Fenchole
Fenchol (1,3,3-trimethyl-2-nor-bornanole) are bicyclic monoterpene - alcohols with molecular formula C 10 H 18 O and the molar mass of 154.25 g · mol -1 . There are four stereoisomers of the natural product isomeric with borneol , namely the α-fenchols [(+) - and (-) - α-fenchol] and the β-fenchols [(+) - and (-) - β-fenchol] which the hydroxyl group is above the levels of the six-membered ring. You come z. As in rosemary , hops , nutmeg oil and pine oil , and fruits such as lime , the grapefruit and peel of orange in front.
properties
Natural fenchol extracted from plants is always a mixture of the four different isomers (CAS number: 1632-73-1) with an overall camphor- like odor, the composition of which depends on the plant species. There is therefore no defined melting point (range from 35 to 40 ° C) or boiling point (~ 200 ° C) for the mixture. The individual isomers each have their own odor, ranging from lime-like to camphor-like to wood-like, earthy . The taste is bitter and lime-like . The fenchols are almost insoluble in water, but easily soluble in ethanol . The (+) - α-isomer has an irritant effect on eyes, skin and mucous membranes.
Isomers
Fenchole | ||||||||||||||
Short name | (+) - α-fenchol | (-) - α-fenchol | (±) -α-fenchol | (±) -α / β-fenchol | (+) - β-fenchol | (-) - β-fenchol | (±) -β-fenchol | |||||||
IUPAC name | (+) - (1 R , 2 R , 4 S ) -α-fenchol | (-) - (1 S , 2 S , 4 R ) -α-fenchol | (+) - (1 S , 2 R , 4 R ) -β-fenchol | (-) - (1 R , 2 S , 4 S ) -β-fenchol | ||||||||||
Structural formula | 1: 1 mixture of (+) - α-fenchol and (-) - α-fenchol | Not further defined mixture of four stereoisomers | 1: 1 mixture of (+) - β-fenchol and (-) - β-fenchol | |||||||||||
CAS number | 2217-02-9 | 512-13-0 | 36386-49-9 | 1632-73-1 | 64439-31-2 | 470-08-6 | 36386-50-2 | |||||||
Physical state | firmly | liquid | ||||||||||||
Brief description | colorless solid | colorless oil | ||||||||||||
Melting point | 47-47.5 ° C | 43.7-48.5 ° C | 38 ° C | 35-40 ° C | 26-27 ° C | 7-8 ° C | 6 ° C | |||||||
boiling point | 94 ° C (20 mmHg) | 200 ° C | ~ 200 ° C | 201 ° C | ||||||||||
solubility | insoluble in water, soluble in ethanol | |||||||||||||
odor | woody, earthy camphor-like |
characteristic lime-like |
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GHS labeling |
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H and P phrases | see above | see above | 315-319-335 | no H-phrases | see above | see above | see above | |||||||
see above | see above | no EUH phrases | no EUH phrases | see above | see above | see above | ||||||||
see above | see above | 261-305 + 351 + 338 | no P-phrases | see above | see above | see above |
Presentation, reactions and use
Fenchols can be prepared by reducing fenchone with sodium in ethanol . The unsaturated fenchene , which are rarely found in essential oils , are formed by dehydrating fenchols .
(-) - α-Fenchol is used as a component in perfumes . Also in bergamot oil contained small amounts fenchol.
Natural fenchol is classified as FEMA GRAS ( G enerally R eported A s S afe , FEMA GRAS # 2480) in the United States and can therefore be used as a food additive . In 2003, 316.67 pounds (= 143.6 kg) of fenchols were used as odorous substances in the USA ; the permitted daily dose was set at 0.533 mg.
Individual evidence
- ↑ a b entry on fenchol. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
- ↑ Michèle Lees: Food authenticity and traceability. Woodhead Publishing, 2003, ISBN 978-1-85573-526-2 , p. 208.
- ↑ a b George A. Burdock: Encyclopedia of Food and Color Additives. CRC Press, 1996, ISBN 978-0-8493-9416-4 , p. 1091.
- ↑ TheGoodsCompany: fenchol
- ↑ a b c d e Fenchole data sheet (PDF) from Carl Roth , accessed on December 14, 2010.
- ↑ JIG Codagan, J. Buckingham, FJ MacDonald, PH Rhodes: Dictionary of organic compounds. 6th edition, pp. 6288, CRC Press, 1996, ISBN 978-0-412-54090-5 .
- ↑ a b c d e f g h i j S. Yanna: Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. CRC Press, 2003, ISBN 978-1-58488-416-3 , pp. 1394-1395
- ↑ a b TheGoodsCompany: Data for (-) - alpha-fenchol
- ↑ Claudia Synowietz (Ed.): Paperback for chemists and physicists . founded by Jean d'Ans, Ellen Lax. 4th edition. Volume II: Organic Compounds . Springer, Berlin 1983, ISBN 3-540-12263-X .
- ↑ Fenchyl alcohol data sheet from Sigma-Aldrich , accessed on April 29, 2011 ( PDF ).
- ^ University of Erlangen : Natural Products Chemistry: Terpenes ( Memento from December 3, 2008 in the Internet Archive ), lecture script.
- ^ Dictionary of Flavors. 2nd edition, Wiley-Blackwell, 2009, ISBN 978-0-8138-2135-1 , p. 78.
- ^ GA Burdock, G. Fenaroli: Fenaroli's handbook of flavor ingredients. 5th edition, CRC Press, 2004, ISBN 978-0-8493-3034-6 , p. 654.