g cm −3 at 25 ° C (racemate)
Melting point	61-61.5 ° C (racemate)
safety instructions
H and P phrases	H: 302-410
	P: 264-273-301 + 312-391-501
Toxicological data	1700 mg kg −1 ( LD 50 , rat , oral ) ; 5000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phantolid is a fragrance and is mainly used in the cosmetics industry. It is a bicyclic, aromatic musk compound derived from indan .

Stereochemistry

Phantolide contains a stereocenter and is therefore chiral . There are two enantiomeric forms, ( R ) -phantolid and ( S ) -phantolide. However, only the racemate [( RS ) -phantolid], i.e. a 1: 1 mixture of ( R ) -phantolid and ( S ) -phantolid:

Enantiomers of phantolide
CAS No .: 1217263-72-3	CAS No .: 1217263-73-4

use

Phantolid is a synthetic fragrance without a natural model. It is a component of detergents , creams , lotions and perfumes . The limit values in the USA are lowest for laundry detergents at 0.015% and highest for perfumes at 0.4%. A total of 19 t of Phantolid were used in Europe in 1998. When phantolid is used as an attractant in attractant traps for fruit flies , its effectiveness against male fruit flies is enhanced. Trimedlure is also used as an insecticide .

environment

In a longitudinal study , Phantolid was found in purified water and in fish from bodies of water in front of a sewage treatment plant on the Ruhr . Initial findings also show that phantolid also accumulates in the human body. It was found in human fat and breast milk .

Individual evidence

↑ ^a ^b Phantolid data sheet from PFW Aroma Chemicals, accessed on October 31, 2017.
^ CL Yaws (Ed.): The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals . Elsevier Verlag, Heidelberg 2015, ISBN 978-0-12-800834-8 , p. 541.
↑ Patent DE1035826 : Perfumes. Published March 23, 1999 , Inventors: Carpenter, Marion S .; Easter, Wm. M., Jr .; Wood, Thomas F ..
↑ AV Grampoloff (ed.): Musk-smelling compounds derived from substituiertem indane . In: Helvetica Chimica Acta , Volume 38, 1955, pp. 1263-1268.
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 1,1,2,3,3,6-hexamethylindan-5-yl methyl ketone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on October 23, 2017, is reproduced from a self-classification by the distributor .
↑ ^a ^b A. J. Wohl: Report to The Research Institute for Fragrance Materials, May 15, 1974.
↑ Patent US4541948 : Perfumes containing polyalkyl substituted indan-1-ones and process for preparing the compounds. Published September 17, 1985 , Inventor: Daniel R. Joulain. ‌
↑ Patent DE10000223 : Microcapsule preparations and washing and cleaning agents containing microcapsules. Published on June 12, 2001 , inventors: Ekkehard Jahns, Dieter Boeckh, Werner Bertleff, Peter Neumann. ‌
↑ DLJ Opdyke (Ed.): Monographs on Fragrance Raw Materials: A Collection of Monographs Originally appearing in Food and Cosmetics Toxicology . Pergamon Press, Frankfurt 1979, ISBN 0-08-023775-4 , p. 33.
↑ J. Heck, B. König & R. Winter (eds.): Fragrances, between stink and scent . Wolfgang Legrum, Springer Spektrum, Marburg 2013, ISBN 978-3-658-07310-7 , e-book, p. 168.
↑ A. Akelah (Ed.): Functionalized Polymeric Materials in Agriculture and the Food Industry . Springer Verlag, New York 2013, ISBN 978-1-4614-7061-8 , e-book, p. 168.
↑ H.-D. Eschke, H.-J. Dibowski, J. Traud (Ed.): Investigations into the occurrence of polycyclic musk fragrances in different environmental compartments . In: Environmental Sciences Europe , Ecomed Verlagsgesellschaft AG & Co., Landsberg 1995, Volume 7, No. 3, pp. 131-138.

[PFW-1] Phantolid data sheet from PFW Aroma Chemicals, accessed on October 31, 2017.

[Yaws-2] CL Yaws (Ed.): The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals . Elsevier Verlag, Heidelberg 2015, ISBN 978-0-12-800834-8 , p. 541.

[DE_Patent-3] Patent DE1035826 : Perfumes. Published March 23, 1999 , Inventors: Carpenter, Marion S .; Easter, Wm. M., Jr .; Wood, Thomas F ..

[Grampoloff-4] AV Grampoloff (ed.): Musk-smelling compounds derived from substituiertem indane . In: Helvetica Chimica Acta , Volume 38, 1955, pp. 1263-1268.

[ECHA-5] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 1,1,2,3,3,6-hexamethylindan-5-yl methyl ketone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on October 23, 2017, is reproduced from a self-classification by the distributor .

[Wohl-6] A. J. Wohl: Report to The Research Institute for Fragrance Materials, May 15, 1974.

[US_Patent-7] Patent US4541948 : Perfumes containing polyalkyl substituted indan-1-ones and process for preparing the compounds. Published September 17, 1985 , Inventor: Daniel R. Joulain. ‌

[DE2_Patent-8] Patent DE10000223 : Microcapsule preparations and washing and cleaning agents containing microcapsules. Published on June 12, 2001 , inventors: Ekkehard Jahns, Dieter Boeckh, Werner Bertleff, Peter Neumann. ‌

[Opdyke-9] DLJ Opdyke (Ed.): Monographs on Fragrance Raw Materials: A Collection of Monographs Originally appearing in Food and Cosmetics Toxicology . Pergamon Press, Frankfurt 1979, ISBN 0-08-023775-4 , p. 33.

[Heck-10] J. Heck, B. König & R. Winter (eds.): Fragrances, between stink and scent . Wolfgang Legrum, Springer Spektrum, Marburg 2013, ISBN 978-3-658-07310-7 , e-book, p. 168.

[Akelah-11] A. Akelah (Ed.): Functionalized Polymeric Materials in Agriculture and the Food Industry . Springer Verlag, New York 2013, ISBN 978-1-4614-7061-8 , e-book, p. 168.

[Eschke-12] H.-D. Eschke, H.-J. Dibowski, J. Traud (Ed.): Investigations into the occurrence of polycyclic musk fragrances in different environmental compartments . In: Environmental Sciences Europe , Ecomed Verlagsgesellschaft AG & Co., Landsberg 1995, Volume 7, No. 3, pp. 131-138.