Perillaldehyde

Perillaldehyde[1]
Skeletal formula of perillaldehyde
Skeletal formula of perillaldehyde
Ball-and-stick model of perillaldehyde
Ball-and-stick model of perillaldehyde
Names
IUPAC name
(S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehyde
Other names
Perilla aldehyde; 4-Mentha-1,8-dien-7-al
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.639 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3 checkY
    Key: RUMOYJJNUMEFDD-UHFFFAOYSA-N checkY
  • InChI=1/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3
    Key: RUMOYJJNUMEFDD-UHFFFAOYAO
  • O=C\C1=C\CC(\C(=C)C)CC1
Properties
C10H14O
Molar mass 150.221 g·mol−1
Appearance Colorless liquid
Density 0.953 g/mL (20 °C)
Boiling point 237 °C (459 °F; 510 K) (745 mmHg)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Perillaldehyde, perillic aldehyde or perilla aldehyde, is a natural organic compound found most abundantly in the annual herb perilla, but also in a wide variety of other plants and essential oils. It is a monoterpenoid containing an aldehyde functional group.

Perillaldehyde, or volatile oils from perilla that are rich in perillaldehyde, are used as food additives for flavoring and in perfumery to add spiciness. Perillaldehyde can be readily converted to perilla alcohol, which is also used in perfumery. It has a mint-like, cinnamon odor and is primarily responsible for the flavor of perilla.

The oxime of perillaldehyde is known as perillartine or perilla sugar and is about 2000 times sweeter than sucrose and is used in Japan as a sweetener. It is presented in lower concentrations in the body odor of persons suffering from Parkinson's disease.[2]

Biosynthesis

In Perilla frutescens, the monoterpene, (S)-limonene, undergoes two oxidation steps. The enzyme (S)-limonene 7-monooxygenase gives (–)-perillyl alcohol and perillyl-alcohol dehydrogenase converts this to perillaldehyde.[3]

2D representation of the chemical structure of Q27089405.
(S)-limonene
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q105177714.
(–)-perillyl alcohol
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q23766753.
(–)-perillaldehyde


See also

References

  1. ^ Merck Index, 12th Edition, 7308.
  2. ^ Trivedi, Drupad K.; Sinclair, Eleanor; Xu, Yun; Sarkar, Depanjan; Walton-Doyle, Caitlin; Liscio, Camilla; Banks, Phine; Milne, Joy; Silverdale, Monty; Kunath, Tilo; Goodacre, Royston; Barran, Perdita (2019). "Discovery of Volatile Biomarkers of Parkinson's Disease from Sebum". ACS Central Science. 5 (4): 599–606. doi:10.1021/acscentsci.8b00879. PMC 6487537. PMID 31041379.
  3. ^ Karp F, Mihaliak CA, Harris JL, Croteau R (1990). "Monoterpene biosynthesis: specificity of the hydroxylations of (−)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves". Arch. Biochem. Biophys. 276 (1): 219–26. doi:10.1016/0003-9861(90)90029-X. PMID 2297225.
  • Wikimedia Commons logo Media related to Perillaldehyde at Wikimedia Commons

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