Misplaced Pages

4-Anisaldehyde: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editNext edit →Content deleted Content addedVisualWikitext
Revision as of 08:34, 15 April 2023 editJohn of Reading (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers767,049 editsm →top: Typo fixing, replaced: an formyl → a formylTag: AWB← Previous edit Revision as of 21:51, 13 November 2023 edit undoJon Kolbert (talk | contribs)Extended confirmed users, Page movers, File movers, IP block exemptions, New page reviewers, Rollbackers, Template editors139,984 editsm Reference edited with ProveIt #proveitTag: ProveIt editNext edit →
Line 2: Line 2:
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 387721524 | verifiedrevid = 387721524
| Reference=<ref>{{Cite book |title=The Merck index: an encyclopedia of chemicals, drugs, and biologicals |date=1994 |publisher=Merck |isbn=978-0-911910-28-5 |editor-last=Budavari |editor-first=Susan |edition=11. ed., 4. print |location=Rahway, NJ |pages=693}}</ref>
| Reference=<ref>''Merck Index'', 11th Edition, '''693'''</ref>
| Name = 4-Anisaldehyde | Name = 4-Anisaldehyde
| ImageFile1 = Anisaldehyde-2D-structure.svg | ImageFile1 = Anisaldehyde-2D-structure.svg
Line 38: Line 38:
|Section2={{Chembox Properties |Section2={{Chembox Properties
| C=8|H=8|O=2 | C=8|H=8|O=2
| Density = 1.119 g/cm<sup>3</sup><ref name=Aldrich>{{cite web | url = http://www.sigmaaldrich.com/catalog/product/aldrich/a88107?lang=en | title = p-Anisaldehyde | publisher = ]}}</ref> | Density = 1.119 g/cm<sup>3</sup><ref name="Aldrich">{{Cite web |title=p-Anisaldehyde |url=http://www.sigmaaldrich.com/catalog/product/aldrich/a88107?lang=en |publisher=]}}</ref>
| MeltingPtC = -1 | MeltingPtC = -1
| MeltingPt_ref = <ref name=Aldrich/> | MeltingPt_ref = <ref name=Aldrich/>
Line 59: Line 59:


== Uses == == Uses ==
Being structurally related to ], 4-anisaldehyde is a widely used in the fragrance and flavor industry.<ref name=Ullmann>{{Ullmann|author1=Karl-Georg Fahlbusch |author2=Franz-Josef Hammerschmidt |author3=Johannes Panten |author4=Wilhelm Pickenhagen |author5=Dietmar Schatkowski |author6=Kurt Bauer |author7=Dorothea Garbe |author8=Horst Surburg |title=Flavors and Fragrances|year=2003|doi=10.1002/14356007.a11_141}}</ref> It is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery. The related ] has a scent of licorice. Being structurally related to ], 4-anisaldehyde is a widely used in the fragrance and flavor industry.<ref name="Ullmann">{{Ullmann|author1=Karl-Georg Fahlbusch |author2=Franz-Josef Hammerschmidt |author3=Johannes Panten |author4=Wilhelm Pickenhagen |author5=Dietmar Schatkowski |author6=Kurt Bauer |author7=Dorothea Garbe |author8=Horst Surburg |title=Flavors and Fragrances|year=2003|doi=10.1002/14356007.a11_141}}</ref> It is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery. The related ] has a scent of licorice.


A solution of ''para''-anisaldehyde in acid and ethanol is a useful stain in thin layer chromatography.<ref></ref> Different chemical compounds on the plate can give different colors, allowing easy distinction. A solution of ''para''-anisaldehyde in acid and ethanol is a useful stain in thin layer chromatography.<ref></ref> Different chemical compounds on the plate can give different colors, allowing easy distinction.
Line 65: Line 65:
==DNA breakage== ==DNA breakage==


Anisaldehyde in combination with copper (II) can induce single- and double-strand breaks in double stranded ].<ref>{{cite journal|doi=10.3109/10715769609088030|pmid=8733936|title=DNA Single and Double Strand Breaks Induced by Aliphatic and Aromatic Aldehydes in Combination with Copper(II)|year=1996|last1=Becker|first1=T. W.|last2=Krieger|first2=G.|last3=Witte|first3=I.|journal=Free Radical Research|volume=24|issue=5|pages=325–332}}</ref> Anisaldehyde in combination with copper (II) can induce single- and double-strand breaks in double stranded ].<ref>{{Cite journal |last=Becker |first=T. W. |last2=Krieger |first2=G. |last3=Witte |first3=I. |year=1996 |title=DNA Single and Double Strand Breaks Induced by Aliphatic and Aromatic Aldehydes in Combination with Copper(II) |journal=Free Radical Research |volume=24 |issue=5 |pages=325–332 |doi=10.3109/10715769609088030 |pmid=8733936}}</ref>


== References == == References ==

Revision as of 21:51, 13 November 2023

4-Anisaldehyde
Structural formula of anisaldehyde
Ball-and-stick model of the anisaldehyde molecule
Ball-and-stick model of the anisaldehyde molecule
Space-filling model of the anisaldehyde molecule
Space-filling model of the anisaldehyde molecule
Names
Preferred IUPAC name 4-Methoxybenzaldehyde
Systematic IUPAC name 4-Methoxybenzenecarbaldehyde
Other names
  • 4-Anisaldehyde
  • p-Anisaldehyde
  • para-Anisaldehyde
  • Anisic aldehyde
  • Anise aldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.185 Edit this at Wikidata
EC Number
  • 204-602-6
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3Key: ZRSNZINYAWTAHE-UHFFFAOYSA-N
  • InChI=1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3Key: ZRSNZINYAWTAHE-UHFFFAOYAA
SMILES
  • COc1ccc(C=O)cc1
Properties
Chemical formula C8H8O2
Molar mass 136.150 g·mol
Density 1.119 g/cm
Melting point −1 °C (30 °F; 272 K)
Boiling point 248 °C (478 °F; 521 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302
Precautionary statements P264, P270, P301+P312, P330, P501
Flash point 108 °C (226 °F; 381 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

4-Anisaldehyde, or p-Anisaldehyde, is an organic compound with the formula CH3OC6H4CHO. The molecule consists of a benzene ring with a formyl and a methoxy group. It is a colorless liquid with a strong aroma. It provides sweet, floral and strong aniseed odor. Two isomers of 4-anisaldehyde are known, ortho-anisaldehyde and meta-anisaldehyde. They are less commonly encountered.

Production

Anisaldehyde is prepared commercially by oxidation of 4-methoxytoluene (p-cresyl methyl ether) using manganese dioxide to convert a methyl group to the aldehyde group. It can also be produced by oxidation of anethole, a related fragrance that is found in some alcoholic beverages, by oxidative cleavage of an alkene.

Uses

Being structurally related to vanillin, 4-anisaldehyde is a widely used in the fragrance and flavor industry. It is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery. The related ortho isomer has a scent of licorice.

A solution of para-anisaldehyde in acid and ethanol is a useful stain in thin layer chromatography. Different chemical compounds on the plate can give different colors, allowing easy distinction.

DNA breakage

Anisaldehyde in combination with copper (II) can induce single- and double-strand breaks in double stranded DNA.

References

  1. Budavari, Susan, ed. (1994). The Merck index: an encyclopedia of chemicals, drugs, and biologicals (11. ed., 4. print ed.). Rahway, NJ: Merck. p. 693. ISBN 978-0-911910-28-5.
  2. ^ "p-Anisaldehyde". Sigma-Aldrich.
  3. ^ Karl-Georg Fahlbusch; Franz-Josef Hammerschmidt; Johannes Panten; Wilhelm Pickenhagen; Dietmar Schatkowski; Kurt Bauer; Dorothea Garbe; Horst Surburg (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_141. ISBN 978-3527306732.
  4. Stains for Developing TLC Plates
  5. Becker, T. W.; Krieger, G.; Witte, I. (1996). "DNA Single and Double Strand Breaks Induced by Aliphatic and Aromatic Aldehydes in Combination with Copper(II)". Free Radical Research. 24 (5): 325–332. doi:10.3109/10715769609088030. PMID 8733936.
Categories: