Cinnamon alcohol

Structural formula
General
Surname	Cinnamon alcohol
other names	trans cinnamon alcohol; ( E ) -cinnamon alcohol; Styron; trans -3-phenylallyl alcohol; trans -3-phenylprop-2-en-1-ol; FEMA 2294 ;
Molecular formula	C 9 H 10 O
Brief description	sweet-balsamic hyacinth-scented needles
External identifiers / databases
EC number	689-359-8
ECHA InfoCard	100.216.224
PubChem	5315892
ChemSpider	21105870
Wikidata	Q204030
properties
Molar mass	134.18 g mol −1
Physical state	firmly
density	1.04 g cm −3 (25 ° C)
Melting point	31-34 ° C
boiling point	258 ° C
Vapor pressure	1.33 hPa (114 ° C)
solubility	poor in water (1.8 g l −1 at 20 ° C)
Refractive index	1.5819 ( cis , 20 ° C); 1.5819 ( trans , 20 ° C);
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-317-319
	P: 280-305 + 351 + 338
Toxicological data	2000 mg kg −1 ( LD 50 , rat , oral )
	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

Cinnamyl alcohol ( 3-phenyl-2-propenol , FEMA 2294 ), also known as Styron referred to is a naturally occurring perfume , in the cosmetics industry is used. Cinnamon alcohol is an aromatic compound and is an unsaturated alcohol with a trans -substituted carbon-carbon double bond in the side chain. The isomeric cis or ( Z ) cinnamon alcohol is of little importance. The information in this article relates only to the trans cinnamon alcohol.

Occurrence

hyacinth

Cinnamon alcohol is found in a wide variety of plants. It is included in:

Extraction and presentation

Cinnamon alcohol can be obtained directly from cinnamon or from cinnamaldehyde by the Meerwein-Ponndorf-Verley reduction in 75% yield.

It is also possible to convert phenylpropargyl alcohol to cinnamon alcohol with the aid of lithium aluminum hydride .

properties

Physical Properties

Cinnamon alcohol forms sweet-balsamic needles that smell of hyacinths. It is poorly soluble in water, readily soluble in diethyl ether and miscible with ethanol .

Chemical properties

Cinnamon alcohol can be oxidized with manganese dioxide at room temperature in ether to form cinnamaldehyde in 87% yield.

use

Cinnamon alcohol is used as an additive (fragrance) in cosmetics (e.g. massage and baby oils, toilet paper) to obtain a violet or hyacinth scent. It is also used to make derivative compounds such as hydrocinnamon alcohol (phenylpropanol).

safety instructions

Cinnamon alcohol is a naturally occurring allergen .

Web links

Commons : Cinnamon Alcohol - Collection of images, videos and audio files

Individual evidence

↑ ^a ^b Entry on FEMA 2294 in the database of the Flavor and Extract Manufacturers Association of the United States .
↑ Entry on cinnamon alcohol. In: Römpp Online . Georg Thieme Verlag, accessed on November 11, 2014.
↑ Entry on 2-propen-1-ol, 3-phenyl- . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed September 24, 2012.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on cinnamon alcohol in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-432.
^ Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , p. 505.
^ Gattermann / Wieland : The practice of organic chemists , 43rd edition, Walter de Gruyter, Berlin · New York 1982, ISBN 3-11-006654-8 , pp. 483-484: Brownstone oxidation of cinnamon alcohol .
↑ Juliane Daphi-Weber, Heike Raddatz, Rainer Müller: Investigation of Fragrances - Controlled Fragrances , pp. 94–95, in Volume V of the series HighChem hautnah - News from food chemistry (published by the Society of German Chemists ) 2010, ISBN 978- 3-936028-64-5 .
↑ K. Jason Dennis and Takayuki Shibamoto: Photochemical Products of trans-Cinnamic Alcohol: Possible Formation of Skin Irritants and Allergens , In: J. Toxicol. Cutan. Ocul. Toxicol. , 1990 , 9 (2), pp. 149-157 ( doi : 10.3109 / 15569529009036319 ).
^ Heinrich Dickel: Implementation of a relational database system in the University Dermatology Clinic in Cologne with the evaluation of a bicontinental multicenter study - BAER study - on the question of allergen frequency in contact allergies . Dissertation, TH Aachen, 1996. DNB 97070903x / 34 .

[FEMA2294-1] Entry on FEMA 2294 in the database of the Flavor and Extract Manufacturers Association of the United States .

[roempp-2] Entry on cinnamon alcohol. In: Römpp Online . Georg Thieme Verlag, accessed on November 11, 2014.

[3] Entry on 2-propen-1-ol, 3-phenyl- . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed September 24, 2012.

[GESTIS-4] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on cinnamon alcohol in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[CRC90_3_432-5] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-432.

[6] Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , p. 505.

[7] Gattermann / Wieland : The practice of organic chemists , 43rd edition, Walter de Gruyter, Berlin · New York 1982, ISBN 3-11-006654-8 , pp. 483-484: Brownstone oxidation of cinnamon alcohol .

[Weber-8] Juliane Daphi-Weber, Heike Raddatz, Rainer Müller: Investigation of Fragrances - Controlled Fragrances , pp. 94–95, in Volume V of the series HighChem hautnah - News from food chemistry (published by the Society of German Chemists ) 2010, ISBN 978- 3-936028-64-5 .

[9] K. Jason Dennis and Takayuki Shibamoto: Photochemical Products of trans-Cinnamic Alcohol: Possible Formation of Skin Irritants and Allergens , In: J. Toxicol. Cutan. Ocul. Toxicol. , 1990 , 9 (2), pp. 149-157 ( doi : 10.3109 / 15569529009036319 ).

[10] Heinrich Dickel: Implementation of a relational database system in the University Dermatology Clinic in Cologne with the evaluation of a bicontinental multicenter study - BAER study - on the question of allergen frequency in contact allergies . Dissertation, TH Aachen, 1996. DNB 97070903x / 34 .