Bornyl acetate

Structural formula
Structure of (-) - bornyl acetate
General
Surname	Bornyl acetate
other names	Borneol acetate Bornyl acetate endo- boronyl acetate 1,7,7-Trimethylbicyclo [2.2.1] hept-2-yl acetate
Molecular formula	C 12 H 20 O 2
Brief description	colorless crystals with a strong smell of spruce colorless crystals or colorless liquid
External identifiers / databases
CAS number 5655-61-8 (-) - bornyl acetate 20347-65-3 (+) - bornyl acetate 76-49-3 (±) -Racemat EC number 200-964-4 ECHA InfoCard 100,000,878 PubChem 6448 Wikidata Q780165
properties
Molar mass	196.29 g · mol -1
Physical state	firmly
density	0.981-0.99 g cm -3
Melting point	25-29 ° C
boiling point	224-226 ° C
solubility	almost insoluble in water easily soluble in ethanol
Refractive index	1.4635 (20 ° C)
safety instructions
GHS hazard labeling no classification available
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

Bornyl acetate is the acetic acid ester of the terpene borneol .

Isomers

Bornyl acetate is always endo -configured, the exo -configuration is called isobornyl acetate . There are two isomeric forms, (-) - and (+) - bornyl acetate [synonyms: (1 S , 2 R , 4 S ) -boronyl acetate and (1 R , 2 S , 4 R ) -boronyl acetate], which are often used as 1: 1 mixture ( racemate ) occur.

Isomers of Bornyl Acetate
Surname	(-) - Bornyl acetate	(+) - Bornyl acetate
other names	(1 S , 2 R , 4 S ) -1,7,7-trimethylbicyclo [2.2.1] hept-2-yl acetate	(1 R , 2 S , 4 R ) -1,7,7-trimethylbicyclo [2.2.1] hept-2-yl acetate
Structural formula
CAS number	5655-61-8	20347-65-3
	76-49-3 (racemate)
EC number	227-101-4	243-750-6
	200-964-4 (racemate)
ECHA info card	100,024,638	100,039,757
	100,000,878 (racemate)
PubChem	442460	6950274
	6448 (racemate)
Wikidata	Q27105264	Q27284125
	Q780165 (racemate)

Occurrence

Chaste tree ( Vitex agnus-castus )

Black spruce ( Picea mariana )

The ester belongs to the drug family of essential oils and is found in many plants available such as in the, conifers fir ( Abies ), pine ( Pinus ), spruce ( Picea ) and larch ( Laryx ), but also in chaste tree ( Vitex agnus- castus ), musk yarrow ( Achillea moschata ), magnolias ( Magnolia ) and wild flowers ( Tanacetum ).

Properties and appearance

Bornyl acetate is a white, crystalline substance that gives the pine and spruce needle oil its characteristic odor. As a pure substance, the compound smells very strongly of spruce or pine and has a burning taste. The characteristic odor can already be perceived in a concentration of 75  ppb or more. Bornyl acetate melts at 25 to 29 ° C to a colorless liquid and can be produced industrially from borneol and acetic acid.

use

Balsam fir needle oil ( Abietis balsameae aetherloeum ) and spruce needle oil ( Piceae aetheroleum ) contain up to 23%, Canada balsam ( Balsamum canadense ) between 4 and 11% bornyl acetate. These essential oils are used for rubbing in, pure bornyl acetate and its isomer isobornyl acetate as an odor component in bath preparations, sprays and soaps , baked goods, puddings and beverages and as a component of pharmaceuticals ( Lindofluid N ).

Individual evidence

1. ↑ ^{a b} entry on bornyl acetate. In: Römpp Online . Georg Thieme Verlag, accessed on June 26, 2014.
2. ↑ European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, p. 545, ISBN 978-3-7692-3962-1 .
3. ↑ ^{a b c} Hermann Ammon (Ed.): Hunnius Pharmaceutical Dictionary . 8th edition, de Gruyter, Berlin 2004, ISBN 3-11-015792-6 .
4. ↑ ^{a b c d e f g} G.A. Burdock: Fenaroli's Handbook Of Flavor Ingredients , 2004, CRC Press , ISBN 0-8493-3034-3 .
5. ↑ Bornyl acetate data sheet from Sigma-Aldrich , accessed on March 30, 2011 ( PDF ).
6. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
7. ↑ U. Schwabe, D. Paffrath: Drug Ordinance Report 2003 , Springer-Verlag , ISBN 3-540-40188-1 .