Bornyl acetate
Structural formula | ||||||||||||||||
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Structure of (-) - bornyl acetate | ||||||||||||||||
General | ||||||||||||||||
Surname | Bornyl acetate | |||||||||||||||
other names |
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Molecular formula | C 12 H 20 O 2 | |||||||||||||||
Brief description |
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properties | ||||||||||||||||
Molar mass | 196.29 g · mol -1 | |||||||||||||||
Physical state |
firmly |
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density |
0.981-0.99 g cm -3 |
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Melting point |
25-29 ° C |
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boiling point |
224-226 ° C |
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solubility |
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Refractive index |
1.4635 (20 ° C) |
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safety instructions | ||||||||||||||||
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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
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
- ↑ a b entry on bornyl acetate. In: Römpp Online . Georg Thieme Verlag, accessed on June 26, 2014.
- ↑ European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, p. 545, ISBN 978-3-7692-3962-1 .
- ↑ a b c Hermann Ammon (Ed.): Hunnius Pharmaceutical Dictionary . 8th edition, de Gruyter, Berlin 2004, ISBN 3-11-015792-6 .
- ↑ a b c d e f g G.A. Burdock: Fenaroli's Handbook Of Flavor Ingredients , 2004, CRC Press , ISBN 0-8493-3034-3 .
- ↑ Bornyl acetate data sheet from Sigma-Aldrich , accessed on March 30, 2011 ( PDF ).
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ U. Schwabe, D. Paffrath: Drug Ordinance Report 2003 , Springer-Verlag , ISBN 3-540-40188-1 .