Pentadecan-15-olide

Structural formula
General
Surname	Pentadecan-15-olide
other names	1-oxa-2-cyclohexadecanone; Oxacyclohexadecan-2-one; 15-hydroxypentadecanoic acid lactone; 15-pentadecanolide; Pentalid; Thibetolide; 15-oxypentadecene lactone; Pentadecalactone; PENTADECALACTONE ( INCI ) ;
Molecular formula	C 15 H 28 O 2
Brief description	white solid
External identifiers / databases
EC number	203-354-6
ECHA InfoCard	100.003.050
PubChem	235414
ChemSpider	205386
Wikidata	Q9251595
properties
Molar mass	240.38 g mol −1
Physical state	firmly
density	0.918 g cm −3 (25 ° C)
Melting point	34-36 ° C
boiling point	137 ° C (3 hPa)
Refractive index	soluble in ethanol and dipropylene glycol ; practically insoluble in water;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Pentadecane-olid 15 , also 1.15 pentadecanolide or exaltolide is a macrocyclic (16-membered) lactone and is among the musk fragrances .

Occurrence

Pentadecan-15-olide is a component of the oil from angelica ( angelica ). It was identified in medicinal angelica oil by Max Kerschbaum von Haarmann & Reimer in the 1920s .

Manufacturing

When 15-bromopentadecanoic acid is heated with potassium carbonate or from 15-hydroxypentadenanoic acid and benzenesulfochloride , pentadecan-15-olide is formed with cyclization. It can also be obtained by hydrogenating 15-pentadecenolide . It is usually present as a mixture of 15-pentadecen-11-olide and 15-pentadecen-12-olide. This double bond isomer mixture is referred to in the present case as 15-pentadecene-11 (12) -olide.

use

Pentadecan-15-olide is a monomer used to make PGA-co-pentadecalactone polymers, which are used in the development of directly compressed, extended-release tablets of poorly soluble drugs such as ketoprofen . Pentadecan-15-olide can also be used for the synthesis of poly (pentadecanolide) (PPDL) by Novozyme 435 catalyzed ring-opening polymerization. It can also be used as a starting reagent for the synthesis of terminally branched iso-fatty acids (iso-C15-C17).

Pentadecan-15-olide can in particular also be used as a fragrance , in perfume compositions, perfume oils or fragrance compositions. Another area of use is hygiene or care products, particularly in the household and personal care sector.

Individual evidence

↑ Entry on PENTADECALACTONE in the CosIng database of the EU Commission, accessed on December 23, 2019.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet pentadecanolide, ≥99.0% (GC) from Sigma-Aldrich , accessed on February 1, 2019 ( PDF ).
↑ ^a ^b ^c Datasheet Pentadecanolide, 98% from AlfaAesar, accessed on February 1, 2019 ( PDF )(JavaScript required) .
↑ Wolfgang Legrum: Fragrances, between stench and fragrance occurrence, properties and use of fragrances and their mixtures . Springer-Verlag, 2015, ISBN 978-3-658-07310-7 , pp. 170 ( limited preview in Google Book search).
↑ Simone Schmitz-Spanke, Thomas Nesseler, Stephan Letzel, Dennis Nowak: Environmental Medicine . ecomed-Storck GmbH, 2017, ISBN 978-3-609-10562-8 , p. 312 ( limited preview in Google Book search).
↑ M. Kerschbaum: About lactones with large rings - the carriers of the vegetable musk scent. In: Reports of the German Chemical Society. 60, 1927, p. 902, doi : 10.1002 / cber.19270600411 .
^ David Rowe: Chemistry and Technology of Flavors and Fragrances . John Wiley & Sons, 2009, ISBN 1-4051-4807-1 , pp. 147 ( limited preview in Google Book search).
↑ Lexikon der Chemie, Spektrum Akademischer Verlag, 1998, Volume 1, ISBN 3-8274-0379-0 , p. 420.
↑ ^a ^b Google Patents: DE10113963A1 - Process for the production of 15-pentadecanolide - Google Patents , accessed on February 1, 2019.

[CosIng-1] Entry on PENTADECALACTONE in the CosIng database of the EU Commission, accessed on December 23, 2019.

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet pentadecanolide, ≥99.0% (GC) from Sigma-Aldrich , accessed on February 1, 2019 ( PDF ).

[Alfa-3] Datasheet Pentadecanolide, 98% from AlfaAesar, accessed on February 1, 2019 ( PDF )(JavaScript required) .

[Wolfgang_Legrum-4] Wolfgang Legrum: Fragrances, between stench and fragrance occurrence, properties and use of fragrances and their mixtures . Springer-Verlag, 2015, ISBN 978-3-658-07310-7 , pp. 170 ( limited preview in Google Book search).

[Simone_Schmitz-Spanke,_Thomas_Nesseler,_Stephan_Letzel,_Dennis_Nowak-5] Simone Schmitz-Spanke, Thomas Nesseler, Stephan Letzel, Dennis Nowak: Environmental Medicine . ecomed-Storck GmbH, 2017, ISBN 978-3-609-10562-8 , p. 312 ( limited preview in Google Book search).

[DOI10.1002/cber.19270600411-6] M. Kerschbaum: About lactones with large rings - the carriers of the vegetable musk scent. In: Reports of the German Chemical Society. 60, 1927, p. 902, doi : 10.1002 / cber.19270600411 .

[David_Rowe-7] David Rowe: Chemistry and Technology of Flavors and Fragrances . John Wiley & Sons, 2009, ISBN 1-4051-4807-1 , pp. 147 ( limited preview in Google Book search).

[Lexikon_der_Chemie-8] Lexikon der Chemie, Spektrum Akademischer Verlag, 1998, Volume 1, ISBN 3-8274-0379-0 , p. 420.

[google.com-9] Google Patents: DE10113963A1 - Process for the production of 15-pentadecanolide - Google Patents , accessed on February 1, 2019.