4-Anisaldehyde

Last updated
4-Anisaldehyde [1]
Anisaldehyde-2D-structure.svg
Ball-and-stick model of the anisaldehyde molecule Anisaldehyde-from-xtal-Mercury-3D-bs.png
Ball-and-stick model of the anisaldehyde molecule
Space-filling model of the anisaldehyde molecule Anisaldehyde-from-xtal-Mercury-3D-sf.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.185 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-602-6
KEGG
PubChem CID
UNII
  • InChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
    Key: ZRSNZINYAWTAHE-UHFFFAOYSA-N
  • InChI=1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
    Key: ZRSNZINYAWTAHE-UHFFFAOYAA
  • COc1ccc(C=O)cc1
Properties
C8H8O2
Molar mass 136.150 g·mol−1
Density 1.119 g/cm3 [2]
Melting point −1 °C (30 °F; 272 K) [2]
Boiling point 248 °C (478 °F; 521 K) [2]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302
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 [77 °F], 100 kPa).
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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.

Contents

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. [3]

Uses

Being structurally related to vanillin, 4-anisaldehyde is a widely used in the fragrance and flavor industry. [3] 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. [4] 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. [5]

Related Research Articles

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<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

<span class="mw-page-title-main">Acetophenone</span> Chemical compound

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<span class="mw-page-title-main">Xylene</span> Organic compounds with the formula (CH3)2C6H4

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<span class="mw-page-title-main">Vanillin</span> Chemical compound

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<span class="mw-page-title-main">Cinnamaldehyde</span> Chemical compound

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<span class="mw-page-title-main">Carvone</span> Chemical compound

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<i>o</i>-Xylene Chemical compound

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In genetics, crosslinking of DNA occurs when various exogenous or endogenous agents react with two nucleotides of DNA, forming a covalent linkage between them. This crosslink can occur within the same strand (intrastrand) or between opposite strands of double-stranded DNA (interstrand). These adducts interfere with cellular metabolism, such as DNA replication and transcription, triggering cell death. These crosslinks can, however, be repaired through excision or recombination pathways.

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In chemical nomenclature, a descriptor is a notational prefix placed before the systematic substance name, which describes the configuration or the stereochemistry of the molecule. Some of the listed descriptors should not be used in publications, as they no longer accurately correspond with the recommendations of the IUPAC. Stereodescriptors are often used in combination with locants to clearly identify a chemical structure unambiguously.

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. 1 2 3 "p-Anisaldehyde". Sigma-Aldrich.
  3. 1 2 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.