Anisaldehyde

Structural formula
General
Surname	Anisaldehyde
other names	4-methoxybenzaldehyde p -methoxybenzaldehyde ANISALDEHYDE ( INCI )
Molecular formula	C 8 H 8 O 2
Brief description	yellowish liquid with a characteristic odor
External identifiers / databases
CAS number 123-11-5 EC number 204-602-6 ECHA InfoCard 100.004.185 PubChem 31244 ChemSpider 21105937 Wikidata Q174937
properties
Molar mass	136.15 g mol −1
Physical state	liquid
density	1.12 g cm −3 (25 ° C)
Melting point	0-2 ° C
boiling point	247-249 ° C
Vapor pressure	1 hPa (20 ° C)
solubility	poor in water (2 g l −1 at 20 ° C)
Refractive index	1.5731
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	3210 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

Anisaldehyde is an aromatic compound , is structurally derived from benzaldehyde or anisole and belongs to the group of methoxybenzaldehydes .

Occurrence

In nature, aniseed aldehyde occurs in anise , fennel and other essential oils. It is synthesized in plants via the shikimic acid route .

Extraction and presentation

Anisaldehyde can be obtained by oxidation (e.g. by nitric acid or chromic acid ) of anethole or 4-methoxytoluene or from anisole by a Vilsmeier reaction .

properties

By reaction of anisaldehyde with oxidizing agents (. Eg Fehling - or silver mirror sample ) can be anisic acid ( p -Methoxybenzoesäure) represent.

use

Anisaldehyde is used as an intermediate in the synthesis of drugs, fragrances and other chemicals.

Anisaldehyde is used in thin-layer chromatography in the form of a spray reagent for the detection of various classes of natural substances (especially terpene derivatives ). For this, 0.5 mL anisaldehyde is mixed with 10 mL glacial acetic acid , 85 mL methanol and 5 mL conc. Sulfuric acid mixed in the order given. After this solution has been sprayed onto the TLC plate and the plate is subsequently heated to approx. 110 ° C. for 5 to 10 minutes, the corresponding zones change color characteristic in daylight. This reagent is listed under the name anisaldehyde reagent R in the European Pharmacopoeia (Ph. Eur.). The reagent is stable for a limited time only. If it turns red-violet, it should be discarded.

safety instructions

The vapors of anisaldehyde can form an explosive mixture with air ( flash point 116 ° C, ignition temperature 220 ° C).

Individual evidence

1. ↑ Entry on ANISALDEHYDE in the CosIng database of the EU Commission, accessed on February 25, 2020.
2. ↑ ^{a b c d e f g h i j} Entry for CAS no. 123-11-5 in the GESTIS substance database of the IFA , accessed on November 7, 2016(JavaScript required) .
3. ↑ CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
4. ^ ^{A b} Egon Stahl, Werner Schild: Isolation and characterization of natural substances . 1st edition. Gustav Fischer Verlag, Stuttgart / New York 1986, ISBN 3-437-30511-5 , p. 173 .
5. ↑ European Pharmacopoeia . 4.00 edition. tape 1 . Deutscher Apotheker Verlag / Govi-Verlag - Pharmazeutischer Verlag GmbH, Stuttgart / Eschborn 2002, ISBN 3-7692-2947-9 , p. 384 .